QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES

A. A. Toropov, A. P. Toropova, I. Raska

Research output: Contribution to journalArticlepeer-review

Abstract

Simplified molecular input line entry system (SMILES) has been utilized in constructing quantitative structure-property relationships (QSPR) for octanol/water partition coefficient of vitamins and organic compounds of different classes by optimal descriptors. Statistical characteristics of the best model (vitamins) are the following: n = 17, R2 = 0.9841, s = 0.634, F = 931 (training set); n = 7, R2 = 0.9928, s = 0.773, F = 690 (test set). Using this approach for modeling octanol/water partition coefficient for a set of organic compounds gives a model that is statistically characterized by n = 69, R2 = 0.9872, s = 0.156, F = 5184 (training set) and n = 70, R2 = 0.9841, s = 0.179, F = 4195 (test set).

Original languageEnglish
Pages (from-to)714-740
Number of pages27
JournalEuropean Journal of Medicinal Chemistry
Volume43
Issue number4
DOIs
Publication statusPublished - Apr 2008

Keywords

  • Octanol/water partition coefficient
  • QSPR
  • SMILES
  • Vitamins

ASJC Scopus subject areas

  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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