title: Discovering H-bonding rules in crystals with inductive logic programming.
abstract: In the domain of crystal engineering, various schemes have been proposed for the classification of hydrogen bonding (H-bonding) patterns observed in 3D crystal structures. In this study, the aim is to complement these schemes with rules that predict H-bonding in crystals from 2D structural information only. Modern computational power and the advances in inductive logic programming (ILP) can now provide computational chemistry with the opportunity for extracting structure-specific rules from large databases that can be incorporated into expert systems. ILP technology is here applied to H-bonding in crystals to develop a self-extracting expert system utilizing data in the Cambridge Structural Database of small molecule crystal structures. A clear increase in performance was observed when the ILP system DMax was allowed to refer to the local structural environment of the possible H-bond donor/acceptor pairs. This ability distinguishes ILP from more traditional approaches that build rules on the basis of global molecular properties.
authors.affiliation: Research Formulations, Pfizer Global Research and Development, Ann Arbor Laboratories, Ann Arbor, Michigan 48105, USA. Howard.Ando@Pfizer.com
authors.forename: Howard Y
authors.initials: HY
authors.lastname: Ando
authors.forename: Luc
authors.initials: L
authors.lastname: Dehaspe
authors.forename: Walter
authors.initials: W
authors.lastname: Luyten
authors.forename: Elke
authors.initials: E
authors.lastname: Van Craenenbroeck
authors.forename: Henk
authors.initials: H
authors.lastname: Vandecasteele
authors.forename: Luc
authors.initials: L
authors.lastname: Van Meervelt
mesh_terms: D001185:Artificial Intelligence; D003198:Computer Simulation; D003460:Crystallization; D003663:Decision Trees; D015195:Drug Design; D001330:Electronic Data Processing; D005544:Forecasting; D006860:Hydrogen Bonding; D008954:Models, Biological; D008968:Molecular Conformation; D015394:Molecular Structure; D012984:Software