CHEBI:69089 - glyasperin C

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ChEBI Name glyasperin C
ChEBI ID CHEBI:69089
Definition A methoxyisoflavan that is (R)-isoflavan substituted by a methoxy group at position 5, hydroxy groups at positions 7, 2' and 4' and a prenyl group at position 6. It has been isolated from Glycyrrhiza uralensis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H24O5
Net Charge 0
Average Mass 356.41230
Monoisotopic Mass 356.16237
InChI InChI=1S/C21H24O5/c1-12(2)4-6-16-19(24)10-20-17(21(16)25-3)8-13(11-26-20)15-7-5-14(22)9-18(15)23/h4-5,7,9-10,13,22-24H,6,8,11H2,1-3H3/t13-/m0/s1
InChIKey RCZMWVKBVFOCEE-ZDUSSCGKSA-N
SMILES COc1c(CC=C(C)C)c(O)cc2OC[C@H](Cc12)c1ccc(O)cc1O
Metabolite of Species Details
Glycyrrhiza uralensis (NCBI:txid74613) Found in root (BTO:0001188). Dried and ground roots extracted with supercritical CO2 with 5% EtOH as modifier See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing glyasperin C (CHEBI:69089) has parent hydride (R)-isoflavan (CHEBI:36101)
glyasperin C (CHEBI:69089) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
glyasperin C (CHEBI:69089) has role plant metabolite (CHEBI:76924)
glyasperin C (CHEBI:69089) is a hydroxyisoflavans (CHEBI:76250)
glyasperin C (CHEBI:69089) is a methoxyisoflavan (CHEBI:77002)
IUPAC Name
4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
Registry Numbers Types Sources
142474-53-1 CAS Registry Number ChemIDplus
5358177 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16142649 PubMed citation Europe PMC
22074222 PubMed citation Europe PMC
Last Modified
18 June 2015