genistein   Click here for help

GtoPdb Ligand ID: 2826

Synonyms: 5,7,4'-trihydroxyisoflavone
PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 90.9
Molecular weight 270.05
XLogP 3.33
No. Lipinski's rules broken 0
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Canonical SMILES Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
Isomeric SMILES Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
InChI InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
1. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
2. Nowak S, Di Pizio A, Levit A, Niv MY, Meyerhof W, Behrens M. (2018)
Reengineering the ligand sensitivity of the broadly tuned human bitter taste receptor TAS2R14.
Biochim Biophys Acta Gen Subj, 1862 (10): 2162-2173. [PMID:30009876]
3. Roland WS, Vincken JP, Gouka RJ, van Buren L, Gruppen H, Smit G. (2011)
Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39.
J Agric Food Chem, 59 (21): 11764-71. [PMID:21942422]
4. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S. (2003)
Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.
Mol Cancer Res, 1 (13): 981-91. [PMID:14638870]
5. Verkman AS, Galietta LJ. (2009)
Chloride channels as drug targets.
Nat Rev Drug Discov, 8 (2): 153-71. [PMID:19153558]
6. Wong CO, Huang Y, Yao X. (2010)
Genistein potentiates activity of the cation channel TRPC5 independently of tyrosine kinases.
Br J Pharmacol, 159 (7): 1486-96. [PMID:20233211]