Mapping Fragmental Drug-Likeness in the MoStBioDat Environment:Intramolecular Hydrogen Bonding Motifs in β-Ketoenols

Title: Mapping Fragmental Drug-Likeness in the MoStBioDat Environment:Intramolecular Hydrogen Bonding Motifs in β-Ketoenols

Volume: 14 Issue: 7

Author(s): Andrzej Bak, Tomasz Magdziarz, Agata Kurczyk and Jaroslaw Polanski

Affiliation:

Keywords: Virtual ligand screening, β-ketoenols, intramolecular hydrogen bonding, Drug, MoStBioDat, ligand-receptor, difunctional building, database, Bioactive Molecule, Chemical Space

Abstract: A detailed knowledge of hydrogen bond geometry and its directional preferences is vital for in silico investigations of the ligand-receptor short-range non-covalent interactions. The spatial arrangement of the carbonyl and hydroxyl groups seems to determine the capability of β-ketoenol derivatives to recognize the surrounding environment by forming inter- and intra-molecular hydrogen bonds (IHB). In the current study we examined the application of the MoStBioDat platform for a massive database screening of the IHB motifs in β-ketoenol subunits (O=C – C=C – OH). Then, the virtual 3D structural data derived from ZINC and PubChem repository were compared to the experimentally determined CSD data. Differences specific for each database were discovered, which indicated inaccuracies in the simulated data.

Cite this article as:

Bak Andrzej, Magdziarz Tomasz, Kurczyk Agata and Polanski Jaroslaw, Mapping Fragmental Drug-Likeness in the MoStBioDat Environment:Intramolecular Hydrogen Bonding Motifs in β-Ketoenols, Combinatorial Chemistry & High Throughput Screening 2011; 14 (7) . https://dx.doi.org/10.2174/138620711796367193