title: Modeling bioconcentration factor (BCF) using mechanistically interpretable descriptors computed from open source tool "PaDEL-Descriptor".
abstract: Predictive regression-based models for bioconcentration factor (BCF) have been developed using mechanistically interpretable descriptors computed from open source tool PaDEL-Descriptor ( http://padel.nus.edu.sg/software/padeldescriptor/ ). A data set of 522 diverse chemicals has been used for this modeling study, and extended topochemical atom (ETA) indices developed by the present authors' group were chosen as the descriptors. Due to the importance of lipohilicity in modeling BCF, XLogP (computed partition coefficient) was also tried as an additional descriptor. Genetic function approximation followed by multiple linear regression algorithm was applied to select descriptors, and subsequent partial least squares analyses were performed to establish mathematical equations for BCF prediction. The model generated from only ETA indices shows importance of seven descriptors in model development, while the model generated from ETA descriptors along with XlogP shows importance of four descriptors in model development. In general, BCF depends on lipophilicity, presence of heteroatoms, presence of halogens, fused ring system, hydrogen bonding groups, etc. The developed models show excellent statistical qualities and predictive ability. The developed models were used also for prediction of an external data set available from the literature, and good quality of predictions (R (2) pred = 0.812 and 0.826) was demonstrated. Thus, BCF can be predicted using ETA and XlogP descriptors calculated from open source PaDEL-Descriptor software in the context of aquatic chemical toxicity management.
authors.affiliation: Drug Theoretics and Cheminformatics Laboratory, Division of Medicinal and Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Kolkata, 700 032, India.
authors.forename: Subrata
authors.initials: S
authors.lastname: Pramanik
authors.forename: Kunal
authors.initials: K
authors.lastname: Roy
mesh_terms: D020003:1-Octanol / Q000737:chemistry; D000465:Algorithms; D006860:Hydrogen Bonding; D016018:Least-Squares Analysis; D016014:Linear Models; D008962:Models, Theoretical; D011078:Polychlorinated Biphenyls / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D012984:Software; D014867:Water / Q000737:chemistry; D014874:Water Pollutants, Chemical / Q000737:chemistry*
chemical_list: D014874:Water Pollutants, Chemical; D014867:Water; D011078:Polychlorinated Biphenyls; D020003:1-Octanol