Ij. Bruno et al., ISOSTAR - A LIBRARY OF INFORMATION ABOUT NONBONDED INTERACTIONS, Journal of computer-aided molecular design, 11(6), 1997, pp. 525-537
Crystallographic and theoretical tab initio) data on intermolecular no
nbonded interactions have been gathered together in a computerised lib
rary ('IsoStar'). The library contains information about the nonbonded
contacts formed by some 250 chemical groupings. The data can be displ
ayed visually-and used to aid protein-ligand docking or the identifica
tion of bioisosteric 'replacements. Data from the library show that th
ere is great variability in the geometrical preferences of different t
ypes of hydrogen bonds, although in general there is a tendency for H-
bonds to form along lone-pair directions. The H-bond acceptor abilitie
s of oxygen and sulphur atoms are highly dependent on intramolecular e
nvironments. The nonbonded contacts formed by many hydrophobic groups
show surprisingly strong directional preferences. Many unusual nonbond
ed interactions are to be found in the library-and are of potential va
lue for designing novel biologically active molecules.