Molecular Descriptors from Two-Dimensional Chemical Structure

Abstract

This chapter presents a review of whole-molecule descriptors obtained from two-dimensional chemical structure. The sections include a short overview of the mathematical foundation (graph theory) that is behind the calculation of topological descriptors. A concise overview, together with practical calculated examples, is provided for major classes of 2-D descriptors, including topological indices, information content descriptors, electrotopological descriptors, and autocorrelation descriptors. Numerous examples of their practical use in QSAR modelling are presented. The examples are dedicated to in silico toxicology modelling applications, including toxicities towards Pimephales promelas, Tetrahymena pyriformis, Daphnia magna, Vibrio fischeri, Chlorella vulgaris, rodents and humans. Also the role of 2-D descriptors in the modelling of soil sorption coefficients is presented. Emphasis is given to the interpretation of topological descriptors in QSAR models. Finally, a state-of-the art overview of available applications for the calculation of molecular descriptors is given together with an extensive bibliography of the relevant literature.