liquiritigenin   Click here for help

GtoPdb Ligand ID: 8899

Immunopharmacology Ligand
Comment: Liquiritigenin is a selective estrogen receptor β agonist isolated from the root of Glycyrrhizae uralensis Fisch (a type of Chinese liquorice) [1]. We show the structure without specified stereochemistry.
The compound exhibits anti-inflammatory actions [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 66.76
Molecular weight 256.07
XLogP 2.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2)O
Isomeric SMILES Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2)O
InChI InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2
InChI Key FURUXTVZLHCCNA-UHFFFAOYSA-N
Bioactivity Comments
Displays 20-fold selectivity for ERβ over ERα and does not activate other nuclear receptors, including the androgen and glucocorticoid receptors [1].
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM3 Hs Channel blocker - 5.2 pIC50 - 2
pIC50 5.2 [2]
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Estrogen receptor-β Hs Agonist Agonist 7.4 pEC50 - 1
pEC50 7.4 (EC50 3.65x10-8 M) [1]
Description: Measuring activation of the ERE tk-Luc reporter by ER&bets; in transfected U2OS cells.