Molecular Descriptors in Chemoinformatics, Computational Combinatorial Chemistry, and Virtual Screening

Abstract

Many contemporary applications in computer-aided drug discovery and chemoinformatics depend on representations of molecules by descriptors that capture their structural characteristics and properties. Such applications include, among others, diversity analysis, library design, and virtual screening. Hundreds of molecular descriptors have been reported in the literature, ranging from simple bulk properties to elaborate three-dimensional formulations and complex molecular fingerprints, which sometimes consist of thousands of bit positions. Knowledge-based selection of descriptors that are suitable for specific applications is an important task in chemoinformatics research. If descriptors are to be selected on rational grounds, rather than guesses or chemical intuition, detailed evaluation of their performance is required. A number of studies have been reported that investigate the performance of molecular descriptors in specific applications and/or introduce novel types of descriptors. Progress made in this area is reviewed here in the context of other computational developments in combinatorial chemistry and compound screening.