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

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.

Experimental and theoretical studies on the molecular properties of ciprofloxacin, norfloxacin, pefloxacin, sparfloxacin, and gatifloxacin in determining bioavailability

“…It is worth mentioning that atomic-contribution methods do not take correction factors into account [16, 20–23]. …”

Exploring the RC-106 Chemical Space: Design and Synthesis of Novel (E)-1-(3-Arylbut-2-en-1-yl)-4-(Substituted) Piperazine Derivatives as Potential Anticancer Agents

“…For each compound, water solubility and lipophilicity were predicted with the SwissADME web tool (Daina et al, 2017 ), which allows to compare the outputs of different computational methods. In detail, five freely available predictive models are employed in SwissADME to estimate log P O/W (i.e., XLOGP3 (Cheng et al, 2007 ), WLOGP (Wildman and Crippen, 1999 ), MLOGP (Souza et al, 2011 ), SILICOS-IT (“Silicos-It | Filter-It™” n.d. 2 ), and iLOGP Daina et al, 2014 ), and the consensus log P O/W is calculated as the arithmetic mean of the values derived from these methods. On the other hand, three different models used to predict water solubility: the ESOL model (Delaney, 2004 ), an adaptation of the one developed by Ali et al ( 2012 ) and the one by SILICOS-IT (“Silicos-It | Filter-It™” n.d.).…”

Computational prediction of octanol–water partition coefficient based on the extended solvent-contact model

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