QSPR modeling of octanol-water partition coefficient and organic carbon normalized sorption coefficient of diverse organic chemicals using Extended Topochemical Atom (ETA) indices.

ABSTRACT

Octanol-water partition coefficient (logKow) and soil organic carbon content normalized sorption coefficient (logKoc) values are two important physicochemical properties in the context of bioaccumulation and environmental fate of organic compounds and their environmental risk assessment. Simple, interpretable and easy-to-derive extended topochemical atom (ETA) indices obtained from 2D structural representation of compounds were used for quantitative structure-property relationship (QSPR) modeling of these two endpoints. Linear regression based models developed using only ETA indices show encouraging statistical and validation results. Based on the information obtained from developed QSPR models, we may conclude that molecular volume, branching pattern, presence of hydrophobic Cl atoms, cyclicity/fusion, polar environment, electron density, unsaturation content, hydrogen bonding propensity or hydrogen bond donor atoms, local topology, presence of heteroatoms and aromaticity are crucial factors in controlling the logKow and logKoc values of the compounds. The suggested explanatory features for different classes of chemicals or the whole diverse set can help in safer designing of chemicals, which is one of the primary agenda of the "Green Chemistry" program.