Standardizer Molecular Cosmetics for Chemoinformatics György Pirok Java Solutions for...
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Transcript of Standardizer Molecular Cosmetics for Chemoinformatics György Pirok Java Solutions for...
Standardizer
Molecular Cosmetics for Chemoinformatics
György Pirok
Java Solutions for Cheminformatics
Why standardize structures?
Canonicalisation Uniformization of structures without changing the chemical content to
recognize duplicates, functional groups (aromatization, mesomers, tautomers, ... )
Beautification Making the structures visually more attractive (dearomatization,
cleaning coordinates, wedge orientation, ... )
Modification Conversion of structures by modifying its original content as a
preparation step for further chemoinformatics tasks (transformations, removing stereo, removing R-groups, ...).
Canonicalisation
making hydrogens explicit
converting to canonical mesomer form
transforming to user defined mesomer form
Hydrogens
aromatizing Kekülé rings
Resonant structures
converting to canonical tautomer form
removing user defined fragments
transforming to user defined tautomer form
Tautomers
expanding stoichiometry
Other
removing small fragments
making hydrogens implicit
setting the chiralflag
Mesomers
Tautomersoxo-enol, enamine-imine
Fragment removal
Specific counterion removal
Solvent removal
Beautification
calculating 2D coordinates
Hydrogens
converting aromaticrings to Kekülé format
Resonant structures
making hydrogens implicit
Cleaning
reallocating wedge bonds
contracting/expanding/ungrouping abbreviated and multiple groups
Groups
template based cleaning
3D geometry optimization
Template-based Cleaning2D-coordinate calculation of macrocycles or bridged systems
query
Template-based Cleaningorienting search results to the query
client
Canonicalization During Database Import
RelationalDatabase
input structures
canonicalization configuration original structurescanonicalized structures
server
StandardizerJChem Base/ Cartridge
client
Sending Query to the Database
RelationalDatabase
serverquery structure
canonicalization configuration canonicalized queryquery is compared
to the canonicalized structures
StandardizerJChem Base/ Cartridge
Displaying Result Structures
RelationalDatabase
original structures
serverclient
beautification configuration
beautified structures
StandardizerJChem Base/ Cartridge
Modification
custom transformations+
API and command line interface
Standardizer st = new Standardizer(new File("standardize.xml"));st.standardize(mol);
standardize input.sdf -c config.xml -o output.smiles
Standardizer GUI
Applications: Virtual Synthesis
Applications: Structure Databases
Acknowledments
Ferenc Csizmadia Nóra Máté István Cseh Szabó Attila Alex Allardyce Szilárd Dóránt Péter Kovács Szabolcs Csepregi
Java Solutions for Cheminformatics