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

A. A. Toropov; A. P. Toropova; I. Raska

doi:10.1016/j.ejmech.2007.05.007

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

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

Istituto di Ricerche Farmacologiche "Mario Negri"

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	714-740
Number of pages	27
Journal	European Journal of Medicinal Chemistry
Volume	43
Issue number	4
DOIs	https://doi.org/10.1016/j.ejmech.2007.05.007
Publication status	Published - 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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title = "QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES",

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).",

keywords = "Octanol/water partition coefficient, QSPR, SMILES, Vitamins",

author = "Toropov, {A. A.} and Toropova, {A. P.} and I. Raska",

year = "2008",

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AU - Toropov, A. A.

AU - Toropova, A. P.

AU - Raska, I.

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N2 - 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).

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