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Int. J. Mol. Sci. 2015, 16(6), 12891-12906;

Quantitative Structure-Antioxidant Activity Models of Isoflavonoids: A Theoretical Study

Departamento de Ciencias Experimentales y Matemáticas, Facultad de Veterinaria y Ciencias Experimentales, Universidad Católica de Valencia San Vicente Mártir, Guillem de Castro-94, E 46001 València, Spain
Institut Universitari de Ciència Molecular, Universitat de València, Edifici d’Instituts de Paterna, P. O. Box 22085, E 46071 València, Spain
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Academic Editor: Paula Andrade
Received: 20 May 2015 / Revised: 1 June 2015 / Accepted: 3 June 2015 / Published: 8 June 2015
(This article belongs to the Special Issue Phenolics and Polyphenolics 2015)
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Seventeen isoflavonoids from isoflavone, isoflavanone and isoflavan classes are selected from Dalbergia parviflora. The ChEMBL database is representative from these molecules, most of which result highly drug-like. Binary rules appear risky for the selection of compounds with high antioxidant capacity in complementary xanthine/xanthine oxidase, ORAC, and DPPH model assays. Isoflavonoid structure-activity analysis shows the most important properties (log P, log D, pKa, QED, PSA, NH + OH ≈ HBD, N + O ≈ HBA). Some descriptors (PSA, HBD) are detected as more important than others (size measure Mw, HBA). Linear and nonlinear models of antioxidant potency are obtained. Weak nonlinear relationships appear between log P, etc. and antioxidant activity. The different capacity trends for the three complementary assays are explained. Isoflavonoids potency depends on the chemical form that determines their solubility. Results from isoflavonoids analysis will be useful for activity prediction of new sets of flavones and to design drugs with antioxidant capacity, which will prove beneficial for health with implications for antiageing therapy. View Full-Text
Keywords: antioxidant; structure-activity relationship; absorption; QSAR; ADMET; poor absorption or permeation antioxidant; structure-activity relationship; absorption; QSAR; ADMET; poor absorption or permeation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Castellano, G.; Torrens, F. Quantitative Structure-Antioxidant Activity Models of Isoflavonoids: A Theoretical Study. Int. J. Mol. Sci. 2015, 16, 12891-12906.

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