CHEBI:310312 - isoliquiritigenin

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ChEBI Name isoliquiritigenin
ChEBI ID CHEBI:310312
Definition A member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43173, CHEBI:6022
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Formula C15H12O4
Net Charge 0
Average Mass 256.25340
Monoisotopic Mass 256.074
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+
InChIKey DXDRHHKMWQZJHT-FPYGCLRLSA-N
SMILES Oc1ccc(cc1)\C=C\C(=O)c1ccc(O)cc1O
Metabolite of Species Details
Dalbergia louveli (IPNI:490305-1) Found in heartwood (PO:0004512). See: PubMed
Pterocarpus marsupium (IPNI:516505-1) Found in bark (BTO:0001301). See: DOI
Pterocarpus marsupium (IPNI:516505-1) Found in heartwood (PO:0004512). See: DOI
Tephrosia toxicaria (IPNI:520970-1) Found in stem (BTO:0001300). See: PubMed
Crinum bulbispermum (NCBI:209086) Found in bulb (BTO:0000159). See: DOI
Glycine max (NCBI:3847) Found in root (BTO:0001188). See: PubMed
Sinofranchetia chinensis (NCBI:41786) See: PubMed
Glycyrrhiza (NCBI:46347) Found in root (BTO:0001188). See: CHEM PHARM BULL, 1978, 26, 144
Glycyrrhiza glabra (NCBI:49827) See: PubMed
Dalbergia odorifera (NCBI:499988) See: PubMed
Platymiscium floribundum (NCBI:500185) See: PubMed
Glycyrrhiza uralensis (NCBI:74613) See: PubMed
Roles Classification
Biological Role(s): EC 1.14.18.1 (tyrosinase) inhibitor
Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
Application(s): GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing isoliquiritigenin (CHEBI:310312) has functional parent trans-chalcone (CHEBI:48965)
isoliquiritigenin (CHEBI:310312) has role biological pigment (CHEBI:26130)
isoliquiritigenin (CHEBI:310312) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
isoliquiritigenin (CHEBI:310312) has role GABA modulator (CHEBI:50268)
isoliquiritigenin (CHEBI:310312) has role metabolite (CHEBI:25212)
isoliquiritigenin (CHEBI:310312) has role NMDA receptor antagonist (CHEBI:60643)
isoliquiritigenin (CHEBI:310312) is a chalcones (CHEBI:23086)
isoliquiritigenin (CHEBI:310312) is conjugate acid of isoliquiritigenin(1−) (CHEBI:77948)
Incoming 2'-O-methylisoliquiritigenin (CHEBI:519567) has functional parent isoliquiritigenin (CHEBI:310312)
isoliquiritigenin(1−) (CHEBI:77948) is conjugate base of isoliquiritigenin (CHEBI:310312)
IUPAC Name
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms Sources
(E)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone ChEMBL
(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-one ChEBI
2',4,4'-Trihydroxychalcone ChemIDplus
2',4,4'-TRIHYDROXYCHALCONE PDBeChem
4,2',4'-Trihydroxychalcone ChemIDplus
Isoliquiritigenin KEGG COMPOUND
trans-2',4,4'-trihydroxychalcone ChEBI
Database Links Databases
C00006925 KNApSAcK
C08650 KEGG COMPOUND
CN101524341 Patent
CN102247339 Patent
CPD-3041 MetaCyc
HCC PDBeChem
Isoliquiritigenin Wikipedia
LMPK12120096 LIPID MAPS
View more database links
Registry Numbers Types Sources
1914296 Beilstein Registry Number Beilstein
1914296 Reaxys Registry Number Reaxys
961-29-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11501051 PubMed citation Europe PMC
11853176 PubMed citation Europe PMC
14510590 PubMed citation Europe PMC
14640516 PubMed citation Europe PMC
15878356 PubMed citation Europe PMC
1622242 PubMed citation Europe PMC
16675659 PubMed citation Europe PMC
19067384 PubMed citation Europe PMC
20146476 PubMed citation Europe PMC
21158449 PubMed citation Europe PMC
21691759 PubMed citation Europe PMC
21720042 PubMed citation Europe PMC
21815175 PubMed citation Europe PMC
21866899 PubMed citation Europe PMC
21945440 PubMed citation Europe PMC
22076338 PubMed citation Europe PMC
9525107 PubMed citation Europe PMC
Last Modified
28 July 2014
General Comment
2012-07-27 CHEM PHARM BULL, 1978, 26, 144