There is an increase in the number of chiral molecules coming into pharmaceutical, agrochemical and fragrance industry and this is due to the advancement in chiral synthetic methods using biocatalysts, and separation technology. However, the impetus in the synthesis of enantiopure drugs may partly be attributed to regulatory policies for chiral pharmaceuticals. Enantiomers and diastereomers collectively the stereoisomers have difference in bio-efficacy, adsorption, metabolism, degradation, and toxicity. In the case of achiral molecules, most of these properties have been modelled by quantitative structure–activity relationship QSAR approach using molecular descriptors that encode various features of the molecules. However, extension of this approach to stereoisomers is not possible with the conventional molecular descriptors as these descriptors have the same numerical values for stereoisomers, that is the conventional molecular descriptors are incapable of differentiating stereoisomers. In order to overcome this limitation several attempts have been taken in developing descriptors that differentiate stereoisomers namely enantiomers and diastereomers. Chirality about carbon atom(s) being the cause for the stereoisomerism these descriptors are mostly called chirality descriptors and the approach is called as numerical characterization of molecular chirality. These descriptors are expected to play a role not only in developing predictive models for the biological and toxicological properties of the chiral molecules but also assist in identifying new molecules for chiral synthesis. This chapter reviews the various chirality descriptors developed to model the bioactivities of chiral molecules.