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CHEBI:69087 - glycycoumarin

ChEBI IDCHEBI:69087
ChEBI Nameglycycoumarin
Stars
DefinitionA member of the class of coumarins that is coumarin substituted by a hydroxy group at position 7, a methoxy group at position 5, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antispasmodic activity.
Last Modified16 January 2014
DownloadsMolfile
FormulaC21H20O6
Net Charge0
Average Mass368.385
Monoisotopic Mass368.12599
SMILESCOc1c(CC=C(C)C)c(O)cc2oc(=O)c(-c3ccc(O)cc3O)cc12
InChIInChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3
InChIKeyNZYSZZDSYIBYLC-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 Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antispasmodic drug  A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
ChEBI Ontology
Outgoing Relation(s)
glycycoumarin (CHEBI:69087) has role antispasmodic drug (CHEBI:53784)
glycycoumarin (CHEBI:69087) has role plant metabolite (CHEBI:76924)
glycycoumarin (CHEBI:69087) is a aromatic ether (CHEBI:35618)
glycycoumarin (CHEBI:69087) is a coumarins (CHEBI:23403)
glycycoumarin (CHEBI:69087) is a resorcinols (CHEBI:33572)
IUPAC Name 
3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Synonym  Source
3-(2,4-dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-oneChemIDplus
Manual XrefsDatabases
LMPK12160018LIPID MAPS
HMDB0038225HMDB
JP2001253823Patent
Registry NumbersSources
Reaxys:5632912Reaxys
CAS:94805-82-0ChemIDplus
Citations