Premium
Batch tautomer generation with MolTPC
Author(s) -
Will Thorsten,
Hutter Michael C.,
Jauch Johann,
Helms Volkhard
Publication year - 2013
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.23397
Subject(s) - tautomer , ring (chemistry) , computer science , chain (unit) , software , limit (mathematics) , enumeration , chemistry , computational chemistry , algorithm , mathematics , stereochemistry , physics , discrete mathematics , quantum mechanics , programming language , mathematical analysis , organic chemistry
Besides all their conformational degrees of freedom, drug‐like molecules and natural products often also undergo tautomeric interconversions. Compared to the huge efforts made in experimental investigation of tautomerism, open and free algorithmic solutions for prototropic tautomer generation are surprisingly rare. The few freely available software packages limit their output to a subset of the possible configurational space by sometimes unwanted prior assumptions and complete neglection of ring‐chain tautomerism. Here, we describe an adjustable fully automatic tautomer enumeration approach, which is freely available and also incorporates the detection of ring‐chain variants. The algorithm is implemented in the MolTPC framework and accessible on SourceForge. © 2013 Wiley Periodicals, Inc.