title: Plane of best fit: a novel method to characterize the three-dimensionality of molecules.
abstract: We describe a computational method, plane of best fit (PBF), to quantify and characterize the 3D character of molecules. This method is rapid and amenable to analysis of large diverse data sets. We compare PBF with alternative literature methods used to assess 3D character and apply the method to diverse data sets of fragment-like, drug-like, and natural product compound libraries. We show that exemplar fragment libraries underexploit the potential of 3D character in fragment-like chemical space and that drug-like molecules in the libraries examined are predominantly 2D in character.
authors.affiliation: Cancer Research UK Cancer Therapeutics Unit, Division of Cancer Therapeutics, The Institute of Cancer Research, 15 Cotswold Road, Sutton, Surrey, SM2 5NG, UK.
authors.forename: Nicholas C
authors.initials: NC
authors.lastname: Firth
authors.forename: Nathan
authors.initials: N
authors.lastname: Brown
authors.forename: Julian
authors.initials: J
authors.lastname: Blagg
mesh_terms: D000465:Algorithms; D001688:Biological Products / Q000737:chemistry*; D062126:Databases, Chemical; D062313:Databases, Pharmaceutical; D015195:Drug Design; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D054852:Small Molecule Libraries / Q000737:chemistry*
chemical_list: D001688:Biological Products; D054852:Small Molecule Libraries