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CHEBI:66727 - papyriflavonol A

ChEBI IDCHEBI:66727
ChEBI Namepapyriflavonol A
Stars
DefinitionA pentahydroxyflavone that is flavone substituted with hydroxy groups at positions 3, 5, 7, 3' and 4' and prenyl groups at positions 6 and 5'. Isolated from Broussonetia papyrifera, it exhibits inhibitory activity against phospholipase A2 and tyrosinase.
Last Modified12 July 2013
DownloadsMolfile
FormulaC25H26O7
Net Charge0
Average Mass438.476
Monoisotopic Mass438.16785
SMILESCC(C)=CCc1cc(-c2oc3cc(O)c(CC=C(C)C)c(O)c3c(=O)c2O)cc(O)c1O
InChIInChI=1S/C25H26O7/c1-12(2)5-7-14-9-15(10-18(27)21(14)28)25-24(31)23(30)20-19(32-25)11-17(26)16(22(20)29)8-6-13(3)4/h5-6,9-11,26-29,31H,7-8H2,1-4H3
InChIKeyNQBROFAEMRVICP-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Broussonetia papyrifera (ncbitaxon:172644) root (BTO:0001188) PubMed (11395279) Previous component: root bark;
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.1.1.4 (phospholipase A2) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
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)
papyriflavonol A (CHEBI:66727) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
papyriflavonol A (CHEBI:66727) has role EC 3.1.1.4 (phospholipase A2) inhibitor (CHEBI:50469)
papyriflavonol A (CHEBI:66727) has role metabolite (CHEBI:25212)
papyriflavonol A (CHEBI:66727) is a 3'-hydroxyflavonoid (CHEBI:27741)
papyriflavonol A (CHEBI:66727) is a flavonols (CHEBI:28802)
papyriflavonol A (CHEBI:66727) is a pentahydroxyflavone (CHEBI:25883)
IUPAC Name 
2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-3,5,7-trihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Synonyms  Source
5,7,3',4'-tetrahydroxy-6,5'-di-(γ,γ-dimethylallyl)-flavonolChEBI
3,5,7,3',4'-pentahydroxy-6,5'-di-(3-methyl-2-butenyl)flavoneChEBI
broussonol EChEBI
Manual XrefsDatabases
KR20050054712Patent
LMPK12112289LIPID MAPS
Registry NumbersSources
Reaxys:8955040Reaxys
Citations