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Issue 3, 2012
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A comparative analysis of the molecular topologies for drugs, clinical candidates, natural products, human metabolites and general bioactive compounds

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Abstract

Natural Products (NPs) and their subset Human Metabolites (HMs) are synthesized in living organisms and, due to their biogenic nature, can be used as starting points for drug discovery projects as well as a source of inspiration for designing new chemical libraries. It is therefore of interest to characterize NPs and HMs in relation to other types of molecules relevant for drug discovery. In this study, a comparative analysis of the molecular topologies was carried out for NPs, HMs, drugs from different time periods, clinical candidates and general bioactive compounds. It is shown that the NP and HM sets have the highest percentage of compounds with only one ring system. NPs have also the highest Ring System Complexity (RSC) of the compared datasets, while general bioactive compounds have the largest number of ring systems. The difference in molecular topology between the datasets is independent of the molecular size and lipophilicity. Further analysis of topological descriptors shows that NPs and HMs have a larger proportion of side chain atoms in relation to their size and have a higher proportion of aliphatic carbons (indicating a more three-dimensional shape) than compounds from the other sets.

Graphical abstract: A comparative analysis of the molecular topologies for drugs, clinical candidates, natural products, human metabolites and general bioactive compounds

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Publication details

The article was received on 16 Sep 2011, accepted on 30 Nov 2011 and first published on 01 Dec 2011


Article type: Concise Article
DOI: 10.1039/C2MD00238H
Med. Chem. Commun., 2012,3, 312-321

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    A comparative analysis of the molecular topologies for drugs, clinical candidates, natural products, human metabolites and general bioactive compounds

    H. Chen, O. Engkvist, N. Blomberg and J. Li, Med. Chem. Commun., 2012, 3, 312
    DOI: 10.1039/C2MD00238H

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