title: Properties of known drugs. 2. Side chains.
abstract: We continue our study of the common features present in drug molecules by looking in detail at drug side chains. Using shape description methods, we divide a database of commercially available drugs into a list of common drug side chains. On the basis of the atom pair shape descriptor (taking into account atom type, hybridization, and bond order), there are 1,246 different side chains among the 5,090 compounds analyzed. The average number of side chains per molecule is 4, and the average number of heavy atoms per side chain is 2. If we ignore the carbonyl side chain, then there are approximately 15,000 occurrences of side chains. Of these 15,000 approximately 11,000 are from the "top 20" group of side chains. This suggests that the diversity that side chains provide to drug molecules is quite low. We discuss ways that this work could be used to provide guidance for molecular design efforts.
authors.affiliation: Vertex Pharmaceuticals, 130 Waverly Street, Cambridge, Massachusetts 02139-4242, USA.
authors.forename: G W
authors.initials: GW
authors.lastname: Bemis
authors.forename: M A
authors.initials: MA
authors.lastname: Murcko
mesh_terms: D002626:Chemistry, Pharmaceutical; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry*
chemical_list: D004364:Pharmaceutical Preparations