The Oxo‐ and Hydroxyimidazoles and their Sulfur Analogues

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 left harpoon over right harpoon 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 pK(a) based-method that utilizes pK(a) values predicted by MoKa. Predicted tautomeric ratios based on pK(a) 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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The Oxo‐ and Hydroxyimidazoles and their Sulfur Analogues

Cited by 2 publications

References 101 publications

Synthesis and photocyclization of some 4‐(5)arylethenylimidazoles

Synthesis and photocyclization of some 4‐(5)arylethenylimidazoles

Tautomer Enumeration and Stability Prediction for Virtual Screening on Large Chemical Databases

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