title: Three-dimensional hydrogen-bond geometry and probability information from a crystal survey.
abstract: An extensive crystal survey of the Cambridge Structural Database has been carried out to provide hydrogen-bond data for use in drug-design strategies. Previous crystal surveys have generated 1D frequency distributions of hydrogen-bond distances and angles, which are not sufficient to model the hydrogen bond as a ligand-receptor interaction. For each hydrogen-bonding group of interest to the drug designer, geometric hydrogen-bond criteria have been derived. The 3D distribution of complementary atoms about each hydrogen-bonding group has been ascertained by dividing the space about each group into bins of equal volume and counting the number of observed hydrogen-bonding contacts in each bin. Finally, the propensity of each group to form a hydrogen bond has been calculated. Together, these data can be used to predict the potential site points with which a ligand could interact and therefore could be used in molecular-similarity studies, pharmacophore query searching of databases, or de novo design algorithms.
authors.affiliation: Department of Pharmacology, University of Cambridge, U.K.
authors.forename: J E
authors.initials: JE
authors.lastname: Mills
authors.forename: P M
authors.initials: PM
authors.lastname: Dean
mesh_terms: D018360:Crystallography, X-Ray; D016208:Databases, Factual; D015195:Drug Design; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011336:Probability