QSAR modeling of anxiolytic activity taking into account the presence of keto- and enol-tautomers by balance of correlations with ideal slopes

Alla P. Toropova, Andrey A. Toropov, Emilio Benfenati, Giuseppina Gini, Danuta Leszczynska, Jerzy Leszczynski

Research output: Contribution to journalArticle

Abstract

Optimal descriptors calculated with simplified molecular input line entry system (SMILES) have been examined as a tool for prediction of anxiolytic activity. Descriptors calculated with SMILES (a) of keto-isomers; (b) of enol-isomers; and (c) of both keto-isomers together with enol-isomers have been studied. Three approaches have been compared: 1. classic 'training-test' system 2. balance of correlations and 3. balance of correlations with ideal slopes. The best statistical characteristics for the external validation set took place for optimal descriptors calculated with SMILES of both keto-form and enol-form (i.e., molecular structure was represented in the format: 'SMILES of keto-form . SMILES of enol-form') by means of balance of correlations with ideal slopes. The predictive potential of this model was checked with three random splits.

Original languageEnglish
Pages (from-to)846-854
Number of pages9
JournalCentral European Journal of Chemistry
Volume9
Issue number5
DOIs
Publication statusPublished - Oct 2011

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Keywords

  • Anxiolytic activity
  • Balance of correlation
  • QSAR
  • SMILES
  • Tautomerism

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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