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CHEBI:310312 - isoliquiritigenin
| Formula | C15H12O4 |
| Net Charge | 0 |
| Average Mass | 256.257 |
| Monoisotopic Mass | 256.07356 |
| SMILES | O=C(/C=C/c1ccc(O)cc1)c1ccc(O)cc1O |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Sinofranchetia chinensis (ncbitaxon:41786) | - | PubMed (11501051) | |
| Dalbergia louveli (IPNI:490305-1) | heartwood (PO:0004512) | PubMed (14640516) | |
| Dalbergia odorifera (ncbitaxon:499988) | - | PubMed (9525107) | |
| Glycyrrhiza uralensis (ncbitaxon:74613) | - | PubMed (16675659) | |
| Pterocarpus marsupium (IPNI:516505-1) | |||
| bark (BTO:0001301) | DOI (10.1021/np50031a029) | ||
| heartwood (PO:0004512) | DOI (10.1021/np50031a029) | ||
| Crinum bulbispermum (ncbitaxon:209086) | bulb (BTO:0000159) | DOI (10.1016/S0031-9422(00)00184-9) | |
| Glycyrrhiza (ncbitaxon:46347) | root (BTO:0001188) | Article (CHEM PHARM BULL, 1978, 26, 144) | |
| Glycine max (ncbitaxon:3847) | root (BTO:0001188) | PubMed (1622242) | |
| Tephrosia toxicaria (IPNI:520970-1) | stem (BTO:0001300) | PubMed (14510590) | |
| Glycyrrhiza glabra (ncbitaxon:49827) | - | PubMed (21866899) | |
| Platymiscium floribundum (ncbitaxon:500185) | - | PubMed (21866899) |
| Roles Classification |
|---|
| Biological Roles: | 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. 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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| Applications: | 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. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| isoliquiritigenin (CHEBI:310312) has functional parent trans-chalcone (CHEBI:48965) |
| isoliquiritigenin (CHEBI:310312) has role antineoplastic agent (CHEBI:35610) |
| 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 geroprotector (CHEBI:176497) |
| isoliquiritigenin (CHEBI:310312) has role metabolite (CHEBI:25212) |
| isoliquiritigenin (CHEBI:310312) has role NMDA receptor antagonist (CHEBI:60643) |
| isoliquiritigenin (CHEBI:310312) is a (E)-2'-hydroxy-chalcones (CHEBI:231427) |
| isoliquiritigenin (CHEBI:310312) is a chalcones (CHEBI:23086) |
| isoliquiritigenin (CHEBI:310312) is conjugate acid of isoliquiritigenin(1−) (CHEBI:77948) |
| Incoming Relation(s) |
| 2'-O-methylisoliquiritigenin (CHEBI:519567) has functional parent isoliquiritigenin (CHEBI:310312) |
| isoliquiritigenin 2'-glucosyl-(1→4)-rhamnoside (CHEBI:197171) 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 | Source |
|---|---|
| Isoliquiritigenin | KEGG COMPOUND |
| 2',4,4'-TRIHYDROXYCHALCONE | PDBeChem |
| (E)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone | ChEMBL |
| 4,2',4'-Trihydroxychalcone | ChemIDplus |
| 2',4,4'-Trihydroxychalcone | ChemIDplus |
| trans-2',4,4'-trihydroxychalcone | ChEBI |
| UniProt Name | Source |
|---|---|
| isoliquiritigenin | UniProt |
| Manual Xrefs | Databases |
|---|---|
| C08650 | KEGG COMPOUND |
| HCC | PDBeChem |
| LMPK12120096 | LIPID MAPS |
| Isoliquiritigenin | Wikipedia |
| CPD-3041 | MetaCyc |
| CN102247339 | Patent |
| CN101524341 | Patent |
| C00006925 | KNApSAcK |
| Registry Numbers | Sources |
|---|---|
| Beilstein:1914296 | Beilstein |
| Reaxys:1914296 | Reaxys |
| CAS:961-29-5 | KEGG COMPOUND |
| CAS:961-29-5 | ChemIDplus |
| Citations |
|---|