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

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

Journal Name: Combinatorial Chemistry & High Throughput Screening

Volume 14 , Issue 7 , 2011

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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.

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

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Article Details

Year: 2011
Page: [560 - 569]
Pages: 10
DOI: 10.2174/138620711796367193
Price: $58

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