Quantitative structure-activity relationships of structurally similar odorless and odoriferous benzenoid musks

Abstract

To reveal the difference of molecular property between structurally similar odorless and odoriferous musk compounds, 10 pairs of benzenoids (monocyclic-, dicyclic- and tricyclic-) were examined. Molecular structures of all compounds were optimized by MNDO (modified neglect of diatomic differential overlap) considering conformation. Parameters effective in discriminating two groups, group A of 10 odorless compounds and group B of 10 musk odor compounds, were searched from 34 candidate parameters by adaptive least squares. The best three parameters found were log P value (octanol/water partition coefficient), the longest side length of hexahedron circumscribing a molecule, and the parameter which expresses structural hindrance to the functional group when a molecule approaches the receptor site. The two groups of compounds were completely discriminated using these three parameters.