Numerical Characterization of Molecular Chirality of Organic Compounds

Abstract

In 2006, 80% of the small molecule drugs approved by Food and Drug Administration (FDA) of USA were chiral and 75% were single enantiomers. It is expected that 200 chiral compounds could enter the development process every year. In order to keep pace with the industry, computational chemists are trying to develop chirality measures to assist and direct asymmetric synthesis and chiral catalysis. Parameterization of chirality and development of chirality metrics, are very important in QSAR approach to be applied to chiral molecules. There are several attempts in the development of chirality measurements and earlier reviews on chirality measures concentrated more on the mathematics involved in their calculations. This review presents in-depth discussions of various chirality measures from the perspective of a QSAR modeler. Keywords: Chirality, chirality measures, chirality index, enantiomers, diastereoisomers, quantitative structure-activity relationship