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      ClogP(alk): a method for predicting alkane/water partition coefficient.

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          Abstract

          Alkane/water partition coefficients (P(alk)) are less familiar to the molecular design community than their 1-octanol/water equivalents and access to both data and prediction tools is much more limited. A method for predicting alkane/water partition coefficient from molecular structure is introduced. The basis for the ClogP(alk) model is the strong (R² = 0.987) relationship between alkane/water partition coefficient and molecular surface area (MSA) that was observed for saturated hydrocarbons. The model treats a molecule as a perturbation of a saturated hydrocarbon molecule with the same MSA and uses increments defined for functional groups to quantify the extent to which logP(alk) is perturbed by the introduction each functional group. Interactions between functional groups, such as intramolecular hydrogen bonds are also parameterized within a perturbation framework. The functional groups and interactions between them are specified substructurally in a transparent and reproducible manner using SMARTS notation. The ClogP(alk) model was parameterized using data measured for structurally prototypical compounds that dominate the literature on alkane/water partition coefficients and then validated using an external test set of 100 alkane/water logP measurements, the majority of which were for drugs.

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          Author and article information

          Journal
          J. Comput. Aided Mol. Des.
          Journal of computer-aided molecular design
          Springer Nature
          1573-4951
          0920-654X
          May 2013
          : 27
          : 5
          Affiliations
          [1 ] Grupo de Estudos em Química Medicinal, NEQUIMED, Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador Sancarlense 400, São Carlos, SP 13560-590, Brazil. pwk.pub.2008@gmail.com
          Article
          10.1007/s10822-013-9655-5
          23737238

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