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Int. J. Mol. Sci. 2011, 12(10), 7250-7264; doi:10.3390/ijms12107250
Article

Estimating the Octanol/Water Partition Coefficient for Aliphatic Organic Compounds Using Semi-Empirical Electrotopological Index

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Received: 8 September 2011 / Revised: 8 October 2011 / Accepted: 14 October 2011 / Published: 24 October 2011
(This article belongs to the Special Issue Advances in Molecular Electronic Structure Calculations)
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Abstract

A new possibility for estimating the octanol/water coefficient (log P) was investigated using only one descriptor, the semi-empirical electrotopological index (ISET). The predictability of four octanol/water partition coefficient (log P) calculation models was compared using a set of 131 aliphatic organic compounds from five different classes. Log P values were calculated employing atomic-contribution methods, as in the Ghose/Crippen approach and its later refinement, AlogP; using fragmental methods through the ClogP method; and employing an approach considering the whole molecule using topological indices with the MlogP method. The efficiency and the applicability of the ISET in terms of calculating log P were demonstrated through good statistical quality (r > 0.99; s < 0.18), high internal stability and good predictive ability for an external group of compounds in the same order as the widely used models based on the fragmental method, ClogP, and the atomic contribution method, AlogP, which are among the most used methods of predicting log P.
Keywords: quantitative structure-property relationship; n-octanol-water partition coefficient; semi-empirical electrotopological index quantitative structure-property relationship; n-octanol-water partition coefficient; semi-empirical electrotopological index
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Souza, E.S.; Zaramello, L.; Kuhnen, C.A.; Junkes, B.S.; Yunes, R.A.; Heinzen, V.E.F. Estimating the Octanol/Water Partition Coefficient for Aliphatic Organic Compounds Using Semi-Empirical Electrotopological Index. Int. J. Mol. Sci. 2011, 12, 7250-7264.

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