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CHEBI:69089 - glyasperin C

ChEBI IDCHEBI:69089
ChEBI Nameglyasperin C
Stars
DefinitionA 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.
Last Modified18 June 2015
DownloadsMolfile
FormulaC21H24O5
Net Charge0
Average Mass356.418
Monoisotopic Mass356.16237
SMILESCOc1c(CC=C(C)C)c(O)cc2c1C[C@H](c1ccc(O)cc1O)CO2
InChIInChI=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
InChIKeyRCZMWVKBVFOCEE-ZDUSSCGKSA-N
Species of MetaboliteComponentSourceComments
Glycyrrhiza uralensis (ncbitaxon:74613) root (BTO:0001188) PubMed (22074222) Dried and ground roots extracted with supercritical CO2 with 5% EtOH as modifier
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:5358177Reaxys
CAS:142474-53-1ChemIDplus
Citations