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Tautomer Enumeration and Stability Prediction for Virtual Screening on Large Chemical Databases
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Molecular Discovery Limited.
, §Università degli Studi di Perugia.
Abstract
Tautomeric rearrangements affect the results of cheminformatics applications that depend on the knowledge of the 2D or 3D structure of a compound, such as tools for database searches, fingerprint generation, virtual screening, and physical-chemical properties prediction. In this paper we present TauThor, a tool to enumerate tautomers and predict tautomer stability in the aqueous medium. The enumeration is based on a recursive process that generates tautomers according to the general scheme HX-Y=Z 
X=Y-ZH. The stability of a tautomer is calculated by using a library of 145 fragments associated with experimental tautomeric percentages in water and a pKa based-method that utilizes pKa values predicted by MoKa. Predicted tautomeric ratios based on pKa calculations were benchmarked against literature data for a set of eleven compounds. The FDA approved drugs database, the NCI database and two vendor databases - Specs Screening Library and Asinex Gold Collection - were used to illustrate the impact of tautomerism on chemical libraries and to evaluate the relative occurrences of alternative tautomeric forms.
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History
- Published In Issue January 26, 2009
- Article ASAPJanuary 06, 2009
- Received: September 18, 2008
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