Isoliquiritigenin

Isoliquiritigenin

Names
IUPAC name (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Other names 6'-deoxychalcone 2',4,4'-Trihydroxychalcone 4,2',4'-Trihydroxychalcone 4'2'4'-trihydroxychalcone 2',4',4-Trihydroxychalcone
Identifiers
CAS Number	961-29-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:310312 N
ChEMBL	ChEMBL129795 N
ChemSpider	553829 N
ECHA InfoCard	100.202.617
EC Number	237-316-5
KEGG	C08650 N
PubChem CID	638278
CompTox Dashboard (EPA)	DTXSID2022466
InChI 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+ N Key: DXDRHHKMWQZJHT-FPYGCLRLSA-N N InChI=1/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+ Key: DXDRHHKMWQZJHT-FPYGCLRLBB
SMILES C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
Properties
Chemical formula	C15H12O4
Molar mass	256.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Isoliquiritigenin is a licorice chalconoid, a type of natural phenols. It is under experimentation phase testing for use as a cancer treatment and as an aide for cocaine addiction. It is a sirtuin-activating compound.

Metabolism

The enzyme 6'-deoxychalcone synthase uses malonyl-CoA, 4-coumaroyl-CoA, NADPH, and H⁺ to produce CoA, isoliquiritigenin, CO₂, NADP⁺, and H₂O.

The enzyme isoliquiritigenin 2'-O-methyltransferase further transforms isoliquiritigenin into 2'-O-methylisoliquiritigenin.

Mechanism of action

Isoliquiritigenin has been found to potent (65 times higher affinity than diazepine) GABA-A benzodiapine receptor positive allosteric modulator.