Sphericity and oblate-prolate indices: 3D shape descriptors for fast shape comparison
Sunghwan Kim, email@example.com, Evan Bolton, firstname.lastname@example.org, and Stephen H. Bryant, email@example.com, National Center for Biotechnology Information, National Institutes of Health, 8600 Rockville Pike, Bethesda, MD 20894
If molecules are structurally similar to each other, they are likely to have similar biological and physicochemical properties. This so-called "similarity principle" is an important concept in ration drug design, which is applied to find potential drug candidates at the initial stage of drug discovery and development. Although the shape-Tanimoto (ST) value between two molecules is considered to be an accurate measure for 3-dimensional (3D) molecular shape comparison, the ST value computation is not fast enough to screen a huge molecular library which typically contains more than billions of conformers. In the present study, the shape quadrupole moments of a molecule were used to devise two 3D shape descriptors (the sphericity index and the oblate-prolate index) that allow a simple and fast shape comparison between molecules.