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CHEBI:69086 - glycyrin

ChEBI IDCHEBI:69086
ChEBI Nameglycyrin
Stars
DefinitionA member of the class of coumarins that is coumarin substituted by methoxy groups at positions 5 and 7, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity.
Last Modified13 November 2013
DownloadsMolfile
FormulaC22H22O6
Net Charge0
Average Mass382.412
Monoisotopic Mass382.14164
SMILESCOc1cc2oc(=O)c(-c3ccc(O)cc3O)cc2c(OC)c1CC=C(C)C
InChIInChI=1S/C22H22O6/c1-12(2)5-7-15-19(26-3)11-20-17(21(15)27-4)10-16(22(25)28-20)14-8-6-13(23)9-18(14)24/h5-6,8-11,23-24H,7H2,1-4H3
InChIKeyFWWGXZYUURXJLK-UHFFFAOYSA-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:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
glycyrin (CHEBI:69086) has role antibacterial agent (CHEBI:33282)
glycyrin (CHEBI:69086) has role metabolite (CHEBI:25212)
glycyrin (CHEBI:69086) has role plant metabolite (CHEBI:76924)
glycyrin (CHEBI:69086) is a aromatic ether (CHEBI:35618)
glycyrin (CHEBI:69086) is a coumarins (CHEBI:23403)
glycyrin (CHEBI:69086) is a hydroxyisoflavans (CHEBI:76250)
IUPAC Name 
3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Synonyms  Source
3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-oneChemIDplus
3-(2',4'-dihydroxyphenyl)-5,7-dimethoxy-2-isopentenylcoumarinChEBI
3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarinLIPID MAPS
Manual XrefsDatabases
WO2004064830Patent
LMPK12160017LIPID MAPS
HMDB0033712HMDB
Registry NumbersSources
Reaxys:1667250Reaxys
CAS:66056-18-6ChemIDplus
Citations