Three-dimensional quantitative structure–activity relationship study for phenylsulfonyl carboxylates using CoMFA and CoMSIA

Abstract

From both the comparative molecular field analysis (CoMFA) and the comparative molecular similarity indices analysis (CoMSIA), the paper describes two three-dimensional quantitative structure–activity relationship (3D-QSAR) models for the acute toxicity logEC 50 (15 min-EC 50 in μmol l −1) of 56 phenylsulfonyl carboxylates on Photobacterium phosphoreum. Two models yield the leave-one-out cross-validated correlation coefficient q 2 values of 0.823 and 0.713, and the conventional correlation coefficient r 2 values of 0.958 and 0.933, respectively. The achievement of higher q 2 and r 2 values of CoMFA model indicates the significance of correlation of steric and electrostatic fields with biological activities. The key features in the CoMFA contour maps are critical to trace the important properties and gain insight into the toxic mechanism of tested compounds. The quality of CoMSIA model is slightly lower than that of CoMFA in terms of q 2 and r 2 values. Not requiring molecular superposition, CoMSIA is faster than CoMFA in data processing.