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

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.

Privileged Structures - Dream or Reality: Preferential Organization of Azanaphthalene Scaffold

“…Typically, the screening procedure takes into account the entire structure or substructure as a search query for identifying the ensemble of compounds fulfilling the global similarity criteria. Substructure or pharmacophore searching in a database locates all of the compounds that share a common user-defined pattern of atoms or bonds in a specified topological or geometric arrangement [177,178]. The algorithms that are essential for the threedimensional substructural moiety specification are mainly based on subgraph-matching techniques [179].…”