QSAR modeling of algal low level toxicity values of different phenol and aniline derivatives using 2D descriptors

Abstract

The deposition of different types of phenol and aniline derivatives in the aquatic environment leads to toxicity to living organisms. Under such condition, evaluation of these toxicants is very much important. Due to non-availability of sufficient experimental data as well as sufficient number of Quantitative Structure-Activity Relationship (QSAR) models for the low level toxicity values for such pollutants, we have employed here the partial least squares (PLS) regression for the development of robust and predictive QSAR models using low level toxicity values against algal species. Here, we have used both Extended Topochemical Atom (ETA) and non-ETA indices as 2D descriptors for model development. The statistical validation parameters ensure the robustness and the predictivity of the developed models. From the insights of the final PLS models, it can be concluded that presence of nitro groups (in the ortho position to phenolic hydroxyl group increasing intramolecular hydrogen bonding capacity), presence of chlorine substituents (influencing lipophilicity) especially at the para position, oxygen and nitrogen at the topological distance three, aliphatic side chain (contributing to hydrophobicity), molecules with large size atoms and higher molecular bulk will increase the toxicity towards the algal species. On the other hand, the phenol ring without any substituent or with a polar substituent (like amino group), presence of chlorine at ortho-ortho or ortho-para position, absence of nitro group, presence of chlorine and oxygen at the topological distance three, presence of lower number of aliphatic groups will decrease the toxic effect towards the algal species.