Fall 2014 — Vol. 66, No. 3

A Publication of the Division of Chemical Information

of the ACS

ISSN: 0364–1910

®

CHEMICALInformation

BULLETIN

Chemical Information BulletinA Publication of the Division of Chemical Information of the ACS Fall 2014 — Vol. 66, No. 3

Message from the Chair 3

Letter from the Editor 5

Assistant Editor Column 6

ACS CINF Social Networking Events at the Fall 2014 ACS Meeting

8

Awards and Scholarships 10

Committee Reports 15

Harry’s Party by Peter F. Rusch and Harry M. Allcock 20

Book Review by Robert E. Buntrock 24

CINF Member Profile by Donna Wrublewski 26

Notes From Our Sponsors 28

Fall 2014 ACS CINF and Cosponsored Symposia Technical Program

33

Fall 2014 ACS CINF Abstracts 56

2014 CINF Officers and Functionaries 132

Future ACS Meetings 135

ISSN: 0364–1910Cover image is courtesy of flickr user Scott Hess (creative commons license).Chemical Information Bulletin © Copyright 2014 by the Division of Chemical Information of the American Chemical Society

Chemical Information Bulletin, 2014, 66 (3) 3

Message from the Chair Greetings from sweltering Philadelphia.

The crisp air and bustle of spring has given way to a hot, humid summer in Philadelphia. Many colleagues and students are on vacation, so it is a great time for an academic to

catch up on ongoing projects, perform research, and perhaps even produce a publication or two. It is also a good time to focus on one’s own professional development, including on the benefits gained and services that can be given to scholarly societies. I have found, over the past fifteen years, that my involvement in ACS and, more particularly in CINF, has offered me leadership and scholarship opportunities that I could not have obtained in any other venue. As the sole chemical information specialist at my university, CINF gives me the opportunity to network with colleagues in similar positions at other institutions and to stay up-to-date with the state-of-the-art in my field.

The most obvious method of networking and learning is through attendance at national meetings, and I’m pleased to report that this fall’s ACS National Meeting in San Francisco offers a wealth of excellent symposia on a wide variety of topics in chemical information and informatics (http://abstracts.acs.org/chem/248nm/program/divisionindex.php select CINF). On Tuesday, help us to celebrate the achievements of Engelbert Zass as he receives the Herman Skolnik Award for his contributions to chemical information. Sunday, Monday, and Tuesday evenings, engage with your colleagues at one of the various receptions and social events sponsored by CINF: the Welcome Reception on Sunday night, complete with the Scholarship for Scientific Excellence poster session and a brief business meeting; Harry’s Party on Monday; and the Herman Skolnik Award Reception on Tuesday. Finally, for those individuals looking to become more active in CINF, please stay tuned for more details about the Committee Dinner, to be held on Saturday, August 9. This is an opportunity for all CINF members to learn about committee activities and get involved.

As we all know, networking and learning are becoming increasingly digital. Even back in 1999, when I started my job, I “met” more of my chemical information colleagues over the CHMINF-L list than I did in person. Making “remote connections” is key to our business, and I am delighted to announce a project, undertaken by the CINF Membership Committee, to begin profiling CINF members and publishing the profiles in the CIB. The first profile appears in this issue; if you wish to be profiled or if you know a CINF member (new or experienced) whose story is particularly interesting, please contact Donna Wrublewski (dtwrub@caltech.edu). I would also like to commend Belinda Hurley, Carmen Nitsche, and the Communications and Publications Committee on an excellent series of CINF Webinars. If you missed any of them or want to know what subjects are forthcoming, please visit http://www.acscinf.org/content/webinars. CINF even has its own YouTube channel: http://www.youtube.com/user/cinfacs! Finally, I would like to thank the multitude of volunteers who responded to the call to join the Careers Committee. This is a very important

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committee and, among other activities, it will be partnering with the ACS Undergraduate Programs Office and the ACS Graduate & Postdoctoral Scholars Office to get out the word about careers in chemical information.

Before I close, I’d like to take this opportunity to welcome the almost 400 individuals who became CINF members during 2014. I look forward to meeting you, working with you, and hearing your stories. In the meanwhile, enjoy the rest of your summer!

With cool thoughts,

Judith CurranoChair, ACS Division of Chemical Information

currano@pobox.upenn.edu

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Letter from the EditorTo remember Harry Allcock (IFI CLAIMS Patent Services and longtime contributor to the CINF division) we have re-printed Harry’s and Peter Rusch’s account of Harry’s Party over the years. My first experience with Harry’s Party was only a few months ago at the ACS Meeting in Dallas, TX earlier this year. All I will say is: yes, it really is that good. Harry’s Party will continue to be an integral component of the CINF social activities.

In this fall 2014 pre-conference issue of the ACS Chemical Information Bulletin (CIB), we have a couple of new features including Member Profiles by Donna T. Wrublewski, and an Assistant Editor Column from Teri Vogel on Science and Popular Culture. Moreover, Bob Buntrock (our Chief Book Reviewer) submitted a review of Mario Markus’ Chemical Poems: One on Each Element. We also have information on the social events, committee reports, notes from our sponsors, and the technical program. Thank you Donna, Teri, Bob and everyone else who submitted content and helped with the production of the CIB! I hope you enjoy reading this issue of the CIB. I’ll see you in San Francisco!

Vincent F. Scalfani, Editorvfscalfani@ua.edu

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Assistant Editor’s Column: Science and Popular CultureJuly in San Diego means one thing: Comic-Con, more than 130,000 people and five days of pop culture, fun, craziness, and long lines. And among the many sessions scheduled is Science of Science Fiction. With scientists and screenwriters among the panelists, it should be a lively discussion about how recent films and television shows have gotten the science right, and maybe not so right. There will also be a second, similar session moderated by the Nerdist science editor, one on the psychology, kinesiology, and neuroscience of Batman, and two panels on the robots, androids and artificial intelligence in entertainment and what we can expect to see in our near future.

Inspired by my favorite event of the year, here are some fun and informative resources that celebrate science and popular culture.

When you think of chemistry and entertainment, one of the first examples to come to mind is probably Breaking Bad. Jyllian Kemsley at Chemical & Engineering News interviewed the show’s creator Vince Gilligan for an article in 2008. When the finale aired in September 2013, she interviewed their science advisor, organic chemist Donna J. Nelson, and in tribute compiled a list of some of her favorite articles, interviews and blog posts about the series.

Analytical chemist Raychelle Burks (aka @DrRubidium) wrote about zombie repellent chemistry and The Walking Dead, and worked with ACS to produce a video based on that blog post: Zombie Apocalypse Survival Chemistry: Death Cologne.

(Spoilers for season 4 of Game of Thrones)When a character was murdered in season four of Game of Thrones, several people speculated on the possible poison involved, including Burks (blog post and ACS Reactions video), forensic toxicologist Justin Brower at Nature’s Poisons, and science journalist Rachel Nuwer at Boing Boing.

The Zombie Research Society has a section on zombie science, with articles on infectious sources and physiology. Neuroscientists Bradley Voytek (University of California San Diego) and Timothy Verstynen (Carnegie Mellon University) have given talks about zombie brains and spoken to Neurology Today and Wired about their work, which also went into this infographic.

Orphan Black, BBCA’s series about a group of women who have discovered they are clones, just completed its second season. Kyle Hill at The Nerdist praised the show for how it deals with cloning and genetics, while ThinkProgress interviewed the show’s science consultant, Cosima Herter.

With the slogan “We come from the future,” the io9 blog has long been one of my daily reads for news about science as well as science fiction. Sometimes they intersect, whether it’s news of using water waves to create a tractor beam, or NASA’s JPL Ops Lab founder answering questions about holodecks and videogame technology.

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Jon Spaihts, who was one of the Prometheus screenwriters is currently working on scripts for The Black Hole and Doctor Strange, recently spoke with Alex Jackson for Nature’s Soapbox Science blog. In the interview he discusses the importance of science in filmmaking and his scripts in particular, and the trade offs that sometimes have to made to preserve the drama of the story. Also from Jackson for the Nature blogs: Behind the Science of Hollywood, which touches on the work of the National Academy of Sciences Science and Entertainment Exchange and it’s role connecting entertainers with scientists and engineers.

A group of science writers recently participated in a blog carnival about the Science of Tatooine, with posts about its water, plant and animal life, and environment. You can read the Tatooine Intergovernmental Report on Climate Change, a naturalist’s piece about the biology of the sarlacc, or an article suggesting that the over hunting of Krayt dragons may have led to the planet’s desertification.

And finally, there is Hollywood Chemistry: When Science Met Entertainment, published in 2013 by the American Chemical Society. You’ll find chapters on particular shows and films from Breaking Bad to The Avengers, and how the public’s understanding of science is influenced by what we see on the large and small screens. The book is available online as part of the ACS Symposium Series, but it can also be purchased in print for a third of what titles in this series typically cost.

Teri Vogel, Assistant Editortmvogel@uscd.edu

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ACS CINF Social Networking Events at the Fall 2014 ACS Meeting

Please Join Us at these Division of Chemical Information Events!

The ACS Division of Chemical Information is pleased to host the following social networking events at the Fall 2014 ACS National Meeting in San Francisco, CA.

(Please check for updates to the Fall 2014 Sponsors in the electronic version of the Fall 2014 Chemical Information Bulletin at http://bulletin.acscinf.org)

o Sunday Welcoming Reception & Scholarships for Scientific Excellence Posters 6:30-8:30pm, Sunday, August 10th – Ralston Room, Palace Hotel * Shuttle Route 1.

Reception co-sponsored by Bio-Rad Laboratories, InfoChem, Kilmorie Clarke, Springer, and AAAS/Science. Scholarships for Scientific Excellence sponsored exclusively by Royal Society of Chemistry.

o Harry’s Party 5:30-8:00pm Monday, August 11th – San Francisco Marriott Marquis, Room TBD.

Sponsored exclusively by ACS Publications.

o Tuesday Luncheon (Ticketed Event – Contact Division Chair, Judith Currano).12:15-1:30 pm Tuesday, August 12th – Telegraph Hill, InterContinental Hotel

Sponsored exclusively by the RSC Publishing.Speaker: Prof. Dr. Barend Mons - Data stewardship, boring or soaring?

o Herman Skolnik Award Reception honoring Dr. Engelbert Zass. 6:30-8:30pm Tuesday, August 12th – Grand Ballroom C, Intercontinental Hotel

Executive sponsors: Elsevier/Reaxys, Thieme Chemistry, ACS Publications and Chemical Abstracts Service.

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Tuesday CINF Luncheon Presentation – ‘Data stewardship, boring or soaring?’ In the eScience era, meaningful pattern recognition in high dimensional and complex data has a major contribution to knowledge discovery in science, specifically chemistry and biology, whether it be in drug discovery or materials development. In order to optimally (re-)use data for this purpose, the data need to be machine-readable. However, many key data sets and databases are not in enabling formats and most research projects do not even have a “data management plan” that deals with the generated data for the duration of the project. Many key data sets therefore go unnoticed or worse, get lost. Data stewardship emphasizes the long-term availability of data for continued use in human and machine meta-analyses. This talk will cover aspects of data publishing in FAIR format (Findable, Accessible, Interoperable and Reusable). It will also show how well stewarded data can serve “in silico knowledge discovery” and may change the metrics of scientific attribution. Specifically interaction between traditionally separated chemical and biological data will be addressed.

BiographyProf. Dr. Barend Mons holds a chair in Biosemantics at the Leiden University Medical Centre and is Head of Node for The Netherlands in ELIXIR. In addition, he acts as a Life Sciences “eScience integrator” in the Netherlands e-Science centre. Barend is also a member of the Executive Committee of the IMI project Open PHACTS, and one of the Founders of the Concept Web Alliance. He also serves on several scientific and technical advisory boards. Currently, he also advises a start up company that was built around nanopublications, called EURETOS.

Barend is a molecular biologist by training and received his MSc in Biology (cum laude) in 1981 and his PhD in 1986 on genetics of malaria parasites, from Leiden University, The Netherlands. Subsequently he performed over a decade of research on malaria genetics and vaccine development in close collaboration with colleagues in developing countries. He served the research department of the European Commission in this field for 3 years as a seconded national expert and gained further experience in science management at the Research Council of The Netherlands (NWO). Barend was a co-founder of three spin-off companies in biotechnological and semantic technologies, and an advisor for several others.

In the year 2000, Barend switched to the development of semantic technologies to manage big data and he founded the www.biosemantics.org Biosemantics group. At present, Barend is Professor in Biosemantics at the at the Department of Human Genetics at the Leiden University Medical Centre with an honorary appointment in the same discipline at the Department of Medical Informatics, Erasmus Medical Centre, University of Rotterdam, both in The Netherlands. From 2009-2014 he was also Scientific Director of the Netherlands Bioinformatics Center (NBIC) and board member of the interim ELIXIR international board. His research is focused on www.nanopub.org nanopublications as a substrate for in silico knowledge discovery.

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Applications Invited for CSA Trust Grant for 2015

The Chemical Structure Association (CSA) Trust is an internationally-recognized organization established to promote the critical importance of chemical information to advances in chemical research. In support of its charter, the Trust has created a unique Grant Program and is now inviting the submission of grant applications for 2015.

Purpose of the Grants: The Grant Program has been created to provide funding for the career development of young researchers who have demonstrated excellence in their education, research or development activities that are related to the systems and methods used to store, process and retrieve information about chemical structures, reactions and compounds. One or more Grants will be awarded annually up to a total combined maximum of ten thousand U.S. dollars ($10,000). Grants are awarded for specific purposes, and within one year each grantee is required to submit a brief written report detailing how the grant funds were allocated. Grantees are also requested to recognize the support of the Trust in any paper or presentation that is given as a result of that support.

Who is Eligible? Applicant(s), age 35 or younger, who have demonstrated excellence in their chemical information related research and who are developing careers that have the potential to have a positive impact on the utility of chemical information relevant to chemical structures, reactions and compounds, are invited to submit applications. While the primary focus of the Grant Program is the career development of young researchers, additional bursaries may be made available at the discretion of the Trust. All requests must follow the application procedures noted below and will be weighed against the same criteria.

Which Activities are Eligible? Grants may be awarded to acquire the experience and education necessary to support research activities, for example, for travel to collaborate with research groups, to attend a conference relevant to one’s area of research, to gain access to special computational facilities, or to acquire unique research techniques in support of one’s research.

Application Requirements:

1. A letter that details the work upon which the Grant application is to be evaluated as well

Chemical Structure Association Trust

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as details on research recently completed by the applicant;

2. The amount of Grant funds being requested and the details regarding the purpose for which the Grant will be used (e.g., cost of equipment, travel expenses if the request is for financial support of meeting attendance, etc.). The relevance of the above-stated purpose to the Trust’s objectives and the clarity of this statement are essential in the evaluation of the application;

3. A brief biographical sketch, including a statement of academic qualifications;

4. Two reference letters in support of the application. Additional materials may be supplied at the discretion of the applicant only if relevant to the application and if such materials provide information not already included in items 1–3. Three copies of the complete application document must be supplied for distribution to the Grants Committee.

Deadline for Applications: The deadline for applications for the 2015 Grant is March 13, 2015. Successful applicants will be notified no later than May 2, 2015.

Address for Submission of Applications: Three copies of the application documentation should be forwarded to: Bonnie Lawlor, CSA Trust Grant Committee Chair, 276 Upper Gulph Road, Radnor, PA 19087, USA. If you wish to enter your application by e-mail, please contact Bonnie Lawlor at chescot@aol.com prior to submission so that she can contact you if the e-mail does not arrive.

Chemical Structure Association Trust: Previous Grant Awardees

2014 – Dr. Adam MadaraszInstitute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences. He was awarded a Grant for travel to study at the University of Oxford with Dr. Robert S. Paton, a 2013 CSA Trust Grant winner, in order to increase his experience in the development of computational methodology which is able to accurately model realistic and flexible transition states in chemical and biochemical reactions.

2014 – MJosé Ojeda MontesDepartment of Biochemistry and Biotechnology, University Rovira i Virgili, Spain. She was awarded a Grant for travel expenses to study for four months at the Freie University of Berlin to enhance her experience and knowledge regarding virtual screening workflows for predicting therapeutic uses of natural molecules in the field of functional food design.

2014 – Dr. David PalmerDepartment of Chemistry, University of Strathclyde, Scotland. He was awarded a Grant

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to present a paper at the fall 2014 meeting of the American Chemical Society on a new approach for representing molecular structures in computers based upon on ideas from the Integral Equation Theory of Molecular Liquids.

2014 – Sona B. WarrierDepartments of Pharmaceutical Chemistry, Pharmaceutical Biotechnology, and Pharmaceutical Analysis, NMIMS University, Mumbai. She was awarded a Grant to attend the International Conference on Pure and Applied Chemistry to present a poster on her research on inverse virtual screening in drug repositioning.

2013 – Dr. Johannes HachmannDepartment of Chemistry and Chemical Biology at Harvard University, Cambridge, MA. He was awarded the Grant for travel to speak on “Structure-property relationships of molecular precursors to organic electronics” at a workshop sponsored by the Centre Européen de Calcul Atomique et Moléculaire (CECAM) that took place October 22 – 25, 2013 in Lausanne, Switzerland.

2013 – Dr. Robert S. PatonUniversity of Oxford, UK. He was awarded the Grant to speak at the Sixth Asian Pacific Conference of Theoretical and Computational Chemistry in Korea on July 11, 2013. Receiving the invitation for this meeting provided Dr. Paton with an opportunity to further his career as a Principal Investigator.

2013 – Dr. Aaron ThorntonMaterial Science and Engineering at CSIRO in Victoria, Australia. He was awarded the Grant to attend the 2014 International Conference on Molecular and Materials Informatics at Iowa State University with the objective of expanding his knowledge of web semantics, chemical mark-up language, resource description frameworks and other online sharing tools. He also visited Dr. Maciej Haranczyk, a prior CSA Trust Grant recipient, who is one of the world leaders in virtual screening.

2012 – Tu LeCSIRO Division of Materials Science & Engineering, Clayton, VIV, Australia. Tu C. was awarded the Grant for travel to attend a cheminformatics course at Sheffield University and to visit the Membrane Biophysics group of the Department of Chemistry at Imperial College London.

2011 – J. B. BrownKyoto University, Kyoto, Japan. J.B. was awarded the Grant for travel to work with Professor Ernst Walter-Knappat the Freie University of Berlin and Professor Jean-Phillipe Vert of the Paris MinesTech to continue his work on the development of atomic partial charge kernels.

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2010 – Noel O’BoyleUniversity College Cork, Ireland. Noel was awarded the grant to both network and present his work on open source software for pharmacophore discovery and searching at the 2010 German Conference on Cheminformatics.

2009 – Laura Guasch PamiesUniversity Rovira & Virgili, Catalonia, Spain. Laura was awarded the Grant to do three months of research at the University of Innsbruck, Austria.

2008 – Maciej HaranczykUniversity of Gdansk, Poland. Maciej was awarded the Grant to travel to Sheffield University, Sheffield, UK, for a 6-week visit for research purposes.

2007 – Rajarshi GuhaIndiana University, Bloomington, IN, USA. Rajarshi was awarded the Grant to attend the Gordon Research Conference on Computer-Aided Design in August 2007.

2006 – Krisztina BodaUniversity of Erlangen, Erlangen, Germany. Krisztina was awarded the Grant to attend the 2006 spring National Meeting of the American Chemical Society in Atlanta, GA, USA.

2005 – Dr. Val Gillet and Professor Peter WillettUniversity of Sheffield, Sheffield, UK. They were awarded the Grant for student travel costs to the 2005 Chemical Structures Conference held in Noordwijkerhout, the Netherlands.

2004 – Dr. Sandra SaundersUniversity of Western Australia, Perth, Australia. Sandra was awarded the Grant to purchase equipment needed for her research.

2003 – Prashant S. KharkarInstitute of Chemical Technology, University of Mumbai, Matunga, Mumbai. Prashant was awarded the Grant to attend the conference, Bioactive Discovery in the New Millennium, in Lorne, Victoria, Australia (February 2003) to present a paper, “The Docking Analysis of 5-Deazapteridine Inhibitors of Mycobacterium avium complex (MAC) Dihydrofolate reductase (DHFR).”

2001 – Georgios GkoutosImperial College of Science, Technology and Medicine, Department of Chemistry. London, UK. Georgios was awarded the Grant to attend the conference, Computational Methods in Toxicology and Pharmacology Integrating Internet Resources, (CMTPI-2001) in Bordeaux, France, to present part of his work on internet-based molecular resource discovery tools.

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®

CINF Scholarship for Scientific Excellence Co-sponsored by InfoChem and Springer

The international scholarship program of the Division of Chemical Information (CINF) of the American Chemical Society (ACS) co-sponsored by InfoChem (www.infochem.de) and Springer (www.springer.com) is designed to reward students in chemical information and related sciences for scientific excellence and to foster their involvement in CINF.

Up to three scholarships valued at $1,000 each will be awarded at the 249th ACS National Meeting in Denver, CO, March 22 – 26, 2015. Student applicants must be enrolled at a certified college or university; postdoctoral fellows are also invited to apply. They will present a poster during the Welcoming Reception of the division on Sunday evening at the national meeting. Additionally, they will have the option to show their poster at the Sci-Mix session on Monday night. Abstracts for the poster must be submitted electronically through MAPS, the abstract submission system of ACS.

To apply, please inform the chair of the selection committee, Guenter Grethe, at ggrethe@att.net, that you are applying for a scholarship. Submit your abstract at http://abstracts.acs.org using your ACS ID. If you do not have an ACS ID, follow the registration instructions and submit your abstract in the CINF program in the session “CINF Scholarship for Scientific Excellence.” MAPS will be open for abstract submissions from August 25, 2014, to October 17, 2014. Additionally, please send Guenter Grethe a 2000 word abstract in electronic form by January 31,2015, describing the work to be presented. Any questions related to applying for one of the scholarships should be directed to the same e-mail address.

Winners will be chosen based on content, presentation, and relevance of the poster and they will be announced during the Sunday reception. The content will reflect upon the student’s work and describe research in the field of cheminformatics and related sciences.

Guenter Grethe

About InfoChemInfoChem GmbH based in Munich, Germany, is a market leader in structure and reaction handling and retrieval. Founded in 1989, InfoChem focuses on the production and marketing of new chemical information products, including structural and reaction databases, and the development of software tools required for these applications. The main software tools provided are the InfoChem Fast Search Engine (ICFSE), the InfoChem Chemistry Cartridge for Oracle (ICCARTRIDGE) and the widely used InfoChem reaction classification algorithm CLASSIFY. InfoChem distributes one of the largest structural and reaction files worldwide, currently containing 7 million organic compounds and facts and 4 million reactions covering the chemical literature published since 1974 (SPRESI). In addition, InfoChem provides tools for the automatic recognition and extraction of chemical entities and their conversion into chemical structures as well as the semantic enrichment of chemical science documents. Springer GmbH (Berlin) has held a majority interest in InfoChem since 1991. For more infromation go to www.infochem.de.

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Report on the Council Agenda for August 13, 2014The Council of the American Chemical Society will meet in San Francisco, CA on Wednesday, August 13, 2014 from 8:00 am until approximately 12:00 pm in the Grand Ballroom B of the Hilton San Francisco Union Square Hotel. All ACS members are welcome to attend, although only Councilors are permitted to vote. A continental breakfast is usually available at 7:00 am for all attendees.

There are a number of items for Council Action, but all are routine. The action items are summarized below.

Nominations and ElectionsCommittee on Committees: Council will vote to fill five slots on the Committee on Committees. There are ten nominees as follows: Spiro D. Alexandratos, Mark A. Benvenuto, Mitchell R. M. Bruce, Judith N. Currano, Jetty L. Duffy-Matzner, Kathleen Gibboney, Bonnie Lawlor, Zaida Morales-Martinez, Robert A. Pribush, and Patricia A. Redden.

Council Policy Committee: Council will vote to fill five slots on the Council Policy Committee. There are ten nominees as follows: Lawrence Barton, Dwight W. Chasar, Lynne P. Greenblatt, Martha G. Holloman, Peter C. Jurs, Pamela D. Kistler, Doris I. Lewis, Christopher Masi, Andrea Twiss-Brooks and Linette M. Watkins.

Committee on Nominations and Elections: Council will vote to fill five slots on the Committee on Nominations and Elections. There are ten nominees as follows: Anthony W. Addison, John W. Finle, Lydia E. M. Hines, Roland F. Hirsch, Robert L. Lichter, Mamie W. Moy, Anne T. O’Brien, Eleanor D. Siebert, Herbert B. Silber, and Ralph A. Wheeler.

CommitteesThe Committee on Committees (ConC) will put forth a recommendation for the continuation of the committees that have been reviewed as required by the Committee Sunset Laws. The committees under consideration are the Committee on Science (ComSci) and the Committee on Patents and Related Matters (CPRM).

ConC will also recognize Councilors who have reached milestone anniversaries of service and committee members and chairs who have reached the statutory limit or completed their terms of service

New Edition of Professional Employment GuidelinesThe Committee on Economic and Professional Affairs (CEPA) is requesting that Council approve the 9th edition of The Professional Employment Guidelines. The document has been revised and updated to reflect current practices in the workplace and changes in U.S. labor laws and policies. The revised document was presented for consideration during the ACS National Meeting in Indianapolis in September 2013. Minor revisions were made to incorporate suggestions by Council members and others.

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Local Section Territory ChangeThe Committee on Local Section Activities (LSAC) will ask Council to vote to approve a request from the Philadelphia Local Section to extend its boundaries to include the Ocean County Local Section. LSAC was prepared to dissolve the Ocean County Local Section due to inactivity and the lack of response to an action plan that would have assisted with reviving the section. Neighboring sections have been polled and they do not object to the request. A majority of ACS members residing in the Ocean County who responded to a poll have favorably indicated that they wish to join the Philadelphia section.

New International Chemical Sciences ChapterA legal application has been received for the formation of the South Africa International Chemical Sciences Chapter. It will consist of the territory of South Africa and is not part of any other Chapter or Local Section of the Society. The petition was initiated and approved by ACS members in good standing and residing in the territory and it meets all of the requirements of Bylaw IX of the Society. The application includes a proposed budget which includes no allotment of funds from the Society. The petition has been reviewed by the ACS Committee on International Activities (IAC). If Council approves, its operations will be contingent upon the approval of the ACS Board of Directors.

Petitions for Vote to Chance the ACS BylawsThere are no petitions to change the ACS Bylaws.

Bylaw Changes for Consideration OnlyNo petitions to change the Bylaws are being presented for consideration at this meeting.

Town Hall MeetingA Town Hall meeting organized by the Committee on Nominations and Elections is scheduled for Sunday, August 10, 2014 in the Imperial Ballroom B of the San Francisco Hilton Union Square Hotel from 4:15pm - 5:15pm. It will highlight a Q&A session with the candidates for Directors-at-Large. All ACS members are encouraged to attend. It is a great way to gather first-hand information and decide for whom you might want to vote in the fall election.

Respectfully submitted July 12, 2014

CINF Councilors

Bonnie LawlorAndrea Twiss-Brooks

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Education CommitteeThe CINF Education Committee will meet Saturday afternoon at the upcoming ACS National Meeting in San Francisco. We will also be present at the Committee Dinner Saturday evening to talk to people who may be interested in joining the Education Committee. People do not have to physically attend all of the ACS Meetings in order to participate in the CINF Education Committee. If you are interested in joining the Education Committee, please contact Grace Baysinger (graceb@stanford.edu).

Information Skills for Graduate StudentsOne of the main agenda items for the CINF Education Committee at the fall ACS National Meeting in San Francisco will be to discuss a draft document on information skills needed for successful graduate students. Please feel free to join the Education Committee’s Meeting and participate in this discussion.

ACS Guidelines for Bachelor’s Degree Programs in ChemistryThe ACS Committee on Professional Training (CPT) has developed new guidelines for undergraduate chemistry programs that will be adopted in 2014. Changes include the guidelines on chemical information skills. For more details, please see links below. White Paper: Proposed Changes to the ACS GuidelinesSummary of Proposed ChangesChemical Information Skills

CPT will hold an open meeting at the 248th ACS National Meeting in San Francisco, California on Sunday, August 10. The time and location have not been determined as of this writing. CPT is organizing a symposium on “Enriching Professional Preparation of Students: Vertical Skill Integration and Capstone Experiences” at the Biennial Conference on Chemical Education at Grand Valley State University on Monday, August 4 from 9:30am to 12:30pm. View the schedule.

Explore Chemical Information Teaching Resources (XCITR)FIZ CHEMIE Berlin was very generous to develop and host the XCITR website, but due to changing circumstances was no longer able to do so. The Royal Society of Chemistry (RSC) graciously agreed to host XCITR for 2013-14. The URL has stayed the same: http://www.xcitr.org.

Submissions of educational materials from information providers, chemistry instructors, and librarians are desired. Submissions can be descriptions with links to web pages or videos on a provider’s website or deposition of documents. Because the audience is broad, XCITR is an excellent way to share information with colleagues and clients. The CINF Education Committee is very interested in any feedback you may have about XCITR. Please send comments to Grace Baysinger (graceb@stanford.edu).

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Biennial Conference on Chemical Education 2014BCCE 2014 will be held on August 3-7th at Grand Valley State University in Allendale, Michigan. Integrating Library and Information Resources into Chemistry Curricula (S61) is a full day program that will be held on Wednesday, August 6th. While the CINF Education Committee did not organize this session, Ye Li, a CINF Education Committee Member, is co-authoring the last presentation in the morning on Wikipedia editing. Please see abstract and links to presentations below.

Integrating Library and Information Resources into Chemistry Curricula (S61)Presider: Charity Lovitt, Seattle University

Information literacy, the ability to find and evaluate information resources, is an important skill for future scientists. For example, students and scientists need to distinguish among information provided by Wikipedia, ChemSpider, research journals, and the New York Times. Professors and librarians often teach this skill through database demonstrations, video tutorials, and lectures. However, it is possible to increase the impact of these activities by designing chemistry projects that incorporate information literacy as a learning outcome. This symposium provides a forum to share activities that help students find and evaluate information resources in the context of a science course. Of particular interest are activities and assignments that integrate information literacy and chemical literacy. All forms of activities are encouraged including videos, course projects, in-class activities, and online activities.

AM P772: Monitoring student abilities and perceptions regarding information literacy in chemistry (9:35 am to 9:55 am) P773: Research strategy for searching the literature more effectively (9:55 am to 10:15 am) P774: Collaborative chemical information literacy: Is it “scholarly?” (10:15 am to 10:35 am) P775: Student engagement through writing: an undergraduate e-journal project (10:35 am to 10:55 am) P776: Designing a library research project to identify credible resources on climate change (11:10 am to 11:30 am) P777: Debunking pseudoscience: video projects and related assignments to promote critical thinking of scientific information by chemistry students (11:30 am to 11:50 am) P778: Wikipedia editing in chemistry classrooms: learning chemistry and improving information competencies simultaneously (11:50 am to 12:10 pm)

PM P873: Engaging non-science majors in the chemistry around us through information literacy (2:05 pm to 2:25 pm) P874: Building information literacy in first-year chemistry students through student-centered learning and experimental design (2:25 pm to 2:45 pm) P875: Integrating and assessing information literacy in a large introductory chemistry course (withdrawn)

Chemical Information Bulletin, 2014, 66 (3) 19

P876: Incorporating library literacy into large classrooms through the laboratory (3:05 pm to 3:25 pm) P877: Integrating information literacy and research strategies into sophomore and senior level college chemistry courses (3:40 pm to 4:00 pm) P878: Reading, writing, review, and analysis: engaging with chemical literature to enhance analytical understanding (4:00 pm to 4:20 pm) P879: Integrating information literacy into the junior level organic chemistry experience (withdrawn)

Respectively, submittedGrace Baysinger

Chair, CINF Education Committee

Chemical Information Bulletin, 2014, 66 (3) 20

Remembering Harry AllcockHarry’s Party has been part of the CINF lore since the 1960’s. In fact, it appears that the party was first held in 1964, meaning that this year is the 50th anniversary of that noble (or ignoble) tradition. Because of its unofficial status, the exact date and location are lost to history. But Harry is not. We remember Harry Allcock on this occasion of his passing, and we also remember the life and enthusiasm he injected into our Division over the years. Reprinted from only a year ago (CIB Vol. 65 No. 1) are Pete Rusch’s and Harry’s reflections on Harry’s Party.

CAUTION: Because people ask, and because I wasn’t aware, I asked Peter Rusch to provide a history of Harry’s Party. I got everything I wanted to know and more. The entire uncensored PG-13 rated version has been included. For those who thought the CINF was a staid group of software developers, cheminformaticians, and librarians (in other words, a bunch of nerds), check it out, but at your own risk.

David Martinsen

Harry at Harry’s Party in Chicago, March 26th, 2007 http://www.acscinf.org/content/harrys-party-chicago-march-26th-2007

Chemical Information Bulletin, 2014, 66 (3) 21

Harry’s Party by Peter F. Rusch and Harry M. Allcock[Reprinted from CIB Vol. 65 No. 1]

“Harry’s Party has been hosted by Harry M. Allcock (IFI/Plenum Data Corporation) at every ACS National Meeting since the early 1960’s. While ‘unofficial’, it has become a divisional tradition to which every attendee looks forward on Monday evening.

Every party is well attended and is always considered as the best place to renew old acquaintances, to make new friends, and to exchange most-up-to-date information, especially on newest trends in information processing as well as who manages whom and what. The best remembered party was the one in the Caesars Palace in Las Vegas on August 25, 1980, when Harry and his associates served drinks standing in a huge decorative bathtub.

The opening paragraphs are from Val Metanomski’s prodigious and detailed history of the ACS Division of Chemical Information (CINF). Our objective is to paint a more complete picture filled with fact, trivia and wit that seemed to pervade all of Harry’s Parties.

Started in 1964 by Harry Allcock when there were few social events for the Division of Chemical Information at ACS National Meetings, it was a famous meeting place for all who attended, generously hosted by Harry until his retirement when FIZ CHEMIE Berlin continued the tradition until 2012.

Harry headed the successful IFI (Information for Industry) part of Plenum Publishing. Their product was a series of databases covering US patents for as long a period as data could be found. IFI even had information that the US Patent and Trademark Office (USPTO) had lost. The databases contained straightforward bibliographic data for US patents and a deeply indexed portion of high value.

For those of you who have met Harry, you know he is truly one of the most gregarious people to ever be in the chemical information business. Can anyone imagine Harry at a National ACS Meeting and not be involved in a party? Of course not!

Getting the ACS to host a party or, frankly, paying hotel prices for a hosted party, ran counter to Harry’s sensibilities. So, Harry took things into his own hands. I was a willing accomplice in many of these, but not at the beginning.

In the early days, Harry and IFI staff would arrange for refreshments, send out the invitations and have great party. One of Harry’s colleagues, Charlie Merrick, who owned and operated Rapid Patent, a patent copy service, was always present. Sadly his participation came to an end when he perished in a helicopter accident while traveling in New Zealand.

Harry continued. Eventually, I (Peter) became involved and it is those parties that I want to share with you.

Chemical Information Bulletin, 2014, 66 (3) 22

How to throw Harry’s Party the old-fashioned way.Hotel accommodationsMake arrangements at one of the hotels at the ACS National Meeting city, preferably through some ACS staff member who knows a good party. Reserve a hotel suite with a bedroom on either side. High floor is good. Arrive at the hotel on Sunday and check-in to the bedrooms. On Monday (the traditional day for Harry’s Party) get the key to the suite. Open the doors for inspection.

In Anaheim, Harry was unable to access the bedroom on the other side of the suite. The hotel manager assured him that the second bedroom would be cleaned and available by the time of the party. Finally, Harry saw a woman on the balcony that connected the bedrooms and the suite. Thinking her to be from the housekeeping staff, he politely thanked her for making up the room. In reality, her business arrangement with the previous occupant was completed and she wasn’t about to clean up anything.

RefreshmentsThis starts on Sunday because what’s needed first is several appropriate boxes. These are easily found at the ACS Exhibition that is setting up. Boxes with corporate logos, such as Plenum Publishing boxes, are essential. Also go by some booth to acquire a dozen plastic bags. Mission accomplished and on to phase two.

Harry’s Party is about liquid refreshments. That means: cheap scotch for Harry and other aficionados, jug (or box) of white wine for those who insist, jug red wine, soft drinks, and beer, lots of beer. The acquisition varies depending on the likely attendance. As more Germans attended, the beer component grew. Additionally, napkins, plastic cups, a bag (or maybe 2 bags) of pretzels. All of this is obtained at a deep-discount liquor store probably (but not always) across town from the hotel. In New Orleans we walked to and from a drug store on Canal Street in the mid-day heat and humidity; in Las Vegas it was one of the many cheap liquor stores and a taxi.

Pack all of the stuff in the boxes prior to arrival at the hotel. Hotels don’t want parties to use outside refreshments. This way, the bell staff will gladly take these boxes of “seminar material” to the suite and receive a generous tip. Use of suitcases is not recommended (once in Anaheim, a bottle broke and the leaking suitcase was a dead give-away in the elevator).

Monday afternoon after the announcement is made (vide infra) the next item required is ice. Take the plastic bags and with the help of one or more accomplices go to every ice machine on all of the adjacent floors, except the floor where the party will be held. That way the closest ice is the reserve.

Fill bathtub with ice. Add beer. Set out bags of pretzels and a few napkins. Place IFI sales brochures next to pretzels. Set up bar. At Caesar’s Palace (vide supra) the bar was the ironing board found in the room. The bath tub was a Roman tub close to the circular bed with a mirror overhead.

Chemical Information Bulletin, 2014, 66 (3) 23

InvitationsOn Monday morning go to the CINF session(s) with a note giving the hotel, room number and time (always 5:00 PM) for Harry’s Party. Have the session chair make announcement.

Believe it or not, there was another “Harry Allcock” who attended most ACS National meetings. He was known to complain bitterly that his phone rang at all hours with callers asking: “Where’s the party?” Even though our Harry Allcock always invited him to the party, he vowed to never attend and never did.

OpeningNo directional signs are necessary as by this time everybody knows where Harry’s Party is. The noise of the gathering crowd is sufficient to direct everyone to the right location. Open the door. Harry is at the bar to greet everyone and make generous drinks.

SecurityOnce the party has started it will get crowded. Standing room only is an understatement. In Caesar’s Palace the heat of the crowd set off the fire alarm prompting a visit from security who asked that we “keep it down.” In Anaheim, one of the guests started a contest to see if she could kick the chandelier. She couldn’t so her escort gave it a beefy right hook. In Atlanta, President Reagan was shot and everyone was on the bed watching TV. In Philadelphia, one of the guests located a trashy paperback book on an outside balcony on the 23rd floor. It was successfully retrieved to the delight of the guests. There was no door to the balcony.

ClosingSooner or later the refreshments are depleted. Even the pretzels are gone. Frankly, not much is done to keep guests from leaving at 7:00 PM. There’s no more food or drink and they all have other commitments anyway.

Clean-upAfter the guests are gone, put all of the empties and other trash in the plastic bags. In high-rise hotels there is bank of service elevators usually in a lobby adjacent to the guest elevators. When the service elevator arrives, look both ways, throw in the bags, push a button for a low floor, and exit the building by another route.

Repeat

Chemical Information Bulletin, 2014, 66 (3) 24

Book ReviewMarkus, Mario. Chemical Poems: One on Each Element. Dos Madres Press Inc. Loveland, OH, 2013. pp. 289 + xiv, ISBN 978-1-933675-98-5 (softcover) $30.

Also reviewed in C&EN:http://cen.acs.org/articles/92/i7/Elemental-Amulets.html

This delightful book combines the factual, historical, data, properties, and use information on the chemical elements with the literary. The factual information for each element appears on the left hand page and the facing page has a poem illustrating the author’s impressions of the scientific information. For each element, the state of matter, density (for liquids and solids), history (including discoverer), sources (including astronomical detection), and selected properties and uses are listed. Terms with asterisks are defined in the glossary and detailed references (375) are given for properties and uses. The subjects of the poems, written without rhyme or meter, concentrate on the discovery, properties, and uses of interest to the author. They tend to lyrically feature the people, mythology, emotional, social, and political aspects associated with each element. For example, use of phosphorus in matches and nerve gasses, often harmful, are poetically described, but uses as an essential plant nutrient and fertilizer are not. Beauty, as in gems, is often contracted with toxicity. Negative political and environmental aspects are often featured.

Although 118 elements are known or have been discovered (through the actinide series), elements 119-122, 126, 164, and 210 are described. These last are predicted to have at least one isotope that may be stable enough (close to an island of stability) for detection and investigation of its chemistry. Since element 113 and above 114 have not yet been named (even if discovered), a table of triple numeric symbols are given on the factual page for element 113 (Uut, also known as eka-thallium). Relativistic effects on the electrons for transuranic elements begin to appear and deviations from periodic relationships are described. Understandably, the properties and possible occurrence of undiscovered elements are items of conjecture, but detection in supernovas as well as residual “halos” from residual radioactive decay may be due to the prior presence of many.

A periodic table and a brief primer on nuclear chemistry are presented at the beginning of the book, including atomic and electronic shell structure as well as a diagram of the peninsula and islands of nuclear stability. Some of the properties and uses of the elements are well known but others are not, intriguing to both the author and reader. I did not spend the time to look up many of the original references, but I plan to do so. There are some errors. Properties and uses of compounds of the elements are not always distinguished from the elements themselves. The density of potassium is incorrectly listed as 8.56 so the decimal point is displaced by one. “Boron perborate” should be sodium perborate. The author is Chilean and was educated and has taught in Germany. The original version of the book was in Spanish and has been translated into German and English by the author.

Chemical Information Bulletin, 2014, 66 (3) 25

I found this book to be a novel and entertaining way to present chemical information. I recommend it to anyone interested in chemistry, chemical history, and poetry.

Robert E. BuntrockOrono, ME

buntrock16@roadrunner.com

Chemical Information Bulletin, 2014, 66 (1) 26

CINF Member Profile – Michael Qiuby Donna T. Wrublewski

Welcome to a new feature of the CIB – Member Profiles. Find out more about your CINF colleagues, what they find valuable about CINF, and even identify potential collaborators! If you’re interested in being interviewed for an upcoming CIB, please e-mail Donna at dtwrub@caltech.edu.

Who are you?Michael Qiu

What do you do?I am a Science and Engineering Librarian at the University of Southern California (USC). I serve as the subject librarian for the Department of Chemistry and the Mork Family Department of Chemical Engineering and Materials Science. My core job duties include:

1. Reference services at the Science and Engineering Library, Leavey Library (undergraduate), Doheny Library (main research library on campus) and virtual chat and e-mail through QuestionPoint

2. Outreach to faculty, students, and the greater USC community

3. Subject-specific instruction in chemistry and general instruction for the Writing program

4. Collection development in my subject areas.

In addition, we have faculty responsibilities to serve on appointed and elected library and university committees. I also am one of the faculty advisors to the USC Libraries Ambassadors, a group of undergraduates that works closely with the library to promote and market library services to undergraduates.

Why are you in the chemical information field?I received my Masters in Library and Information Science from UCLA in 2013 before starting my position at the USC. Before that, I received my BS in Chemistry from Iowa State University (Ames, Iowa) in 2011. When I was an undergraduate I started as a biochemistry major and I really, really, really wanted to go to medical school, but soon realized that I did not enjoy biology and biochemistry. I ultimately pursued chemistry because I enjoyed the field and the career possibilities after graduation. In addition, when I was in school, I

Chemical Information Bulletin, 2014, 66 (1) 27

was involved with my university library’s special collections and the local public library. I decided that I wanted to pursue librarianship as a way to work with people, but also stay in a scholarly and academic environment. I only learned during graduate school that science librarians were in high demand and that having a science background was a strength. I was lucky enough to have several opportunities to become a science librarian, specifically a chemistry librarian, after graduate school. Being a librarian, specifically my university’s chemical information specialist, has brought together everything I was looking for in a career. I not only get to be involved in the science I enjoyed so much as an undergraduate, but I also get to use my expertise as a librarian to help further research and education at USC.

What makes CINF valuable to you?In general, I believe that professional organizations are extremely important and they have the ability to bring leaders, movers and shakers, and novices and newbies (like me) into the same space where we are able to network, learn, and advance our field together. ACS CINF is a leading group for chemical information professionals and chemistry librarians and the most logical place with which to affiliate myself. In addition, CINF has provided me the opportunity to take on a role that is challenging, but also extremely valuable serving on the Fundraising Committee for 2014.

Want to learn more about Michael?

Get in Touch!

Michael QiuScience and Engineering LibrarianUniversity of Southern Californiaqium@usc.edu

Chemical Information Bulletin, 2014, 66 (3) 28

Notes From Our Sponsors

Division of Chemical Information Sponsors Fall 2014

The American Chemical Society Division of Chemical Information is very fortunate to receive generous financial support from our sponsors. Their support allows us to maintain the high quality of the Division’s programming and to promote communication between members at social functions at the ACS fall 2014 National Meeting in San Francisco, CA, and to support other divisional activities during the year, including scholarships to graduate students in chemical Information. Please check for updates to the Fall 2014 Sponsors in the Fall 2104 CIB at http://bulletin.acscinf.org

The Division gratefully acknowledges contributions from the following sponsors:

Gold ACS Publications Elsevier/Reaxys

Silver Bio-Rad Laboratories Chemical Abstracts Service

Royal Society of ChemistryRSC Publishing

Bronze InfoChem Kilmorie Clarke PerkinElmer Springer Thieme Chemistry Contributors AAAS/Science Opportunities are available to sponsor Division of Chemical Information events, speakers, and material. Our sponsors are acknowledged on the CINF web site, in the Chemical Information Bulletin, on printed meeting materials, and at any events for which we use your contribution. For more information please review the sponsorship brochure at http://www.acscinf.org/PDF/CINF_Sponsorship_Brochure.pdf. Please feel free to contact me if you would like more information about supporting CINF.

Phil HellerChair, Fundraising Committee Email: Fundraising@acscinf.orgTel: 917-450-4591The ACS CINF Division is a non-profit tax-exempt organization with taxpayer ID no. 52-6054220.

Chemical Information Bulletin, 2014, 66 (3) 29

PerkinElmer Launches New Version of ChemBioOffice SuiteSciFinder Search Provides Access to Comprehensive and Authoritative Chemistry Content

WHAT: PerkinElmer, Inc., a global leader focused on the health and safety of people and the environment, today announced the launch of a new version of its ChemBioOffice offering, an integrated suite of personal productivity tools that enables chemists and biologists to capture, store, retrieve and share data and information on compounds, reactions, materials and their properties.

HOW: The ChemBioDraw Ultra program, a component of the ChemBioOffice suite, is a digital drawing tool that chemists and biologists use to create publication-ready, scientifically intelligent drawings for use in electronic lab notebooks (ELNs), databases and publications. A popular new capability in our ChemBioDraw Ultra software allows scientists to draw structures or reactions and directly launch a search via a SciFinder button without time-consuming cutting and pasting of structures between different chemical drawing tools.

SciFinder® is a research discovery application that provides access to the world’s most comprehensive and authoritative source of references, substances and reactions in chemistry and related sciences, which are collected, organized and indexed by Chemical Abstracts Service (CAS) scientists.

“We are pleased to roll out our new version of the ChemBioOffice suite, providing scientists in chemistry and biology with enhanced capabilities for searching and productivity,” said Karen Madden, President, Informatics, PerkinElmer. “Our customers have found our direct access to the SciFinder search capability to be an invaluable tool for quickly locating relevant chemical information from CAS.”

MORE: Subscribers to the ChemBioOffice Ultra software will be entitled to deploy a special version of the ChemDraw for iPad mobile application, CDSLTM, throughout their organizations at no extra charge. This application provides convenient mobile access to the ChemDraw software application functionality with the ability to move and share files between the desktop and mobile versions.

The ChemBioOffice software suite (ChemBioDraw Ultra, ChemBio3D, ChemBioFinder, ChemBioFinde for Microsoft Office, ChemDraw for Microsoft Excel and ChemScript offerings) has been qualified for use with the Microsoft Windows 8.1 (32 and 64 bit) operating system and Microsoft Office 2013 (32 bit) suite. ChemBioDraw software has been qualified for use with the Mac OS 10.9 operating system (Mavericks)

Chemical Information Bulletin, 2014, 66 (3) 30

For more information on the SciFinder application and CAS content, visit www.cas.org.

For more information on PerkinElmer’s Informatics solutions, please visit www.perkinelmer.com/informatics.

About PerkinElmer, Inc.

PerkinElmer, Inc. is a global leader focused on improving the health and safety of people and the environment. The Company reported revenue of approximately $2.2 billion in 2013, has about 7,600 employees serving customers in more than 150 countries, and is a component of the S&P 500 Index. Additional information is available through 1-877-PKI-NYSE, or at www.perkinelmer.com.

Media Contact:Brian Willinskybrian.willinsky@perkinelmer.com781-663-5728

Chemical Information Bulletin, 2014, 66 (3) 31

Reaxys Facilitates and Accelerates Research for ChemistsWhether researching cutting-edge fields such as green chemistry or nanochemistry or working in drug development, chemists can more easily find relevant and reliable answers via a simple search query with Reaxys. Offered among other Elsevier Life Science Solutions, Reaxys provides access to key chemical formulas, physicochemical properties and experimental procedures extracted from chemistry journals and patents. Built by chemists for chemists, Reaxys enable researchers in every field of chemistry to drive their work forward. Combining a database that covers every chemistry-related field with customizable ways to execute search queries, Reaxys delivers relevant answers, saving time for researches. For chemistry questions, “ask Reaxys.” To learn more about Reaxys, please visit us at http://www.elsevier.com/online-tools/reaxys.

Chemical Information Bulletin, 2014, 66 (3) 32

New Thieme Chemistry Website

We are delighted to announce the relaunch of the Thieme Chemistry website www.thieme-chemistry.com.

Since the end of May a new and modern interface is available and provides useful information as well as easy access to all of our Thieme Chemistry products. The consistent, attractive design of the new website detailing information about our products (print and online) also allows users to switch smoothly between actual information pages and the online product of interest. All pages are linked directly with Thieme Connect, our online resource for electronic content.

Go to www.thieme-chemistry.com to

• find product information• access Thieme Chemistry e-products• sign-up for free trials of our online products• purchase books• find general news about Thieme Chemistry and our author community

The following products are covered:

• The Journals SYNTHESIS, SYNLETT and SYNFACTS: the peer-reviewed Thieme Chemistry journals have a long tradition in publishing excellent research in all fields of synthetic organic chemistry.

• The reference work Science of Synthesis, the full-text resource for methods in synthetic organic chemistry. It provides a critical review of the synthetic methodology developed from the early 1800s to date for the entire field of organic and organometallic chemistry.

• The reference work Pharmaceutical Substances, which is designed to be a complete reference guide to every pharmaceutical compound of significance. It provides a compendium of some 2,500 active pharmaceutical ingredients of interest to the chemical and pharmaceutical industries.

• The encyclopedia ROEMPP, our renowned German language encyclopedia covering chemistry and related topics.

• A selected program of Monographs complements our core program, each monograph highlighting a different aspect of organic chemistry.

Chemical Information Bulletin, 2014, 66 (3) 33

Technical Program

ACS Chemical Information Division (CINF)248th ACS National Meeting, Fall 2014

San Francisco, CA (August 10-14, 2014) CINF Symposia Erin Bolstad, Program Chair

**This meeting program was generated on July 14, 2014. The ACS meetings website will contain more up-to-date information.

Sunday, August 10, 2014

Nature’s Second Act: Revisiting Natural Products - AM Session

Palace Hotel Room: Marina Roger Schenck, Organizer Roger Schenck, Presiding

9:40 am - 12:00 pm

9:40 - Introductory Remarks

9:45 - 1 - Applying Royal Society of Chemistry cheminformatics skills to support the PharmaSEA project Antony J Williams1, tony27587@gmail.com, Valery Tkachenko1, Alexey Pshenichnov1, Ken Karapetyan1, David Sharpe2, Colin Batchelor2.

10:15 - 2 - From publishing to recognition – indexing literature for natural products David Evans1, david.evans@reedelsevier.ch, Pieder Caduff1, Juergen Swienty-Busch2.

10:45 - Intermission

11:00 - 3 - Hazardous substances data bank: A tool for natural product information and research Shannon M. Jordan, shannon.jordan1@nih.gov,

11:30 - 4 - Real structures for real natural products − really getting them right and getting them faster Patrick Wheeler1, pwheeler@yahoo.com, Antony Williams3, Mikhail Elyashberg2, Rostislav Pol2, Arvin Moser1.

Sunday, August 10, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - AM Session

Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding

8:40 am - 12:00 pm

8:40 - Introductory Remarks

8:50 - 5 - When your language is science: Abstracting, classifying, and

Chemical Information Bulletin, 2014, 66 (3) 34

indexing patents in the Derwent World Patents Index Donald Walter, don.walter@thomsonreuters.com,

9:20 - 6 - Chemistry and reactions from non-US patents Daniel M Lowe, daniel@nextmovesoftware.com, Roger A Sayle.

9:50 - 7 - Teach Document-to-Structure to be trilingual: Extract, display, and search chemical information within English, Chinese, and Japanese patents David Deng, ddeng@chemaxon.com, Daniel Bonniot.

10:20 - Intermission

10:35 - 8 - Chemically aware text mining platform David Milward, David.Milward@linguamatics.com, Andrew Hinton, andrew.hinton@linguamatics.com.

11:05 - 9 - CHEMDNER task: Automatic recognition of chemical entities in text Martin Krallinger1, Obdulia Rabal2, Florian Leitner1, Julen Oyarzabal2, julenoyarzabal@unav.es, Alfonso Valencia1.

11:35 - 10 - Structuring the unstructured: Creating knowledge through visual analytics and the use of Tibco Spotfire with Attivio for text analytics of scientific patents Philip J Skinner1, philip.skinner@perkinelmer.com, Joshua A Bishop1, Josh.Bishop@PERKINELMER.COM, Alexandia Vamvakidou1, Megean Schoenberg1, Sameer Nori2, Matt Connon2.

11:55 - Concluding Remarks

Sunday, August 10, 2014

Computational Methods and the Development/Production of Biologics and Biosimilars - AM Session

Palace Hotel Room: California Parlor Rachelle Bienstock, Organizer Rachelle Bienstock, Presiding

8:30 am - 9:35 am

8:30 - Introductory Remarks

8:35 - 11 - Classification, representation, and analysis of cyclic peptides and peptide-like analogs Roger A Sayle, roger@nextmovesoftware.com, Daniel M Lowe, Noel M O’Boyle.

8:55 - 12 - Non-covalent interactions in protein-ligand interactions: Applications of halogen bonds and carbon bonds in designing PTSD drugs Suman Sirimulla, suman.sirimulla@nau.edu,

9:15 - 13 - BCL:Conf A knowledge based ligand flexibility algorithm and application in computational drug discovery like online drug design game Foldit Sandeepkumar K Kothiwale1, sandeepkumar.k.kothiwale@vanderbilt.edu, Jens Meiler1,2, Will Lowe1.

Sunday, August 10, 2014

Science and the Law: How the Communication of Science Influences Science-Based Policy Development in the Environment, Food, Health, and Transport Sectors - PM Session

Palace Hotel Room: Marina Cosponsored by AGFD

Chemical Information Bulletin, 2014, 66 (3) 35

William Town, Organizer William Town, Presiding

1:15 pm - 5:25 pm

1:15 - Introductory Remarks

1:20 - 14 - Coming out from under the cloud of “Climategate”: Are scientists effectively communicating with the public on climate change? Frederick W Stoss, fstoss@buffalo.edu,

1:50 - 15 - Carbon accounting for indirect land use change (ILUC) in biofuels policy: The co-evolution of science and policy Hanna Breetz, hbreetz@berkeley.edu,

2:20 - 16 - Communicating the risk of nicotine delivery products Jim Solyst, jim.solyst@smna.com,

2:50 - Intermission

3:00 - 17 - PEPFAR - a US Government program that is helping to keep millions alive around the world George Lunn, george.lunn@fda.hhs.gov,

3:30 - 18 - Does science or communications have greater influence in formulating policy? A UK perspective Tamora Langley, Tlangley@webershandwick.com,

4:00 - 19 - Consumer communication of nutrition science and impact on public health David P Richardson, info@dprnutrition.com,

4:30 - 20 - Communicating controversial science: The case of tobacco harm reduction and the ethics of blanket censorship Sarah Cooney, sarah_cooney@bat.com,

Christopher Proctor.

5:00 - Panel Discussion

5:20 - Concluding Remarks

Sunday, August 10, 2014

Nature’s Second Act: Revisiting Natural Products - PM Session

Palace Hotel Room: Presidio Roger Schenck, Organizer Roger Schenck, Presiding

1:00 pm - 5:20 pm

1:00 - Introductory Remarks

1:05 - 21 - Evaluation of genus species coverage in chemical abstract Matthew J McBride, mmcbride@cas.org,

1:35 - 22 - Natural products information resources and the role of Dictionary of Natural Products Fiona M Macdonald, fiona.macdonald@informa.com, John Buckingham, Steve Walford.

2:05 - 23 - Garlic and other alliums: The lore and the science Eric Block, eblock@albany.edu,

2:35 - 24 - Rediscovering macrocyclic natural products as drug leads Roger Schenck, rschenck@cas.org,

3:05 - Intermission

3:20 - 25 - MarinLit: Database and essential tools for the marine natural products community Serin Dabb1, dabbs@rsc.org, John Blunt2, Murray Munro2.

Chemical Information Bulletin, 2014, 66 (3) 36

3:50 - 26 - RÖMPP natural products: An online encyclopedia Guido F. Herrmann, guido.herrmann@thieme.de, Manfred Köhl, Klaus Köberlein, Ute Rohlf.

4:20 - 27 - ChEMBL - linking chemistry and biology to enable mapping onto molecular pathways Louisa J Bellis, ljbellis@ebi.ac.uk, Anna Gaulton, Anne Hersey, A Patricia Bento, Jon Chambers, Mark Davies, Felix Kruger, Yvonne Light, Nathan Dedman, Shaun McGlinchey, Michal Nowotka, George Papadatos, Rita Santos, John P Overington.

4:40 - 28 - Treatment of Bifenthrin against subterranean termite damage to structural wood works in a semi-arid tropical urban system Sammaiah Chintha, sammaiah_ch@yahoo.com,

5:00 - 29 - Bioisosteres in accessible chemistry space Tim Cheeseright, tim@cresset-group.com, Mark Mackey, Rae Lawrence, Martin Slater.

Sunday, August 10, 2014

The Impact of the IUPAC InChI on Finding and Linking Information on Chemicals - PM Session

Palace Hotel Room: California Parlor Cosponsored by CHED, COMP Stephen Heller, Organizer Stephen Heller, Presiding

1:30 pm - 4:35 pm

1:30 - 30 - InChI project

Stephen Heller, steve@hellers.com,

1:40 - 31 - Moving the standard ever onwards: The role of the InChI Trust in supporting and developing the InChI David Evans, david.evans@reedelsevier.ch,

2:00 - 32 - How the InChI identifier is used to underpin our online chemistry databases at the Royal Society of Chemistry Antony J. Williams1, williamsa@rsc.org, Valery Tkachenko1, Karen Karapetyan1, Alexey Pshenichnov1, Colin Batchelor2.

2:35 - Intermission

2:50 - 33 - Data linking in PubChem using InChI Evan Bolton, bolton@ncbi.nlm.nih.gov,

3:25 - 34 - QR InCHI codes Jeremy G Frey, j.g.frey@soton.ac.uk, Andrew J Milsted, Simon J Coles.

4:00 - 35 - International chemical identifier for reactions (RInChI) Guenter Grethe1, ggrethe@att.net, Jonathan M Goodman2, Chad Allen2.

Sunday, August 10, 2014

CINF Scholarships for Scientific Excellence - EVE Session Palace Hotel Room: Ralston Guenter Grethe, Organizer

6:30 pm - 8:30 pm

36 - Toward quantitative structure-activity relationship (QSAR) models for nanoparticles Katarzyna Odziomek1,2, kjodziomek@lbl.gov, Daniela Ushizima2, Tomasz Puzyn1,

Chemical Information Bulletin, 2014, 66 (3) 37

Maciej Haranczyk2.

37 - Targeting androgen receptor DNA-binding domain using structure-based methods to overcome resistance Huifang Li, janelhf@gmail.com, Fuqiang Ban, Kush Dalal, Eric Leblanc, Paul S. Rennie, Artem Cherkasov.

38 - Carbon bond: A noncovalent interaction Chelsea Traina, cdt64@nau.edu, Erik M. Chavez, Erin Carter, Suman Sirimulla.

39 - Random walk-based prediction of novel drug-target interactions Abhik Seal, abseal@indiana.edu, Yong Yeol Ahn, David J Wild.

40 - Pred-hERG: A novel web-accessible computational tool for predicting cardiac toxicity of drug candidates Vinícius M Alves1, viniciusm.alves@gmail.com, Rodolpho C Braga1, rodolphobraga@yahoo.com, Meryck B Silva1, Eugene Muratov2, Denis Fourches2, Alexander Tropsha2, Carolina H Andrade1, carolina@ufg.br.

41 - Mining chemical space for novel molecules: A graphical tool for working with fragment spaces Florian Lauck, lauck@zbh.uni-hamburg.de, Matthias Rarey.

42 - BCL::EvoGen: An evolutionary algorithm for focused library design Alexander R Geanes, alexander.r.geanes@vanderbilt.edu, Edward W Lowe, Jens Meiler.

Monday, August 11, 2014

Global Challenges in the Communication of Scientific Research -

AM Session

Palace Hotel Room: Marina David Martinsen, Norah Xiao, Organizers David Martinsen, Norah Xiao, Presiding

8:05 am - 11:40 am

8:05 - Introductory Remarks

8:10 - 43 - Utility-based analysis of solar energy technologies Collin Perry, collinperry@my.unt.edu, William Justin Youngblood.

8:40 - 44 - New IUPAC organic nomenclature: From bottle label to update of databases Andrey Yerin, erin@acdlabs.ru,

9:10 - 45 - New strategies to engage more of the world with scientific app development and content deployment Steven M Muskal, smuskal@eidogen-sertanty.com,

9:40 - 46 - Dealing with the complex challenge of managing diverse chemistry data online Antony J Williams, williamsa@rsc.org, Valery Tkachenko, Ken Karapetyan, Alexey Pshenichnov.

10:10 - Intermission

10:20 - 47 - Amplifying the role of collaboration globally for neglected and commercial disease drug discovery Barry A. Bunin, bbunin@collaborativedrug.com, Charlie Weatherall, charlie@collaborativedrug.com.

10:50 - 48 - Why there needs to be open data for ultrarare and rare disease drug discovery

Chemical Information Bulletin, 2014, 66 (3) 38

Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2, Jill Wood3, Lori Sames4, Allison Moore5.

11:20 - 49 - Supporting the exploding dimensions of the chemical sciences via global networking Valery Tkachenko1, TkachenkoV@rsc.org, Anthony Williams1, Sergey Vatsadze2.

Monday, August 11, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - AM Session

Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding

9:05 am - 12:00 pm

9:05 - Introductory Remarks

9:10 - 50 - Recent enhancements in the accuracy of CLiDE tool for extracting chemical structure data from patents and other documents Aniko T Valko1, Aniko.Valko@keymodule.co.uk, Peter Johnson2.

9:40 - 51 - Structure Clipper: An interactive tool for extracting chemical structures from patents Christopher E Kibbey, christopher.kibbey@pfizer.com, Jacqueline L Klug-McLeod.

10:10 - 52 - Computer-assisted Markush structures curation from patent documents David Deng, ddeng@chemaxon.com, Arpad Figyelmesi.

10:40 - Intermission

10:55 - 53 - Use of reverse text-mining to establish whether indexing and classification of chemical patents is still necessary Robert A Stembridge, bob.stembridge@thomsonreuters.com,

11:25 - 54 - Extraction of chemical reactions from full text documents: From n-tuples of value attribute pairs toward the automated construction of reaction databases Lutz Weber, lutz.weber@ontochem.com, Matthias Irmer, Claudia Bobach.

11:55 - Concluding Remarks

Monday, August 11, 2014

The Impact of the IUPAC InChI on Finding and Linking Information on Chemicals - AM Session

Palace Hotel Room: California Parlor Cosponsored by CHED, COMP Stephen Heller, Organizer Stephen Heller, Presiding

8:30 am - 12:00 pm

8:30 - 55 - InChIs are not just for small molecules Keith T Taylor, keith.taylor@laderaconsultancy.com,

9:05 - 56 - NCI/CADD Group’s InChI usage and analysis of tautomerism for InChI V2 Marc C Nicklaus, mn1@helix.nih.gov,

9:40 - 57 - Intersecting crystallographic databases using InChI Ian J Bruno1, bruno@ccdc.cam.ac.uk,

Chemical Information Bulletin, 2014, 66 (3) 39

Tjelvar SG Olsson1, Sanchayita Sen2, Gary M Battle2, Jose M Dana2, Sameer Velankar2.

10:15 - Intermission

10:30 - 58 - Data formats for elementary gas phase kinetics: Unique representations of reactions Donald R Burgess1, dburgess@nist.gov, Jeffrey A Manion1, Carrigan J Hayes2.

11:05 - 59 - International Chemical Identifier (InChI) at Wiley: Strengths and limitations Graeme E. Whitley1, gwhitley@wiley.com, Bernd Berger2, bberger@wiley.com.

11:40 - 60 - InChIKeys as chemical entity ids to enable in-context text indexing and to identify engine-ranked chemically similar documents Stephen Boyer, sboyer@us.ibm.com, Tom Griffin, Cassidy Kelly, Eric Louie, Jacques Labrie, Scott Spangler, Ying Chen, Ru Fang, Su Yan.

Monday, August 11, 2014

Global Challenges in the Communication of Scientific Research - PM Session

Palace Hotel Room: Marina David Martinsen, Norah Xiao, Organizers David Martinsen, Norah Xiao, Presiding

1:15 pm - 5:25 pm

1:15 - Introductory Remarks

1:20 - 61 - Building BRICK by BRICK sometimes works: How ACS Editors’ participation in ACS on Campus has brought publishing best practices

to thousands of authors in BRICKS countries, an overview of challenges and successes S. Sara Rouhi1, s_rouhi@acs.org, Kirk S. Schanze3, schanze-office@ami.acs.org, Prashant V. Kamat2, pkamat@nd.edu.

2:00 - 62 - Article-impact assessment in the age of open copyright and social networking Frederick F Fenter, frederick.fenter@frontiersin.org, Costanza Zucca.

2:30 - 63 - Chemistry journals in China and chemical papers from China: What is the future? Xiaowen Zhu, zhuxiaowen74@126.com,

3:00 - 64 - Globalization of scholarly publishing: Meeting the needs of international researchers Amy Beisel, amy.beisel@researchsquare.com, Keith Collier, Ben Mudrak.

3:30 - Intermission

3:45 - 65 - Beyond open access Martin Hicks, mhicks@beilstein-institut.de,

4:15 - 66 - Supporting and facilitating the publication of chemical science research: A global view Daping Zhang, ZhangD@rsc.org,

4:45 - 67 - Enabling international collaboration using the Eureka Research Workbench Stuart Chalk1, schalk@unf.edu, Robert Belford2, Phuc Tran2, Thanit Pewnim3.

5:05 - 68 - Combatting chemophobia: Speaking science to distrust and engaging with empathy, online, and face-to-face Leigh K Boerner2, Ljkboerner@gmail.com, Raychelle Burks6,8, rmburks@gmail.

Chemical Information Bulletin, 2014, 66 (3) 40

com, Matthew Hartings4, hartings@american.edu, Chad Jones5, chemist.jones@gmail.com, Kevin Shanks7, forensictoxguy@gmail.com, Janet D Stemwedel1, dr.freeride@gmail.com, Brandi VanAlphen3, branvanchemist@gmail.com. (1) Department of Philosophy, San Jose State University, San Jose, CA 95192-0096, United States, (2) Unaffiliated, United States, (3) Unaffiliated, United States, (4) Department of Chemistry, American University, Washington, DC 20016, United States, (5) Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, United States, (6) Center of Nanohybrid Functional Materials, University of Nebraska, Lincoln, NE 68508, United States, (7) Department of Forensic Toxicology, AIT Laboratories, Indianapolis, IN, United States, (8) Department of Chemistry, Doane College, Crete, NE 68333, United States Monday, August 11, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - PM Session

Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding

1:30 pm - 4:55 pm

1:30 - Introductory Remarks

1:35 - 69 - ChemInfoCloud: Opensource based Cloud compatible chemical textmining tools for harvesting largescale medical literature Muthukumarasamy Karthikeyan, karthincl@gmail.com,

2:05 - 70 - Knowledge mining by

structure search Jinbo Lee, rhotchandani@scilligence.com,

2:35 - 71 - Toward extracting analytical science metrics from the RSC archives Stuart Chalk1, schalk@unf.edu, Antony Williams2, Valery Tkachenko2, Colin Batchelor3.

3:05 - Intermission

3:20 - 72 - SureChEMBL: An open system for exploration of patent chemistry space Michal M. Nowotka, mnowotka@ebi.ac.uk, John P. Overington, Mark Davies.

3:50 - 73 - Computer analysis of the scientific literature Scott Spangler1, Olivier Lichtarge1, Meena Nagarajan1, MeenaNagarajan@us.ibm.com, Angela Dawn Wilkins1, Lawrence Allen Donehower2, Curtis Reid Pickering2, Sam Julian Regenbogen2, Benjamin Judson Bachman2, Ioana Roxana Stanoi1, Ying Chen1, Jacques J Labrie1, Linda Kato1, Maria Elisa Terron2, Anbu Karani Adikesavan2, Stephen K Boyer1.

4:20 - 74 - Using the BRAIN, biorelations and intelligence network, for knowledge discovery Albert Mons1, albert.mons@euretos.com, Barend Mons3, Aram Krol1, Arie Baak1, Antony Williams2, Valery Tkachenko2.

4:50 - Concluding Remarks

Monday, August 11, 2014

Sci-Mix - EVE Session Moscone Center, North Bldg. Room: Hall D Erin Bolstad, Organizer

8:00 pm - 10:00 pm

Chemical Information Bulletin, 2014, 66 (3) 41

3 - Hazardous substances data bank: A tool for natural product information and research Shannon M. Jordan, shannon.jordan1@nih.gov,

4 - Real structures for real natural products − really getting them right and getting them faster Patrick Wheeler1, pwheeler@yahoo.com, Antony Williams3, Mikhail Elyashberg2, Rostislav Pol2, Arvin Moser1.

13 - BCL:Conf A knowledge based ligand flexibility algorithm and application in computational drug discovery like online drug design game Foldit Sandeepkumar K Kothiwale1, sandeepkumar.k.kothiwale@vanderbilt.edu, Jens Meiler1,2, Will Lowe1.

27 - ChEMBL - linking chemistry and biology to enable mapping onto molecular pathways Louisa J Bellis, ljbellis@ebi.ac.uk, Anna Gaulton, Anne Hersey, A Patricia Bento, Jon Chambers, Mark Davies, Felix Kruger, Yvonne Light, Nathan Dedman, Shaun McGlinchey, Michal Nowotka, George Papadatos, Rita Santos, John P Overington.

36 - Toward quantitative structure-activity relationship (QSAR) models for nanoparticles Katarzyna Odziomek1,2, kjodziomek@lbl.gov, Daniela Ushizima2, Tomasz Puzyn1, Maciej Haranczyk2.

37 - Targeting androgen receptor DNA-binding domain using structure-based methods to overcome resistance Huifang Li, janelhf@gmail.com, Fuqiang Ban, Kush Dalal, Eric Leblanc, Paul S. Rennie, Artem Cherkasov.

39 - Random walk-based prediction of novel drug-target interactions Abhik Seal, abseal@indiana.edu, Yong Yeol Ahn, David J Wild.

40 - Pred-hERG: A novel web-accessible computational tool for predicting cardiac toxicity of drug candidates Vinícius M Alves1, viniciusm.alves@gmail.com, Rodolpho C Braga1, rodolphobraga@yahoo.com, Meryck B Silva1, Eugene Muratov2, Denis Fourches2, Alexander Tropsha2, Carolina H Andrade1, carolina@ufg.br.

41 - Mining chemical space for novel molecules: A graphical tool for working with fragment spaces Florian Lauck, lauck@zbh.uni-hamburg.de, Matthias Rarey.

42 - BCL::EvoGen: An evolutionary algorithm for focused library design Alexander R Geanes, alexander.r.geanes@vanderbilt.edu, Edward W Lowe, Jens Meiler.

60 - InChIKeys as chemical entity ids to enable in-context text indexing and to identify engine-ranked chemically similar documents Stephen Boyer, sboyer@us.ibm.com, Tom Griffin, Cassidy Kelly, Eric Louie, Jacques Labrie, Scott Spangler, Ying Chen, Ru Fang, Su Yan.

75 - Benchmark study: Structural similarity search methods for identifying read-across analogs Jie Shen, jshen@rifm.org,

76 - Activity cliffs on chemotype-based activity landscapes Jaime Pérez-Villanueva1, jpvillanueva@correo.xoc.uam.mx, José L. Medina-Franco2, Oscar Méndez-Lucio3, Olivia

Chemical Information Bulletin, 2014, 66 (3) 42

Soria-Arteche1.

77 - Uncovering activity cliff-forming compounds using SALI values José L Medina-Franco1, MedinaFranco.Jose@mayo.edu, Kai Fan Cheng2, Mingzhu He2, Yousef Al-Abed2, Nathalie Meurice1.

78 - Unified modeling language schema for scientific and technical data and information Donald R Burgess, dburgess@nist.gov,

79 - How to communicate effectively about chemicals with non-chemists Chad A. Jones1, chemist.jones@gmail.com, Janet D. Stemwedel2, Raychelle Burks3,4, Brandi VanAlphen6.

80 - Activity landscape modeling of AKT/PKB inhibitors Pedro J. Trejo-Soto1, piter_jo@comunidad.unam.mx, Rodrigo Aguayo-Ortiz1, Oscar Méndez-Lucio2, Alicia Hernández-Campos1, Rafael Castillo1.

81 - Pursuit of activity enrichment in phenotypic screening using chemotype-driven approaches Joachim L Petit, petit.joachim@mayo.edu, José L Medina-Franco, Nathalie Meurice.

116 - DNA methyltransferase Dnmt1: Regulation and novel drug-design strategies Zeljko M Svedruzic1, zsvedruz@biol.pmf.hr, Patrik Nikolic2.

124 - Scilligence’s ELN for research laboratories and academia Rajeev Hotchandani, rhotchandani@scilligence.com,

131 - Multicriteria drug discovery: Using CoMFA models to drive target

specificity Lei Wang, lei.wang@certara.com, Brian Masek, Fabian Boes, Bernd Wendt, Stephan Nagy. Tuesday, August 12, 2014

The Herman Skolnik Award Symposium - AM Session The Publication Chain Revisited: Old Links and New Connections

Palace Hotel Room: PresidioAndrea Twiss-Brooks, Organizer Andrea Twiss-Brooks, Presiding 9:15 am - 12:00 pm

9:15 - Introductory Remarks

9:20 - 82 - Evolution and transformation of journals in a digital environment Grace Baysinger, graceb@leland.stanford.edu,

9:50 - 83 - What do the readers think? The role of the end user in the evolution of publications Andrea Twiss-Brooks, atbrooks@uchicago.edu,

10:20 - 84 - Context and connection: Visualizing library data Martin Brändle, mpbraendle@gmail.com,

10:50 - Intermission

11:00 - 85 - Predicted future of science and scientific publishing within the framework of a changing world René Deplanque, rene@deplanque.de,

11:30 - 86 - Chemical Publications revisited Guido Herrmann, Guido.Herrmann@thieme.de,

Tuesday, August 12, 2014

Chemical Information Bulletin, 2014, 66 (3) 43

The Herman Skolnik Award Symposium - PM Session The Publication Chain Revisited: Old Links and New Connections Palace Hotel Room: PresidioAndrea Twiss-Brooks, Organizer Andrea Twiss-Brooks, Presiding

2:00 pm - 5:05 pm

2:00 - 87 - CAS databases: Reflecting the changes in how chemical discoveries have been disclosed Matthew J. Toussant, mtoussant@cas.org,

2:30 - 88 - InChI & the publication and information chain Stephen Heller, steve@hellers.com,

3:00 - 89 - From virtual communities to Web 2.0, social media, and beyond: A publishing perspective Wendy Warr, wendy@warr.com,

3:30 - Intermission

3:40 - 90 - Digital transformation - the long and winding road David Evans1, david.evans@REEDELSEVIER.CH, Pieder Caduff2, Jürgen Swienty-Busch3.

4:10 - 91 - Of a landmark total synthesis yet unpublished in full experimental detail – vitamin B12 Engelbert Zass, zass@chem.ethz.ch,

4:55 - Award Presentation

Wednesday, August 13, 2014

It Takes Two To Tango: Chemistry Librarians Partnering with Publishers and Researchers To Advance the

Chemical Sciences - AM Session Symposium in Honor Dana Roth

Palace Hotel Room: Marina Ted Baldwin, Judith Currano, Organizers Judith Currano, Ted Baldwin, Presiding

8:35 am - 12:00 pm

8:35 - Introductory Remarks

8:40 - 92 - Chemical information ecosystems at research universities: Users, libraries, and information providers Grace Baysinger, graceb@stanford.edu,

9:00 - 93 - “What happened to my library?” revisited Susanne J Redalje, curie@u.washington.edu,

9:20 - 94 - Products, policies, pricing: How collaboration with libraries has shaped the evolution of ACS Publications 3Ps S. Sara Rouhi, s_rouhi@acs.org,

9:40 - 95 - New dance steps: Emerging areas connecting us to our researchers Ted W. Baldwin, BALDWITW@UCMAIL.UC.EDU,

10:00 - Intermission

10:15 - 96 - Academic libraries and CAS: A match made in heaven Roger Schenck, rschenck@cas.org,

10:35 - 99 - Evolving library services in the ever-changing world of chemical information: From printed to electronic to networked Donna T. Wrublewski, dtwrublewski@library.caltech.edu, George S. Porter, Joy Painter, Kristin Buxton, Lindsay B. Cleary.

Chemical Information Bulletin, 2014, 66 (3) 44

10:55 - 98 - Navigating chemistry requirements for data management and electronic notebooks: A case study Leah R McEwen1, lrm1@cornell.edu, Antony J Williams2, Valery Tkachenko2, Jeremy G Frey3, Simon J Coles3, Aileen E Day2, Cerys Willoughby3, William R Dichtel1.

11:15 - 97 - “Dancing” lessons: Teaching non-chemist librarians to communicate with chemists Judith N. Currano, currano@pobox.upenn.edu,

11:35 - Discussion

11:55 - Concluding Remarks

Wednesday, August 13, 2014

Inspiring the Next Generation To Pursue Computational Chemistry and Cheminformatics - AM Session

Palace Hotel Room: Presidio Antony Williams, Leah McEwen, Organizers Antony Williams, Leah McEwen, Presiding

8:20 am - 11:05 am

8:20 - Introductory Remarks

8:25 - 100 - Examples of how to inspire the next generation to pursue computational chemistry/cheminformatics Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2.

8:50 - 101 - Implementing an interactive cheminformatics course for the acceleration of graduate chemical research

O. Maduka Ogba, ogbao@onid.oregonstate.edu, Paul H.-Y. Cheong.

9:15 - 102 - Leveraging history to develop community sourced best practices in chemical information systems development: An interactive online teaching module Leah McEwen1, lrm1@cornell.edu, Evan Smith2.

9:40 - Intermission

9:55 - 103 - Who knew I would get here from there: How I became the ChemConnector Antony J. Williams, tony27587@gmail.com,

10:20 - 104 - Chemical Informatics Project >inspires >chemistry majors Stuart Chalk, schalk@unf.edu,

10:40 - 105 - Enabling cheminformatic exploration at the academic level: Enterprise tools, academic availability Erin Bolstad, erinbolstad@gmail.com,

Wednesday, August 13, 2014

The IUPAC Solubility Data Series: 100 Volumes of Solubility Data Online - PM Session

Palace Hotel Room: Marina Cosponsored by ANYL, HIST David Martinsen, M. Clara Magalhães, Organizers David Martinsen, M. Clara Magalhães, Presiding

1:30 pm - 5:10 pm

1:30 - Introductory Remarks: IUPAC Projects

Chemical Information Bulletin, 2014, 66 (3) 45

1:40 - 106 - Objectives of the Solubility Data Series Mark Salomon, Mark.Salomon@maxpowerinc.com,

2:05 - 107 - NIST Standard Reference Data and the Solubility Data Series Allan H. Harvey1, allan.harvey@nist.gov, Donald R. Burgess2.

2:30 - 108 - REST API for the IUPAC Solubility Data Series: A “Skunkworks” project Stuart Chalk, schalk@unf.edu,

2:55 - 109 - Database on ionic liquids solubilities in molecular solvents: Progress and prospects Zdeněk Wagner1, Johan Jacquemin2, Magdalena Bendová1, bendova@icpf.cas.cz.

3:20 - Intermission

3:30 - 110 - Critical evaluation of stability constant data by IUPAC Glenn Hefter, G.Hefter@murdoch.edu.au,

3:55 - 111 - Models to evaluate experimental solubility data for crystalline nonelectrolyte solutes in organic mono-solvents and solvent mixtures William E. Acree, Jr., acree@unt.edu,

4:20 - 112 - Thermodynamics of electrolyte solubility in mixed solvents: Silver halides Earle Waghorne, earle.waghorne@ucd.ie,

4:45 - 113 - Possible contributions from the Solubility Data Project for arsenic and carbon dioxide environmental impacts mitigation M. Clara F. Magalhães, mclara@ua.pt,

Wednesday, August 13, 2014

ChemEpInformatics: In the Pursuit of Epidrugs Using Chemoinformatics and Computational Approaches - PM Session

Palace Hotel Room: Presidio Jose Medina-Franco, Nathalie Meurice, Organizers Jose Medina-Franco, Nathalie Meurice, Presiding

1:15 pm - 5:20 pm

1:15 - Introductory Remarks

1:20 - 114 - Targeting HDAC8 with derivatives of valproic acid: Design, synthesis, theoretical, and experimental evaluation as anticancer agents Jose Correa Basurto, corrjose@gmail.com,

1:45 - 115 - Development of isoform-selective protein arginine methyltransferase inhibitors Y. George Zheng1, yzheng@uga.edu, Ivaylo Ivanov2, Kun Qian1, Chunli Yan2.

2:10 - 116 - DNA methyltransferase Dnmt1: Regulation and novel drug-design strategies Zeljko M Svedruzic1, zsvedruz@biol.pmf.hr, Patrik Nikolic2.

2:35 - 117 - Identification and design of new C5-DNA methyltransferase inhibitors and their biological activity Paola Barbara Arimondo, paola.arimondo@etac.cnrs.fr,

3:00 - 118 - Drug repurposing and epigenetics: Olsalazine is a hypomethylating compound active in a cellular context José L. Medina-Franco1, Oscar Méndez-

Chemical Information Bulletin, 2014, 66 (3) 46

Lucio2, Joachim Petit1, Jeremy Tran3, James Bogenberger1, Mark Muller3, Raoul Tibes1, Nathalie Meurice1, Meurice.Nathalie@mayo.edu.

3:25 - Intermission

3:40 - 119 - Computer-aided hit/probe discovery for methyllysine reader proteins Bradley M. Dickson, Lindsey I. James, Brandi M. Baughman, Stephen V. Frye, Dmitri Kireev, dmitri.kireev@unc.edu.

4:05 - 120 - Molecular design approaches to target histone methyltransferases Alberto Del Rio, alberto.delrio@gmail.com,

4:30 - 121 - Structural basis for selective inhibition of hSirt2 by ligand induced rearrangement of the active site Tobias Rumpf1, tobias.rumpf@pharmazie.uni-freiburg.de, Matthias Schiedel1, Berin Karaman2, Claudia Rössler3, Brian J North5, Kathrin I Ladwein1, Markus Gaier1, David A Sinclair5, Mike Schutkowski3, Wolfgang Sippl2, Oliver Einsle4, Manfred Jung1.

4:55 - 122 - Decoding genetic and epigenetic networks for vitamin C mediated cell reprogramming Panwen Wang, Yan Wang, Junwen Wang, junwen@hku.hk.

Wednesday, August 13, 2014

Exploring the Application of New Technologies in Chemical Research and Education - PM Session Palace Hotel Room: California Parlor Cosponsored by CHED David Martinsen, Organizer David Martinsen, Presiding

1:30 pm - 5:15 pm

1:30 - Introductory Remarks

1:35 - 123 - New target prediction and visualization tools incorporating open source molecular fingerprints for TB mobile version 2 Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2, Malabika Sarker3.

2:05 - 124 - Scilligence’s ELN for research laboratories and academia Rajeev Hotchandani, rhotchandani@scilligence.com,

2:35 - 125 - Accessing 3D printable chemical structures online Vincent F. Scalfani1, vfscalfani@ua.edu, Antony J. Williams2, Robert M. Hanson3, Jason E. Bara4, Aileen Day2, Valery Tkachenko2.

3:05 - Intermission

3:15 - 126 - Libraries as hubs for emerging technologies Jeffrey R. Lancaster, jeffrey.lancaster@columbia.edu,

3:45 - 127 - Global science capacity building and the Maker Movement: Do-it-yourself lab equipment with Tekla Labs Julea Vlassakis, jvlassakis@berkeley.edu,

4:15 - 128 - Google Glass based immunochromatographic diagnostic test analysis Steve Feng1,2, stevewfeng@gmail.com, Romain Caire1,2, Bingen Cortazar1,2, Mehmet Turan1,2, Andrew Wong1,2, Aydogan Ozcan1,2,3,4.

4:45 - 129 - Frugal science and global

Chemical Information Bulletin, 2014, 66 (3) 47

health: Democratizing access to scientific tools Manu Prakash, manup@stanford.edu,

Thursday, August 14, 2014

General Papers - AM Session Computational Chemistry and Informatics

Palace Hotel Room: Marina Erin Bolstad, Organizers Erin Bolstad, Presiding

9:40 am - 12:05 pm

9:40 - Introductory Remarks

9:45 - 130 - Ten years of innovative collaborative drug discovery Barry A. Bunin, bbunin@collaborativedrug.com,

10:05 - 131 - Multicriteria drug discovery: Using CoMFA models to drive target specificity Lei Wang, lei.wang@certara.com, Brian Masek, Fabian Boes, Bernd Wendt, Stephan Nagy.

10:25 am 132 WITHDRAWN

10:45 - Intermission

11:00 - 133 - Conditional structure-activity-similarity (SAS) maps Gerry Maggiora2,3, gerry.maggiora@gmail.com, Martin Vogt1, Preeti Iyer1, Jurgen Bajorath1.

11:20 - 134 - Fragment-based computational approach to study the phase behavior of biopolymers Jan-Willem Handgraaf1, janwillem.

handgraaf@culgi.com, Rubèn Serral Gracià1, Peter Schiffels2, Johannes G. E. M. Fraaije1,3.

11:40 - 135 - Future of large-scale computational screening of porous materials Jihan Kim, jihankim@kaist.ac.kr,

Thursday, August 14, 2014

General Papers - AM Session Toolkits and Databases

Palace Hotel Room: Presidio Erin Bolstad, Organizers Erin Bolstad, Presiding

9:45 am - 12:25 pm

9:45 - Introductory Remarks

9:50 - 136 - Integrating Jmol/JSpecView into the Eureka Research Workbench Stuart Chalk1, schalk@unf.edu, Matthew Morse1, Israel Hurst1, Anthony Williams2, Valery Tkachenko2, Alexey Pshenichnov2, Robert Hanson3.

10:15 - 137 - Open innovation and chemistry data management contributions from the Royal Society of Chemistry resulting from the Open PHACTS project Antony J Williams1, tony27587@gmail.com, Valery Tkachenko1, Ken Karapetyan1, Alexey Pshenichnov1, Colin Batchelor2, Jon Steele2, David Sharpe2.

10:35 - 138 - Using outreach to inform, maintain, and evaluate your collection Kiyomi Deards, kdeards2@unl.edu,

10:55 - 139 - PubChem: Celebrating ten

Chemical Information Bulletin, 2014, 66 (3) 48

years online Evan Bolton, bolton@ncbi.nlm.nih.gov,

11:15 - Intermission

11:25 - 140 - Clustering the Royal Society of Chemistry chemical repository to enable enhanced navigation across millions of chemicals Ken Karapetyan1, karapetyank@rsc.org, Valery Tkachenko1, Antony J Williams1, Oliver Kohlbacher2, Phillipp Thiel2.

11:45 - 141 - Experiences and adventures with noSQL and its applications to cheminformatics data Valery Tkachenko1, tkachenkov@rsc.org, Antony Williams1, Ken Karapetyan1, Alexey Pshenichnov1, Mikhail Rybalkin2.

12:05 - 142 - Building an online data repository for 100,000 dyes David Hinks1, david_hinks@ncsu.edu, Valery Tkachenko2.

Thursday, August 14, 2014

General Papers - PM Session Toolkits and Databases Palace Hotel Room: Marina Erin Bolstad, Organizers Erin Bolstad, Presiding

1:30 pm - 3:20 pm

1:30 - 143 - Mining PubChem data: Interfaces, approaches, and best practices Evan Bolton, bolton@ncbi.nlm.nih.gov,

1:50 - 144 - The Royal Society of Chemistry and its adoption of semantic web technologies for chemistry at the epoch of a federated world Antony J Williams, tony27587@gmail.com, Valery Tkachenko, Ken Karapetyan,

Alexey Pshenichnov.

2:10 - Intermission

2:20 - 145 - Dereplication applications for computer-assisted structure elucidation (CASE) and the ChemSpider database Patrick Wheeler1, info@acdlabs.com, Arvin Moser1, Joe DiMartio1, Mikhail Elyashberg2, Kirill Blinov3, Sergey Molodstov4, Anthony Williams5.

2:40 - 146 - Faculty profiling and searching in the Eureka Research Workbench using VIVO and ScientistsDB Stuart Chalk1, schalk@unf.edu, Matthew Morse1, Israel Hurst1, Anthony Williams2, Valery Tkachenko2, Alexey Pshenichnov2.

3:00 - 147 - Semantic enrichment of ChemSpider data: Usage and applications Valery Tkachenko, TkachenkoV@rsc.org,

Chemical Information Bulletin, 2014, 66 (3) 49

Cosponsored SymposiaCOMP, Emilio Esposito, Scott Wildman Monday, August 11, 2014 Ameri-QSAR - PM Session Why Should the Europeans Have All the Fun?

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Emilio Esposito, Scott Wildman, Organizers Emilio Esposito, Scott Wildman, Presiding

1:30 pm - 5:30 pm

1:30 - 112 - Might template CoMFA integrate structure-based and ligand-based design? Richard D Cramer

2:00 - 113 - What good are QSAR models if chemists don’t use them? Daniel Ortwine

2:30 - 114 - From QSAR To MQSPR and beyond: Using materials informatics to predict the mechanical and dielectric properties of polymers and nanocomposites using a combination of heuristic and physics-based methods Curt M Breneman, Ke Wu, Linda Schadler, Cate Brinson, Yang Li, Tim Krentz, Richard Zhao, Yanhui Huang.

3:00 - Intermission

3:15 - 115 - Semi-quantitative SAR using Bayesian modelling on activity cliffs Tim Cheeseright, Mark Mackey, Rae Lawrence, Martin Slater.

3:45 - 116 - Datasets: Curation and evaluations Heather A Carlson

4:15 - 117 - Protein-family virtual screening (PFVS) with accuracy comparable to experimental HTS: Tool compounds and leads for selective kinase inhibitors Eric Martin, Li Tian.

4:45 - Discussion

COMP, Emilio Esposito, Scott Wildman Sunday, August 10, 2014 Drug Discovery - AM Session Delving Into That Tricky World of ADMe/Tox #stickyWicket

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Hector Gonzalez, Presiding

8:30 am - 11:45 am

8:30 - 1 - Is there a role for the integral equation theory of molecular liquids in chemical informatics? David S Palmer, Maxim V Fedorov.

9:00 - 2 - Predicting drug bioavailability using physiologically-based pharmacokinetic modeling and Global Sensitivity Analysis to identify sensitive parameters

Pankaj R. Daga, Michael B. Bolger, Ian S. Haworth, Robert D. Clark, Eric Martin. 9:30 - 3 - CypRules: A rule-based P450 inhibition prediction server Chi-Yu Shao, Yufeng J. Tseng.

10:00 - Intermission

10:15 am 4 WITHDRAWN

10:45 - 5 - Improving the chance of success when an outcome can’t be predicted Matthew Segall, Edmund J. Champness,

Chemical Information Bulletin, 2014, 66 (3) 50

Iskander Yusof.

11:15 - 6 - Looking beyond a few hard cutoffs in assessing ADMET RiskTM Robert D. Clark, Robert Fraczkiewicz, Michael B. Bolger, Walter S. Woltosz.

COMP, Emilio Esposito, Scott Wildman Sunday, August 10, 2014 Drug Discovery - PM Session Using the Information Gained To Explain What Has Happened. #informatics

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Zheng Yang, Presiding

1:30 pm - 5:15 pm

1:30 - 37 - Chiral and isotopic matched pair identification and data analysis on physicochemical and in vitro endpoints for drug discovery Yongjin Xu, Jeffrey T. Bagdanoff, Eric Martin, Gavin Dollinger.

2:00 - 38 - Modeling a crowdsourced definition of molecular complexity Edward C Sherer, Robert P Sheridan, Nicolas Zorn, Louis-Charles Campeau, Charlie Chang, Jared Cumming, Matt L Maddess, Philippe G Nantermet, Chris J Sinz, Paul O’Shea.

2:30 - 39 - RegMol: Registration and assay database for biologics and small molecules from scilligence Jinbo Lee

3:00 - 40 - Gilead Sciences structure portal: An integrated solution to organize and disseminate 3D structural project data Johannes H Voigt, Jayaraman Chandrasekhar, George Lane, Mark Kenney, Derek Stonich, Uli Schmitz.

3:30 - Intermission

3:45 - 41 - PubChem BioAssay, a public information resource for drug discovery: A bibliometric analysis on PubChem application Yanli Wang

4:15 - 42 - Chemist-defined toxicophore identification toolkit Sharang Phatak, Tamsin E Mansley, Shikha O’Brien.

4:45 - 43 - Collaborative sharing of molecules and data in the mobile age Sean Ekins, Alex M Clark, Joel S Freundlich.

COMP, Emilio Esposito, Scott Wildman Monday, August 11, 2014 Drug Discovery - AM Session Harnessing the Power of the Ligand To Improve Itself. #ligandBasedDesign

Moscone Center, West Bldg.

Room: 2005

Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Shuneize Slater, Presiding

8:30 am - 11:45 am

8:30 - 77 - Complementarity between PubChem 2D and 3D neighbors Sunghwan Kim, Evan E Bolton, Stephen H Bryant.

9:00 - 78 - Expanding the metabolite mimic approach to identify hits for Mycobacterium tuberculosis Sean Ekins, Joel S Freundlich, Malabika Sarker, Carolyn Talcott, Peter Madrid, Barry A Bunin, Gyanu Lamichhane.

9:30 - 79 - Extending profile-QSAR to

Chemical Information Bulletin, 2014, 66 (3) 51

diverse protein families: GPCRs, CYPs, proteases, and non-kinase adenosine-binding proteins Li Tian, Eric Martin.

10:00 - Intermission

10:15 - 80 - Analysing selectivity through multi-dimensional activity cliff analysis Tim Cheeseright, Mark Mackey, Rae Lawrence, Martin Slater.

10:45 - 81 - Diamidine compounds for selective inhibition of protein arginine methyltransferase 1 Chunli Yan, Leilei Yan, Kun Qian, Xinyang Zhao, Yunjun George Zheng, Ivaylo Ivanov.

11:15 - 82 - Conformer free energies, ligand strain, and ligand flexibility Christopher I. Bayly, Stanislaw Wlodek.

COMP, Emilio Esposito, Scott Wildman Tuesday, August 12, 2014 Drug Discovery - AM Session #methodMadness For Everyone!

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Edward Sherer, Presiding

8:30 am - 11:45 am

8:30 - 153 - Binding site prediction algorithms in pharmaceutical discovery Dusanka Janezic, Janez Konc.

9:00 - 154 - Statistical learning from multiple-source datasets: Mind the gap! Floriane Montanari, Santiago D Villalba, Gerhard F Ecker.

9:30 - 155 - Reaction driven molecular invention: Generating synthetically feasible

design ideas Brian B Masek, Stephan Nagy, David Baker, Fred Soltanshahi, Roman Dorfman.

10:00 - Intermission

10:15 - 156 - Peptide design reloaded Gisbert Schneider, Petra Schneider, Jan A Hiss.

10:45 - 157 - Using fluorine to optimise affinity: Direct interactions and pre-organisation in lipid binding to CD1d Stephen J Fox, Annie Tocheva, Stephanie Gourdain, Salah Mansour, Bruno Linclau, Stephan Gadola, Tim Elliot, Chris-Kriton Skylaris, Jonathan W Essex.

11:15 - 158 - Accuracy assessment of free energy calculations in drug design Thomas Fox, Clara Christ.

COMP, Emilio Esposito, Scott Wildman Tuesday, August 12, 2014 Drug Discovery - PM Session A Full Day of #drugDisco #methodMadness! #whoLovesYa? @acsCOMP Does. That’s Who.

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Chinthaka Ratnaweera, Presiding

1:30 pm - 5:15 pm

1:30 - 190 - One parameter QSAR: Prediction by general similarities (PGS) Terry R Stouch, Geoffrey Skillman, David Buttar, Thomas Darden, Anthony Nicholls.

2:00 - 191 - Nonparametric regression for iterative experimental compound screening Ramgopal R Mettu, Ryan H Lilien. 2:30 - 192 - Contour® growth algorithm creates novel drug-like molecules

Chemical Information Bulletin, 2014, 66 (3) 52

complementing hydrophobic and hydrophilic features of protein binding pockets Zhijie Liu, Kristi Fan, Yajun Zheng, Peter R Lindblom, David A Claremon, Richard D Gregg, Suresh B Singh.

3:00 - 193 - Identification of diverse and potent LRRK2 kinase inhibitors using a funnel-based virtual screening workflow Huifen Chen

3:30 - Intermission

3:45 - 194 - Challenges of decision making using uncertain data Edmund J Champness, Matthew D Segall.

4:15 - 195 - Study of protein-protein interface inhibition through molecular dynamics and free energy simulations: Application to staple peptides, small molecules, and antibodies Goran Krilov, Woody Sherman, Zuojun Guo, Kristina Streu, Udayan Mohanty, Tomi Sawyer.

4:45 - 196 - Molecular simulation and kinetic network models: New tools for designing peptidomimetics Vincent A Voelz

COMP, Emilio Esposito, Scott Wildman Wednesday, August 13, 2014 Drug Discovery - AM Session Closing Out the Week with Structural Bioinformatics and Target-Based #drugDisco #informationisPower

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Katrina Lexa, Presiding

8:30 am - 11:45 am

8:30 - 404 - Discovery and optimization of novel Arp2/3 complex inhibitors via computer-aided drug design George Patargias, Byron Hetrick, Juliana Han, Michael Montgomery, Bradley Nolen, Zoe Cournia.

9:00 - 405 - Mechanistic lessons of targeting HIV-1 capsid assembly by small molecules Eric Hu, Stephen Yant, Anita Niedziela-Majka, Manuel Tsiang, Randall Halcomb, Roman Sakowicz, Tomas Cihlar, Uli Schmitz.

9:30 - 406 - Identification of novel small molecule CXCR4 inhibitors as anti-HIV agents Debananda Das, Kenji Maeda, Yasuhiro Hayashi, Navnath Gavande, Darshan V Desai, Simon B Chang, Arun K Ghosh, Hiroaki Mitsuya.

10:00 - Intermission

10:15 - 407 - Prospective virtual screening for small molecule TLR2 antagonists and binding mode investigation Manuela S Murgueitio, Sandra Santos-Sierra, Gerhard Wolber.

10:45 - 408 - Structure-based virtual screening approach for discovery of covalently bound ligands Dora Toledo Warshaviak, Gali Golan, Kenneth W. Borrelli, Kai Zhu, Ori Kalid.

11:15 - 409 - Design of pyoverdine analogs with antibacterial activity Christine Cezard, Natacha Farvacques, Viviane Silva-Pires, Pascal Sonnet.

Chemical Information Bulletin, 2014, 66 (3) 53

COMP, Emilio Esposito, Scott Wildman Wednesday, August 13, 2014 Drug Discovery - PM Session Leveraging That Sweet Structural Information for Better Drugs. #informationisPower

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Trent Balius, Presiding

1:30 pm - 5:15 pm

1:30 - 441 - From neurotransmitters to hormones and back: Thyroid hormone action on GABA transporters confirmed by virtual screening Andreas Jurik, Barbara Zdrazil, Marion Holy, Thomas Stockner, Harald H Sitte, Gerhard F Ecker.

2:00 - 442 - Does flexibility control the specificity of protein-protein and protein-drug interfaces? Klaus R Liedl

2:30 - 443 - Interaction type differences as proposed determinants of monoamine transporter selectivity for amphetamines Amir Seddik, Thomas Steinkellner, Thomas Stockner, Walter Sandtner, Michael Freissmuth, Harald H Sitte, Gerhard F Ecker.

3:00 - 444 - Docking study of binding to TRPV1 structure: Agonists vs. antagonists Daria Goldmann, Gerhard F. Ecker.

3:30 - Intermission

3:45 - 445 - Predicting new molecular targets for existing drugs by constructing a Stochastic Pocket Ensemble and integrating drug-target expression data Hammad Naveed, Xin Gao.

4:15 - 446 - Molecular dynamics study of human lactate dehydrogenase A inhibitors Yun Shi, B. Mario Pinto.

4:45 - 447 - Rational molecular design supported by ligand-based NMR techniques Ionut Onila, Kai Fredriksson, Adam Mazur, Luca Codutti, Teresa Carlomagno, Heiko M. Möller, Christian Griesinger, Thomas E. Exner.

COMP, Emilio Esposito, Scott Wildman Thursday, August 14, 2014 Drug Discovery - AM Session #lastDay of #drugDisco: We’re Sad Too #informationisPower

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Eleonora Gianti, Presiding

8:30 am - 12:15 pm

8:30 - 481 - Analysis of the DFG-out binding pocket in kinases Christine Yueh, Dima Kozakov, Sandor Vajda.

9:00 - 482 - Novel bradykinin B2 receptor antagonists identified by virtual screening Marcel Bermudez, Gerhard Wolber.

9:30 - 483 - Assessing drugability of gram negative bacterial (G-) targets or other target classes that require specific ligand properties Valery R Polyakov, Johanna Jansen, Eric Martin, Hooman Shadnia, Chris Williams, Heinz Moser.

10:00 - 484 - Predicting macromolecular binding sites on protein binding partners

Chemical Information Bulletin, 2014, 66 (3) 54

Scott E Mottarella, Dima Kozakov, Sandor Vajda.

10:30 - Intermission

10:45 - 485 - Screening and structural strategies for the design of selective Leucine-rich repeat kinase 2 (LRRK2) inhibitors Ijen Chen, Laurent David.

11:15 - 486 - Identification and optimization of toll-like receptor 7 agonists: A retrospective structure-based analysis Jason K Perry, Randall L Halcomb, Paul A Roetthe, Ryan M McFadden.

11:45 - 487 - Structure-based lead optimization of a novel glycogen synthase kinase 3 beta (GSK-3β) inhibitor Shuneize E Slater, Gang Fu, Manal Nael, Mitchell A Avery, Robert J Doerksen.

COMP, Emilio Esposito, Scott Wildman

Thursday, August 14, 2014

Drug Discovery - PM Session We Appreciate You Staying This Long. And We Reward You with More #awesome #drugDisco talks! #informationisPower

Moscone Center, West Bldg. Room: 2005 Cosponsored by CINF, MEDI Scott Wildman, Y. Jane Tseng, Organizers Ryan Coleman, Presiding

1:30 pm - 4:45 pm 1:30 - 517 - Abrogating Ras abnormal function by targeting Ras oligomers: Identification of dimer interface for oncogenic K-Ras Priyanka P Srivastava, Drew Dolino, Alemayehu A Gorfe.

2:00 - 518 - Insights into the selectivity

profile of OXA-232 carbapenemase using covalent docking and molecular dynamics simulations Thierry Naas, Saoussen Oueslati, Cheickna Cissé, Pascal Retailleau, Bogdan I Iorga.

2:30 pm 519 WITHDRAWN

3:00 - Intermission

3:15 - 520 - FEP from Schrodinger: A robust solution for accurate free energy predictions in drug discovery Woody Sherman

3:45 - 521 - Knowledge-guided docking: Accurate prospective prediction of bound configurations of novel ligands Ann E. Cleves, Ajay N. Jain.

4:15 - 522 - Quantum mechanics-based macromolecular X-ray refinement: The impact of advanced refinement methods on our understanding of protein:ligand structure and function Oleg Borbulevych, Joshua A Plumley, Lance M Westerhoff.

SCHB, Joseph Sabol Monday, August 11, 2014 Cyber Security for Small Businesses - AM Session

Moscone Center, South Bldg. Room: Esplanade Ballroom 301 Cosponsored by CINF Joseph Sabol, Michael Nordstrom, Organizers Michael Nordstrom, Presiding

9:30 am - 11:40 am

9:30 - Introductory Remarks

Chemical Information Bulletin, 2014, 66 (3) 55

9:35 - 12 - WITHDRAWN

10:00 - 13 - Protecting intellectual property from world-wide threats and intrusions Robert Scherer

10:25 - 14 - Cyber security, threats, and intrusions: Perspective from law enforcement Malcolm K. Palmore

10:50 - Panel Discussion

11:35 - Concluding Remarks

Chemical Information Bulletin, 2014, 66 (3) 56

Sunday, August 10, 2014

Nature’s Second Act: Revisiting Natural Products - AM Session Palace Hotel Room: Marina Roger Schenck, Organizer Roger Schenck, Presiding

9:40 am - 12:00 pm

9:40 - Introductory Remarks

9:45 - 1 - Applying Royal Society of Chemistry cheminformatics skills to support the PharmaSEA project Antony J Williams1, tony27587@gmail.com, Valery Tkachenko1, Alexey Pshenichnov1, Ken Karapetyan1, David Sharpe2, Colin Batchelor2. (1) Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States, (2) eScience, Royal Society of Chemistry, Cambridge, United Kingdom The collaborative project PharmaSea brings European researchers to some

of the deepest, coldest and hottest places on the planet. Scientists from the UK, Belgium, Norway, Spain, Ireland, Germany, Italy, Switzerland and Denmark are working together to collect and screen samples of mud and sediment from huge, previously untapped, oceanic trenches. The large-scale, four-year project is backed by almost 10 million euros of funding and brings together 24 partners from 13 countries from industry, academia and non-profit organisations. The PharmaSea project focuses on biodiscovery research and the development and commercialisation of new bioactive compounds from marine organisms, including deep-sea sponges and bacteria, to evaluate their potential as novel drug leads or ingredients for nutrition or cosmetic applications. The Royal Society of Chemistry is responsible for developing a number of capabilities to support the Pharmasea project including a chemical registration system for new compounds, dereplication technologies to assist in the identification of new compounds and search techniques for mass spectrometrists within the

Technical Program Abstracts

ACS Chemical Information Division (CINF)248th ACS National Meeting, Fall 2014

San Francisco, CA (August 10-14, 2014) CINF Symposia Erin Bolstad, Program Chair

**This meeting program was generated on July 14, 2014. The ACS meetings website will contain more up-to-date information.

Chemical Information Bulletin, 2014, 66 (3) 57

project. This presentation will provide an overview of the project and our progress to contributing chemical information technologies to support the effort.

10:15 - 2 - From publishing to recognition – indexing literature for natural products David Evans1, david.evans@reedelsevier.ch, Pieder Caduff1, Juergen Swienty-Busch2. (1) Reed Elsevier Properties SA, Neuchâtel, Switzerland, (2) Elsevier Information Systems GmbH, Frankfurt, Germany Natural products build an inspiring source for Medicinal Chemists in their ever-challenging journey of developing new and more efficient drugs. Finding reliable information about natural products quickly, including their isolation from biological sources, their total synthesis and their bioactive properties is becoming more and more important in a highly competitive industry and environment. We will explain Reaxys content excerption rules for this exciting scientific field and demonstrate use cases showing how the information can be retrieved and applied in Medicinal Chemistry information workflows

10:45 - Intermission

11:00 - 3 - Hazardous substances data bank: A tool for natural product information and research Shannon M. Jordan, shannon.jordan1@nih.gov, National Institutes of Health, National Library of Medicine, Bethesda, MD 20894, United States The National Library of Medicine (NLM) Hazardous Substances Data Bank (HSDB) is a database that contains a wealth of information on many types of chemicals including natural products. Increasingly, professionals and the general public

seek and utilize information about natural products for various purposes. In response to this demand, the HSDB development team has increased the number of natural product records within the database and updated existing records. Natural product records in HSDB contain, but are not limited to the following information: chemical structure, human health effects, animal toxicity, pharmacology, metabolism and pharmacokinetics, environmental fate and exposure, safety and handling, manufacturing, use, laboratory methods, and more. The data extraction team along with a Scientific Review Panel (SRP) utilizes dozens of sources to build, update, and peer-review HSDB records on a four month cycle. As new articles on natural products are published, HSDB serves as an information resource that captures historical and emerging science. NLM will continue to develop and market HSDB as a tool for researchers and the general public covering all types of natural products from phytochemicals to venoms and toxins.

11:30 - 4 - Real structures for real natural products − really getting them right and getting them faster Patrick Wheeler1, pwheeler@yahoo.com, Antony Williams3, Mikhail Elyashberg2, Rostislav Pol2, Arvin Moser1. (1) Advanced Chemistry Development, Toronto, Ontario M5C 1B5, Canada, (2) Advanced Chemistry Development, Moscow, Russian Federation, (3) Royal Society of Chemistry, London, United Kingdom Structure determination for natural products has been revolutionized by the advance of NMR technology and application of innovative experimental techniques. Notably, it is possible to obtain structures from small amounts of material that are not accessible to single crystal X-ray diffraction. Still, the interpretation of

Chemical Information Bulletin, 2014, 66 (3) 58

this data can be arduous, requires great expertise, and is error-prone. Of course, other techniques are used to confirm structures as well: synthetic reproduction of natural products has a long tradition of success in the elucidation of molecules containing intricate elements, including multiple stereo centers. However, despite rigorous analysis by qualified chemists, these methods still sometimes arrive at erroneous results1-5.

Astute application of modern technology can speed the rate at which structures are solved, while also vastly reducing errors that result either from synthetic methods or from unassisted analysis of instrumental data. Computer Assisted Structure Elucidation (CASE) has developed over the past decades to relieve the burden of work in proving correct structures. In this presentation, we will discuss how CASE is used to objectively analyze complex sets of NMR data in order to test structural hypotheses, conduct de novo structure elucidation, and query large databases of known structures for matches of already identified natural products.

Sunday, August 10, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - AM Session Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding

8:40 am - 12:00 pm

8:40 - Introductory Remarks

8:50 - 5 - When your language is science: Abstracting, classifying, and indexing patents in the Derwent World Patents Index

Donald Walter, don.walter@thomsonreuters.com, IP Solutions, Thomson Reuters, Alexandria, VA 22314, United States The Derwent World Patents Index® (DWPISM) collects patents from 50 countries in 30 languages – not all of them using the Roman alphabet – and creates from them high quality English abstracts, classifications and indexes. This talk will outline how we deal with them, including our human, and human assisted translations by language and technical experts; how we organize the information into fielded abstracts using clear editorial guidelines to provide consistent records; and how we correct errors in the information sent to us from the patent offices for use in DWPI.

9:20 - 6 - Chemistry and reactions from non-US patents Daniel M Lowe, daniel@nextmovesoftware.com, Roger A Sayle. NextMove Software, Cambridge, Cambridgeshire CB4 0EY, United Kingdom All US patents from 1976 onwards are freely available in computer-readable formats providing a large corpus for chemical text mining. Other patent offices are increasingly also offering their back-catalogues as XML, allowing chemical text mining to be performed in the same way as for recent US patents. We investigate how much chemistry is found in non-US patents (compared to US patents) and, where the chemistry is present in publications from multiple patent offices, how long were the delays between these publications. We show that non-US patents can be text mined for a large number of chemical reactions and analyse the overlap with reactions from US patents. Finally we use all the extracted chemical reactions to explore whether models for predicting

Chemical Information Bulletin, 2014, 66 (3) 59

reaction yield may be built from features such as the reaction type and its reaction conditions (as text mined from the patent text).

9:50 - 7 - Teach Document-to-Structure to be trilingual: Extract, display, and search chemical information within English, Chinese, and Japanese patents David Deng, ddeng@chemaxon.com, Daniel Bonniot. ChemAxon, Cambridge, MA 02142, United States By expanding Naming, a reliable chemical name-to-structure technology, ChemAxon has developed a suite of chemistry text mining tools. The core application is Document-to-Structure, which can extract chemical information from patent and other documents. Document-to-Structure includes numerous functions to overcome the challenges in patent mining:

1. Implemented OCR technology for non-text patent document. A correction algorithm will identify OCR errors and correct the names before converting to structures.

2. Easy Integration with different image-to-structure software to extract structure images.

3. In addition to English, Asian language support for Chinese and Japanese patent mining.

4. Annotate a document with a single mouse click: create a new document with chemical information “annotated”. Mouse over the chemical name to display the structures.

5. With ChemAxon’s chemistry search function, the extracted structure information can be searched, which makes identifying a compound in a patent document

much faster and easier.

This presentation will demonstrate various text mining applications, including extracting structures from chemical patents using Document-to-Structure; searching the patent structure database with Document-to-Database; and interactively displaying chemical information in patent documents with Document Annotation.

10:20 - Intermission

10:35 - 8 - Chemically aware text mining platform David Milward, David.Milward@linguamatics.com, Andrew Hinton, andrew.hinton@linguamatics.com. Linguamatics Limited, 324 Cambridge Science Park, Milton Road, Cambridge CB4 0WG, United Kingdom The greater availability of patent content in recent years has led to several chemically aware search systems providing unprecedented access to chemical information in patents. In this paper we will describe a chemically aware text mining system and show how this can provide finer-grained access to patent information in both English and Chinese, addressing challenges of patent searchers and medicinal chemists. This work resulted from a research partnership between Linguamatics and Chemaxon, leading to a close integration of chemical name to structure, structure drawing, substructure and similarity searching into the Linguamatics I2E text mining platform. We will show progress in addressing automatic extraction of structure activity relationships (SAR) from patents, including understanding of data found within tables, and connection of information originating from different parts of the document. We will also discuss Markush structure recognition including linking of chemical scaffolds and R-group information within

Chemical Information Bulletin, 2014, 66 (3) 60

particular claims.

11:05 - 9 - CHEMDNER task: Automatic recognition of chemical entities in text Martin Krallinger1, Obdulia Rabal2, Florian Leitner1, Julen Oyarzabal2, julenoyarzabal@unav.es, Alfonso Valencia1. (1) Structural Biology and Computational Biology, Spanish National Cancer Research Centre (CNIO), Madrid, Spain, (2) Small Molecule Discovery Platform, Center for Applied Medical Research (CIMA) - University of Navarra, Pamplona, Spain There is an increasing interest, both on the academic side as well as for industry, to facilitate more efficient access to information on chemical compounds and drugs (chemical entities) described in repositories of unstructured data, including scientific articles, patents or health agency reports. In order to achieve this goal, a crucial aspect is to be able to identify mentions of chemical compounds automatically within text as well as to index whole documents with the compounds described in them. The recognition of chemical entities is also crucial for other subsequent text processing strategies, such as detection of drug-protein interactions, adverse effects of chemical compounds and their associations to toxicological endpoints or the extraction of pathway and metabolic reaction relations. Despite its importance, only a very limited number of publicly accessible chemical compound recognition systems have been released. In contrast to this, a considerable number of methods and strategies to recognize chemicals in text have been proposed. One of the main bottlenecks currently encountered to implement and compare the performance of such systems is the (a) lack of suitable training/test data, (b) the intrinsic difficulty in defining annotation guidelines of what actually

constitutes a chemical compound or drug, (c) heterogeneity in terms of scope and textual data sources used, as well as (d) limited evaluation efforts carried out so far. A total of 27 teams submitted results for the proposed CHEMDNER task. Teams were provided with the manual annotations of 7,000 abstracts to implement and train their systems and then had to return predictions for the 3,000 test set abstracts during a short period of time. When directly comparing the automated results against the manually labeled Gold Standard annotations, the best team reached an F-score (the harmonic mean between precision of coverage) of 87% on the Chemical Entity Mention (CEM) task (http://www.biocreative.org/tasks/biocreative-iv/chemdner)

11:35 - 10 - Structuring the unstructured: Creating knowledge through visual analytics and the use of Tibco Spotfire with Attivio for text analytics of scientific patents Philip J Skinner1, philip.skinner@perkinelmer.com, Joshua A Bishop1, Josh.Bishop@PERKINELMER.COM, Alexandia Vamvakidou1, Megean Schoenberg1, Sameer Nori2, Matt Connon2. (1) PerkinElmer, Waltham, Massachusetts 02451, United States, (2) Attivio, Newton, MA 02466, United States The growing adoption of visual analytics tools such as Tibco Spotfire has revolutionized the way that scientists interpret structured data, such as SAR analyses conducted by medicinal chemists. There remains, however, a wealth of valuable insight contrained within unstructured content sources such such as patents and scientific literature, where critical information is contained. These text based sources do not fit nicely within the traditional model of organizing information as database records and require other

Chemical Information Bulletin, 2014, 66 (3) 61

techniques to derive insight from them. Text analytics technologies such as those developed by Attivio, in combination with visual analytics tools, can uncover new trends and patterns within unstructured content sources. We will outline relevant usecases where such technologies were applied to develop the research strategies of scientific organizations by incorporating analysis around identification of research adjacencies, key opinion leaders and geographical and historical trends of research.

11:55 - Concluding Remarks

Sunday, August 10, 2014

Computational Methods and the Development/Production of Biologics and Biosimilars - AM Session Palace Hotel Room: California Parlor Rachelle Bienstock, Organizer Rachelle Bienstock, Presiding

8:30 am - 9:35 am

8:30 - Introductory Remarks

8:35 - 11 - Classification, representation, and analysis of cyclic peptides and peptide-like analogs Roger A Sayle, roger@nextmovesoftware.com, Daniel M Lowe, Noel M O’Boyle. NextMove Software, Cambridge, CAMBS CB4 0EY, United Kingdom Wikipedia defines a cyclic peptide as a polypeptide chain wherein the amino terminus and the carboxyl terminus, amino terminus and sidechain, carboxyl terminus and sidechain or sidechain and sidechain are linked to form a ring. The awkwardness of this definition reflects the multitude of ways that peptide-like sequences can cross-link to form macrocycles.

Together with the great diversity of non-standard amino acid monomers, the myriad topologies and architectures available to cyclic peptides enable the chemical diversity that has resulted in their prevalence amongst natural products and synthetic small molecule libraries. In this presentation, we consider some of the informatics challenges of recognizing and representing homodetic and heterodetic peptides, stapled peptides, disulfide bridge patterns and other polycyclic peptides. Amongst the complications are that covalently cross-linked sidechains may have multiple possible (degenerate) primary sequences, requiring the selection of a preferred canonical form during biological registration. This talk will present examples and statistics drawn from the PubChem and ChEMBL databases.

8:55 - 12 - Non-covalent interactions in protein-ligand interactions: Applications of halogen bonds and carbon bonds in designing PTSD drugs Suman Sirimulla, suman.sirimulla@nau.edu, Chemistry & Biochemistry, Northern Arizona University, Flagstaff, Az 86011, United States Currently, there is a growing attention for non-covalent interactions such as halogen bonds and carbon bonds in protein-ligand interactions. Data mining of halogen bonds and carbon bonds in the Protein data bank was performed and the statisical analysis of these results will be presented. Successful applications of these non-covalent interactions will be illustrated in designing drugs for Post-Traumantic Stress Disorder (PTSD) syndrome.

9:15 - 13 - BCL:Conf A knowledge based ligand flexibility algorithm and application in computational drug discovery like online drug design game Foldit

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Sandeepkumar K Kothiwale1, sandeepkumar.k.kothiwale@vanderbilt.edu, Jens Meiler1,2, Will Lowe1. (1) Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States, (2) Pharmacology, Vanderbilt University, Nashville, Tennessee 37235, United States The three-dimensional conformation a small molecule can adopt is critical for its binding to a target protein. Therefore, rapid and accurate prediction of the conformational space of a small molecule is critical for both structure- and ligand-based drug discovery algorithms such as docking or quantitative structure-activity relationships, respectively. Here we have derived a database of small molecule fragments frequently sampled in experimental structures within the crystallographic structure database (CSD) and the protein databank (PDB). Likely conformations of these fragments are stored as rotamers in analogy to amino acid side chain rotamer libraries used for rapid sampling of protein conformational space – an approach that will allow integration of BCL::Conf into respective computational biology programs such as Rosetta or Scwrl. A conformational ensemble for small molecules can now be generated by recombining fragment rotamers with a Monte Carlo search strategy. BCL::Conf was benchmarked against other conformer generator methods including Moe, Confab, and Frog2, in its ability to recover native-like protein bound conformation of small molecules, diversity of conformational ensembles, and sampling rate. BCL::Conf recovers 97% of molecules within a root mean square deviation of 2Å to the native conformation. The rapid rotamer sampling approach allows integration into Rosetta suite of macromolecular modeling and drug design module of the online protein folding game, Foldit. Conformer generation

using multiple threads allows easy integration into high-throughput docking experiments using RosettaLigand.

Sunday, August 10, 2014

Science and the Law: How the Communication of Science Influences Science-Based Policy Development in the Environment, Food, Health, and Transport Sectors - PM Session Palace Hotel Room: Marina Cosponsored by AGFD William Town, Organizer William Town, Presiding

1:15 pm - 5:25 pm

1:15 - Introductory Remarks

1:20 - 14 - Coming out from under the cloud of “Climategate”: Are scientists effectively communicating with the public on climate change? Frederick W Stoss, fstoss@buffalo.edu, University at Buffalo--SUNY, Buffalo, New York 14260, United States The strategies, resources, and tools of these groups challenge scientists’ communicating with the public, and are discussed and various STEM-base information, communication and education resources. Communicating with the public is not a traditional role of scientists, but is increasingly importance in today’s virtually-connect world. It is incumbent that the public understands the basic scientific principles of the environments in which they live, work, learn, and play. Climate change emerged in the 21st Century as one of the most complex, and controversial environmental problems. Enhanced scientific communication by scientists and their proxies is a response to the theft of emails and documents from the University

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of East Anglia in November 2009, and strategically “leaked” days before the United Nations Framework Convention on Climate Change in Copenhagen. Climate change deniers attacked researchers, and Conservative radio talk-shows dispersed allegations of fraud, withholding and manipulation of data, and suppression of publications. “Climategate” neutered the UN negotiations, and more lastingly, created public confusion and mistrust about the scientific consensus on climate change. Scientific organizations challenged scientists to evaluate their roles as communicators and set the stage for increasing the proactive discussion of their research in terms of how their research contributes to a more informed decision-making process that is necessary to transform our ways of thinking from living in a greenhouse gas constrained world, to a world not constrained by greenhouse gases.

1:50 - 15 - Carbon accounting for indirect land use change (ILUC) in biofuels policy: The co-evolution of science and policy Hanna Breetz, hbreetz@berkeley.edu, University of California, Berkeley, Berkeley CA, California 94720, United States Over the last several years, policy-makers in the US, EU, and California have been grappling with how to account for land use change emissions in biofuel regulations. One of the great challenges is that the modeling of land use change emissions has rapidly evolved since initial estimates were published by Searchinger et al. (2008). This paper explores how the science and policy have co-evolved during this period. In particular, it traces and compares how the process of policy-making responded to emerging models and data, with a particular focus on how the science was portrayed by public

discourse and interest group advocacy. The policies include the U.S. Renewable Fuel Standard (RFS), California Low Carbon Fuel Standard (LCFS), and the E.U. Fuel Quality Directive (FQD) and Renewable Energy Directive (RED).

2:20 - 16 - Communicating the risk of nicotine delivery products Jim Solyst, jim.solyst@smna.com, Swedish Match North America, Severna Park, Maryland Md. 21146, United States The rapid increase in the use of electronic cigarettes by smokers of tobacco cigarettes has highlighted the risk perception and communication challenge facing the US Food and Drug Administration (FDA) in characterizing nicotine delivery products. Tobacco smokers believe that by switching to electronic cigarettes they are reducing their risk level; which is likely true, but the scientific evidence is only now being collected. FDA is a public health and science-based agency, and cannot communicate the risk reduction potential of electronic cigarettes until they have sufficient evidence, regardless of the intuitive risk reduction potential of the product.

The 2009 Tobacco Control Act provides authority to FDA Center for Tobacco Products to regulate tobacco products, including electronic cigarettes. Section 911 of the Act –Modified Risk Tobacco Product (MRTP)--provides a scientific evidence based process by which a company can apply for and receive a MRTP order. If a product can be demonstrated to reduce harm to the individual and benefit the overall public health then it may be characterized as modified risk and FDA may communicate that information to the public.

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There are products –Swedish snus for example—for which there is a great deal of human health evidence and may at some time be granted a MRTP order; but there is no such human health evidence for electronic cigarettes due to the recent introduction of the product to the market. So what does FDA say to the tobacco smoker who is considering switching to electronic products? The best advice is not to use nicotine products at all, but does FDA have an obligation to inform smokers of the obvious benefits of switching, even if the evidence is not complete?

2:50 - Intermission

3:00 - 17 - PEPFAR - a US Government program that is helping to keep millions alive around the world George Lunn, george.lunn@fda.hhs.gov, Food and Drug Administration, Silver Spring, Maryland MD 20993, United States The President’s Emergency Plan for AIDS relief was announced by President George W. Bush in 2003 with the aim of preventing infections, treating infected people, and caring for infected individuals and orphans in resource-limited countries. In a unique arrangement, low-cost manufacturers submit New Drug Applications or Abbreviated New Drug Applications for antiretroviral drugs to treat AIDS to the FDA and these applications are reviewed to the same standards as applications for products that are destined for the US market. To expedite the preparation and submission of these applications, the FDA has reached out to the manufacturers, distributers, and other interested parties. At the beginning of 2014 FDA had taken an action on 168 applications and 6.7 million people worldwide are being treated with these antiretroviral drugs.

3:30 - 18 - Does science or

communications have greater influence in formulating policy? A UK perspective Tamora Langley, Tlangley@webershandwick.com, Healthcare Public Affairs, Weber Shandwick, United Kingdom The dynamic and principles of the scientific environment are starkly at odds with the dynamic of the political environment in which policies are made or broken. While a scientific approach is rational, evidence-based and formed through consensus of experts, the political environment is emotional, driven by communications and adversarial. Although decision-makers aspire to evidence-based policy-making, in contested areas the side with the most effective communications often seems to ‘win’. The recent economic crisis in the UK and across mainland Europe has necessitated drastic cuts in public spending, impressing on officials the need to make savings and squeeze more value out of public resources. In the UK, the government marked out the health budget as one of only two areas of public spending to be shielded from the cuts. Still, relatively flat health spending has been outstripped by rising demand for services, and so any new policies requiring additional resources remain in theory unaffordable. Where new health policies have been introduced, such as the Cancer Drugs Fund (CDF), they have been driven not by scientific developments so much as by public opinion and political decision-making. Similarly, attempted policy change driven by or expressed in terms of economic or rational imperatives (such as attempts to reconfigure health services, or attempts to change statutory regulation of dispensing medicines), have failed in the face of patient and professional campaigns. To conclude that those who shout loudest will always win, is to over-simplify. Besides, in some policy debates, patient and professional advocacy groups

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are divided. Even if policies are pushed through by noisy campaigns, they can be reversed or stalled by the public officials who ‘outlive’ their political masters and realise they are in practice unworkable or inefficient. The answer? Begin with the science, but recognise that the communication of science is just as critical.

4:00 - 19 - Consumer communication of nutrition science and impact on public health David P Richardson, info@dprnutrition.com, School of Chemistry, Food and Pharmacy, University of Reading, Reading, Berkshire RG6 6UR, United Kingdom Dietary interventions for vulnerable groups such as the elderly, women of childbearing age, children and adolescents can contribute beneficially to help reduce the risk of suboptimal intakes and deficiencies of micronutrients, to control costs of healthcare, and to promote the health and quality of life of people globally. Examples include the communication of the scientific evidence for (a) the use of folic acid/folate to reduce the risk of neural tube defects, (b) the reduction in prevalence of iron-deficiency anaemia, (c) the relationship of calcium and vitamin D to bone health and reduced risk of osteoporosis, and (d) the modulation of the age-related decline in most organ functions and reduction in the development and/or progression of many chronic diseases. The paper will highlight the need for evidence-based healthcare and communication policies, including the use of nutrition and health claims on food products to raise awareness of the role of diet in health.

4:30 - 20 - Communicating controversial science: The case of tobacco harm reduction and the ethics of blanket censorship Sarah Cooney, sarah_cooney@bat.com,

Christopher Proctor. British American Tobacco, Southampton, United Kingdom It has long been accepted that cigarette smoking causes serious disease and death, and public policy has focused on reducing tobacco use. In the US, the Food & Drug Administration (FDA) has had regulatory jurisdiction over tobacco products since 2009 and is committed to an evidence-based approach for regulatory decision making anchored by sound science. In an effort to generate much more data about tobacco science, the FDA has established an interagency partnership with the National Institutes of Health (NIH), which is making available billions of research dollars to study priority questions about tobacco science to inform FDA regulations. This new funding should attract many new researchers, creating a larger and more diverse, transparent and results-orientated tobacco science community. The FDA has set an example in acknowledging tobacco manufacturers both as an important stakeholder and as a potential source of valuable scientific expertise. Perhaps as a result, there is a general increase in scientific publications resulting from research undertaken by tobacco industry scientists. Additionally, most tobacco manufacturers are even more committed to developing products substantially less risky than cigarettes, and the science to evaluate the potential of such products to promote harm reduction. At the same time there is an increase in the number of scientific journals introducing blanket bans on publishing science from tobacco manufacturers, with the British Medical Journal being a recent example. This paper looks at the ethical dilemmas surrounding scientific censorship and the role of peer review in protecting scientific integrity.

5:00 - Panel Discussion

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5:20 - Concluding Remarks

Sunday, August 10, 2014

Nature’s Second Act: Revisiting Natural Products - PM Session Palace Hotel Room: Presidio Roger Schenck, Organizer Roger Schenck, Presiding 1:00 pm - 5:20 pm

1:00 - Introductory Remarks

1:05 - 21 - Evaluation of genus species coverage in chemical abstract Matthew J McBride, mmcbride@cas.org, Science IP, Chemical Abstracts Service, Columbus, OH 43202, United States Comprehensive retrieval of natural products reported in the public literature – patents, journal articles and other sources – requires thorough indexing of biological organisms at both common names and Genus species. CAS Registry and Chemical Abstracts (available in SciFinder and STN) provides the most complete publicly disclosed coverage of substance and literature information, however little has been reported on organism coverage, nor the impact on substances derived from such indexing. This session presents an overview of Genus species coverage in Chemical Abstracts, and focuses specifically on a case study on plant species in Chemical Abstracts and examples of how natural products and secondary metabolites are indexed in the database.

1:35 - 22 - Natural products information resources and the role of Dictionary of Natural Products Fiona M Macdonald, fiona.macdonald@informa.com, John Buckingham, Steve

Walford. Taylor & Francis, Boca Raton, FL 33487, United States Originally envisaged as a spin-off from the Dictionary of Organic Compounds, the Dictionary of Natural Products (DNP) was first published in 1991 and contained 79,000 compounds. Updated continuously since then, it now contains 260,000 compounds and is published biannually on DVD and online. Its role in natural product research will be reviewed, and plans for future enhancements revealed.

2:05 - 23 - Garlic and other alliums: The lore and the science Eric Block, eblock@albany.edu, Department of Chemistry, University at Albany, SUNY, Albany, New York 12222, United States It has been written “Cultivation of leek, onion and garlic is as old as the history of the human race, and as extensive as civilization itself. References to these plants in the Bible and the Koran reflect their importance to ancient civilizations both as flavorful foods and as healing herbs” (1). Clearly, adequately reporting on both the newest and oldest knowledge about these healing herbs and flavorful foods, including their natural products chemistry, requires more than a routine search of scientific data bases. In the course of writing a monograph on “Allium science”, the author used rare book collections in major libraries and botanical gardens to view old herbals and botanical mongraphs, spoke to botanists, visited archeological sites to see historical depictions of plants, and even found useful material in used book stores. Visits to farms in the U.S. and abroad, to overseas spice markets as well as to manufacturers and processors of alliums all proved helpful in better understanding agricutural aspects of these plants,

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while visits to museums, onion-domed churches, and even theaters, revealed the role alliums play in culture and the arts. Even cookbooks can be a useful source of information when considering the chemistry that occurs in the kitchen with common vegetables, which could be described as “chemistry in a salad bowl.” When writing about plants that have been known for centuries, researchers should find it very helpful, as well as enjoyable, to utilize non-traditional sources and locations, and view the plants in cultivation and in the wild. References (1) Eric Block, Garlic and Other Alliums: The Lore and the Science, Royal Society of Chemistry, Cambridge, 2009 (hardback), 2010 (paperback).

2:35 - 24 - Rediscovering macrocyclic natural products as drug leads Roger Schenck, rschenck@cas.org, Marketing, Chemical Abstracts Service, Columbus, Ohio 43202, United States While natural products are being rediscovered as drug leads, macrocyclic natural products have been largely ignored as therapeutic leads. Containing rings with 12 or more atoms, these macrocyclic natural products generally exceed the rule-of-five but still exhibit positive drug-like physicochemical and pharmacokinetic properties. This talk will focus on some recent examples from the CAS databases and conclude with a study of synthetic pathways for making these valuable synthetic targets in the lab.

3:05 - Intermission

3:20 - 25 - MarinLit: Database and essential tools for the marine natural products community Serin Dabb1, dabbs@rsc.org, John Blunt2, Murray Munro2. (1) Royal Society of Chemistry, Cambridge, United Kingdom,

(2) University of Canterbury, Christchurch, New Zealand MarinLit is the premier database for marine natural products research. The database contains comprehensive bibliographic information for published articles related to all aspects of marine natural products. The unusual genesis of this database, originally designed as an in-house system in the 1980s to fulfil the needs of the University of Canterbury Marine Group, led to features that are unique, or seldom found in other chemistry databases. These features, in addition to complete bibliographic details, include: taxonomy, ecology, biogeography, key words, and for compounds, structures, trivial names, syntheses, biosyntheses, bioactivities and NMR and UV data. In addition to easy access to these indexed data for the individual compounds, MarinLit is a very powerful dereplication tool. There are two aspects to this. The first is biogeography. The availability of collection site and depth data gives spatial answers to all possible search profiles. Additionally, all compounds (23,500) in the database have been analysed by a unique algorithm that populates 44 individually searchable fields with the numbers of each structural feature that can be readily recognised by 1H-NMR spectroscopy. This presentation will describe the unique functionality and searching capability of the database, the editorial process, and demonstrate how it can be used to aid dereplication in a research environment.

3:50 - 26 - RÖMPP natural products: An online encyclopedia Guiido F. Herrmann, guido.herrmann@thieme.de, Manfred Köhl, Klaus Köberlein, Ute Rohlf. Georg Thieme Verlag, Stuttgart, Germany The chemical encyclopedia “RÖMPP” has been founded by Dr. Hermann RÖMPP

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in 1947. About 250 authors have been contributing to the work over the last years and today RÖMPP contains more than 63000 entries and 14000 structural formulas. For more than a decade RÖMPP is published online (https://roempp.thieme.de/) and there are now monthly updates. The coverage of Natural Products and Secondary Metabolites has always been a central topic for the RÖMPP. The first German print edition “Naturstoffe” was published in 1997 with contributions by more than 40 authors. The German version was followed by an English edition in 2001. This edition covers about 6000 relevant natural compounds including 2200 formulas. Today, about 8% of the content of the online version of RÖMPP covers Natural Products. Our talk will highlight:

• how RÖMPP covers natural products (secondary and –to a lesser extent- primary metabolites) including additional information such as genus/species and their geographic location, analytical methods, biological and physical properties, indices with Latin species names;

• how the Editorial Board and Authors have handled the content curation over the years and decide upon updates and new entries;

• how researchers are using RÖMPP and the Natural Products sections;

• how we communicate with our users and improve the content of RÖMPP;

• how we cooperate with our Advisory Board (Dr. Sabine Angel, BASF; Dr. Andreas Barth, FIZ Karlsruhe und Dr. Engelbert Zass, ETH Zürich);

• how we have developed the graphical user interface and the underlying technologies;

4:20 - 27 - ChEMBL - linking chemistry and biology to enable mapping onto molecular pathways Louisa J Bellis, ljbellis@ebi.ac.uk, Anna Gaulton, Anne Hersey, A Patricia Bento, Jon Chambers, Mark Davies, Felix Kruger, Yvonne Light, Nathan Dedman, Shaun McGlinchey, Michal Nowotka, George Papadatos, Rita Santos, John P Overington. ChEMBL Group, European Bioinformatics Institute (EMBL-EBI), Hinxton, Cambridgeshire CB10 1SD, United Kingdom ChEMBL is an open access, large-scale bioactivity database (https://www.ebi.ac.uk/chembl) containing over 11 million bioactivity data points and 1.6 million compounds, primarily curated from scientific literature. Systems biology plays a central role in drug discovery by integrating both chemical and biological processes. Understanding a drug’s mode of action, from the consideration of its target to how it affects a molecular pathway is crucial and so combining systems biology with cheminformatics is necessary. ChEMBL is one such database that extracts data and then displays clear links between the chemical compounds, their bioactivity endpoints and associated protein targets. Showing these clear links is essential if a database is to be successfully used for drug discovery. A major stumbling block in such bioinformatic databases has, historically, been the number of different activity types and units published, thereby making it difficult to compare results from different papers. ChEMBL uses their own standardization technique to give an activity type, pChEMBL, to unite these disparate activity types and values into a

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uniform set that can be compared across multiple sources. pChEMBL is defined as –Log(molar IC50, XC50, EC50, AC50, Ki, Kd or Potency). This symposium will aim to show how ChEMBL can be used for mapping onto molecular pathways, in order to understand the modulated nodes and the chemical tools available. We will present some examples from our research, where we have developed informatics approaches to automatically annotate pathways with ChEMBL data. A second use case for systems biology is the assembly of thematic views of ChEMBL, for example in ADME systems biology.

4:40 - 28 - Treatment of Bifenthrin against subterranean termite damage to structural wood works in a semi-arid tropical urban system Sammaiah Chintha, sammaiah_ch@yahoo.com, DEPARTMENT OF ZOOLOGY,KAKATIYA UNIVERSITY, DEPARTMENT OF ZOOLOGY, WARANGAL, ANDHRA PRADESH 506009, India Subterranean termites cause damage to structural wood and other articles in different types of houses and its control was investigated in a semi-arid tropical urban system. Ten species of termites were recorded within urban houses, of which six viz Coptotermes ceylonicus, Holmgren (Rhinotermitidae), Odontotermes brunneus (Hagen), Odontotermes redemanni (Wasmann), Odontotermes wallonensis (wasmann), Odontotermes bellahunisensis Holmgren and Holmgren and Microtermes obesi Holmgren (Termitidae) were found damaging different wood works such as door frames and panels, windows- sashes, joists rafter etc. The termite damage was controlled by chemical treatment of the site at the foundation level, timber at the time of construction or by drilling holes

and treating buildings (105) with Bifenthrin (pyrethroid insecticide). The results of controls carried out during the last three year will be discussed.

5:00 - 29 - Bioisosteres in accessible chemistry space Tim Cheeseright, tim@cresset-group.com, Mark Mackey, Rae Lawrence, Martin Slater. Cresset, Cambridge, Cambs Sg80SS, United Kingdom Searching for bioisosteric replacements is a valuable part of a medicinal chemist’s toolbox. A bioisosteric core replacement can solve an ADMET or IP issue and move development into a new lead series, while bioisosteric replacements for leaf groups enable fine tuning of molecular properties without affecting the fundamental activity. A fundamental limitation of most current bioisosteric replacement search tools is the synthesisability of their suggestions. Existing computational synthesizability assessments tend to perform poorly in this context. We present an alternative approach in which the chemist is able to define the accessible synthetic space around the core of their lead molecule. The search for bioisosteres is confined to this space, so that the results are all known to be synthesisable using accessible reagents. In order to do this, multiple databases of fragments are created from the reagent sets and classified according to the synthons present and the desired chemistries. Despite the very large number of chemical reactions in the modern medicinal chemistry tool set, we have found that a very limited number of synthetic transforms are needed to fully represent this space. By focusing on the structural transformation rather than the chemical reaction, many different chemistries can be summarized into a small set of rules. We implement these rules in a special-purpose chemical

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transformation language, ATPAT. The ATPAT language combines a molecular regular expression syntax that is simpler, more extensible and more powerful than SMARTS with a set of simple transformation procedures that can be automatically applied on a successful match. The ATPAT engine allows new chemical transformation rules to be generated effortlessly. The result is an integrated system that allows the chemist to easily process his or her available reagents into a list of potential molecules to make. Wrapping this system in a KNIME or Pipeline Pilot wrapper allows automation and simple integration into existing cheminformatics systems.

Sunday, August 10, 2014

The Impact of the IUPAC InChI on Finding and Linking Information on Chemicals - PM Session Palace Hotel Room: California Parlor Cosponsored by CHED, COMP Stephen Heller, Organizer Stephen Heller, Presiding

1:30 pm - 4:35 pm

1:30 - 30 - InChI project Stephen Heller, steve@hellers.com, BMD, NIST, Gaithersburg, MD 20899-8362, United States This presentation will provide the background for the InChI symposium presentations.

1:40 - 31 - Moving the standard ever onwards: The role of the InChI Trust in supporting and developing the InChI David Evans, david.evans@reedelsevier.ch, Reed Elsevier Properties SA, Neuchâtel, Switzerland and InChI Trust, United Kingdom

Since its inception over 10 years ago by IUPAC and with support from NIST, the InChI standard has been widely used in the publishing, database, and life sciences industries, as well as securing a strong foothold in academic research and the information community. The InChI Trust, a UK based not-for-profit, was founded in 2009 in order to support the continued development of the InChI. The vision for the InChI Trust is to provide a freely available Open Source structure representation algorithm to link and find information on defined chemical structures and to provide standards, apps, and other tools that will facilitate its use. In this presentation we will discuss the current status of the InChI projects, and show how the InChI Trust and IUPAC can continue to support the development of the InchI standard and how the community can help in this work.

2:00 - 32 - How the InChI identifier is used to underpin our online chemistry databases at the Royal Society of Chemistry Antony J. Williams1, williamsa@rsc.org, Valery Tkachenko1, Karen Karapetyan1, Alexey Pshenichnov1, Colin Batchelor2. (1) US Cheminformatics, Royal Society of Chemistry, Wake Forest, NC 27587, United States, (2) eScience, Royal Society of Chemistry, Cambridge, United Kingdom The Royal Society of Chemistry hosts a growing collection of online chemistry content. For much of our work the InChI identifier is an important component underpinning our projects. This enables the integration of chemical compounds with our archive of scientific publications, the delivery of a reaction database containing millions of reactions as well as a chemical validation and standardization platform developed to help improve

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the quality of structural representations on the internet. The InChI has been a fundamental part of each of our projects and has been pivotal in our support of international projects such as the Open PHACTS semantic web project integrating chemistry and biology data and the PharmaSea project focused on identifying novel chemical components from the ocean with the intention of identifying new antibiotics. This presentation will provide an overview of the importance of InChI in the development of many of our eScience platforms and how we have used it to provide integration across hundreds of websites and chemistry databases across the web. We will discuss how we are now expanding our efforts to develop a platform encompassing efforts in Open Source Drug Discovery and the support of data management for neglected diseases

2:35 - Intermission

2:50 - 33 - Data linking in PubChem using InChI Evan Bolton, bolton@ncbi.nlm.nih.gov, National Center for Biotechnology Information, National Institutes of Health, Bethesda, MD 20894, United States PubChem is an open archive of chemical substances and their biological activities. It is a sizeable resource with many tens of millions of records provided by the chemical biology community. The IUPAC InChI and InChIKey can play a key role in accessing information in PubChem when using a chemical structure. This talk will provide an overview of the many ways one can use InChI and InChIKey with the PubChem resource. Particular emphasis will be placed on its role in linked data approaches.

3:25 - 34 - QR InCHi codes Jeremy G Frey, j.g.frey@soton.ac.uk,

Andrew J Milsted, Simon J Coles. Chemistry, University of Southampton, Southampton, United Kingdom The combination of QR codes with imbedded logos and InChI offers many opportunities for labelling and provision of machine and human readable information about materials and samples. We have developed a web based system to allow providers to create these InChI QR codes with a link to resources about a sample. This link is mediated via an InChI site and can be presented via smart phone apps. As well as enabling resource and stock control this type of label proves a very flexible way to present information to the emergency services. The service options considered will be summarised and example of the service demonstrated.

4:00 - 35 - International chemical identifier for reactions (RInChI) Guenter Grethe1, ggrethe@att.net, Jonathan M Goodman2, Chad Allen2. (1) Unaffliliated, Alameda, CA 94502-7409, United States, (2) Department of Chemistry, University of Cambridge, Cambridge, United Kingdom An open-access software for creating a unique, text-based identifier for reactions (RInChI) was developed at Cambridge University based on the IUPAC

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International Chemical Identifier (InChI) standard. RInChIs describe the substances (reactants, products, reagents and solvents) participating in a reaction with their respective InChIs. The structure of RInChIs is analogous to that of InChIs. In addition to generate RInChIs from widely used Rxnfiles and RDfiles, the software also includes the generation of long- and short-form, hashed representations – RInChIKeys. Furthermore, the software allows the reversible conversion between CT-files and RInChIs, to search for specific substances and their specific roles in reactions and to analyze databases. All these functions are available through web-based tools. An easy-to-use and freely accessible website is available at http://www-rinchi.ch.cam.ac.uk/ . We will discuss details of the program and the status of the RInChI project.

Sunday, August 10, 2014

CINF Scholarships for Scientific Excellence - EVE Session Palace Hotel Room: Ralston Guenter Grethe, Organizer

6:30 pm - 8:30 pm

36 - Toward quantitative structure-activity relationship (QSAR) models for nanoparticles Katarzyna Odziomek1,2, kjodziomek@lbl.gov, Daniela Ushizima2, Tomasz Puzyn1, Maciej Haranczyk2. (1) Faculty of Chemistry, Laboratory of Environmental Chemometrics, University of Gdansk, Gdansk, Poland, (2) Computational Research Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States For decades the implementation of combined chemometric and computational

tools has successfully aided scientists in predicting properties of new chemical compounds, based on their molecular structure. Quantitative structure-activity relationship (QSAR) methods, for example, which use linear and non-linear combinations of molecular descriptors, can be utilized to predict physical-chemical and/or biological properties of a molecule. QSAR approaches require well-defined structures of the considered molecules. Similar approaches are envisioned to predict relevant properties of nanoparticles (NPs), which are common form of chemicals used in cosmetics, pharmaceuticals and even food products. Due to their nature, NPs exhibit different characteristics than bulk materials. Nanoparticle samples are typically non-uniform and present various shapes and sizes, which give rise to their properties. Using conventional QSAR techniques is therefore not possible. Our goal is to develop new approaches that will facilitate QSAR-type modeling for nanoparticles. Our strategy is to incorporate new nanoparticle descriptors into existing, proven QSAR methods. We used scanning electron microscopy (SEM) images to obtain valuable visual information based on the morphology and topography of nanoparticles. Using computer vision algorithms, we have analyzed the SEM images and obtained descriptors of regions of interest (i.e. potential NPs), such as shape, size, surface area, roughness etc. These descriptors can be used to group and classify the nanoparticles. Next, we plan to build statistical models correlating nano and microscale parameters with physical-chemical and biological characteristics. We demonstrate applications of our methodology by investigating hydroxyapatite-based bionanomaterials. Hydroxyapatite, (hydroxylapatite, bioapatite, HAp), Ca10(PO4)6(OH)2, is a naturally occurring

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calcium phosphate mineral and has a wide range of biomedical applications, such as bone implants.

37 - Targeting androgen receptor DNA-binding domain using structure-based methods to overcome resistance Huifang Li, janelhf@gmail.com, Fuqiang Ban, Kush Dalal, Eric Leblanc, Paul S. Rennie, Artem Cherkasov. Vancouver Prostate Centre, University of British Columbia, Vancouver, B.C. V6H 3Z6, Canada The human androgen receptor (AR) is considered as a master regulator in the development and progression of prostate cancer (PCa). As resistance to current antiandrogens remains a major challenge for the treatment of advanced PCa, there is a continuing need to pursue new anti-AR therapeutic avenues. In this study, we identified a plausible binding site on the DNA binding domain (DBD) of the AR, and small-molecule inhibitors through initial screening against this site. Through exploring the related chemical space of a moderately active initial hit compound, an analogue with 10-fold improved activity was identified, and with the preliminary structure-activity relationship (SAR) on this chemical class, we obtained a lead compound of equal potency as current drug Enzalutamide. The site-directed mutagenesis demonstrates the developed inhibitors do interact with the proposed binding site on the AR DBD, suggesting a novel mechanism of action that is fundamentally different from conventional targeting of the AR through its ligand binding domain (LBD). Furthermore, they effectively inhibit the growth of cells with resistance to Enzalutamide and blocks the transcription of constitutively active AR splice variants, which lack the entire LBD and play a critical role in the development of resistance to conventional

antiandrogens. The current study provides an initial proof of principle for selectively targeting the AR DBD, which may be a novel and viable approach for the treatment of advanced and resistant PCa.

38 - Carbon bond: A noncovalent interaction Chelsea Traina, cdt64@nau.edu, Erik M. Chavez, Erin carter, Suman Sirimulla. Chemistry & Biochemistry, Northern Arizona University, Flagstaff, Az 86011, United States Nonbonding interactions between atoms are crucial to stabilizing and directing molecular formation in solutions and solids. Interactions such as hydrogen and halogen bonding have been studied to elicit these stabilizing and directing features. Another interaction, the carbon bond, also has similar capabilities and could prove to be essential in many molecular interactions, specifically in drug design. A quantitative evaluation was performed using the Cambridge Structural Database (CSD) and protein database (PDB)to analyze the carbon bond interaction. The search criterion was based upon van der Waals radii distances and avoidance of weak hydrogen bonds. This allowed us to measure the interactions between the carbon atom and nucleophile. The molecular configurations that were searched in the CSD were F/O/Cl-C…N/O/S/Cl/F. The O-C…O species yielded the greatest amount of hits at 39066. The F-C…S species generated only 125 hits. The statistical analyses of the results are presented.

39 - Random walk-based prediction of novel drug-target interactions Abhik Seal, abseal@indiana.edu, Yong Yeol Ahn, David J Wild. School of Informatics and Computing, Indiana University, bloomington, INDIANA 47408,

Chemical Information Bulletin, 2014, 66 (3) 74

United States Predicting novel drug–target associations is important not only for developing new drugs, but also for understanding how drugs work and what are their modes of action. As more data about drugs, targets, and their interactions becomes available, computational approaches are becoming more viable in drug-target association discovery. In this paper, we apply Random Walk with Restart (RWR) method on a heterogeneous network of drugs and targets to predict novel drug-target associations. From DrugBank, we construct the heterogeneous drug-target networks using four types of chemical fingerprints, sequence similarity, and interaction profiles. We find that our method produces reliable prediction with respect to the choice of chemical fingerprint types. We use ChEMBL, an external dataset with 2,763 associations, to evaluate the performance of our approach, finding that it correctly predict nearly 45% of the interactions that are only present in the ChEMBL dataset. We also verify several associations between drugs and mode-of-actions, such as strong associations between hair loss and cardiovascular drug Simvastatin. Finally, the associations between 110 popular drugs and 3,519 targets are analyzed as a case study. In summary, we demonstrate the effectiveness and promise of the approach—RWR on heterogeneous networks—for identifying novel drug target interactions.

40 - Pred-hERG: A novel web-accessible computational tool for predicting cardiac toxicity of drug candidates Vinícius M Alves1, viniciusm.alves@gmail.com, Rodolpho C Braga1, rodolphobraga@yahoo.com, Meryck B Silva1, Eugene Muratov2, Denis Fourches2, Alexander Tropsha2, Carolina H

Andrade1, carolina@ufg.br. (1) Laboratory for Molecular Modeling and Drug Design, Faculty of Pharmacy, Federal University of Goiás, Goiania, Goias 74605170, Brazil, (2) Laboratory for Molecular Modeling, Division of Chemical Biology and Medicinal Chemistry, University of North Carolina, Chapel Hill, North Carolina 27599, United States Several non-cardiovascular drugs have been withdrawn from the market due to their critical side effect of inhibiting the human ether-à-go-go related gene (hERG) K+ channels, which may lead to heart arrhythmia and death. Thus, hERG safety testing is an indispensable process that is required by the US FDA. There is considerable interest in developing computational tools to filter out potential hERG blockers in early stages of drug discovery. In this work, we describe the development of a new tool for the rapid identification of potential cardiotoxic compounds by hERG inhibition. We have compiled the largest publicly available dataset of hERG binding, containing 11,958 compounds from the ChEMBL database. Once curated, this dataset contained 4,980 compounds for modeling. Several types of QSAR models have been developed and validated according to the OECD principles. The external classification accuracies discriminating blockers from non-blockers were 0.83-0.93 on external set. Model interpretation revealed several SAR rules, which can guide structural optimization of some hERG blockers into non-blockers. Virtual screening of the WDI chemical library using selected QSAR models identified 4,945 compounds as potential hERG blockers. The developed models can reliably identify blockers and non-blockers, which could be useful for the scientific community. A freely accessible web server has been developed allowing users to

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identify putative hERG blockers and non-blockers in chemical libraries of their interest (http://labmol.farmacia.ufg.br/predherg).

41 - Mining chemical space for novel molecules: A graphical tool for working with fragment spaces Florian Lauck, lauck@zbh.uni-hamburg.de, Matthias Rarey. Universität Hamburg - Center for Bioinformatics, Hamburg, Germany Mining chemical space for novel molecules with desirable properties proves difficult. The collective strategy is to limit search space so that it is easier to consider only those molecules with suitable physicochemical and topological properties. One therefore requires methods and data structures for efficiently modeling this chemical subspace, as well as user-friendly tools to access this functionality. Here, we present a graphical user interface for creating, manipulating, and searching large chemical space. As a model we use a fragment space, i.e., a combinatorial chemical space consisting of molecular fragments and connection rules. Each fragment has at least one reaction site that corresponds to an open valence. These sites are modeled as artificial atoms with a defined type, called link atoms. The connection rules determine compatibility of such link atoms. When two fragments are connected, the link atoms are removed and a bond in accordance with the connection rule is introduced. A number of algorithms and strategies for working with fragment spaces have been developed in the past but were only available as separate command-line tools. Our new software combines these tools into one user-friendly application, able to visualize the contents of a fragment space (fragments and connection rules), as well as search results (novel molecules).

For generating fragment spaces, an automated approach was incorporated using a set of molecules and cut rules, i.e., SMARTS pattern that define where a molecule should be cleaved and link atoms should be introduced. For retrieving molecules with structural similarity we provide two query-based search methods utilizing molecular similarity (reduced graph descriptors) and substructure search (SMARTS pattern matching). In addition, a new approach for constraint-based enumeration complements these algorithms, allowing a search based on physicochemical properties rather than structural similarity. Finally, specialized fragment spaces can be created by filtering fragments via numerous properties.

42 - BCL::EvoGen: An evolutionary algorithm for focused library design Alexander R Geanes, alexander.r.geanes@vanderbilt.edu, Edward W Lowe, Jens Meiler. Department of Chemistry, Vanderbilt University, Nashville, TN 37235, United States In recent years, virtual high-throughput screening (vHTS) techniques have been successfully applied in the drug discovery process. In many cases, these vHTS techniques are leveraged to prioritize subsets of chemical libraries for acquisition and testing in physical screens. However, for computer-aided drug design (CADD), it is advantageous to have algorithms which are capable of designing new chemical entities for a specific biological target. An evolutionary algorithm was implemented as part of the BCL::ChemInfo suite within the Biochemistry Library (BCL), a C++ library developed at Vanderbilt University, to iteratively generate chemical species with high predicted biological activities for use in focused library design for hit-to-lead optimization. Quantitative structure activity relationships based on machine

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learning techniques were used to predict the biological activity of compounds in each generation. The compounds with the highest predicted activity, as well as a smaller number of lower activity species, were subjected to combination, crossover, and mutation to form the subsequent generation. Termination criteria were based on a percentage of compounds in a single generation achieving a predicted activity above a pre-determined cutoff, or after reaching a pre-set number of generations in the event the first criterion could not be satisfied. This method was benchmarked using a previously published set of 9 datasets designed for the validation of novel CADD methods. Each of the datasets was compiled from publicly available HTS data taken from PubChem, and contain a minimum of 150 active compounds each. In addition, the datasets span a range of protein targets including GPCRs, ion channels, and enzymes. Here we present the results of this focused library design application, BCL::EvoGen.

Monday, August 11, 2014

Global Challenges in the Communication of Scientific Research - AM Session Palace Hotel Room: Marina David Martinsen, Norah Xiao, Organizers David Martinsen, Norah Xiao, Presiding 8:05 am - 11:40 am

8:05 - Introductory Remarks

8:10 - 43 - Utility-based analysis of solar energy technologies Collin Perry, collinperry@my.unt.edu, William Justin Youngblood. Department of Chemistry, University of North Texas, Denton, Texas 76203, United States We explore the Von Neumann-

Morgenstern utility theorem to compare the overall utility of different solar energy technologies. As part of this approach, we seek to define the variables that can be manipulated to maximize the utility of photovoltaic research with regards to economic developments, the protection of the natural environment, the advancement of basic and applied science, and the quality of life for human populations.

8:40 - 44 - New IUPAC organic nomenclature: From bottle label to update of databases Andrey Yerin, erin@acdlabs.ru, Advanced Chemistry Development, Inc. (ACD/Labs), Toronto, Ontario M5C 1B5, Canada International Union of Pure and Applied Chemistry (IUPAC) recently published new recommendations on nomenclature of organic chemistry (IUPAC Blue Book 2013). The most important part of these recommendations is a concept of “Preferred IUPAC Name” (PIN) established by hierarchical order of criteria allowing to derive the unique systematic name intended for registrations, patents, regulations and other official purposes. Together with introduction of PIN concept new IUPAC recommendations introduce several principle changes in naming procedures that will change systematic names for many classes of organic structures. While strict following of IUPAC recommendations is not mandatory, the gradual change of naming conventions is expected and will affect chemical publications and databases. An introduction of these changes makes organic nomenclature not only stricter but at the same more difficult to memorize, thus increasing the role of automatic naming tools. The presentation will illustrate the most principle changes of naming principles with examples of the corresponding classes of chemicals.

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The overall impact of application of new nomenclature rules will be estimated via comparison of systematic names generated by ACD/Labs naming tools according to the previous and new naming principles for large compound libraries.

9:10 - 45 - New strategies to engage more of the world with scientific app development and content deployment Steven M Muskal, smuskal@eidogen-sertanty.com, Eidogen-Sertanty, Inc., Oceanside, CA 92056, United States Over 70% of the world’s population, i.e. 5 billion people will routinely use mobile devices in the next few years. In this age of immediate access and connectivity, an unprecedented “global conversation” and capability has arisen creating many new opportunities for content capture, manipulation, and dissemination. Unfortunately, the number of people developing cloud-based mobile applications is far too small to meet the global need. To this end, we have been engaged with Accelrys on a multi-year project to extend their popular Pipeline Pilot framework to interface directly with hand-held devices to leverage mobile capabilities including image capture, upload and annotation, geo-location tagging, audio and video capture, and other forms of content capture and manipulation. Earlier this year, we released the “ScienceCloud Tasks” mobile app (freely available to the world in the Apple Appstore), and have plans to develop an Android version. By better interfacing mobile devices with server-based, cloud-deployed pipelining technologies, we expect to dramatically simplify mobile-cloud app development and deployment in general, and hope to open-up new possibilities in workflows (i.e. “tasks”) associated with publication assembly, submission, editing, and distribution.

9:40 - 46 - Dealing with the complex challenge of managing diverse chemistry data online Antony J Williams, williamsa@rsc.org, Valery Tkachenko, Ken Karapetyan, Alexey Pshenichnov. US Cheminformatics, Royal Society of Chemistry, Wake Forest, NC 27587, United States The Royal Society of Chemistry has provided access to data associated with millions of chemical compounds via our ChemSpider database for over 5 years. During this period the richness and complexity of the data has continued to expand dramatically and the original vision for providing an integrated hub for structure-centric data has been delivered across the world to hundreds of thousands of users. With an intention of expanding the reach to cover more diverse aspects of chemistry-related data including compounds, reactions and analytical data, to name just a few data-types, we are in the process of implementing a new architecture to build a Chemistry Data Repository. The data repository will manage the challenges of associated metadata, the various levels of required security (private, shared and public) and exposing the data as appropriate using semantic web technologies. Ultimately this platform will become the host for all chemicals, reactions and analytical data contained within RSC publications and specifically supplementary information. This presentation will report on how our efforts to manage chemistry related data has impacted chemists and projects across the world and will review specifically our contributions to projects involving natural products for collaborators in Brazil and China, for the Open Source Drug Discovery project in India, and our collaborations with scientists in Russia.

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10:10 - Intermission

10:20 - 47 - Amplifying the role of collaboration globally for neglected and commercial disease drug discovery Barry A. Bunin, bbunin@collaborativedrug.com, Charlie Weatherall, charlie@collaborativedrug.com. Management, Collaborative Drug Discovery (CDD), Burlingame, CA 94010, United States Collaborative innovation is uniquely able to realize the economics of well-integrated specialization required for drug discovery. Particularly in the neglected infectious disease areas lacking a profit motive, better collaborative tools are fundamentally important to catalyze faster progress. Layering unique collaborative capabilities upon requisite drug discovery database functionality unlocks and amplifies synergy between biologists and chemists. Researchers need to have tools that balance individual needs for robust, intuitive registration and bioactivity analyses while at the same time facilitating collaborations with secure data partitioning, communication, and group engagement. Recent results shared publicly for Tuberculosis, Malaria, and Kinetoplastids, as well as an unusual collaboration among hundreds of undergraduates students developing novel compounds for Neglected Disease applications amply demonstrate these bold suppositions are true and general. Since collaborative technology is “therapeutic area agnostic”, it has generally been proven equally applicable for commercial applications. Representative commercial case studies include broad consortia such as the NIH Neuroscience Blueprint collaboration between drug discovery companies, CROs, together with seven leading academic biology laboratories as part of a 5-year government contract to

advance new CNS drugs into the clinic. As well as more focused examples following the lean venture funded model such as the collaboration between Acetyton Pharmaceuticals with Harvard and a Chinese CRO to bring a selective HDAC inhibitor into the clinic. Finally, by spanning the continuum of private, collaborative and public modes, researchers globally can now seamlessly collaborate across the pre-competitive and competitive landscape.

10:50 - 48 - Why there needs to be open data for ultrarare and rare disease drug discovery Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2, Jill Wood3, Lori Sames4, Allison Moore5. (1) Collaborations in Chemistry, Fuquay Varina, NC 27526, United States, (2) Molecular Materials Informatics,, Montreal, Quebec H3J 2S1, Canada, (3) Jonah’s Just Begun, Brooklyn, NY 11215, United States, (4) Hannah’s Hope Fund., Rexford, NY 12148, United States, (5) Hereditary Neuropathy Foundation., New York, NY 10016, United States Individual parents and patients are increasingly doing more to fund, discover and develop treatments for rare and ultra-rare diseases that afflict their children, themselves or their friends. They are performing many roles in driving the science that are equivalent to professional scientists. Through their efforts and that of the collaborative networks which they have developed, they may be in position to disrupt drug discovery. But what is missing is accessibility to scientific data and publications. This can be illustrated using three different ultra-rare disease parent / patient advocate groups and the diseases for which they are developing treatments. Each group encountered difficulties in accessing information. Perhaps what could be proposed is an open data commons or

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database dedicated to rare and ultra-rare diseases. This could encompass chemistry and biology data. Our efforts with the mobile app Open Drug Discovery Teams (ODDT) will be described to catalyze such efforts. Challenges will likely come from industry which sees this as a lucrative field. Our aim is to discuss the pros and cons of Open Data for Ultra-Rare and Rare Disease Drug Discovery and suggest mechanisms for this to occur to benefit everyone.

11:20 - 49 - Supporting the exploding dimensions of the chemical sciences via global networking Valery Tkachenko1, TkachenkoV@rsc.org, Anthony Williams1, Sergey Vatsadze2. (1) Royal Society of Chemistry, Wak Forest, NC 27587, United States, (2) Department of Chemistry, Moscow State University, United States The Royal Society of Chemistry is building is a comprehensive federated platform for chemical informatics in a Big Research Data world. The resulting platform is a blend of social, informatics and knowledge components which itself produces new dimensions in the chemical sciences to support activities such as Open Innovation and sharing of data. The platform itself would be isolated and insular unless a broad collaboration between societies, industry and universities is created in a federated and open way. In this presentation we will talk about one of these efforts, between RSC and Moscow State University, to facilitate the development, population and use of a global networking platform for the chemical sciences.

Monday, August 11, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - AM Session

Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding 9:05 am - 12:00 pm

9:05 - Introductory Remarks

9:10 - 50 - Recent enhancements in the accuracy of CLiDE tool for extracting chemical structure data from patents and other documents Aniko T Valko1, Aniko.Valko@keymodule.co.uk, Peter Johnson2. (1) R&D, Keymodule Ltd., Leeds, United Kingdom, (2) School of Chemistry, University of Leeds, Leeds, United Kingdom We present an enhanced version of CLiDE, which is a long-term project aimed at detecting chemical structure diagrams rendered in images and converting these diagrams into chemical connection tables. The enhancement was achieved by introducing a feedback mechanism into CLiDE’s interpretation process. This mechanism makes use of a series of domain- and spatial-specific rules for identifying drawing features that convey a complex or an ambiguous meaning. Once such a feature is found, CLiDE automatically corrects the structural information being compiled and passed through subsequent interpretation steps. This enhancement has a considerable effect on CLiDE’s accuracy in reconstructing chemical structures and auto-detecting interpretation errors. A detailed study of CLiDE’s performance on a large validation corpus will be presented. The validation corpus will include benchmark sets created by other projects and a set of non-Markush structures collected from patent documents.

9:40 - 51 - Structure Clipper: An interactive tool for extracting chemical

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structures from patents Christopher E Kibbey, christopher.kibbey@pfizer.com, Jacqueline L Klug-McLeod. Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Groton, Connecticut 06340, United States Medicinal chemists rely on patent intelligence at three distinct junctures of a research project: inception of an idea, ongoing competitive intelligence during project development, and preparation of the patent application. Knowledge of the competitive landscape provides medicinal chemists with insight into competitor’s strategies for improving potency and decreasing ADME liabilities. While comprehensive databases of chemical structures obtained from patents are available, medicinal chemists generally focus their analysis on a few patents at a time. In addition to identifying “key” compounds within a competitor’s patent, medicinal chemists are interested in obtaining bioassay results, synthetic route, yield and analytical characterization related to these compounds. Medicinal chemists spend considerable effort locating chemical structures within a patent, and tools to facilitate compound annotation and traceability are highly desired. Structure Clipper is an interactive tool that combines image processing, image-to-structure (OSRA) conversion, optical character recognition (OCR), chemical name annotation, spelling correction, and chemical name-to-structure conversion to automatically identify and extract chemical structures from electronic documents, such as patents and journal articles. Chemical structures generated by Structure Clipper are tagged with the page number and rectangular coordinates on the page on which the original chemical text or image is located. In addition, chemical structures are assigned the identifier (e.g., example

number, synthetic step, intermediate, etc.) described in the source document. Structure Clipper provides a direct link between chemical structures and their origin within the source document. Extracted structures may be manually annotated with related information, such as bioassay results, synthetic yield, and spectroscopic characterization. Lastly, Structure Clipper provides an interface for semi-automated enumeration of structures from Markush tables spanning multiple pages in the source document.

10:10 - 52 - Computer-assisted Markush structures curation from patent documents David Deng, ddeng@chemaxon.com, Arpad Figyelmesi. ChemAxon, Cambridge, Massachusetts 02142, United States Markush structures (or generic structures) are widely used in chemical patents and combinatorial chemistry to define large chemical spaces. ChemAxon provides powerful Markush structure drawing, Markush search, overlap analysis and visualization functionalities. These Markush functionalities are widely available in our products, including Marvin, JChem Base, JChem Cartridge and Instant JChem. In this presentation, the latest development of the new Patent Curation Tool will be introduced. The curation tool provides an intuitive interface to the user to read patents and curate the Markush structures side-by-side. It features ChemAxon’s chemistry text mining functionality to extract R-group definitions from patent documents, and allows easy importing of these R-group fragments in bulk. The tool takes full consideration of various Markush complexities (e.g. nested R-groups, multiple R-group attachment points). Once the Markush structure is curated, the user may also enumerate the Markush structure. ChemAxon also

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provides powerful search capability allowing structure search in the Markush chemical space. The latest improvement also allows overlap analysis between two Markush structures, and hit result analysis. Both features will be demonstrated in this presentation as well.

10:40 - Intermission

10:55 - 53 - Use of reverse text-mining to establish whether indexing and classification of chemical patents is still necessary Robert A Stembridge, bob.stembridge@thomsonreuters.com, IP & Science, Thomson Reuters, London, United Kingdom With the success of chemical structure name recognition techniques to identify chemical entities within patent documents (at least for specific entities - textual Markush structure recognition still remains a challenge), is there still a place for indexing and classification of chemical patents? This presentation will examine this question by “reverse text-mining” i.e. by analysis of data sets retrieved with indexing and classification using text-mining techniques to identify the success or otherwise of comprehensiveness and precision of recall.

11:25 - 54 - Extraction of chemical reactions from full text documents: From n-tuples of value attribute pairs toward the automated construction of reaction databases Lutz Weber, lutz.weber@ontochem.com, Matthias Irmer, Claudia Bobach. IT Solutions, OntoChem GmbH, Halle (Saale), Sachsen-Anhalt 06120, Germany Computer aided extraction of chemical reactions from natural language text documents represents a problem of

high complexity. Thus, chemicals may be mentioned as starting materials, catalysts, supports, solvents, side products or products – all representing different roles to be captured. Further, additional information includes temperature, yield or other quantitative or qualitative data that increases the value of the information on a particular chemical reaction. We will present a semantic text mining system that uses chemical ontologies on chemical compounds, chemical classes and substituents in conjunction with a chemical reaction relationship model to extract information on chemical reactions from scientific publications. The system first identifies all named entities such as chemical named entities, classifies chemical names as specific compounds, chemical compounds classes, substituent lists or general reaction related named entities. In addition, relevant units, numeric or qualitative value and terms such as for example “excellent yield of >90%” are identified. In a second step, terms are combined into complex, nested named entities to facilitate a syntax based rule assignment of specific roles the identified chemical named entities. Reaction specific syntax rules are implemented to understand and classify chemical reactions – from metabolic reactions up to the range of well-known named chemical reactions.

As a result, the presented text mining system allows to scan millions of text documents in few days and extract chemical reaction information in CML or other chemistry aware data file formats for filling chemical reaction databases. As a

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case study we will present the automated generation of a metabolic database for phytochemicals.

11:55 - Concluding Remarks

Monday, August 11, 2014

The Impact of the IUPAC InChI on Finding and Linking Information on Chemicals - AM Session Palace Hotel Room: California Parlor Cosponsored by CHED, COMP Stephen Heller, Organizer Stephen Heller, Presiding

8:30 am - 12:00 pm

8:30 - 55 - InChIs are not just for small molecules Keith T Taylor, keith.taylor@laderaconsultancy.com, Ladera Consultancy LLC, Sparks, Nevaa 89436, United States The success of the InChI for small, drug-like molecules has driven the need to extend its coverage. Progress with enhncements to support enhanced stereochemistry, organometallics, biologics, polymers, and mixtures will be described.

9:05 - 56 - NCI/CADD Group’s InChI usage and analysis of tautomerism for InChI V2 Marc C Nicklaus, mn1@helix.nih.gov, CADD Group, CBL, CCR, National Cancer Institute, NIH, Frederick, MD 21702, United States We are presenting a brief overview of the current status of the usage of InChI and InChIKey in several free web services of the NCI/CADD Group at http://cactus.nci.nih.gov, as well as in the underlying

very large database of small molecules aggregated from screening sample collections and other sources. We also present a status update of the efforts to analyze, and if needed modify, the current rules in the InChI algorithm of calculating tautomers and thus ensuring InChI’s design goal of being a tautomer-invariant identifier with view of a possible revamping of the handling of tautomerism for a version 2 of InChI.

9:40 - 57 - Intersecting crystallographic databases using InChI Ian J Bruno1, bruno@ccdc.cam.ac.uk, Tjelvar SG Olsson1, Sanchayita Sen2, Gary M Battle2, Jose M Dana2, Sameer Velankar2. (1) The Cambridge Crystallographic Data Centre, Cambridge, United Kingdom, (2) Protein Data Bank in Europe, EMBL-European Bioinformatics Institute (EMBL-EBI), Cambridge, United Kingdom Knowledge derived from small-molecule crystal structure data has a role to play in helping protein crystallographers refine models of ligands crystallised with biological macromolecules. The Cambridge Crystallographic Data Centre (CCDC) and the Protein Data Bank in Europe (PDBe) are thus engaged in a collaborative project that aims to make coordinates of structures from the Cambridge Structural Database (CSD) available in the worldwide Protein Data Bank (wwPDB) chemical component dictionaries. This requires us to identify molecules in the CSD that match ligands in the Protein Data Bank (PDB), a task for which InChI is ideally suited. This presentation will describe how we have been able to take advantage of InChI to intersect these two resources of 3D structural information and will discuss the challenges encountered in reliably generating InChIs for structures in the CSD where the chemistry is diverse and

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crystallographic artefacts abound. This work is funded by a grant from the BBSRC, UK, Reference BB/K016970/1.

10:15 - Intermission

10:30 - 58 - Data formats for elementary gas phase kinetics: Unique representations of reactions Donald R Burgess1, dburgess@nist.gov, Jeffrey A Manion1, Carrigan J Hayes2. (1) Chemical and Biochemical Reference Data Division, National Institute of Standards and Technology, Gaithersburg, MD 20899, United States, (2) Department of Chemistry, Otterbein University, Westerville, OH 43081, United States A method of extending the IUPAC International Chemical Identifier (InChI) to describe and identify elementary reactions in a standard computer readable notation was developed. Denoted InChI-ER, the method is based on the existing InChI formalism, with certain refinements including a more complete identification of molecular entities. Using this base notation, an identifier for elementary reactions on a molecular level can be created by adding additional layers in a conceptually similar and extensible manner. Two of the layers describe the atoms involved in the transition-state and the connectivity changes that occur during the reaction. Additional layers classify the reactions on the basis of the connectivity changes, providing chemical information useful in organizing and searching kinetic data sets found in databases or used in detailed kinetic modeling. Important aspects of the method are that the proposed layers are optional, that they do not interfere with existing InChI specifications, and that they retain extensibility should further refinements be desired in the future. Its utility for organizing data is illustrated

by implementation for a well-employed combustion mechanism.

11:05 - 59 - International Chemical Identifier (InChI) at Wiley: Strengths and limitations Graeme E. Whitley1, gwhitley@wiley.com, Bernd Berger2, bberger@wiley.com. (1) Global Research, Research Innovations, Wiley, Hoboken, NJ 07030, United States, (2) Global Technology Solutions, Wiley-VCH, Weinheim, Baden-Württemberg 69469, Germany Wiley’s adoption of the InChI as a chemical indentifier is pervasive across its publications and databases. We will provide use-case examples that highlight the standard’s core strengths and fundamental limitations. Areas to be covered will include compound identity matching, stereochemistry, and organometallics.11:40 - 60 - InChIKeys as chemical entity ids to enable in-context text indexing and to identify engine-ranked chemically similar documents Stephen Boyer, sboyer@us.ibm.com, Tom Griffin, Cassidy Kelly, Eric Louie, Jacques Labrie, Scott Spangler, Ying Chen, Ru Fang, Su Yan. IBM Almaden Research Center, San Jose, CA 95120, United States Chemical name annotators that find and standardize chemical names in scientific papers and patent text documents usually generate tables of SMILES or InChIs. In order to make the most use of identified compounds for text analytics, we convert the found compound names into InChIKeys and insert the InChIKey values into the original document text beside the compound name, along with the literal word “inchikey” as an entity type marker. The augmented documents are then indexed as full text using Solr/Lucene

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resulting in a search service with useful capabilities such as co-occurence analysis, e.g., finding all cases of any text synonym of aspirin within 10 words of cancer, finding cases of any chemical compound (any entity marker “inchikey”) within 10 words of “produced” AND within 10 words of “yield”. This indexing technique also supports finding chemically similar documents. The selected compounds’ InChIKeys are entered together as a set of query “words”, returning an engine-ranked list of documents with the most compounds overlapping the target’s. Full engine capabilities such as boolean filter terms are still available to refine the set with full engine performance. The indexed augmented text also facilitates other data mining capabilities such as batch searches for large numbers of molecules over millions of documents. Our team is developing a comprehensive chemical pedia containing structure representations and attributes for millions of molecules derived from patents and other sources such as Medline Abstracts. On-going work includes entity insertions simultaneously performed on gene, drug and disease annotation types, enabling rich entity/text combination queries with no search engine modifications needed.

Monday, August 11, 2014

Global Challenges in the Communication of Scientific Research - PM Session Palace Hotel Room: Marina David Martinsen, Norah Xiao, Organizers David Martinsen, Norah Xiao, Presiding

1:15 pm - 5:25 pm

1:15 - Introductory Remarks

1:20 - 61 - Building BRICK by BRICK

sometimes works: How ACS Editors’ participation in ACS on Campus has brought publishing best practices to thousands of authors in BRICKS countries, an overview of challenges and successes S. Sara Rouhi1, s_rouhi@acs.org, Kirk S. Schanze3, schanze-office@ami.acs.org, Prashant V. Kamat2, pkamat@nd.edu. (1) Library Relations, ACS Publications, Washington, DC 20036, United States, (2) Department of Chemistry & Biochemistry and Radiation Laboratory, University of Notre Dame, Notre Dame, IN 46556, United States, (3) Department of Chemistry, University of Florida, Gainesville, FL 32611, United States The ACS on Campus program, spearheaded by ACS Publications in 2010 and now an ACS-wide program, was developed to help graduate students, post-docs, and faculty address the challenges of a career in the sciences, principal among those: getting published in top journals. This presentation will feature ACS on campus team members and ACS Editors sharing their experiences of teaching publishing best practices to the biggest source of science research today, the BRICKS countries. ACS on Campus team lead, Sara Rouhi, will outline the various publishing modules offered to students: Getting Started Writing a Manuscript, What is Peer-Review?, Technical Writing for Non-native Speakers, and Copyright and Ethics in Scholarly Communication. ACS Editors-in-Chief Prashant Kamat and Kirk Schanze will share their experiences delivering these best practices to students around the world during their participation in ACS on Campus. Drs. Kamat and Schanze have attended over 15 ACS on Campus events ranging from Beijing to Calcutta to Rio de Janeiro. Sara Rouhi created the ACS on Campus program in 2010 and current

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manages the international arm of the program.

2:00 - 62 - Article-impact assessment in the age of open copyright and social networking Frederick F Fenter, frederick.fenter@frontiersin.org, Costanza Zucca. Frontiers Media, Lausanne, Vaud 1015, Switzerland Two trends in scientific publishing are the increased use of social networks and the dissemination of articles under open public copyright licenses. In this presentation, we wiill discuss how these will affect the impact metrics –both traditional and new – used to indicate the inherent scientific merit of an article.

2:30 - 63 - Chemistry journals in China and chemical papers from China: What is the future? Xiaowen Zhu, zhuxiaowen74@126.com, University & Higher Education Press, Tianjin, Tianjin, China There are more than 5,000 academic journals in China and only about 60 on chemistry or chemical engineering. From 2009 to 2013, the number of SCI articles in chemistry is more than 160,000 but only 20 chemistry journals are indexed by SCI in China. Most of the chemical papers from China are published outside. To make the domestic journals more international and get more influence are a national strategy. The government put a big financial support in 2012 and 2013. The English language journals including Chinese Chem. Lett., Chinese J. Chem., Sci. China Chem., Chinese J. Polym. Sci., Chinese J. Chem. Eng., and Front. Chem. Sci. Eng. got the financial support.Building an international editorial broad, getting the best papers from Chinese scientists and other countries scientists, using international reviewers, collaborating with

the international publisher are the main ways at this moment.

3:00 - 64 - Globalization of scholarly publishing: Meeting the needs of international researchers Amy Beisel, amy.beisel@researchsquare.com, Keith Collier, Ben Mudrak. Research Square, LLC, Durham, NC 27701, United States Science is truly an international endeavor, with significant investments in research being made around the globe. The fundamentals of research may be universal, but language and lack of familiarity with scholarly publishing conventions represent considerable barriers to the broad dissemination of research findings for many scientists. Publishers are receiving an increasing proportion of their submissions from researchers who are not native English speakers. What can be done to simplify the submission process for these authors while still ensuring that they are sending high-quality and well-matched manuscripts? At Research Square, we assist researchers worldwide in their efforts to disseminate research results. Previously, we surveyed a sample of our customers to determine the biggest challenges they faced when submitting manuscripts to English-language journals. Specific suggestions we have heard from international researchers include their desire for assistance with certain aspects of the publishing process and an appreciation for clearly defined journal policies. Using these survey results and additional insight gained by our ongoing conversations with international investigators, we can provide a greater context for how the current trends in scholarly publishing affect researchers around the world. In some cases, simple changes to the publication processes can lead to better, long-lasting relationships

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with authors. Overall, by meeting the needs of international scientists, we enable the creation of an efficient publication process driven by a diverse community, which increases the pace of scientific discovery itself.

3:30 - Intermission

3:45 - 65 - Beyond open access Martin Hicks, mhicks@beilstein-institut.de, Beilstein-Institut, Frankfuty, Germany Open Access has now become established within scientific publishing. The advantages of having scientific discoveries and research results made freely available for the global scientific community is self-evident. Authors benefit in retaining full copyright and being able to archive the final version of their own articles without restriction. The Beilstein Open Access journals engage the scientific community worldwide, through the removal of price barriers for authors and readers. But what does the scientific community really want when it comes to publishing? The serials crisis is still ongoing, peer-review is straining, more and more papers are being submitted and published, plagiarism is a problem, data reproducibility and integrity is at times questionable – and big data is looming on the horizon. It is essential to ensure that data published by researchers really is useable by all members of the global scientific community. The Beilstein-Institut supports and coordinates two international projects with the aim of ensuring data integrity in enzyme and glycan data reporting.

4:15 - 66 - Supporting and facilitating the publication of chemical science research: A global view Daping Zhang, ZhangD@rsc.org, Royal Society of Chemistry, United States

The Royal Society of Chemistry is the fastest growing chemical society publisher in the world. Over the last five years its published output has increased by a factor of five, from approximately 5000 articles in 2008 to approximately 25000 articles in 2013. As is well known in the publishing community, the majority of these submissions now come from countries with a rapidly expanding research base, such as China, India and Brazil. Not yet producing the same level of output but making rapid progress nonetheless are countries from territories such as the Middle East and Africa. To support this growing trend and provide chemists from these countries with the tools and assistance to publish in English-language journals, the Royal Society of Chemistry has over recent years significantly expanded the reach and scale of its international development and publishing innovation activity: establishing local editorial teams (in China, India, Japan and the US); forging co-publishing partnerships with sister chemical societies; organizing publishing internships, students clubs and “how to publish” training workshops; hosting international conferences; and investing in capacity-building initiatives. This presentation will provide an overview of some of the Royal Society of Chemistry’s recent initiatives in the fields of international co-operation, capacity building and publishing innovation, including the RSC Frontiers journals in China, activities and partnerships established in India and Japan, and the principles and aims of the Pan-African Chemistry Network.

4:45 - 67 - Enabling international collaboration using the Eureka Research Workbench Stuart Chalk1, schalk@unf.edu, Robert Belford2, Phuc Tran2, Thanit Pewnim3. (1) Department of Chemistry, University

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of North Florida, Jacksonville, FL 32224, United States, (2) Department of Chemistry, University of Arkansas at Little Rock, Little Rock, AR 72204, United States, (3) Department of Chemistry, Silpakorn University, Nakhon Pathom Province 73000, Thailand The Eureka Research Workbench (http://eureka.sourceforge.net) is an online environment for capturing the scientific process that is currently under development. This presentation discusses the initial use of Eureka for international collaborative research on eco-toxicological investigations of the generation of estrogen mimics in the early aquatic food chain, (the biochemical conversion of nonylphenol ethoxylate to nonylphenol by the microalgae chlorella vulgaris). Specimens are collected in Thailand with initial extraction and sample preparation occurring at Silpakorn University, where data is directly entered into Eureka. Samples are then sent to analytical laboratories at UALR and UNF for separation and spectroscopic analysis with all data also being uploaded to Eureka. Through Eureka both the data and metadata are stored in one place enabling collaborative research across three distinct geographic regions and time zones. A discussion of the process and future plans for refinement of the system will be included.

5:05 - 68 - Combatting chemophobia: Speaking science to distrust and engaging with empathy, online, and face-to-face Leigh K Boerner2, Ljkboerner@gmail.com, Raychelle Burks6,8, rmburks@gmail.com, Matthew Hartings4, hartings@american.edu, Chad Jones5, chemist.jones@gmail.com, Kevin Shanks7, forensictoxguy@gmail.com, Janet D Stemwedel1, dr.freeride@gmail.com,

Brandi VanAlphen3, branvanchemist@gmail.com. (1) Department of Philosophy, San Jose State University, San Jose, CA 95192-0096, United States, (2) Unaffiliated, United States, (3) Unaffiliated, United States, (4) Department of Chemistry, American University, Washington, DC 20016, United States, (5) Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, United States, (6) Center of Nanohybrid Functional Materials, University of Nebraska, Lincoln, NE 68508, United States, (7) Department of Forensic Toxicology, AIT Laboratories, Indianapolis, IN, United States, (8) Department of Chemistry, Doane College, Crete, NE 68333, United States Chemists should serve the broader public, including better educating people in the nature and uses of chemistry. This requires communicating with different segments of the public and engaging in different modes of communication. Whether talking to media or to people online, speaking on behalf of professional organizations like ACS or speaking to our neighbors, our attempts to communicate impact people’s understanding of chemistry and of the kind of people chemists are. Participants in this panel discussion will describe their chemistry outreach experiences, engaging with groups whose opinions on chemistry range from curiosity and misunderstanding to concern and mistrust. Panelists will describe what has made their own attempts to communicate successful and lessons learned from less successful attempts. We examine a diverse array of outreach efforts to build a repertoire of strategies for engaging with different communities. Leigh Krietsch Boerner writes about the science of consumer products and works to address chemophobia from product marketing and rampant misinformation on the internet.

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Brandi VanAlphen examines impacts of industry supported messages on the public’s understanding of chemistry and of chemists, and discusses how corporations can convey a better understanding of science while addressing the public’s distrust of their motives. Matthew Hartings uses food and cooking to engage large groups of non-scientists with chemistry in the classroom and in public lectures and will discuss how his outreach has been informed by the science of communicating science. Chad Jones explores audiovisual outreach (podcasts and videos) as a way to make chemistry exciting and accurate. Raychelle Burks is a blogger and activities coordinator using the intersection of chemistry and pop culture as an outreach tool. Kevin Shanks is a forensic toxicologist and drug chemist whose activities include community and media outreach through social media and blogging about toxicology, drug laws, and other things forensic.

Monday, August 11, 2014

Hunting for Hidden Treasures: Chemistry Text Mining in Patents and Other Documents - PM Session Palace Hotel Room: Presidio Wei Deng, Organizer Wei Deng, Presiding

1:30 pm - 4:55 pm

1:30 - Introductory Remarks

1:35 - 69 - ChemInfoCloud: Opensource based Cloud compatible chemical textmining tools for harvesting largescale medical literature Muthukumarasamy Karthikeyan, karthincl@gmail.com, Digital Information Resource Centre, CSIR-National Chemical

Laboratory, Pune, Maharastra 411008, India Text mining involves recognizing useful patterns from a wealth of information hidden latent in unstructured text and deducing explicit relationships among data entities by using data mining tools. Harvesting chemical data from textual information is a challenging task. Text mining of Biomedical literature is essential for building biological network connecting genes, proteins, drugs, therapeutic categories, side effects etc. related to diseases of interest. We present an approach for chemically significant textmining biomedical literature mostly in terms of not so obvious hidden relationships and build biological network applied for the textmining of scientific literature related to human diseases like Tuberculosis and Malaria. The methods, tools and data used for building biological networks using a distributed computing environment previously used for ChemXtreme and ChemStar applications will be discussed. The architecture of open source based tool CheminfoCloud developed for this purpose will be presented.

2:05 - 70 - Knowledge mining by structure search Jinbo Lee, rhotchandani@scilligence.com, Scilligence, Burlington, MA 01803, United States With prevalence of cross-organization collaborations, R&D reorganizations and company merger & acquisition, knowledge can be easily lost in a large pile of unstructured data such as PPT, Word, Excel and PDF. Through a case study example, knowledge mining and preservation by structure searching makes possible by Scilligence’s informatics tools.

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2:35 - 71 - Toward extracting analytical science metrics from the RSC archives Stuart Chalk1, schalk@unf.edu, Antony Williams2, Valery Tkachenko2, Colin Batchelor3. (1) Department of Chemistry, University of North Florida, Jacksonville, FL 32224, United States, (2) Royal Society of Chemistry, Wake Forest, NC 27587, United States, (3) eScience, Royal Society of Chemistry, Cambridge, Cambridgeshire CB4 0WF, United Kingdom The Royal Society of Chemistry has an archive of over 300,000 articles containing rich chemistry data in the form of chemicals, reactions, property data and analytical spectra. In this work, we propose the development of standards for organization, representation, and annotation of analytical science information, based around the definition of a Chemical Analysis Metadata Platform (ChAMP). This involves development of specifications for metadata collection, ontologies to link the metadata semantically, and automated extraction of the metadata from the RSC archives. Integration with synergistic activities at RSC, such as the Analytical Abstracts database and the Chemistry Methodology Ontology (CMO), will be explored. This presentation will provide an overview of the vision and scope of this project and initial developments.

3:05 - Intermission

3:20 - 72 - SureChEMBL: An open system for exploration of patent chemistry space Michal M. Nowotka, mnowotka@ebi.ac.uk, John P. Overington, Mark Davies. ChEMBL, The European Bioinformatics Institute, Cambridge, Cambridgeshre CB10 1SD, United Kingdom In December 2013, EMBL-EBI acquired

the SureChem (rebranded SureChEMBL) chemical patent extraction system from Digital Science Ltd. The acquisition has resulted in free and open access to regularly updated chemical data extracted in the patent literature to the research community, which previously would have only been accessible through paywalled systems. SureChEMBL joins ChEMBL as a resource linking bioactive molecule structures to targets and clinical utility, and is based at the EMBL-EBI, alongside resources such as UniProt, Ensembl and the 1000 genomes project. The presentation will cover how existing tools and methods developed within our group, used to extract chemical and biological data from the scientific literature, will be used to enhance the SureChEMBL data extraction process. It will address image segmentation, extraction and classification techniques as well as providing an overview of text extraction methods. Finally, future plans for extending the functionality of the SureChEMBL platform will be discussed. These plans include improving the integration with other resources such as Europe PubMed Central, the extraction of new entity types (e.g. targets, disease, cell-lines and assays) and improved API and KNIME support.

3:50 - 73 - Computer analysis of the scientific literature Scott Spangler1, Olivier Lichtarge1, Meena Nagarajan1, MeenaNagarajan@us.ibm.com, Angela Dawn Wilkins1, Lawrence Allen Donehower2, Curtis Reid Pickering2, Sam Julian Regenbogen2, Benjamin Judson Bachman2, Ioana Roxana Stanoi1, Ying Chen1, Jacques J Labrie1, Linda Kato1, Maria Elisa Terron2, Anbu Karani Adikesavan2, Stephen K Boyer1. (1) Watson, IBM, San Jose, CA 95120, United States, (2) College of Medicine, Baylor

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College of Medicine, Huston, Tx, United States We have extended our ealier work in capturing and analyzing chemical and biological entities to programmatically identifying important relationships between these various entities. The programs further extract and model complex N-point associations between entities using Natural Language Processing techniques thus establishing a framework that allows scaling multiple analytics applications over extracted data and metadata. Two reasoning frameworks will be presented that have proven to generate useful, verifiable hypotheses in the P53 biology space.

4:20 - 74 - Using the BRAIN, biorelations and intelligence network, for knowledge discovery Albert Mons1, albert.mons@euretos.com, Barend Mons3, Aram Krol1, Arie Baak1, Antony Williams2, Valery Tkachenko2. (1) Euretos, Delft, The Netherlands, (2) Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States, (3) Netherlands bioinformatics center, Nijmegen, The Netherlands In life sciences and biomedical research, public data is essential to the knowledge discovery process. Getting useful results from public data sources however is very challenging: there is too much relevant data and information is stored in too many disconnected data sources. Manually searching all these sources is time consuming; the results are at best incomplete and making the connections between results found is simply impossible. This situation is one of the biggest frustrations of life scientists today. For over 10 years academic data researchers have been trying to

address these issues. At the level of manually curated data great progress has been made and clear proof exists that extracting these explicit data manually from sources is highly valuable. However, it is also proven that manual curation is not scalable and thus many scientific discoveries are hidden in the data, waiting to be ‘discovered’ This presentation will report the Euretos’ Bio Relations and Intelligence Network [BRAIN[Ξ]] allowing for high quality in silico knowledge discovery. The platform brings together a wide range of scientifically high value data sources, harmonised in an interoperable format and semantically identified in terms of the concepts they represent The result of this process is a comprehensive network of concepts and their relations derived from all the underlying data sources. BRAIN[Ξ] thus provides one single, accessible view on all underlying data sources involving both the manually curated as well as the computer inferred implicit relations that have either escaped manual extraction or have not been made explicit at all. This allows unearthing ‘hidden gems’ at an unprecedented scale.

4:50 - Concluding Remarks

Monday, August 11, 2014

Sci-Mix - EVE Session Moscone Center, North Bldg. Room: Hall D Erin Bolstad, Organizer

8:00 pm - 10:00 pm

3 - Hazardous substances data bank: A tool for natural product information and research Shannon M. Jordan, shannon.jordan1@nih.gov, National Institutes of Health, National Library of Medicine, Bethesda, MD 20894, United States

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The National Library of Medicine (NLM) Hazardous Substances Data Bank (HSDB) is a database that contains a wealth of information on many types of chemicals including natural products. Increasingly, professionals and the general public seek and utilize information about natural products for various purposes. In response to this demand, the HSDB development team has increased the number of natural product records within the database and updated existing records. Natural product records in HSDB contain, but are not limited to the following information: chemical structure, human health effects, animal toxicity, pharmacology, metabolism and pharmacokinetics, environmental fate and exposure, safety and handling, manufacturing, use, laboratory methods, and more. The data extraction team along with a Scientific Review Panel (SRP) utilizes dozens of sources to build, update, and peer-review HSDB records on a four month cycle. As new articles on natural products are published, HSDB serves as an information resource that captures historical and emerging science. NLM will continue to develop and market HSDB as a tool for researchers and the general public covering all types of natural products from phytochemicals to venoms and toxins.

4 - Real structures for real natural products − really getting them right and getting them faster Patrick Wheeler1, pwheeler@yahoo.com, Antony Williams3, Mikhail Elyashberg2, Rostislav Pol2, Arvin Moser1. (1) Advanced Chemistry Development, Toronto, Ontario M5C 1B5, Canada, (2) Advanced Chemistry Development, Moscow, Russian Federation, (3) Royal Society of Chemistry, London, United Kingdom Structure determination for natural products has been revolutionized by

the advance of NMR technology and application of innovative experimental techniques. Notably, it is possible to obtain structures from small amounts of material that are not accessible to single crystal X-ray diffraction. Still, the interpretation of this data can be arduous, requires great expertise, and is error-prone. Of course, other techniques are used to confirm structures as well: synthetic reproduction of natural products has a long tradition of success in the elucidation of molecules containing intricate elements, including multiple stereo centers. However, despite rigorous analysis by qualified chemists, these methods still sometimes arrive at erroneous results1-5. Astute application of modern technology can speed the rate at which structures are solved, while also vastly reducing errors that result either from synthetic methods or from unassisted analysis of instrumental data. Computer Assisted Structure Elucidation (CASE) has developed over the past decades to relieve the burden of work in proving correct structures. In this presentation, we will discuss how CASE is used to objectively analyze complex sets of NMR data in order to test structural hypotheses, conduct de novo structure elucidation, and query large databases of known structures for matches of already identified natural products.

13 - BCL:Conf A knowledge based ligand flexibility algorithm and application in computational drug discovery like online drug design game Foldit Sandeepkumar K Kothiwale1, sandeepkumar.k.kothiwale@vanderbilt.edu, Jens Meiler1,2, Will Lowe1. (1) Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States, (2) Pharmacology, Vanderbilt University, Nashville, Tennessee 37235, United States

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The three-dimensional conformation a small molecule can adopt is critical for its binding to a target protein. Therefore, rapid and accurate prediction of the conformational space of a small molecule is critical for both structure- and ligand-based drug discovery algorithms such as docking or quantitative structure-activity relationships, respectively. Here we have derived a database of small molecule fragments frequently sampled in experimental structures within the crystallographic structure database (CSD) and the protein databank (PDB). Likely conformations of these fragments are stored as rotamers in analogy to amino acid side chain rotamer libraries used for rapid sampling of protein conformational space – an approach that will allow integration of BCL::Conf into respective computational biology programs such as Rosetta or Scwrl. A conformational ensemble for small molecules can now be generated by recombining fragment rotamers with a Monte Carlo search strategy. BCL::Conf was benchmarked against other conformer generator methods including Moe, Confab, and Frog2, in its ability to recover native-like protein bound conformation of small molecules, diversity of conformational ensembles, and sampling rate. BCL::Conf recovers 97% of molecules within a root mean square deviation of 2Å to the native conformation. The rapid rotamer sampling approach allows integration into Rosetta suite of macromolecular modeling and drug design module of the online protein folding game, Foldit. Conformer generation using multiple threads allows easy integration into high-throughput docking experiments using RosettaLigand.

27 - ChEMBL - linking chemistry and biology to enable mapping onto molecular pathways Louisa J Bellis, ljbellis@ebi.ac.uk,

Anna Gaulton, Anne Hersey, A Patricia Bento, Jon Chambers, Mark Davies, Felix Kruger, Yvonne Light, Nathan Dedman, Shaun McGlinchey, Michal Nowotka, George Papadatos, Rita Santos, John P Overington. ChEMBL Group, European Bioinformatics Institute (EMBL-EBI), Hinxton, Cambridgeshire CB10 1SD, United Kingdom ChEMBL is an open access, large-scale bioactivity database (https://www.ebi.ac.uk/chembl) containing over 11 million bioactivity data points and 1.6 million compounds, primarily curated from scientific literature. Systems biology plays a central role in drug discovery by integrating both chemical and biological processes. Understanding a drug’s mode of action, from the consideration of its target to how it affects a molecular pathway is crucial and so combining systems biology with cheminformatics is necessary. ChEMBL is one such database that extracts data and then displays clear links between the chemical compounds, their bioactivity endpoints and associated protein targets. Showing these clear links is essential if a database is to be successfully used for drug discovery. A major stumbling block in such bioinformatic databases has, historically, been the number of different activity types and units published, thereby making it difficult to compare results from different papers. ChEMBL uses their own standardization technique to give an activity type, pChEMBL, to unite these disparate activity types and values into a uniform set that can be compared across multiple sources. pChEMBL is defined as –Log(molar IC50, XC50, EC50, AC50, Ki, Kd or Potency). This symposium will aim to show how ChEMBL can be used for mapping onto molecular pathways, in order to understand the modulated nodes and the chemical tools available.

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We will present some examples from our research, where we have developed informatics approaches to automatically annotate pathways with ChEMBL data. A second use case for systems biology is the assembly of thematic views of ChEMBL, for example in ADME systems biology.

36 - Toward quantitative structure-activity relationship (QSAR) models for nanoparticles Katarzyna Odziomek1,2, kjodziomek@lbl.gov, Daniela Ushizima2, Tomasz Puzyn1, Maciej Haranczyk2. (1) Faculty of Chemistry, Laboratory of Environmental Chemometrics, University of Gdansk, Gdansk, Poland, (2) Computational Research Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States For decades the implementation of combined chemometric and computational tools has successfully aided scientists in predicting properties of new chemical compounds, based on their molecular structure. Quantitative structure-activity relationship (QSAR) methods, for example, which use linear and non-linear combinations of molecular descriptors, can be utilized to predict physical-chemical and/or biological properties of a molecule. QSAR approaches require well-defined structures of the considered molecules. Similar approaches are envisioned to predict relevant properties of nanoparticles (NPs), which are common form of chemicals used in cosmetics, pharmaceuticals and even food products. Due to their nature, NPs exhibit different characteristics than bulk materials. Nanoparticle samples are typically non-uniform and present various shapes and sizes, which give rise to their properties. Using conventional QSAR techniques is therefore not possible. Our goal is to develop new approaches that will facilitate

QSAR-type modeling for nanoparticles. Our strategy is to incorporate new nanoparticle descriptors into existing, proven QSAR methods. We used scanning electron microscopy (SEM) images to obtain valuable visual information based on the morphology and topography of nanoparticles. Using computer vision algorithms, we have analyzed the SEM images and obtained descriptors of regions of interest (i.e. potential NPs), such as shape, size, surface area, roughness etc. These descriptors can be used to group and classify the nanoparticles. Next, we plan to build statistical models correlating nano and microscale parameters with physical-chemical and biological characteristics. We demonstrate applications of our methodology by investigating hydroxyapatite-based bionanomaterials. Hydroxyapatite, (hydroxylapatite, bioapatite, HAp), Ca10(PO4)6(OH)2, is a naturally occurring calcium phosphate mineral and has a wide range of biomedical applications, such as bone implants.

37 - Targeting androgen receptor DNA-binding domain using structure-based methods to overcome resistance Huifang Li, janelhf@gmail.com, Fuqiang Ban, Kush Dalal, Eric Leblanc, Paul S. Rennie, Artem Cherkasov. Vancouver Prostate Centre, University of British Columbia, Vancouver, B.C. V6H 3Z6, Canada The human androgen receptor (AR) is considered as a master regulator in the development and progression of prostate cancer (PCa). As resistance to current antiandrogens remains a major challenge for the treatment of advanced PCa, there is a continuing need to pursue new anti-AR therapeutic avenues. In this study, we identified a plausible binding site on the DNA binding domain (DBD) of the AR,

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and small-molecule inhibitors through initial screening against this site. Through exploring the related chemical space of a moderately active initial hit compound, an analogue with 10-fold improved activity was identified, and with the preliminary structure-activity relationship (SAR) on this chemical class, we obtained a lead compound of equal potency as current drug Enzalutamide. The site-directed mutagenesis demonstrates the developed inhibitors do interact with the proposed binding site on the AR DBD, suggesting a novel mechanism of action that is fundamentally different from conventional targeting of the AR through its ligand binding domain (LBD). Furthermore, they effectively inhibit the growth of cells with resistance to Enzalutamide and blocks the transcription of constitutively active AR splice variants, which lack the entire LBD and play a critical role in the development of resistance to conventional antiandrogens. The current study provides an initial proof of principle for selectively targeting the AR DBD, which may be a novel and viable approach for the treatment of advanced and resistant PCa.

39 - Random walk-based prediction of novel drug-target interactions Abhik Seal, abseal@indiana.edu, Yong Yeol Ahn, David J Wild. School of Informatics and Computing, Indiana University, bloomington, INDIANA 47408, United States Predicting novel drug–target associations is important not only for developing new drugs, but also for understanding how drugs work and what are their modes of action. As more data about drugs, targets, and their interactions becomes available, computational approaches are becoming more viable in drug-target association discovery. In this paper, we apply Random Walk with Restart (RWR)

method on a heterogeneous network of drugs and targets to predict novel drug-target associations. From DrugBank, we construct the heterogeneous drug-target networks using four types of chemical fingerprints, sequence similarity, and interaction profiles. We find that our method produces reliable prediction with respect to the choice of chemical fingerprint types. We use ChEMBL, an external dataset with 2,763 associations, to evaluate the performance of our approach, finding that it correctly predict nearly 45% of the interactions that are only present in the ChEMBL dataset. We also verify several associations between drugs and mode-of-actions, such as strong associations between hair loss and cardiovascular drug Simvastatin. Finally, the associations between 110 popular drugs and 3,519 targets are analyzed as a case study. In summary, we demonstrate the effectiveness and promise of the approach—RWR on heterogeneous networks—for identifying novel drug target interactions.

40 - Pred-hERG: A novel web-accessible computational tool for predicting cardiac toxicity of drug candidates Vinícius M Alves1, viniciusm.alves@gmail.com, Rodolpho C Braga1, rodolphobraga@yahoo.com, Meryck B Silva1, Eugene Muratov2, Denis Fourches2, Alexander Tropsha2, Carolina H Andrade1, carolina@ufg.br. (1) Laboratory for Molecular Modeling and Drug Design, Faculty of Pharmacy, Federal University of Goiás, Goiania, Goias 74605170, Brazil, (2) Laboratory for Molecular Modeling, Division of Chemical Biology and Medicinal Chemistry, University of North Carolina, Chapel Hill, North Carolina 27599, United States Several non-cardiovascular drugs have been withdrawn from the market due

Chemical Information Bulletin, 2014, 66 (3) 95

to their critical side effect of inhibiting the human ether-à-go-go related gene (hERG) K+ channels, which may lead to heart arrhythmia and death. Thus, hERG safety testing is an indispensable process that is required by the US FDA. There is considerable interest in developing computational tools to filter out potential hERG blockers in early stages of drug discovery. In this work, we describe the development of a new tool for the rapid identification of potential cardiotoxic compounds by hERG inhibition. We have compiled the largest publicly available dataset of hERG binding, containing 11,958 compounds from the ChEMBL database. Once curated, this dataset contained 4,980 compounds for modeling. Several types of QSAR models have been developed and validated according to the OECD principles. The external classification accuracies discriminating blockers from non-blockers were 0.83-0.93 on external set. Model interpretation revealed several SAR rules, which can guide structural optimization of some hERG blockers into non-blockers. Virtual screening of the WDI chemical library using selected QSAR models identified 4,945 compounds as potential hERG blockers. The developed models can reliably identify blockers and non-blockers, which could be useful for the scientific community. A freely accessible web server has been developed allowing users to identify putative hERG blockers and non-blockers in chemical libraries of their interest (http://labmol.farmacia.ufg.br/predherg).

41 - Mining chemical space for novel molecules: A graphical tool for working with fragment spaces Florian Lauck, lauck@zbh.uni-hamburg.de, Matthias Rarey. Universität Hamburg - Center for Bioinformatics, Hamburg, Germany

Mining chemical space for novel molecules with desirable properties proves difficult. The collective strategy is to limit search space so that it is easier to consider only those molecules with suitable physicochemical and topological properties. One therefore requires methods and data structures for efficiently modeling this chemical subspace, as well as user-friendly tools to access this functionality. Here, we present a graphical user interface for creating, manipulating, and searching large chemical space. As a model we use a fragment space, i.e., a combinatorial chemical space consisting of molecular fragments and connection rules. Each fragment has at least one reaction site that corresponds to an open valence. These sites are modeled as artificial atoms with a defined type, called link atoms. The connection rules determine compatibility of such link atoms. When two fragments are connected, the link atoms are removed and a bond in accordance with the connection rule is introduced. A number of algorithms and strategies for working with fragment spaces have been developed in the past but were only available as separate command-line tools. Our new software combines these tools into one user-friendly application, able to visualize the contents of a fragment space (fragments and connection rules), as well as search results (novel molecules). For generating fragment spaces, an automated approach was incorporated using a set of molecules and cut rules, i.e., SMARTS pattern that define where a molecule should be cleaved and link atoms should be introduced. For retrieving molecules with structural similarity we provide two query-based search methods utilizing molecular similarity (reduced graph descriptors) and substructure search (SMARTS pattern matching). In addition, a new approach for constraint-

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based enumeration complements these algorithms, allowing a search based on physicochemical properties rather than structural similarity. Finally, specialized fragment spaces can be created by filtering fragments via numerous properties.

42 - BCL::EvoGen: An evolutionary algorithm for focused library design Alexander R Geanes, alexander.r.geanes@vanderbilt.edu, Edward W Lowe, Jens Meiler. Department of Chemistry, Vanderbilt University, Nashville, TN 37235, United States In recent years, virtual high-throughput screening (vHTS) techniques have been successfully applied in the drug discovery process. In many cases, these vHTS techniques are leveraged to prioritize subsets of chemical libraries for acquisition and testing in physical screens. However, for computer-aided drug design (CADD), it is advantageous to have algorithms which are capable of designing new chemical entities for a specific biological target. An evolutionary algorithm was implemented as part of the BCL::ChemInfo suite within the Biochemistry Library (BCL), a C++ library developed at Vanderbilt University, to iteratively generate chemical species with high predicted biological activities for use in focused library design for hit-to-lead optimization. Quantitative structure activity relationships based on machine learning techniques were used to predict the biological activity of compounds in each generation. The compounds with the highest predicted activity, as well as a smaller number of lower activity species, were subjected to combination, crossover, and mutation to form the subsequent generation. Termination criteria were based on a percentage of compounds in a single generation achieving a predicted activity above a pre-determined cutoff, or after reaching a pre-set number of

generations in the event the first criterion could not be satisfied. This method was benchmarked using a previously published set of 9 datasets designed for the validation of novel CADD methods. Each of the datasets was compiled from publicly available HTS data taken from PubChem, and contain a minimum of 150 active compounds each. In addition, the datasets span a range of protein targets including GPCRs, ion channels, and enzymes. Here we present the results of this focused library design application, BCL::EvoGen.

60 - InChIKeys as chemical entity ids to enable in-context text indexing and to identify engine-ranked chemically similar documents Stephen Boyer, sboyer@us.ibm.com, Tom Griffin, Cassidy Kelly, Eric Louie, Jacques Labrie, Scott Spangler, Ying Chen, Ru Fang, Su Yan. IBM Almaden Research Center, San Jose, CA 95120, United States Chemical name annotators that find and standardize chemical names in scientific papers and patent text documents usually generate tables of SMILES or InChIs. In order to make the most use of identified compounds for text analytics, we convert the found compound names into InChIKeys and insert the InChIKey values into the original document text beside the compound name, along with the literal word “inchikey” as an entity type marker. The augmented documents are then indexed as full text using Solr/Lucene resulting in a search service with useful capabilities such as co-occurence analysis, e.g., finding all cases of any text synonym of aspirin within 10 words of cancer, finding cases of any chemical compound (any entity marker “inchikey”) within 10 words of “produced” AND within 10 words of “yield”. This indexing technique also supports finding chemically similar documents. The selected compounds’

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InChIKeys are entered together as a set of query “words”, returning an engine-ranked list of documents with the most compounds overlapping the target’s. Full engine capabilities such as boolean filter terms are still available to refine the set with full engine performance. The indexed augmented text also facilitates other data mining capabilities such as batch searches for large numbers of molecules over millions of documents. Our team is developing a comprehensive chemical pedia containing structure representations and attributes for millions of molecules derived from patents and other sources such as Medline Abstracts. On-going work includes entity insertions simultaneously performed on gene, drug and disease annotation types, enabling rich entity/text combination queries with no search engine modifications needed.

75 - Benchmark study: Structural similarity search methods for identifying read-across analogs Jie Shen, jshen@rifm.org, Research Institute for Fragrance Materials, Inc., Woodcliff Lake, New Jersey 07677, United States As alternative approaches to fulfill data gaps in chemical safety assessment, in silico methods, such as read-across and quantitative structure activity relationship (QSAR), have generated much attention. Such approaches have been used in ECHA (European Chemicals Agency) submissions of chemical dossiers for REACH (Registration, Evaluation, Authorisation and Restriction of Chemicals). Searching and identifying suitable structural analogs for the chemical of interest is prerequisite for read-across. Although several methodologies and programs are available for analog searching, there are limited practical strategies or guidance for conducting

analog search. This work compared several popular analog search programs using 3 different fragrance materials (as indicated in Fig. 1) reported in a published paper by Blackburn et.al.1 As shown in Fig. 1, for each material, 8 different analog search methods from 5 different programs were conducted. The top 100 analogs with Tanimoto similarity2 more than 0.5 were compared with the suitable analogs reported in Blackburn et al.’s paper.1 As shown in Fig. 1, Pipeline Pilot with FCFP4 fingerprint outperforms other methods in all 3 cases. Most of the methods have higher enrichment rate for lauryl alcohol, and have lower recovery rate for 2, 6-Dimethyl-4-heptanone. Based on this and our experience, Pipeline Pilot (FCFP4/1024 bits) is primarily used to identify suitable analogs.

Fig. 1. The enrichment rate of suitable analogs identified for 3 fragrance materials using 8 different search methods from 5 different programs. Top 100 analogs with a Tanimoto score more than 0.5 were compared with the analogs reported by Blackburn et.al.1 1. Blackburn, K.; Bjerke, D.; Daston, G.; Felter, S.; Mahony, C.; Naciff, J.; Robison, S.; Wu, S., Case studies to test: A framework for using structural, reactivity, metabolic and physicochemical similarity to evaluate the suitability of analogs for SAR-based toxicological assessments. Regulatory Toxicology and Pharmacology 2011, 60 (1), 120-135. 2. Rogers, D. J.; Tanimoto, T. T., A Computer Program for Classifying Plants. Science 1960, 132 (3434), 1115-1118.

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76 - Activity cliffs on chemotype-based activity landscapes Jaime Pérez-Villanueva1, jpvillanueva@correo.xoc.uam.mx, José L. Medina-Franco2, Oscar Méndez-Lucio3, Olivia Soria-Arteche1. (1) Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana - Xochimilco, Mexico, DF 04960, Mexico, (2) Department of Research, Mayo Clinic, Scottsdale, Arizona 85259, United States, (3) Department of Chemistry, University of Cambridge, Cambridge, Cambridgeshire CB2 1EW, United Kingdom Activity landscape modeling methods are useful tools to analyze structure-activity relationships (SAR). Among them, structure-activity similarity (SAS) maps are important representations to aid the SAR characterization of molecular databases. SAS maps are constructed by plotting pairwise comparisons of the structural similarity against the absolute value of the activity difference (or activity similarity). These maps can be employed to detect activity cliffs (compounds where small structural changes lead to large activity differences) and activity cliff generators (molecules that form an increased number of activity cliffs compared with other molecules in the dataset). In addition, pairs of compounds in the smooth regions of the SAR and scaffold hops are also easily identified in these maps. Herein we describe the activity cliff analysis of three molecular databases employing SAS maps that integrate chemotype information. The results reveal different tendencies in local landscapes for subsets of molecules classified in the most frequent chemotypes. Also, quantitative characterization of activity cliffs for compound pairs that fall in each chemotype class was carried out employing the Activity Cliff Enrichment Factor (ACEF), a new index proposed in this work. Finally, chemotype classes

enriched in activity cliffs are discussed and analysed employing the activity cliff generator concept. This approach helps to analyse the behaviour of each chemotype in a given activity landscapes and to identify scaffolds with high probability to form activity cliffs.

77 - Uncovering activity cliff-forming compounds using SALI values José L Medina-Franco1, MedinaFranco.Jose@mayo.edu, Kai Fan Cheng2, Mingzhu He2, Yousef Al-Abed2, Nathalie Meurice1. (1) Department of Research, Mayo Clinic, Scottsdale, Arizona 85259, United States, (2) Center for Molecular Innovation, Feinstein Institute for Medical Research, Manhasset, New York 11030, United States Activity cliffs have a significant impact on a number of tasks relevant in medicinal chemistry and chemoinformatics such as lead optimization, development of methods to predict the biological activity and selection of queries for similarity searching. Therefore, the identification of compounds highly associated with activity cliffs in biological data sets i.e., ‘activity cliff generators’, is of prime significance [1]. The identification of activity cliff generators based on Structure-Activity Similarity (SAS) maps and frequency counts has been reported [1]. Herein we propose two complementary approaches to identify activity cliff generators based on the distribution of the Structure-Activity Landscape Index (SALI) values [2]. To illustrate the approach, we discuss the SAR and the activity cliff generators identified in screening data sets from our effort to identify inhibitors of the migration inhibitory factor MIF. [1] Méndez-Lucio, O. et al. Mol. Inf., 2012, 31, 837. [2] Guha, R and Van Drie, JH. J. Chem. Inf. Model., 2008, 48, 646.

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78 - Unified modeling language schema for scientific and technical data and information Donald R Burgess, dburgess@nist.gov, Chemical Sciences Division, National Institute of Standards and Technology, Gaithersburg, MD 20899, United States The overall goal of this project was to develop a prototype for a web-accessible online editable database for atmospheric and combustion chemistry consistent with existing workflow/formats used by national evaluation panels. The chemical informatics and IT tasks were to modernize legacy implementations, while maintaining and codifying well-established workflows that meet the scientific and technical needs of experts. Many of the databases are legacy print databases produced by IUPAC, NASA/JPL, and other committees and provided in journal articles and reports. One goal is to move toward a dynamic, regularly updated evaluated electronic database, rather than the multistep manual process that exists now. In our presentation, we will provide an overview of the needs and requirements and present a Scientific and Technical Data and Information Unified Modeling Language (SDTI-UML) schema that we have developed which provides a framework for efficient collection, rapid dissemination, identification and indexing, and facile discovery of data and information. The UML developed extends down from root Libraries containing wrapped objects Folders or Documents which contain different classes of Content and Primitive Content (documents, blobs, tables, etc) each tagged with descriptive metadata for indexing and relational associations. The UML includes the ability to included chemical information and bibliographic information with each object.

79 - How to communicate effectively

about chemicals with non-chemists Chad A. Jones1, chemist.jones@gmail.com, Janet D. Stemwedel2, Raychelle Burks3,4, Brandi VanAlphen6. (1) Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, United States, (2) Department of Philosophy, San Jose State University, San Jose, CA 95112, United States, (3) Department of Chemistry, Doane College, Crete, NE 68333, United States, (4) Center of Nanohybrid Functional Materials, University of Nebraska - Lincoln, Lincoln, NE 68508, United States, (6) Unaffiliated, United States The fear of chemicals and the chemical industry is widespread among the general public and the media. How should chemists best attempt to remedy this? What techniques are effective in making scientists influential among non-scientists? The use of factual information to counter scientifically incorrect statements is satisfying for scientists. However, this ‘deficit model’ has been shown to be a poor means of actually changing public opinion, broadly or on an individual level. Chemists should shift away from the “facts and lecture” deficit model approach to a conversational approach that seeks to listen to and understand their audience. Knowing their audience’s cultural context and building trusting relationships have been shown to be more influential techniques. For chemists, sharing details about their personal backgrounds and training may be helpful in establishing that chemists are not only knowledgeable, but trustworthy and empathetic about public concerns. Through these methods, chemists can change minds and spread their influence more effectively about chemicals, counter misinformation and share our love of chemistry.

Chemical Information Bulletin, 2014, 66 (3) 100

80 - Activity landscape modeling of AKT/PKB inhibitors Pedro J. Trejo-Soto1, piter_jo@comunidad.unam.mx, Rodrigo Aguayo-Ortiz1, Oscar Méndez-Lucio2, Alicia Hernández-Campos1, Rafael Castillo1. (1) Pharmacy Deparment, Universidad Nacional Autónoma de México, Mexico city, Mexico, (2) Department of Chemistry, Unilever Centre for Molecular Science Informatics, University of Cambridge, Lensfield Road, Cambridge, United Kingdom The AKT kinase, also known as protein kinase B or PKB, is a serine-threonine kinase that phosphorylates other proteins and molecules that act as second messengers, which are involved involved in important cellular processes, such as cell proliferation and growth, signaling, absorption and metabolism of glucose. AKT is frequently amplified and over-expressed in human cancer cells, therefore its inhibition is an atractive therapeutic target in anticancer drug development. There are three known subtypes, AKT-1, AKT-2 and AKT-3. Each subtype is associated with different types of cancers. In particular, AKT-2 is amplified in pancreatic, breast and ovarian tumors. AKT-3 is over expressed in breast and prostate cancers, the presence of AKT-1 in tumors is less common. Small molecules targeting the ATP-binding site have been reported; however, it is important to study the factors that determine the selectivity of these inhibitors in each subtype of AKT, also to determine the factors that favor the multitarget activity. Herein, we present a systematic characterization of the SAR of 50 compounds screened against the three AKT subtypes. The activity landscape across multiple AKT subtypes was characterized using the dual and triple activity difference (DAD/TAD) maps. We also employed SAS maps

to systematically identify and analyze the activity cliff generators present in the dataset. Analysis of pairs of compounds with high structure similarity revealed the presence of single-, dual, and pan-receptor activity cliffs. Moreover, single-target and dual-target activity cliff generators for AKT-1/AKT-2, AKT-2/AKT-3 and AKT-1/AKT-3 were identified. In addition, docking studies were performed with the compounds that were classified as cliff generators in order to analyze the factors that are involved in the ligand-enzyme interactions. The analysis of the chemical structures in this work points to specific structural features that are helpful for the design of new AKT inhibitors.

81 - Pursuit of activity enrichment in phenotypic screening using chemotype-driven approaches Joachim L Petit, petit.joachim@mayo.edu, José L Medina-Franco, Nathalie Meurice. Department of Research, Mayo Clinic, Scottsdale, AZ, United States At the biology-chemistry interface, phenotypic and functional screening campaigns aim at identifying small molecules modulating biological pathways and/or processes relevant to disease, without target knowledge or bias. Activity landscapes are generated that challenge the classical concept of structure-activity relationships. Activity classes are primarily defined based on bioprofile similarity to bioactivities of reference controls, and active classes include groups of hits that affect biological pathways similarly but are not necessarily similar in structures. In this context, the transition of actives in biological space to confirmed hits and early leads in chemical space requires a careful investigation of chemotype organization across activity classes. And to advance drug discovery programs, the value of chemotype-based analysis in driving hit

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enrichment through iterative screening and assay workflows has to be reassessed. Herein we discuss the significance of chemotype-based approaches to drive activity enrichment in iterative phenotypic screening. To illustrate the approach, we discuss chemotypic classes in light of bioprofile similarities and activity enrichment identified in in-house screening data sets resulting from our effort to identify novel therapeutics for Multiple Myeloma.

116 - DNA methyltransferase Dnmt1: Regulation and novel drug-design strategies Zeljko M Svedruzic1, zsvedruz@biol.pmf.hr, Patrik Nikolic2. (1) Faculty of Medicine, Biomedical Technology, University of Rijeka, Rijeka, Croatia, (2) Faculty of Medicine, Biomedical Technology, University of Rijeka, Campus Trsat, Radmile Matejčić 2, Rm 823, Rijeka, Croatia DNA methyltransferase Dnmt1 is the key enzyme in functional organization of the human genome. For almost 30 years, Dnmt1 has been unsuccessfully targeted in different drug-design efforts. Most of those failures can be attributed to inadequate understanding of diverse mechanisms that regulate the enzyme activity. Dnmt1 is a large enzyme with multiple flexible domains and phosphorylation sites. Dnmt1 can functionally interact with about 40 different molecules involved in DNA repair, chromatin organization, or RNA-directed-DNA methylation. The interacting molecules include proteins, poly(ADP-ribose), and methylated and unmethylated single-stranded and double-stranded non-coding RNA molecules. We are developing inhibitors and activators of Dnmt1 using a combination of enzyme assays, computational structural analysis, and numerical evaluation of enzyme

activity. Knowledge of dynamic reversible processes in the active site of Dnmt1 were used to create novel mechanism-based inhibitors that do not cause DNA damage. Molecular docking and QM/MM MD simulations were used to optimize inhibitors’ geometry, flexibility, interaction with the solvent in the active site, and finally formation of a reversible covalent adduct with the enzyme. Different strategies for optimization of the PK/PD properties have been suggested. A dynamic active site loop has been identified as a part of the lock mechanism that controls allosteric regulation and processivity. Enzymatic assays and numerical methods have been developed to study processivity on the DNA substrate and the affinity for binding at the allosteric site. The presented approach allows screening for specific allosteric activators and inhibitors.

124 - Scilligence’s ELN for research laboratories and academia Rajeev Hotchandani, rhotchandani@scilligence.com, Scilligence, Burlington, MA 01803, United States The dawn of digital age and innovative companies like Google have made access to information much easily in our daily life. However, various laboratories and academic research is lagging behind in this trend. Although a trend has started in academia research groups and organic chemistry labs, a lot of these institutions are still using paper notebooks to document their everyday work. This makes knowledge preservation and sharing much more difficult. Through case study examples in this presentation, knowledge preservation, IP protection and team collaboration can be made efficient by Scilligence informatics in your laboratory environments.

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131 - Multicriteria drug discovery: Using CoMFA models to drive target specificity Lei Wang, lei.wang@certara.com, Brian Masek, Fabian Boes, Bernd Wendt, Stephan Nagy. Certara, St. Louis, MO 63101, United States A successful drug candidate will not only need to overcome ADME, physical and safety properties, but also often need to achieve a selectivity profile against related targets. The approach we present here combines a de novo design method with powerful ligand-based scoring function that consists of three different 3D QSAR models for different targets to generate selective inhibitors. A training set was developed with literature and public information where 50 molecules with activities for FactorXa, Trypsin and Thrombin were selected. Three different Topomer CoMFA models were built using the training set. By combining predictions of the activity profile with different weights and penalty score, a scoring function was created that can drive the invention of new and selective compounds.

Tuesday, August 12, 2014

The Herman Skolnik Award Symposium - AM Session The Publication Chain Revisited: Old Links and New Connections

Palace Hotel Room: Presidio Andrea Twiss-Brooks, Organizer Andrea Twiss-Brooks, Presiding

9:15 am - 12:00 pm

9:15 - Introductory Remarks

9:20 - 82 - Evolution and transformation of journals in a digital environment Grace Baysinger, graceb@leland.stanford.edu, Swain Chemistry and Chemical Engineering Library, Stanford University, Stanford, CA 94305, United States During the past two decades, STM journals have migrated from print to online. Manuscript submission systems, author tools, publication cycles, peer review, IP rights and subscription management, content delivery, user services, discovery tools, and preservation methods have all undergone rapid transformation. This presentation will review changes that have occurred in journals and expected trends for them in the near-term future.

9:50 - 83 - What do the readers think? The role of the end user in the evolution of publications Andrea Twiss-Brooks, atbrooks@uchicago.edu, John Crerar Library, University of Chicago, Chicago, IL 60637, United States Research publications are ultimately intended to be read by the scientists. What do these scientists want and need in a publication? How do they gather their information and decide what to read? When and how much do they read? User studies of various kinds have been done to try and find answers to these questions. The results of these studies are used by libraries to make decisions about

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collections and services, as well as by publishers and vendors to create better products related to scientific publication. A brief overview of selected user studies and methods will be presented, including a description of and preliminary results from a recent study that included University of Chicago students.

10:20 - 84 - Context and connection: Visualizing library data Martin Brändle, mpbraendle@gmail.com, Unaffiliated, Switzerland Visualization leverages our ability to find patterns and connections inside the complex data networks that exist in library catalogs, document and data repositories. This talk aims to present an overview of some of the initiatives libraries have taken to visualize and let users explore their data, and discusses open source tools and requirements.10:50 - Intermission

11:00 - 85 - Predicted future of science and scientific publishing within the framework of a changing world René Deplanque, rene@deplanque.de, Technical University Berlin, Germany

11:30 - 86 - Chemical Publications revisited Guido Herrmann, Guido.Herrmann@thieme.de, George Thieme Verlag KG, Stuttgart, Germany Thieme has been a chemistry publisher since 1909. The basic categories and formats (i.e., journals, reference works, encyclopedia, monographs and textbooks) have proven to be very robust and stable for more than a hundred years. In contrast the published formats (digital vs. print), the user expectations, the production processes, and the distribution channels

have seen significant change over the last decade. Similarly the basic role of a publisher has remained, however the actual operations and production processes have changed drastically. The talk will look into these processes and will highlight one important and distinct aspect of chemical publishing: the strong ties and connections between the full text information and the information embedded in the chemical structures and reactions. In this area significant progress has been made over the last few years.

Tuesday, August 12, 2014

The Herman Skolnik Award Symposium - PM Session The Publication Chain Revisited: Old Links and New Connections Palace Hotel Room: Presidio Andrea Twiss-Brooks, Organizer Andrea Twiss-Brooks, Presiding

2:00 pm - 5:05 pm

2:00 - 87 - CAS databases: Reflecting the changes in how chemical discoveries have been disclosed Matthew J. Toussant, mtoussant@cas.org, Chemical Abstracts Service, United States Chemical Abstracts Service (CAS) has always been a leader in providing scientists with access to chemical information. This presentation will illustrate how CAS has adapted to the phenomenal growth in chemical information being published today. Beginning in 1907 with a group of worldwide abstractors indexing the journal literature, CAS extended its reach into the patent world. Adding other sources of chemical information, like dissertations, meeting abstracts, and conference proceedings, CAS now covers

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more than 1000 ahead of print journals, valuable web sources, commercial chemical suppliers and regulatory inventories to create its databases. Starting with the CAS REGISTRY in 1965, CAS has leveraged rapid changes in technology and evolving sources of disclosed chemistry, to fulfill its mission to provide the world’s best digital research environment to search, retrieve, analyze and link chemical information. This presentation will cover some ways in which CAS has kept pace with the worldwide growth in disclosed chemistry and will close with some predictions about the future of chemical information.

2:30 - 88 - InChI & the publication and information chain Stephen Heller, steve@hellers.com, BMD, NIST, Gaithersburg, MD 20899-8362, United States The International Chemical Identifier (InChI) chemical structure standard is starting to play a major role in changing the links and connections to chemical information. In the past few years, for the first time any journal article can freely add an InChI which will be same InChI that any other article, database, chemical catalog, and so on, can also have enabling linking and connections to the vast amounts of chemical information and data available to help and support basic and applied research and development in the chemical, biological, and medical sciences. This presentation will describe the past, present, and future of how InChI is the key to linking information.

3:00 - 89 - From virtual communities to Web 2.0, social media, and beyond: A publishing perspective Wendy Warr, wendy@warr.com, Wendy Warr & Associates, Cheshire, United Kingdom

Since 1992 the World Wide Web has radically changed the way that we live and work. For most of us, living without the Internet would be like living without water or electricity. As research has become increasingly collaborative, possibilities for communication and collaboration on the Web have also increased. Virtual communities in science such as EiVillage and BioMedNet began to spring up in the 1990s. The earliest virtual community in chemistry, ChemWeb.com, was announced in August 1996 and launched in April 1997. At its peak it offered access to books, journals and databases, and member-generated content, together with discussion groups, virtual conferences and a chemistry preprint server. Eventually its owners started to lose interest; if only they had known what would follow with the advent of Web 2.0 in 2004. The world has since moved on from “e-everything” (e-mail, e-journals, e-commerce) to mobile technologies and “i-everything”, and experimentation in publishing has moved on too. An example is ScienceOpen, an open access scholarly publisher with a new network-based approach, and the mantra “access, network, organize, publish”. It was launched at the end of 2013 with more than one million freely accessible papers in multiple disciplines. It offers authors tools to collect feedback in one place, manage draft versions and share files, to make collaborating on a paper together easy. Its scientific network forms the basis for public, post-publication peer review. ChemWeb.com was ahead of its time. Is the chemistry world now ready for new ventures such as ScienceOpen? In the world of open access, open data and open science what might happen next?

3:30 - Intermission

3:40 - 90 - Digital transformation - the

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long and winding road David Evans1, david.evans@REEDELSEVIER.CH, Pieder Caduff2, Jürgen Swienty-Busch3. (1) Reed Elsevier Properties SA, Neuchâtel, Switzerland, (2) Reed Elsevier Properties SA, Switzerland, (3) Elsevier Information Systems GmbH, Germany

4:10 - 91 - Of a landmark total synthesis yet unpublished in full experimental detail – vitamin B12 Engelbert Zass, zass@chem.ethz.ch, Laboratory of Organic Chemistry, ETH Zürich, Zürich, Switzerland While publication habits have changed since then, for total syntheses in the last century one could reasonably expect publications in journals with full experimental details. There were important exceptions, however, even then: most remarkably, the total synthesis of vitamin B12, considered a landmark in organic synthesis, involving the research groups of R.B. Woodward and A. Eschenmoser with about 100 chemists participating. While almost all of the ETH work was done by Ph.D. students, with their theses fully published already at that time in print (later also electronically), the Harvard part was done exclusively by postdoctoral fellows whose detailed reports are (as usual) not publicly available. An attempt to publish the full details beyond published lectures and summaries about the syntheses was already started at ETH in 1980, but had to be given up in 1986. A progress report is presented, and the intentions why and how to resume this publication project more than 40 years after completion of the syntheses will be discussed.

4:55 - Award Presentation

Wednesday, August 13, 2014

It Takes Two To Tango: Chemistry Librarians Partnering with Publishers and Researchers To Advance the Chemical Sciences - AM Session Symposium in Honor Dana Roth

Palace Hotel Room: Marina Ted Baldwin, Judith Currano, Organizers Judith Currano, Ted Baldwin, Presiding

8:35 am - 12:00 pm

8:35 - Introductory Remarks

8:40 - 92 - Chemical information ecosystems at research universities: Users, libraries, and information providers Grace Baysinger, graceb@stanford.edu, Swain Chemistry and Chemical Engineering Library, Stanford University, Stanford, CA 94305-5081, United States Librarians work closely with users to help meet their research and instructional information needs. Librarians also work in close partnership with information providers. Discussions may cover a full range of the life cycle for a product – development, interface design, licensing and pricing, usage data, training and support as well as marketing. Venues for discussions may be one-on-one meetings, advisory groups, surveys, email exchanges, webinars, etc. This talk will highlight the value of these partnerships and the value that they ultimately bring to users.

9:00 - 93 - “What happened to my library?” revisited Susanne J Redalje, curie@u.washington.edu, University Libraries, University of Washington, Seattle, Seattle, Washington 98195, United States

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A session at the ACS Spring National Conference, 2010, held in San Francisco, focused on the impact of the trend of closing branch libraries. The University of Washington Chemistry Library, along with several other UW science branches, was amongst those that closed. Collections were merged into a much larger library covering many disciplines, no longer providing a clear location for users, physically or virtually. It is now 5 years later. The Library world and technology continue to change, providing new options and new challenges. This paper will examine the continuing impact of these closures on users and address the changes in outreach that are required both by the closures and the ever changing expectations of the users. A variety of methods have been used to date, including posters in the reference area which focus on science topics which were both to highlight the chosen topics and also to say clearly `we are here’. Focus groups and surveys have been used to determine user needs, many focusing on graduate students who were particularly hard hit by the changes. Communication continues to be a main issue, complicated by a major increase in interdisciplinary research groups and centers.

9:20 - 94 - Products, policies, pricing: How collaboration with libraries has shaped the evolution of ACS Publications 3Ps S. Sara Rouhi, s_rouhi@acs.org, Library Relations, ACS Publications, Washington, DC 20009, United States ACS Publications collaboration with libraries is ongoing and evolving. This presentation will outline the evolution of the ACS Librarian Advisory Board (now ACS Academic Roundtable); our collaborations with libraries to develop ACS on Campus; our ongoing library summit strategy; the

role of librarian input in refining ACS Value-Based pricing and package options, and in providing insight into shared challenges, such as Open Access, Data Management, Library Systems, etc.. This presentation will feature representatives from ACS Publications sales and library relations teams as well as librarian partners we’ve had the privilege of collaborating with over the years. Dana Roth has played a crucial role with his insight and frank feedback on all our initiatives. We look forward to participating in this well-deserved recognition!

9:40 - 95 - New dance steps: Emerging areas connecting us to our researchers Ted W. Baldwin, BALDWITW@UCMAIL.UC.EDU, Science and Engineering Libraries, University of Cincinnati, Cincinnati, OH 45221, United States The University of Cincinnati’s Science and Engineering libraries are moving ahead in a number of exciting and strategic ways, in partnership with researchers in chemistry and related sciences, as well as with others across the campus. This talk will highlight our progress in these new directions, and how we are establishing new relationships with our researchers. For physical spaces, including collections and technology, changes are underway to meet emerging research needs and to increase the library’s perceived value. New types of staffing, including a science informationist, increase our capacity for specialized consultation and instruction directed at the workflows of chemistry researchers. Finally, our participation in a multi-institutional shared development process for a new digital repository (based on the Hydra framework) is opening up new channels for dialogue with researchers.

10:00 - Intermission

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10:15 - 96 - Academic libraries and CAS: A match made in heaven Roger Schenck, rschenck@cas.org, Marketing, Chemical Abstracts Service, Columbus, Ohio 43202, United States As a division of the ACS, fostering academic research is core to CAS’s mission. In the endeavor to meet this goal, CAS has built and sustained long-lasting, beneficial relationships with academic libraries, and academic librarians, around the world in its efforts to provide the most current, comprehensive and complete chemical and related information for scientific discovery. Going well beyond simply using CAS’s products and services, from printed Chemical AbstractsTM to CA on CDTM to STN® to SciFinder®, academic libraries and their librarians and education professionals collaborate closely with CAS to develop and enhance CAS services that more efficiently enable academic research and scientific discoveries. From helping CAS to promote the FUTURE LEADERS in Chemistry initiative, to training students and faculty, to spreading the word on important chemistry developments in CAS products, academic librarians have been an invaluable resource for CAS. In this presentation, we will explore the many ways in which CAS’s successful collaboration with academic libraries has helped to ensure CAS products and services remain timely and relevant.

10:35 - 99 - Evolving library services in the ever-changing world of chemical information: From printed to electronic to networked Donna T. Wrublewski, dtwrublewski@library.caltech.edu, George S. Porter, Joy Painter, Kristin Buxton, Lindsay B. Cleary. Caltech Library, California Institute of Technology, Pasadena, CA 91125, United States

Access to chemical information has evolved dramatically over the past 50 years, from printed to electronic to networked. Channeling and focusing this torrent of information to meet the specific needs of researchers has increased exponentially over time, and has required librarians to become beta testers, instructors, and negotiators. Dana Roth’s contributions to chemical information, and to the field of librarianship as a whole, cannot be overestimated. This talk will highlight key contributions that Roth has made to the relationships between the Caltech Library and publishers, and between the Library and the campus research community. These relationships continue to fluorish and expand, and examples of past efforts and current projects from across the Caltech Library will be discussed.

10:55 - 98 - Navigating chemistry requirements for data management and electronic notebooks: A case study Leah R McEwen1, lrm1@cornell.edu, Antony J Williams2, Valery Tkachenko2, Jeremy G Frey3, Simon J Coles3, Aileen E Day2, Cerys Willoughby3, William R Dichtel1. (1) Cornell University, Ithaca, NY 14853, United States, (2) Royal Society of Chemistry, United Kingdom, (3) University of Southampton, United Kingdom Research data management is an ever-present and growing concern for academic chemistry laboratories, libraries, scholarly societies and publishers. Coordinating data management requirements with electronic notebook platform development is an excellent opportunity to consider the process of articulation and resolution among disparate perspectives in depth. When the project group is separated by over three thousand miles and includes an academic team developing an open source ELN, a cheminformatics team developing

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spectral handling capability and an organic chemist with over a dozen students who will ultimately utilize the platform, onsite management and coordination of the needs, training and information flow is critical. This presentation will report observations from a case study involving developers, user scientists and the role of an onsite librarian in coordinating and managing stakeholder objectives.

11:15 - 97 - “Dancing” lessons: Teaching non-chemist librarians to communicate with chemists Judith N. Currano, currano@pobox.upenn.edu, Chemistry Library, University of Pennsylvania, Philadelphia, PA 19104-6323, United States Establishing relationships with the scientists who use one’s facility is key to providing chemical information services to researchers; however, many new chemistry librarians and library liaisons have little or no formal training in the discipline that they support. Since the late 1990s, the Chemistry Division of the Special Libraries Association (SLA) has provided support and training to inexperienced chemistry librarians through continuing education course offerings. This presentation describes the history and evolution of the Chemistry for the Non-Chemist Librarian course and gives glimpses into ways that research chemists can work with their non-chemist librarians to increase their comfort with the language of chemistry.

11:35 - Discussion

11:55 - Concluding Remarks

Wednesday, August 13, 2014

Inspiring the Next Generation To Pursue Computational Chemistry and

Cheminformatics - AM Session Palace Hotel Room: Presidio Antony Williams, Leah McEwen, Organizers Antony Williams, Leah McEwen, Presiding

8:20 am - 11:05 am

8:20 - Introductory Remarks

8:25 - 100 - Examples of how to inspire the next generation to pursue computational chemistry/cheminformatics Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2. (1) Collaborations in Chemistry, Fuquay Varina, NC 27526, United States, (2) Molecular Materials Informatics,, Montreal, Quebec H3J 2S1, Canada If we are to have a future generation of scientists that focus on computational chemistry or cheminformatics we need to consider what we can do to promote the topic. Many people arrive or are drawn to the field from outside, they have a chemistry, biology, physics, information technology or other background. What can we do to bring to the field others so that we have a diverse ecosystem. This in turn may provide us with new ideas, technologies and approaches. If we are to prevent stagnation we need to consider what methods we can use to attract new students. Several examples will be provided of ways in which we can do more to inspire the next generation to pursue computational chemistry.

8:50 - 101 - Implementing an interactive cheminformatics course for the acceleration of graduate chemical research O. Maduka Ogba, ogbao@onid.oregonstate.edu, Paul H.-Y. Cheong. Department of Chemistry, Oregon State

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University, Corvallis, Oregon 97331, United States We have established a cheminformatics course at Oregon State University. This project-based, individualized course was designed to train chemistry researchers with programming and informatics tools to automate and accelerate research projects. First third of the course was focused on a top-down approach of teaching students the basics of structures and algorithms necessary to mine large amounts of chemical data. Second third was focused on interactively learning the Python programming language through hands-on sessions whereby the participants generated and refined scripts with the instructor and their colleagues. The last third was focused on bottom-up approach whereby the students planned, designed, and coded a Python software to achieve automation and acceleration of their own research. The lectures, assignments, and topics were tailored to fit each student’s research interests based on three anonymous evaluations by the students. This individualized learning experience was key to the success of the course, and the projects completed in this course are currently being utilized rigorously to expedite scholarly research.

9:15 - 102 - Leveraging history to develop community sourced best practices in chemical information systems development: An interactive online teaching module Leah McEwen1, lrm1@cornell.edu, Evan Smith2. (1) Cornell University, United States, (2) Princeton University, United States As digital research tools and cheminformatics methods attain ever-greater prominence in 21st-century chemistry, chemical information literacy

has become a pressing challenge. The chemistry research community has engaged in more than a century of capturing, representing, organizing and re-using chemical principles, data and expert interpretation through IUPAC and other national and international initiatives. The history of chemical information and machine documentation is an enormous untapped resource in better understanding current challenges in the design of chemical information systems and chemistry educational programming. The authors are engaged in developing interactive online teaching modules using change over time in systematic nomenclature and machine representation. These tools will help chemistry students unlock the power of information regimes as scientific instruments and directly engage in mapping historically-informed best practices in chemical information notation.

9:40 - Intermission

9:55 - 103 - Who knew I would get here from there: How I became the ChemConnector Antony J. Williams, tony27587@gmail.com, Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States As the ChemConnector and one of the people responsible for creating ChemSpider I have become well known in the chemical information world. I get to connect with some of the brightest minds in the domain, have participated in meetings with Microsoft, Google, various government institutions and with some of the top chemical and pharmaceutical companies. While my path to this point feels at some times like a random walk, and certainly I never set a trajectory to become a chemical information specialist as I am a spectroscopist by training, I

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look back upon my career with a lot of satisfaction. We are now at a time when information is becoming so important to support and guide the discovery process. At the same time the opportunity to communicate your science to the masses is upon us. I will discuss how I became the ChemConnector, my Twitter handle, and why I believe entering the field of cheminformatics at this time holds incredible potential for influence.

10:20 - 104 - Chemical Informatics Project >inspires >chemistry majors Stuart Chalk, schalk@unf.edu, Department of Chemistry, University of North Florida, Jacksonville, FL 32224, United States In Fall 2013 students in the Chemical Information Science course at the University of North Florida were given a final project to generate a database (as a group) of chemical information that would be useful to chemistry majors. Students were required to find a dataset, download and import it into Excel, clean up the data, and organize and annotate the data and metadata using an Excel template prior to ingestion into a MySQL database. The presentation will talk about the technical approach to implementing this project and a review of its potential to open the eyes of chemistry majors in this semantic world.

10:40 - 105 - Enabling cheminformatic exploration at the academic level: Enterprise tools, academic availability Erin Bolstad, erinbolstad@gmail.com, ChemAxon, Budapest, Hungary

Wednesday, August 13, 2014

The IUPAC Solubility Data Series: 100 Volumes of Solubility Data Online - PM Session Palace Hotel

Room: Marina Cosponsored by ANYL, HIST David Martinsen, M. Clara Magalhães, Organizers David Martinsen, M. Clara Magalhães, Presiding

1:30 pm - 5:10 pm

1:30 - Introductory Remarks: IUPAC Projects

1:40 - 106 - Objectives of the Solubility Data Series Mark Salomon, Mark.Salomon@maxpowerinc.com, MaxPower, Inc., Harleysville, PA 19438, United States Many scientists rely on handbooks to find solubility data for their studies in which solubility is not their prime objective. Some handbook tables give very brief evaluations but normally no indication about the reliability of the tabulated solubility data. Many tables simply list solubilities without comments on reliability, precision and/or accuracy and do not provide the source to the tabulated data. Moreover, handbooks generally list one solubility value without error limits, without literature citation, and without mention of other, often more precise or accurate, data that were not considered. The IUPAC Solubility Data Project (SDP) addresses these problems by producing the Solubility Data Series (SDS) in which all available published literature to date on solubility data from all available literature sources for a specific solute/solvent system are succinctly detailed providing information on experimental methods and errors. Where sufficient literature data exist, contributors to the SDS provide critical evaluations comparing the literature data classifying them by either rejecting poorly conceived experimental methods and incorrect solubility values, recommending

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the best experimental values available, or specifying which data should be classified as tentative when literature comparisons cannot be made. At the time of this presentation, Volume 100 of the SDS will have been published, and in discussion future volumes will be described in addition to the future plans of the SDP.

2:05 - 107 - NIST Standard Reference Data and the Solubility Data Series Allan H. Harvey1, allan.harvey@nist.gov, Donald R. Burgess2. (1) Applied Chemicals and Materials Division, National Institute of Standards and Technology, Boulder, CO 80305, United States, (2) Chemical Sciences Division, National Institute of Standards and Technology, Gaithersburg, MD 20899, United States Beginning with Volume 66 in 1998, the IUPAC Solubility Data Series became the IUPAC-NIST Solubility Data Series, no longer published as monographs but instead as articles in the Journal of Physical and Chemical Reference Data. We describe this fruitful cooperation from the perspective of the journal and in the context of NIST’s mission to promote the dissemination of “reference data” for use by science and industry. We will also share some thoughts about how the data compiled by the SDS and published in JPCRD might be made more accessible and useful in the future. An effort is described to make the contents of the pre-1998 volumes available on the Web in a format that will be easily searchable by researchers.

2:30 - 108 - REST API for the IUPAC Solubility Data Series: A “Skunkworks” project Stuart Chalk, schalk@unf.edu, Department of Chemistry, University of North Florida, Jacksonville, FL 32224, United States

The National Institute of Standards and Technology (NIST) publishes a large amount of scientific data across the disciplines. As science increasingly moves online and scientists eagerly seek quality data it makes sense that the data published by NIST be made available in a more web-enabled format. This presentation focuses on a proof of concept project to scrape data and metadata from pages of the IUPAC Solubility Data Series (http://srdata.nist.gov/solubility/) and make it available via a REST API on the authors website. Search and browse functionality are made available via the interface and data points/datasets are published at unique REST URLs for referencing. Finally, multiple export options (HTML, XML, JSON, JSON-LD) are available to allow both human and software usage of the data.

2:55 - 109 - Database on ionic liquids solubilities in molecular solvents: Progress and prospects Zdeněk Wagner1, Johan Jacquemin2, Magdalena Bendová1, bendova@icpf.cas.cz. (1) E. Hala Laboratory of Separation Processes, Institute of Chemical Process Fundamentals AS CR. v. v. i., Prague 6, Czech Republic, (2) School of Chemistry and Chemical Engineering, Queen’s University Belfast, Belfast, United Kingdom Since ionic liquids are classified as novel designer and green solvents, an evaluation of their mutual solubilities with traditionally used solvents is of particular interest in the design and optimization of numerous industrial processes, such as separations, as well as in environmental remediation. Due to the increasing number of published datasets, which range significantly in their quality and robustness, a critical evaluation of this data is needed urgently for the field to move into practical application. The

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IUPAC Project # 2011-065-3-500 Database on liquid-liquid equilibria of binary mixtures of ionic liquids and molecular compounds is aimed at compiling available literature data on solubility and liquid phase equilibria in binary systems ionic liquid + molecular solvent, critical review of the apparatuses used to measure the solubility data, and evaluation of the data with the respect to the experimental techniques used as well as to the purity of the ionic liquid/solvent measured. Critical evaluation of the compiled data will be carried out using a robust gnostic method as well as UNIFAC model parameters to provide a statistical analysis and in view of presenting eventually a set of recommended values. Data will be stored in a web-based interface that may readily be made public later for general use. In the present contribution, a report on the progress of the project will be given, along with examples of how the database is created and administrated. The individual stages of data addition and of their approval by the database administrators will be explained. An example of a critical evaluation of a selected dataset will equally be given to justify the choice of methods based on mathematical gnostics for this task.

3:20 - Intermission

3:30 - 110 - Critical evaluation of stability constant data by IUPAC Glenn Hefter, G.Hefter@murdoch.edu.au, Chemistry Department, Murdoch University, Murdoch, WA 6150, Australia Stability (formation) constants of metal-ion complexes with inorganic and organic ligands in aqueous solution are employed widely for modelling chemical speciation in areas as diverse as medicine, engineering, process control, extractive metallurgy, environmental management and so on.

The available data are both extensive and widely dispersed across the scientific literature, which creates difficulties for potential users of such data. Fortunately, there has been a long-standing tradition of serious attempts at compiling stability constant and related thermodynamic data, starting with the efforts of Sillén and Martell for the UK Chemical Society and more recently in the form of electronic data bases. Unfortunately, most of these compilations do not attempt to distinguish reported results according to their reliability, that is, they are not “critical”. This is a major disadvantage for the non-expert user of such data. This situation was recognised a long time ago by key researchers in the field who set up a group within IUPAC in the 1970s to oversee production of critical evaluations of stability constant and related thermodynamic data. Having gone through a number of transformations, this work continues as part of the activities of the IUPAC Sub-Committee on Solubility and Equilibrium data. This talk will provide an overview of the many contributions that have been made by the IUPAC group to this important task.

3:55 - 111 - Models to evaluate experimental solubility data for crystalline nonelectrolyte solutes in organic mono-solvents and solvent mixtures William E. Acree, Jr., acree@unt.edu, Chemistry, University of North Texas, Denton, Texas 76203, United States Methods used in the critical evaluation of published solubility data for crystalline nonelectrolytes dissolved in neat organic mono-solvents and organic solvent mixtures depend to a large extent on the quantity and type of experimental data to be evaluated. In those instances where independent measurements exist, one can

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compute the mean value and standard deviation, and see how the individual replicate measurments differ from each other. If replicate measurements are not available one can obtain an indication of the internal consistency of a data set by using solution models. The presentation will discuss the applicability of the following models: the Combined Nearly Ideal Binary Solvent (NIBS)/Redlich-Kister model for evaluating measured solubility data in binary solvent mixtures; the Abraham general solvation parameter model for evaluating solubility data of a given solute dissolved in a series of organic solvents; and the Apelblat and Buchowski λh models for evaluating how the measured solubility data varies with temperature. In addition the predictive aspects of the Combined NIBS/Redlich-Kister and Abraham general solvetion models will be illustrated. The Combined NIBS/Redlich-Kister model allows one to predict solute solubility in ternary and higher-order multicomponent solvent mixtures using the equation coefficients calculated from the measured solubility data for the solute dissolved in the contributing sub-binary solvent mixtures. The Abraham general solvation parameter model enables one to predict solute solubility in additional organic solvents from solute descriptors calculated from the measured solubility of the solute in select organic mono-solvents

4:20 - 112 - Thermodynamics of electrolyte solubility in mixed solvents: Silver halides Earle Waghorne, earle.waghorne@ucd.ie, UCD School of Chemistry and Chemical Biology, University College Dublin, Dublin, Ireland Values for the solubility products, KS0, the enthalpies of solution, ΔsolHº, and the equilibrium products for AgXi

(i−1)− silver halide complexes,βi, of the silver halides

in three non-aqueous solvents: methanol, acetonitrile and dimethylsulfoxide, and in their aqueous mixtures, are reviewed. The solvent systems provide examples for three types of mixed aqueous solvent system: aqueous alcohol mixtures and aqueous mixtures with dipolar aprotic solvents that are weakly or strongly basic. As is clear from the figures, the solubilities depend on both the concentration and nature of the organic co-solvent. It can also be seen that variations in the solution enthalpies don’t simply mirror those in the solubility products. The data are discussed in terms of solvent – solute and solvent – solvent interactions present in the systems.

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4:45 - 113 - Possible contributions from the Solubility Data Project for arsenic and carbon dioxide environmental impacts mitigation M. Clara F. Magalhães, mclara@ua.pt, Department of Chemistry and CICECO, University of Aveiro, Aveiro, Portugal Arsenic is progressively becoming a major environmental problem in some parts of the world, being the responsible for large-scale disasters involving thousands of people in particular regions of Asia, Africa, and Central and South America. The crystallization of arsenic containing solid phases can be the process that ensures a long-term immobilization of arsenic in the environment. However, in order to understand which solid phases are stable under given environmental conditions, it is necessary to know each solid phase stability conditions. Solubility data are very important tools to calculate thermodynamic parameters that will help in the construction of stability field diagrams. Nevertheless, only a few data exist and much more work has to be developed on this subject. On the other hand, the progressive increase of the concentrations of carbon dioxide in the atmosphere has been considered one of the responsible for the increase of the global atmosphere average temperature. Oceans have been thought as possible sinks for carbon dioxide. In order to decrease the amounts of atmospheric carbon dioxide new technologies are being developed in which carbon dioxide is injected under pressure, in deep geological structures. In order to optimize the predictive models actually used, accurate data for the high-pressure solubility of carbon dioxide in different solvents are needed. Arsenic and carbon dioxide are two of many examples of environmental global problems, where critically evaluated solubility and related equilibria data can provide useful

information in order to their mitigation

Wednesday, August 13, 2014

ChemEpInformatics: In the Pursuit of Epidrugs Using Chemoinformatics and Computational Approaches - PM Session Palace Hotel Room: Presidio Jose Medina-Franco, Nathalie Meurice, Organizers Jose Medina-Franco, Nathalie Meurice, Presiding

1:15 pm - 5:20 pm

1:15 - Introductory Remarks

1:20 - 114 - Targeting HDAC8 with derivatives of valproic acid: Design, synthesis, theoretical, and experimental evaluation as anticancer agents Jose Correa Basurto, corrjose@gmail.com, SEPI, Escuela Superior de Medicina, IPN, Mexico, D.F. 11340, Mexico Valproic acid (VPA) is extensively used as an anticonvulsive agent and as a treatment for other neurological disorders. It has been shown that VPA exerts an anti-proliferative effect on several types of cancer cells by inhibiting the activity of histone deacetylases (HDACs). However, VPA has some disadvantages, among which are poor water solubility and hepatotoxicity. Therefore, the aim of our research was to explore the binding site of VPA on HDAC8 using docking and molecular dynamics simulations, then, a set of VPA derivatives were designed and evaluated computationally to improve its physicochemical properties and anti-proliferative, which were synthesize and tested biologically. The results demonstrate that VPA is recognized at HDAC8 hydrophobic channel whereas

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its derivatives bind on different HDAC8 sites by hydrogen bonds, hydrophobic interactions and p-p interactions. The IC50 values of the VPA derivatives determined using HeLa cells are in mM range. This result indicates that VPA derivatives have greater anti-proliferative effects than VPA. Hence, these results suggest that these VPA derivatives may represent a good alternative for anticancer treatment.

1:45 - 115 - Development of isoform-selective protein arginine methyltransferase inhibitors Y. George Zheng1, yzheng@uga.edu, Ivaylo Ivanov2, Kun Qian1, Chunli Yan2. (1) Department of Pharmaceutical & Biomedical Sciences, University of Georgia, Athens, Georgia 30602, United States, (2) Department of Chemistry, Georgia State University, Atlanta, Georgia 30302, United States Protein arginine methylation is an epigenetic modification mark critical for a variety of biological processes, including chromatin restructuring, RNA splicing, and signal transduction. Misregulation of protein arginine methyltransferase (PRMT) expression and activities have been linked to cardiovascular disorders, immune disease, cancer, and many other pathological conditions.The enzymatic reaction of arginine methylation is catalyzed by pprotein arginine methyltransferases (PRMTs) which transfer the methyl group from S-adenosyl-L-methionine (AdoMet) to the guanidino group of arginine residues in protein substrates, resulting in mono and di-methylarginine residues in substrate proteins. Several PRMT genes and proteins have been validated as new disease biomarkers and therapeutic targets in various cancer models. Developing selective PRMT inhibitors is a challenging task for both academic labs

and pharmaceutical companies. Most current PRMT inhibitors display limited specificity and selectivity, indiscriminately targeting many methyltransferase enzymes that use AdoMet as a cofactor. We report the identification and characterization of diamidine compounds that specifically inhibit PRMT1, the primary type I arginine methyltransferase. Docking, molecular dynamics and MM/PBSA analysis were conducted to understand the binding modes of these inhibitors and the molecular basis of selective inhibition for PRMT1. Kinetic assays showed that furamidine, one lead inhibitor, functions predominantly by competing with the H4 peptide substrate instead of the cofactor SAM when binding the target enzyme. Furthermore, cellular studies revealed the inhibitor is permeable across the plasma membranes and can effectively inhibit intracellular PRMT1 activity and block cell proliferation in a set of leukemia cell lines with different genetic lesions. This work represents one of the best isoform-selective PRMT inhibitors to date.

2:10 - 116 - DNA methyltransferase Dnmt1: Regulation and novel drug-design strategies Zeljko M Svedruzic1, zsvedruz@biol.pmf.hr, Patrik Nikolic2. (1) Faculty of Medicine, Biomedical Technology, University of Rijeka, Rijeka, Croatia, (2) Faculty of Medicine, Biomedical Technology, University of Rijeka, Campus Trsat, Radmile Matejčić 2, Rm 823, Rijeka, Croatia DNA methyltransferase Dnmt1 is the key enzyme in functional organization of the human genome. For almost 30 years, Dnmt1 has been unsuccessfully targeted in different drug-design efforts. Most of those failures can be attributed to inadequate understanding of diverse mechanisms that regulate the enzyme activity. Dnmt1

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is a large enzyme with multiple flexible domains and phosphorylation sites. Dnmt1 can functionally interact with about 40 different molecules involved in DNA repair, chromatin organization, or RNA-directed-DNA methylation. The interacting molecules include proteins, poly(ADP-ribose), and methylated and unmethylated single-stranded and double-stranded non-coding RNA molecules. We are developing inhibitors and activators of Dnmt1 using a combination of enzyme assays, computational structural analysis, and numerical evaluation of enzyme activity. Knowledge of dynamic reversible processes in the active site of Dnmt1 were used to create novel mechanism-based inhibitors that do not cause DNA damage. Molecular docking and QM/MM MD simulations were used to optimize inhibitors’ geometry, flexibility, interaction with the solvent in the active site, and finally formation of a reversible covalent adduct with the enzyme. Different strategies for optimization of the PK/PD properties have been suggested. A dynamic active site loop has been identified as a part of the lock mechanism that controls allosteric regulation and processivity. Enzymatic assays and numerical methods have been developed to study processivity on the DNA substrate and the affinity for binding at the allosteric site. The presented approach allows screening for specific allosteric activators and inhibitors.

2:35 - 117 - Identification and design of new C5-DNA methyltransferase inhibitors and their biological activity Paola Barbara Arimondo, paola.arimondo@etac.cnrs.fr, USR3388 - ETaC, CNRS-Pierre Fabre, Toulouse, France DNA methylation is involved in the regulation of gene expression and plays an important role in normal developmental

processes and disease. In particular, the epigenetic landscape is altered in cancers where abnormal hypermethylation leads to silencing of certain genes such as tumor suppressor genes. In mammals, DNA methyltransferases are the enzymes responsible for DNA methylation on the position 5 of cytidine in a CpG context. Few direct enzyme inhibitors are known and those have several drawbacks. In order to identify novel inhibitors, we developed three chemical strategies. First a fluorescent High-Throughput Screening for the inhibition of the murine catalytic Dnmt3a/3L complex on the chemical library of the Muséum Naturelle d’Histoire Naturelle and found twelve hits with low micromolar activities. Interestingly, they showed little cytotoxicity. Dichlone, a small halogenated naphthoquinone, classically used as pesticide and fungicide, showed the lowest EC50 at 460 nM. Two molecules including Dichlone, efficiently reactivated YFP gene expression in a stable HEK293 cell line by promoter demethylation. Their efficacy was comparable to the DNMT inhibitor of reference 5-azacytidine. Second, based on molecular modeling studies of quinoline inhibitor SGI1027 in the crystal structure of M.Hha I C5 DNA methyltransferase, suggesting that the quinoline and the aminopyridimine are important for the interaction with the substrates and the protein, we synthesized twenty five new derivatives. Among them, four compounds showed an activity comparable to parent compound SGI-1027. The compounds were more potent against human catalytic DNMT3A than against human DNMT1 and induced the reexpression of a reporter gene, controlled by a methylated CMV promoter, in leukemia KG-1 cells. We carried out structure activity relationship studies to point out the substituents important for inhibition. Third, we carried out a modulation study of the non-nucleoside

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inhibitor N-Phthaloyl-L-tryptophan or RG108. The indole, carboxylate and phthalimide moieties were modified. Homologated and conformationally constrained analogs were prepared. Among them, two constrained compounds and two NPys derivatives were found at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. Altogether, these studies provide insights for the design of the next-generation of DNMT inhibitors. References: Ceccaldi A, Rajavelu A, Ragozin S, Sénamaud-Beaufort C, Bashtrykov P, Testa N, Dali-Ali H, Maulay-Bailly C, Amand S, Guianvarc’h D, Jeltsch A, Arimondo PB. Identification of Novel Inhibitors of DNA Methylation by Screening of a Chemical Library. ACS Chem Biol. 2013 8(3):543-8. Rilova E., ErdmannA., GrosC., MassonV., AussaguesY., Poughon-CassaboisV., RajaveluA., JeltschA., MenonY., NovosadN., Gregoire J.M., VispéS., SchambelP., AusseilA., Sautel F., ArimondoPB and CantagrelF.Design, synthesis and biological evaluation of 4-amino-N-(4-aminophenyl)-benzamides analogues of quinoline-based SGI-1027 as inhibitors of DNA methylation.Chem.Med.Chem 2014 in press. Asgatay S, Champion C, Marloie G, Drujon T, Senamaud-Beaufort C, Ceccaldi A, Erdmann A, Rajavelu A, Schambel P, Jeltsch A, Lequin O, Karoyan P, Arimondo PB, Guianvarc’h Synthesis and Evaluation of Analogues of N-Phthaloyl-l-tryptophan (RG108) as Inhibitors of DNA Methyltransferase 1. J Med Chem. 2014 57(2):421-34.

3:00 - 118 - Drug repurposing and epigenetics: Olsalazine is a hypomethylating compound active in a cellular context

José L. Medina-Franco1, Oscar Méndez-Lucio2, Joachim Petit1, Jeremy Tran3, James Bogenberger1, Mark Muller3, Raoul Tibes1, Nathalie Meurice1, Meurice.Nathalie@mayo.edu. (1) Department of Research, Mayo Clinic, Scottsdale, Arizona 85259, United States, (2) Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico, (3) College of Medicine, University of Central Florida, Orlando, Florida 32827, United States DNA hypomethylating drugs that inhibit DNA methyltransferases (DNMTs) are promising compounds for the treatment of cancer and other diseases. Herein, we describe the characterization of olsalazine, an approved anti-inflammatory drug, as a novel DNA hypomethylating agent [1]. Olsalazine was identified by a fast computer-guided similarity searching of DrugBank, a database of approved drugs to a previously identified inhibitor of DNMTs [2]. In order to examine the ability of olsalazine to inhibit DNMT activity, we utilized a novel DNA methylation re-programming system that operates in the context of living cells [3]. The cell based screen used in this study is highly tractable, internally controlled and well-suited for a drug repurposing strategy in epigenetics. Olsalazine very closely mimics the action of 5-aza-2’-deoxycytidine, a known hypomethylating drug used in the clinic for the treatment of myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML), with minimal cytotoxicity at the concentrations tested. Based on this proof of concept, a more systematic study of the similarity relationships of approved drugs to known epigenetic agents had been undertaken, and will assess the significance of these compounds to MDS and AML. [1] Mendez-Lucio, O. et al. ChemMedChem, 2014, 9, 560. [2] Kuck, D. et al. Bioorg. Med. Chem.

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2010, 18, 822 [3] Morano, A. et al. Nucl. Acids Res., 2014, 42, 804.

3:25 - Intermission

3:40 - 119 - Computer-aided hit/probe discovery for methyllysine reader proteins Bradley M. Dickson, Lindsey I. James, Brandi M. Baughman, Stephen V. Frye, Dmitri Kireev, dmitri.kireev@unc.edu. Center for Integrative Chemical Biology and Drug Discovery, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, United States Chemical marks on histones, collectively called the histone code, are involved in regulation of gene expression, cell cycle and genome stability. Proteins that mediate the histone signaling by binding to the histone marks constitute a largely untapped source of therapeutic targets. The Center for Integrative Chemical Biology and Drug Discovery is involved in the discovery of chemical probes for methyllysine (Kme) readers since 2009. In silico approaches have been instrumental in all stages of this endeavor. For instance, pharmacophore- and structure-based virtual screening has lead to identification of small-molecule hits for L3MBTL1 [1], a malignant brain tumor (MBT) protein. Structure-based design was used throughout the probe development for L3MBTL3 [2], another MBT protein. Molecular simulations were helpful in understanding structural mechanisms of UHRF1, a ubiquitin ligase [3]. Current work includes hit/probe design for UHRF1 and identification of endogenous histone substrates for dual-domain readers. The talk will provide a brief overview of the past work and a discussion of new results. [1] Kireev et al, Identification of non-peptide malignant brain tumor (MBT) repeat antagonists by virtual screening

of commercially available compounds. J Med Chem 2010, 53 (21), 7625-7631 [2] James et al, Discovery of a chemical probe for the L3MBTL3 methyllysine reader domain. Nat Chem Biol 2013, 9 (3), 184-191 [3] Rothbart et al, Multivalent histone engagement by the linked tandem Tudor and PHD domains of UHRF1 is required for the epigenetic inheritance of DNA methylation. Genes & Development 2013, 27 (11), 1288-1298

4:05 - 120 - Molecular design approaches to target histone methyltransferases Alberto Del Rio, alberto.delrio@gmail.com, Institute of Organic Synthesis and Photoreactivity (ISOF), National Research Council (CNR), Bologna, Bologna 40129, Italy and Department of Experimental, Diagnostic and Specialty Medicine (DIMES), Alma Mater Studiorum, University of Bologna, Bologna, Bologna 40126, Italy In the last years the study of histone post-translational modifications (PTMs) marked an extraordinary progression and a great number of epigenetic modifications has been identified and associated to different fundamental biological processes and pathological conditions. Consistently, several drug discovery programs aimed to devise small-molecules able to pharmacologically modulate epigenetic enzymes have been initiated. In this framework, computer-aided approaches spanning from ligand to structure-based methods promise to play an essential role to speed-up the identification of new chemical entities. Herein we provide an overview of molecular design approaches to target protein lysine methyltransferases (PKMT), which are a group of histone-modifying enzymes that emerged recently as important targets for cancer therapy. We will present a typical computer-aided

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approach to search for novel inhibitors of SMYD3, a PKMT found to be upregulated in colorectal cancer cells and tissues. Results of in vitro and cell-based assays demonstrate that small-molecules identified with in silico techniques can modulate the activity of SMYD3, thus supporting the usage of computational approaches as a valuable set of tools for the early-stage identification of new epihits.

4:30 - 121 - Structural basis for selective inhibition of hSirt2 by ligand induced rearrangement of the active site Tobias Rumpf1, tobias.rumpf@pharmazie.uni-freiburg.de, Matthias Schiedel1, Berin Karaman2, Claudia Rössler3, Brian J North5, Kathrin I Ladwein1, Markus Gaier1, David A Sinclair5, Mike Schutkowski3, Wolfgang Sippl2, Oliver Einsle4, Manfred Jung1. (1) Institute of Pharmaceutical Sciences, Albert-Ludwigs-University Freiburg, Freiburg, Baden-Württemberg 79104, Germany, (2) Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, Halle, Sachsen-Anhalt 06120, Germany, (3) Institute for Biochemistry and Biotechnology, Martin-Luther-University Halle-Wittenberg, Halle, Sachsen-Anhalt 06120, Germany, (4) Institute for Biochemistry BIOSS Centre for Biological Signalling Studies, Albert-Ludwigs-University Freiburg, Freiburg, Baden-Württemberg 79104, Germany, (5) Department for Genetics, Havard Medical School, Boston, Massachusetts 02115, United States Sirtuins are a unique and highly conserved class of NAD+-dependent lysine deacylases. Among these the human isotype Sirt2 has been implicated in the pathogenesis of cancer, inflammation and neurodegenerative diseases but a rational basis for the development of optimized inhibitors was lacking so far. Here we present the first high-resolution structures

of human Sirt2 in complex with highly selective drug-like inhibitors that show a unique inhibitory mechanism. Potency and the unprecedented selectivity towards Sirt2 are based on a ligand-induced structural rearrangement of the active site. Application of the most potent of these Sirtuin-rearranging ligands, termed SirReal2, leads to tubulin hyperacetylation in Hela cells and induces degradation of the checkpoint protein BubR1 consistent with Sirt2-inhibition in vivo.

4:55 - 122 - Decoding genetic and epigenetic networks for vitamin C mediated cell reprogramming Panwen Wang, Yan Wang, Junwen Wang, junwen@hku.hk. Department of Biochemistry, The University of Hong Kong, Hong Kong, Hong Kong NA, China Somatic cells can be transformed into induced Pluripotent Stem Cells (iPSCs), a process called reprogramming. Recently, researchers found that vitamin C, a natural molecule that is essential for human health, can promote reprogramming. However, the complete mechanism underlying this process remains unknown. Here we aim to develop a computational framework to uncover the mechanism including signaling pathway, genetic and epigenetic regulatory networks based on our previous work ChIP-Array (Qin, et al., 2011) and EpiRegNet (Wang, et al., 2011). ChIP-Array uses ChIP-seq and transcriptome profiling data to find direct and indirect targets of a particular transcription factors. EpiRegNet explores the regulatory relations between histone modifiers and target genes, buy investigating the correlations of the modifiers’ ChIP-seq signals and the expression of their potential their targets. We will extend these strategies to identify signaling, regulatory and epi-regulatory networks for vitamin C

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mediated cell reprogramming. For the signaling pathway, we use a tissue-specific protein-protein interaction network that is weighted by the known pathways and co-express correlation, and apply a fast Random Walk with Restart algorithm to it. The initial pathways are generated and then optimized by the Depth-First Search algorithm. Several case studies demonstrate the effectiveness of our computational framework. The framework will lead more thorough understanding of the mechanism of cell reprogramming and discover transcription factors or epigenetic modifiers that are suitable for potential drug targets. Reference: Qin, J., et al. ChIP-Array: combinatory analysis of ChIP-seq/chip and microarray gene expression data to discover direct/indirect targets of a transcription factor. Nucleic Acids Res 2011;39(Web Server issue):W430-436. Wang, L.Y., et al. EpiRegNet: constructing epigenetic regulatory network from high throughput gene expression data for humans. Epigenetics 2011;6(12):1505-1512.

Wednesday, August 13, 2014

Exploring the Application of New Technologies in Chemical Research and Education - PM Session Palace Hotel Room: California Parlor Cosponsored by CHED David Martinsen, Organizer David Martinsen, Presiding

1:30 pm - 5:15 pm

1:30 - Introductory Remarks

1:35 - 123 - New target prediction and visualization tools incorporating open source molecular fingerprints for TB mobile version 2

Sean Ekins1, ekinssean@yahoo.com, Alex M Clark2, Malabika Sarker3. (1) Collaborative Drug Discovery, inc, Burlingame, CA, United States, (2) Molecular Materials Informatics,, Montreal, Quebec, Canada, (3) SRI International, CA, United States We recently developed a freely available mobile app (TB Mobile) for both iOS and Android platforms that displays Mycobacterium tuberculosis (Mtb) active molecule structures and their targets with links to associated data. The app was developed to make target information available to as large an audience as possible and therefore has utility for education and researchers. We now report a major update of the iOS version of the app. This includes enhancements that use an implementation of ECFP_6 fingerprints that we have made open source. Using these fingerprints, the user can propose compounds with possible anti-TB activity, and view the compounds within a cluster landscape. Proposed compounds can also be compared to existing target data, using a näive Bayesian scoring system to rank probable targets. We have curated an additional 60 new compounds and their targets for Mtband added these to the original set of 745 compounds. We have also curated 20 further compounds (many without targets in TB Mobile) to evaluate this version of the app with 805 compounds and associated targets. TB Mobilecan now manage a small collection of compounds that can be imported from external sources, or exported by various means such as email or app-to-app inter-process communication. This means that TB Mobilecan be used as a node within a growing ecosystem of mobile apps for cheminformatics. It can also cluster compounds and use internal algorithms to help identify potential targets based on molecular similarity. TB Mobile represents

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a valuable dataset, data-visualization aid and prediction tool.

2:05 - 124 - Scilligence’s ELN for research laboratories and academia Rajeev Hotchandani, rhotchandani@scilligence.com, Scilligence, Burlington, MA 01803, United States The dawn of digital age and innovative companies like Google have made access to information much easily in our daily life. However, various laboratories and academic research is lagging behind in this trend. Although a trend has started in academia research groups and organic chemistry labs, a lot of these institutions are still using paper notebooks to document their everyday work. This makes knowledge preservation and sharing much more difficult. Through case study examples in this presentation, knowledge preservation, IP protection and team collaboration can be made efficient by Scilligence informatics in your laboratory environments.

2:35 - 125 - Accessing 3D printable chemical structures online Vincent F. Scalfani1, vfscalfani@ua.edu, Antony J. Williams2, Robert M. Hanson3, Jason E. Bara4, Aileen Day2, Valery Tkachenko2. (1) University Libraries, University of Alabama, Tuscaloosa, AL 35487, United States, (2) eScience, Royal Society of Chemistry, Cambridge, Cambridgeshire CB4 0WF, United Kingdom, (3) Department of Chemistry, St, Olaf College, Northfield, MN 55057, United States, (4) Department of Chemical & Biological Engineering, University of Alabama, Tuscaloosa, AL 35487, United States We have been exploring routes to create 3D printable chemical structure files (.WRL and .STL). These digital 3D files can be

generated directly from crystallographic information files (.CIF) using a variety of software packages such as Jmol, PyMol, or Chimera. After proper conversion to the .STL (or .WRL) file format, the chemical structures can be fabricated into tangible plastic models using 3D printers. This technique can theoretically be used for any molecular or solid structure. Researchers and educators are no longer limited to building models via traditional piecewise plastic model kits. As such, 3D printed molecular models have tremendous value for teaching and research. As the number of available 3D printable structures continues to grow, there is a need for a robust chemical database to store these files. This presentation will discuss our efforts to incorporate 3D printable chemical structures within the Royal Society of Chemistry’s online compound database.

3:05 - Intermission

3:15 - 126 - Libraries as hubs for emerging technologies Jeffrey R. Lancaster, jeffrey.lancaster@columbia.edu, Science & Engineering Libraries, Columbia University Libraries, New York, NY 10027, United States Libraries occupy a neutral space that is increasingly recognized as a fertile home for innovation. Though this new position is sometimes at odds with its traditional identity, libraries are beginning to develop services built around emerging technologies, changing user needs, and evolving modes of research. I will discuss what Columbia University Libraries is currently doing to support these changing patron expectations, and I will address our current thinking around building service models for these new technologies. With several case studies, I will focus on how chemists – faculty and students – are adapting to using the new technologies

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for their research, teaching, and personal interests. Additionally, I will discuss some possible future directions for these technologies, reasons why libraries will continue to add value to new technologies, and areas where libraries can partner with others, including publishers, professional societies, and industrial organizations in supporting and developing emerging technologies.

3:45 - 127 - Global science capacity building and the Maker Movement: Do-it-yourself lab equipment with Tekla Labs Julea Vlassakis, jvlassakis@berkeley.edu, Bioengineering, UC Berkeley, United States Scientific research and technological innovation are critical for sustainable economic growth in resource-limited settings, but commercial laboratory equipment is prohibitively expensive. Similarly, educators around the world cannot afford to purchase basic laboratory equipment that would enhance their ability to bring science to life in their classrooms. Tekla Labs, a UC Berkeley/UCSF-based student organization, has started an online community for sharing designs to build reliable, low-cost laboratory equipment. Our goal is to empower scientists and educators to build their own research infrastructure using local and repurposed supplies. Our talk will describe our efforts to engage and connect the DIY community with scientists and educators through our online community and competitions, such as our recent international BuildMyLab design contest. We received 174 creative designs and instructions for building DIY laboratory equipment through the competition, which was held with Instructables.com. Winners such as the hotplate and laminar flow hood and others such as centrifuges and

digital microscopes are essential items in many life sciences laboratories. These DIY alternatives are constructed from readily available raw materials and electronics components and are a small fraction of the cost of similar commercial systems. We will integrate these instructions into our existing repository of DIY lab equipment designs available to researchers and educators worldwide. We will also discuss the challenges of mediating international partnerships, with examples from our current efforts to perform test builds of our designs with collaborators in need worldwide. Finally, we will share our vision for the future of DIY laboratory equipment as an enabler for technological and economic development in resource-poor settings, and for improved immersive scientific education around the world.

4:15 - 128 - Google Glass based immunochromatographic diagnostic test analysis Steve Feng1,2, stevewfeng@gmail.com, Romain Caire1,2, Bingen Cortazar1,2, Mehmet Turan1,2, Andrew Wong1,2, Aydogan Ozcan1,2,3,4. (1) Department of Electrical Engineering, University of California, Los Angeles, Los Angeles, CA 90095, United States, (2) Department of Bioengineering, University of California, Los Angeles, Los Angeles, CA 90095, United States, (3) California NanoSystems Institute, University of California, Los Angeles, Los Angeles, CA 90095, United States, (4) Department of Surgery, David Geffen School of Medicine, University of California, Los Angeles, Los Angeles, CA 90095, United States Recent advances in wearable computing devices such as smart glasses provide new opportunities for performing various diagnostic tasks. We demonstrate the ability for one such smart device, the Google Glass, to perform qualitative

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decisions and quantitative measurements on lateral flow immunochromatographic diagnostic tests using a hands-free voice-controllable rapid diagnostic test (RDT) reader software application without any external hardware attachments. After users run our application to image RDTs with attached Quick Response (QR) code identifiers generated though a web tool, the images are digitally transferred to our servers for automated evaluation of all RDTs in the image.

The resulting diagnoses are returned to the user’s Glass device and made available along with their QR code data and other associated information (e.g. geographic) on a central server, which provides the test results via tabular and geospatial (i.e., world map with geo-tagged data) representations. We demonstrate this system’s ability to evaluate qualitative (i.e., yes/no) human immunodeficiency virus (HIV) and quantitative prostate-specific antigen (PSA) tests. For the quantitative PSA tests, we imaged and measured both Free and Total PSA tests at concentrations ranging from 0 to 200 ng/mL and generated calibration curves mapping image line intensities to absolute PSA concentrations. Providing real-

time spatiotemporal tracking of various diseases and medical conditions, hands-free sensing and imaging platforms on wearable computing devices such as Google Glass could prove quite useful for epidemiology, mobile health and telemedicine applications.

4:45 - 129 - Frugal science and global health: Democratizing access to scientific tools Manu Prakash, manup@stanford.edu, Stanford University, United States Somebody once said, “What a damn fool can do for a dollar, an engineer can do for a nickel.” Thinking about cost as an engineering constraint brings new life to ideas. This is what makes the difference between an idea influencing a hundred people or a billion. With our planet literally teaming with problems, it’s time to take cost constraints into serious consideration. As physicists, we like to make stuff. We use these skills (and field work) to design solutions for extremely resource constrained settings, specially in the field of global health. I will discuss our current work from field diagnostics to high-throughput vector ecology and hands on science education.

Thursday, August 14, 2014

General Papers - AM Session Computational Chemistry and Informatics Palace Hotel Room: Marina Erin Bolstad, Organizers Erin Bolstad, Presiding

9:40 am - 12:05 pm

9:40 - Introductory Remarks

9:45 - 130 - Ten years of innovative

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collaborative drug discovery Barry A. Bunin, bbunin@collaborativedrug.com, Management, Collaborative Drug DIscovery (CDD), Burlingame, CA 94010, United States Today, as chemical and biological information grows, researchers increasingly need simple tools to simultaneously manage their own and their collaborators’ data. In addition there is a growing need to securely integrate public data with private data. New approaches that would allow scientists to do research more effectively need to handle chemical complexity (registration, stereochemistry, mixtures, batches) and biological complexity (enzyme, phenotypic, cell, animals, IC50, Z/Z’, and metadata), as well as natural workflows for secure collaborations. This presentation will describe the creation and use cases with hosted web-database technologies like the CDD Vault that provides a more collaborative hosted informatics technology for commercial and neglected disease applications. The major components of effective scientific-community based research include: (1) unifying goal or focus on common therapeutic areas/diseases; (2) multiple research areas/expertise; (3) uniform database platform for effective data accumulation and management; (4) easy access and sharing of information; (5) potential for unlimited growth. The Collaborative Drug Discovery (CDD) Vault was built utilizing innovative web technologies in order to provide a platform that allows scientists to archive, mine, and securely share research data with an initial focus on infectious diseases of the developing world. Since the technology is “therapeutic area agnostic” it has general been proven equally applicable for commercial applications. Collaborative technology allows researchers to securely collaborate with technical experts around

therapeutic or target areas thus advancing research facilitating the discovery of new drug candidates. It also allows scientists to speed up research by sharing unpublished data. Approved examples working with small companies, academics, large collaborations and funding bodies using the CDD Vault database platform will be presented.

10:05 - 131 - Multicriteria drug discovery: Using CoMFA models to drive target specificity Lei Wang, lei.wang@certara.com, Brian Masek, Fabian Boes, Bernd Wendt, Stephan Nagy. Certara, St. Louis, MO 63101, United States A successful drug candidate will not only need to overcome ADME, physical and safety properties, but also often need to achieve a selectivity profile against related targets. The approach we present here combines a de novo design method with powerful ligand-based scoring function that consists of three different 3D QSAR models for different targets to generate selective inhibitors. A training set was developed with literature and public information where 50 molecules with activities for FactorXa, Trypsin and Thrombin were selected.

Three different Topomer CoMFA models

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were built using the training set. By combining predictions of the activity profile with different weights and penalty score, a scoring function was created that can drive the invention of new and selective compounds.

10:25 am 132 WITHDRAWN

10:45 - Intermission

11:00 - 133 - Conditional structure-activity-similarity (SAS) maps Gerry Maggiora2,3, gerry.maggiora@gmail.com, Martin Vogt1, Preeti Iyer1, Jurgen Bajorath1. (1) Department of Life Science Informatics, Rheinische Friedrich-Wilhelms-Universitat, Bonn, Germany, (2) University of Arizona Bio5 Research Institute, Tucson, Arizona 85721, United States, (3) Translational Genomics Research Institute, Phoenix, Arizona 85004, United States SAS maps provide a simple and compact two-dimensional graphical portrayal of the activity differences and similarities of compound pairs. Different regions of these maps correspond to different pairwise features, namely, activity cliffs, similarity cliffs, and “smooth” SAR. Although this provides a useful representation of SARs it suffers from the fact that all of the data is pairwise. A new method is described for generating SAS maps with respect to specific reference compounds yielding unique maps that are“conditioned on” the reference compounds used in their construction. This approach provides a more compound-centric view that facilitates the analysis of SAR properties. An analysis is also presented that describes a means for assessing the statistical properties of the specific features in each conditional SAS map.

11:20 - 134 - Fragment-based

computational approach to study the phase behavior of biopolymers Jan-Willem Handgraaf1, janwillem.handgraaf@culgi.com, Rubèn Serral Gracià1, Peter Schiffels2, Johannes G. E. M. Fraaije1,3. (1) Culgi B.V., Leiden, The Netherlands, (2) Fraunhofer-Institut für Fertigungstechnik und Angewandte Materialforschung, Bremen, Germany, (3) Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands The computational study of molecular processes in nature, such as polymer dynamics or aggregation, are for the most part still out of reach for conventional simulation methods such as Molecular Dynamics or Monte Carlo. Here we present a fragmentation engine designed to handle in principle any molecular architecture. The methodology is based on the well-known notion that atomic groups in molecules can be lumped into single particles, or “beads” [1]. This so-called “coarse-graining” allows for (much) larger length and time scales that can typically be attained by conventional simulation methods.

The problem of fragmenting an atomistally detailed molecule is transformed to a global minimization problem. A scoring function determines how good or bad a given fragmentation is. Then the algorithm is reduced to finding the global minimum of the scoring function. The global minimization is performed by a Monte Carlo evolution where the lowest scoring fragmentation is stored [3]. This typically succeeds finding the global minimum for a given molecular architecture within a reasonable amount of time. From a fundamental chemical informatics point of view, it is interesting to note that that we can represent a collection of different molecules by a much smaller set of distinct fragments, and that the

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frequency distribution of fragments follows Heap’s power law. Extrapolation indicates that one could fragment the entire PubChem database into a mere few thousands distinct fragments. The great practical advantage is that in this way, by pre-parameterization, one can in principle speed up molecular affinity calculations of thermodynamic accuracy by many orders of magnitude, while still maintaining chemical specificity.

So far we have successfully applied the fragment-based computational approach to molecular systems and architectures found in the chemical [3], oil [4] and pharmaceutical industry. The method has been refined and validated against industrially relevant data. Here we will demonstrate the versatility of the methodology by applying it to the biopolymer lignin. First we discuss the problem of generating atomic structures of lignin oligomers from 2D NMR data, followed by a description of the actual fragmentation to coarse-grained lignin models. We finally discuss the application of these coarse-grained lignin models by performing simulations to study the phase behavior in aqueous solution. 1. See: Carbone, P.; Karimi-Varzaneh, H. A.; Müller-Plathe, F. Faraday Discuss. 2010, 144, 25–42, and references therein. 2. Fraaije, J. G. E. M., Nath, S. K., van Male, J., Becherer, P., Klein Wolterink, J., Handgraaf, J.-W., Case F., Tanase,, C. Serral Gracià, R., Culgi Manual version 8.0, www.culgi.com (2013) (ISBN: 978-90-817846-0-3). 3. Handgraaf, J.-W.; Serral Gracià, R.; Nath, S. K.; Chen Z.; Chou, S.-H.; Ross, R. B.; Schultz, N. E.; Fraaije, J. G. M. E., Macromolecules 2011, 44, 1053-1061. 4. Fraaije, J. G. E. M.; Tandon, K.; Jain, S.; Handgraaf, J.-W.; Buijse, M., Langmuir 2013, 29, 2136-2151.

11:40 - 135 - Future of large-scale computational screening of porous materials Jihan Kim, jihankim@kaist.ac.kr, Department of Chemical and Biomolecular Engineering, KAIST, Daejeon, Republic of Korea Porous materials such as zeolites and metal-organic frameworks are seen as promising materials for a wide range of energy and environmental related applications, which include carbon capture, gas storage and separations. Unfortunately, the number of porous material that can be experimentally synthesized is extremely large, making it very time-consuming to identify the optimal structures for a given application. In this presentation, I will discuss some of the computational methods and techniques developed to efficiently screen a large database of porous materials. There will be additional discussions with regards to some future technologies and methods that can lead to further advancements in efficient materials screening. Finally, new ideas and concepts that can help increase the general public’s interest in porous materials screening will be introduced to stimulate further discussions.

Thursday, August 14, 2014

General Papers - AM Session Toolkits and Databases Palace Hotel Room: Presidio Erin Bolstad, Organizers Erin Bolstad, Presiding

9:45 am - 12:25 pm

9:45 - Introductory Remarks

9:50 - 136 - Integrating Jmol/JSpecView into the Eureka Research Workbench

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Stuart Chalk1, schalk@unf.edu, Matthew Morse1, Israel Hurst1, Anthony Williams2, Valery Tkachenko2, Alexey Pshenichnov2, Robert Hanson3. (1) Department of Chemistry, University of North Florida, Jacksonville, FL 32224, United States, (2) Royal Society of Chemistry, Wake Forest, NC 27587, United States, (3) Department of Chemistry, St. Olaf College, Northfield, MN 55057, United States The Eureka Research Workbench (http://eureka.sourceforge.net) is an online environment for capturing the scientific process currently under development. This presentation discusses the integration of the Jmol/JSpecView into the environment to enable experimental data stored in ExptML files (http://exptml.sourceforge.net) to be viewed. Ideas to semantically link data into Jmol will also be discussed.

10:15 - 137 - Open innovation and chemistry data management contributions from the Royal Society of Chemistry resulting from the Open PHACTS project Antony J Williams1, tony27587@gmail.com, Valery Tkachenko1, Ken Karapetyan1, Alexey Pshenichnov1, Colin Batchelor2, Jon Steele2, David Sharpe2. (1) Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States, (2) eScience, Royal Society of Chemistry, Cambridge, Cambridgeshire, United Kingdom The Royal Society of Chemistry was pleased to contribute to the Open PHACTS project, a 3 year project funded by the Innovative Medicines Initiative fund from the European Union. For three years we developed our existing platforms, created new and innovative widgets and data platforms to handle chemistry data, extended existing chemistry ontologies and embraced the semantic web open

standards. As a result RSC served as the centralized chemistry data hub for the project. With the conclusion of the Open PHACTS project we will report on our experiences resulting from our participation in the project and provide an overview of what tools, capabilities and data have been released into the community as a result of our participation and how this may influence future projects. This will include the Open PHACTS open chemistry data dump including the chemistry related data in chemistry and semantic web consumable formats as well as some of the resulting chemistry software released to the community. The Open PHACTS project resulted in significant contributions to the chemistry community as well as the supporting pharmaceutical companies and biomedical community.

10:35 - 138 - Using outreach to inform, maintain, and evaluate your collection Kiyomi Deards, kdeards2@unl.edu, Department of Research and Instructional Services, University of Nebraska-Lincoln, Lincoln, NE 68506, United States Increasing responsibilities, coupled with larger student bodies and corresponding increases in teaching and research faculty and staff, have made it difficult for many librarians and information professionals to spend time on collection development. This presentation will demonstrate how both formal and informal outreach efforts can inform collection development of Chemistry resources, the evaluation of existing resources, and guide collection maintenance efforts.

10:55 - 139 - PubChem: Celebrating ten

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years online Evan Bolton, bolton@ncbi.nlm.nih.gov, National Center for Biotechnology Information, National Institutes of Health, Bethesda, MD 20894, United States PubChem is an open archive of chemical substances and their bioactivities celebrating ten years of service. With humble beginnings, PubChem has grown substantially through the years entirely from voluntary contributions by the chemical biology community, including chemical suppliers, universities, publishers, government agencies, domestic and international resources. This talk will give a brief overview of PubChem and explore some of the historical aspects of the project and future directions.11:15 - Intermission

11:25 - 140 - Clustering the Royal Society of Chemistry chemical repository to enable enhanced navigation across millions of chemicals Ken Karapetyan1, karapetyank@rsc.org, Valery Tkachenko1, Antony J Williams1, Oliver Kohlbacher2, Phillipp Thiel2. (1) Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States, (2) Applied Bioinformatics Group, University of Tuebingen, Tuebingen, Germany The Royal Society of Chemistry has hosted the ChemSpider database and associated platforms for over five years. Technologies made significant progress over that period but, more importantly, the community needs in terms of the variety of data types as well as search performance have increased. The preprocessing of chemicals for improved similarity searching and compound database navigation is seen as one crucial component of major development efforts to architect a new data repository. This component is engineered

and implemented in collaboration with the group of Professor Oliver Kohlbacher at University of Tübingen. They have developed an approach for clustering large chemical libraries based on a fast, parallel, and purely CPU-based algorithm for 2D binary fingerprint similarity calculation. Using this method, the complete similarity network of our seed set with tens of millions of chemicals has been analyzed at a Tanimoto threshold of 0.6 and all similarity links were fed into our database. The latter is highly beneficial and will allow us to create more complex and enriching visualizations of similar compounds with associated bioactivity data and physicochemical properties for the RSC chemical repository users. This presentation will provide an overview of our experiences in applying clustering to our compound data and how it will be used to enrich data navigation on the RSC data repository.

11:45 - 141 - Experiences and adventures with noSQL and its applications to cheminformatics data Valery Tkachenko1, tkachenkov@rsc.org, Antony Williams1, Ken Karapetyan1, Alexey Pshenichnov1, Mikhail Rybalkin2. (1) Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States, (2) Cheminformatics, GGA Software Services, St Petersburg, Russian Federation The Royal Society of Chemistry hosts an increasing number of chemistry related databases and have utilized SQL-based technologies for our development platforms in general. In recent years the interest in noSQL databases has exploded as the associated technologies have developed and have shown great promise in terms of enhanced performance. We have collaborated with GGA Software Services to implement their noSQL technologies

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and have integrated it into the compound repository presently being developed as part of the underpinning architecture for compound data management at the RSC. This presentation will provide an overview of the reasons why we have integrated a noSQL solution, quantitative analysis of the benefits of inclusion and our thoughts regarding further approaches to optimize search performance for the chemical compound repository.12:05 - 142 - Building an online data repository for 100,000 dyes David Hinks1, david_hinks@ncsu.edu, Valery Tkachenko2. (1) North Carolina State University, Raleigh, NC, United States, (2) Royal Society of Chemistry, Wake Forest, NC 27587, United States The Max Weaver Dye Library housed at the College of Textiles at North Carolina State University contains a physical sample library of almost 100,000 dyes. Over the next few years these dyes will be mirrored in the form of a web-accessible collection of electronic chemical structure representations and, as data is generated, will include access to associated spectroscopic, crystallographic and organic synthesis data. As one of the world’s largest physical collections of dyes the release of the data to the community will allow access to a database allowing for molecular modeling. This presentation will provide an overview of the progress to put the data repository of chemical and analytical data online as a community resource and our future plans for this rich data collection.

Thursday, August 14, 2014

General Papers - PM Session Toolkits and Databases Palace Hotel Room: Marina Erin Bolstad, Organizers

Erin Bolstad, Presiding

1:30 pm - 3:20 pm

1:30 - 143 - Mining PubChem data: Interfaces, approaches, and best practices Evan Bolton, bolton@ncbi.nlm.nih.gov, National Center for Biotechnology Information, National Institutes of Health, Bethesda, MD 20894, United States PubChem is a sizeable resource of chemical biology information with many tens of millions of chemical structures, hundreds of millions biological activity outcomes, and many billions of cross references: to external resources, to biological assays, to related chemicals, to the biomedical literature, to proteins, to genes, to pathways, and more. How does one efficiently access such a massive corpus of information? This talk will give an overview of PubChem programmatic interfaces, data access approaches, and best practices to help empower researchers to efficiently access information contained within PubChem.

1:50 - 144 - The Royal Society of Chemistry and its adoption of semantic web technologies for chemistry at the epoch of a federated world Antony J Williams, tony27587@gmail.com, Valery Tkachenko, Ken Karapetyan, Alexey Pshenichnov. Cheminformatics, Royal Society of Chemistry, Wake Forest, North Carolina 27587, United States Semantic web technologies have quickly penetrated all areas of traditional and new database systems and have become the de facto standard in information exchange and communication. The Royal Society of Chemistry has built a new chemistry data repository with the semantic web at the core of the system. Every module of

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the data repository contains a semantic web layer and is able to interact internally and externally using standard approaches and formats including RDF, appropriate ontologies, SPARQL querying and so on. In this presentation we will review the challenges associated with developing this new system based on semantic web technologies and how the approach that we have taken offers distinct advantages over the original data model designed to produce the ChemSpider database. Its advantages include extensibility, an ontological underpinning, federated integration and the adoption of modern standards rather than the constraints of a standard SQL model.

2:10 - Intermission

2:20 - 145 - Dereplication applications for computer-assisted structure elucidation (CASE) and the ChemSpider database Patrick Wheeler1, info@acdlabs.com, Arvin Moser1, Joe DiMartio1, Mikhail Elyashberg2, Kirill Blinov3, Sergey Molodstov4, Anthony Williams5. (1) Advanced Chemistry Development, Toronto, ON, Canada, (2) Moscow Department, Advanced Chemistry Development, Russian Federation, (3) Pr-t, 33 k.1 kv. 51, Molecule Apps, LLC, Moscow, Russian Federation, (4) Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russian Federation, (5) Royal Society of Chemistry, Wake Forest, NC 27587, United States Many Computer-Assisted Structure Elucidation (CASE) applications focus on a structure generation process [1,2] while neglecting a crucial dereplication step. Structure dereplication is a pre-screening search to locate an identical structure or fragment, thus, speeding up the elucidation

of a “known unknown” compound, and potentially saving many hours of work. ACD/Structure Elucidator, a widely used CASE tool, already supports such dereplication methods through the use of internal databases and an available database from PubChem. A key collaboration of ACD/Labs and the Royal Society of Chemistry expands the ACD/Structure Elucidator tools to search across a ChemSpider library using MS and/or NMR data. This presentation will highlight the workflow, substructure filtering and the ranking process for structure identification. ChemSpider is a free chemical structure database of over 22,000,000 compounds, so this addition vastly expands the structure space which can be searched by this already useful CASE tool.2:40 - 146 - Faculty profiling and searching in the Eureka Research Workbench using VIVO and ScientistsDB Stuart Chalk1, schalk@unf.edu, Matthew Morse1, Israel Hurst1, Anthony Williams2, Valery Tkachenko2, Alexey Pshenichnov2. (1) Department of Chemistry, University of North Florida, Jacksonville, FL 32224, United States, (2) Royal Society of Chemistry, Wake Forest, NC 27587, United States The Eureka Research Workbench (http://eureka.sourceforge.net) is an online environment for capturing the scientific process currently under development. This presentation discusses the integration of the VIVO platform (http://vivoweb.org) and ScientistsDB (http://www.scientistsdb.com) for collaboration of scientists – extending the scope of Eureka outside of the faculty members research group. The new VIVO API is used to provided federated search of faculty profiles, identify related scientists, and subsequently extract recent publications and grants. Infobox metadata from ScientistsDB are searched using the

Chemical Information Bulletin, 2014, 66 (3) 131

Mediawiki API. Management of a faculty members VIVO/ScientistsDB profile information will also be discussed.

3:00 - 147 - Semantic enrichment of ChemSpider data: Usage and applications Valery Tkachenko, TkachenkoV@rsc.org, Royal Society of Chemistry, Wake Forest, NC 27587, United States ChemSpider is a free, online database for chemical information that is maintained by the Royal Society of Chemistry. Previously, ChemSpider data was only represented using HTML, a human-accessible format, with a small fraction of the data made accessible to machines via a mixture of web services (WSDL) and REST Web services. This reduced the potential for data integration, and restricted the ability of software developers to reuse ChemSpider data in their consumer applications. In this paper, we describe the enrichment of the ChemSpider database using Semantic Web technologies. We also present an exemplar consumer application that supports data discovery and visualisation. The ChemSpider data is given structure and semantics (meaning) using a suite of schemata and ontologies that are developed using RDF and OWL, and is exposed as Linked Data via dereferencable URIs and a SPARQL endpoint. As a larger fraction of the ChemSpider data is represented using machine-accessible formats, both the potential for data integration and the ability of programmers to develop consumer applications are greatly enhanced. The new system is also highly extensible, scalable and was designed to be a part of larger Linked Data federated systems.

Chemical Information Bulletin, 2014, 66 (3) 132

2014 CINF Officers and Functionaries

ChairJudith CurranoUniversity of Pennsylvaniacurrano@pobox.upenn.edu

Chair ElectRachelle BienstockNational Institute of EnvironmentalHealth Sciences

Past ChairAntony WilliamsRoyal Society of Chemistrywilliamsa@rsc.org

SecretaryLeah McEwenCornell Universitylrm1@cornell.edu

TreasurerRob McFarlandWashington Universityrmcfarland@wustl.edu

CouncilorBonnie Lawlorchescot@aol.com

CouncilorAndrea Twiss-BrooksUniversity of Chicagoatbrooks@uchicago.edu

Alternate CouncilorCharles HuberUniversity of California, Santa Barbarahuber@library.ucsb.edu

Alternate CouncilorGuenter GretheScientific Research Consultantggrethe@att.net

Archivist/HistorianBonnie LawlorSee Councilor

Audit Committee ChairTBD

Awards Committee ChairAndrea Twiss-BrooksSee Councilor

Careers Committee Co-ChairsPamela ScottPfizerpamela.j.scott@pfizer.com

Sue CardinalUniversity of Rochesterscardinal@library.rochester.edu

Communications and PublicationsCommittee ChairDavid MartinsenAmerican Chemical Societyd_martinsen@acs.org

Constitution, Bylaws & ProceduresSusanne RedaljeUniversity of Washingtoncurie@u.washington.edu

Chemical Information Bulletin, 2014, 66 (3) 133

Education Committee ChairGrace BaysingerStanford Universitygraceb@stanford.edu

Finance Committee ChairRob McFarlandSee Treasurer

Fundraising Committee ChairPhil HellerThieme Publishersphillip.heller@thieme.com

Membership Committee ChairGregory BanikBio-Rad Laboratories, Inc.gregory_banik@bio-rad.com

Nominating Committee ChairAntony Williamssee Past Chair

Program Committee ChairErin BolstadChemAxonerinbolstad@gmail.com

Tellers Committee ChairSusan Cardinalsee Careers Committee Chair

Chemical Information Bulletin EditorSummer and WinterSvetlana KorolevUniversity of Wisconsin, Milwaukeeskorolev@uwm.edu

Chemical Information Bulletin EditorFall and SpringVincent F. Scalfani The University of Alabamavfscalfani@ua.edu

Chemical Information Bulletin Assistant Editors

Teri VogelUC San Diego Librarytmvogel@ucsd.edu

David ShobePatent Information Agentavidshobe@yahoo.com

WebmasterDanielle DennieConcordia Universitydanielle.dennie@concordia.ca

Chemical Information Bulletin, 2014, 66 (3) 134

Articles and FeaturesJudith CurranoTeri VogelBonnie LawlorGrace BaysingerRobert E. BuntrockDonna T. WrublewskiPeter F. RuschHarry M. Allcock (deceased)

Sponsor InformationGraham DouglasPhil Heller

Technical ProgramDavid Martinsen

ProductionVincent F. ScalfaniTeri VogelDanielle DennieDavid MartinsenBonnie LawlorWendy Warr

Fall 2014 CINF Bulletin Contributors

Chemical Information Bulletin, 2014, 66 (3) 135

Schedule of Future ACS National Meetings

248th Aug. 10–14 2014 San Francisco, CA Chemistry and Global Stewardship

249th Mar. 22–26 2015 Denver, CO Chemistry of Natural Resources

250th Aug. 16–20 2015 Boston, MA Innovation from Discovery to Application

251st Mar. 13–17 2016 San Diego, CA Computers in Chemistry

252nd Aug. 21–25 2016 Philadelphia, PA Chemistry of the People, by the People, and for the People

253rd Apr. 2–6 2017 San Francisco, CA TBD

254th Aug. 20–24 2017 Washington, DC TBD

255th Mar. 18–22 2018 New Orleans, LA ״

256th Aug. 19–23 2018 Boston, MA ״

257th Mar. 31–Apr. 4 2019 Orlando, FL ״

258th Aug. 25–29 2019 San Diego, CA ״

259th Mar. 22–26 2020 Philadelphia, PA ״