Structure Database (LMSD)
Common Name
Isoliquiritigenin
Systematic Name
(E)-2',4,4'-Trihydroxychalcone
Synonyms
- Trihydroxychalcone
3D model of Isoliquiritigenin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Isoliquiritigenin is a flavonoid that is found in Glycyrrhizae species and has diverse biological activities including anticancer, anti-steatotic, antioxidant, anti-inflammatory, gastroprotective, and estrogenic properties.1,2,3,4,5 It reduces tumor growth in an NCI-H1975 non-small cell lung cancer (NSCLC) mouse xenograft model when administered at doses of 1 and 5 mg/kg.1 Isoliquiritigenin (10 mg/kg per day) inhibits hepatic steatosis, as indicated by reduced hepatic fat and triglyceride accumulation, and increases in hepatic thiobarbituric acid-reactive substances (TBARS), inducible nitric oxide synthase (iNOS), and COX-2 levels in mice fed a high-fat diet.4 It also inhibits LPS-induced increases in IL-1β and IL-6 levels in J774A.1 murine macrophages (IC50s = 7.2 and 7.16 μM, respectively).2 Isoliquiritigenin (5 and 10 mg/kg) reduces gastric acid secretion and gastric ulcer formation in pylorus-ligated rats.3 It is an estrogen receptor α (ERα) and ERβ agonist (IC50s = 16 and 7.8 μM, respectively) and induces estrogen-responsive alkaline phosphatase activity in Ishikawa endometrial cancer cells (EC50 = 2.7 μM).5 Isoliquiritigenin is also a histamine H2 receptor and liver X receptor α (LXRα) antagonist.3,4
This information has been provided by Cayman Chemical
References
5. Thiyagarajan, P., Chandrasekaran, C.V., Deepak, H.B., et al. Modulation of lipopolysaccharide-induced pro-inflammatory mediators by an extract of Glycyrrhiza glabra and its phytoconstituents. Inflammopharmacology 19(4), 235-241 (2011).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
Robinia pseudoacacia
(#35938)
Magnoliopsida
(#3398)
Condensed tannins. 13. Interrelationships of flavonoid components from the heartwood of Robinia pseudacacia.,
Biochem J, 1962
Biochem J, 1962
Pubmed ID:
14038809
String Representations
InChiKey (Click to copy)
DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChi (Click to copy)
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
SMILES (Click to copy)
C1(O)=CC=C(C(=O)/C=C/C2C=CC(O)=CC=2)C(O)=C1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
2
Aromatic Rings
2
Rotatable Bonds
3
Van der Waals Molecular Volume
235.58
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
2.70
Molar Refractivity
71.24
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Created at
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Updated at
27th Jan 2025