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CHEBI:8048 - phellamurin

ChEBI IDCHEBI:8048
ChEBI Namephellamurin
Stars
DefinitionA member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a β-D-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from Phellodendron amurense and Commiphora africana, it exhibits inhibition of intestinal P-glycoprotein.
Secondary ChEBI IDCHEBI:66743
Last Modified5 April 2018
DownloadsMolfile
FormulaC26H30O11
Net Charge0
Average Mass518.515
Monoisotopic Mass518.17881
SMILESCC(C)=CCc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c2c1O[C@H](c1ccc(O)cc1)[C@@H](O)C2=O
InChIInChI=1S/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1
InChIKeyGRDZTDZJQRPNCN-YIANMRPHSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Phellodendron amurense (ncbitaxon:68554) - DOI (10.1016/S0031-9422(00)91328-1)
Commiphora africana (ncbitaxon:181237) stem wood (BTO:0001469) PubMed (15679332)
Phellodendron wilsonii (IPNI:774789-1) leaf (BTO:0000713) PubMed (11859464)
Roles Classification
Biological Role:
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)
phellamurin (CHEBI:8048) has functional parent (+)-dihydrokaempferol (CHEBI:15401)
phellamurin (CHEBI:8048) has role metabolite (CHEBI:25212)
phellamurin (CHEBI:8048) is a 4'-hydroxyflavanones (CHEBI:140331)
phellamurin (CHEBI:8048) is a dihydroflavonols (CHEBI:48039)
phellamurin (CHEBI:8048) is a flavanone glycoside (CHEBI:72730)
phellamurin (CHEBI:8048) is a monosaccharide derivative (CHEBI:63367)
phellamurin (CHEBI:8048) is a trihydroxyflavanone (CHEBI:38739)
phellamurin (CHEBI:8048) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside
Synonyms  Source
PhellamurinKEGG COMPOUND
8-Prenyldihydrokaempferol 7-glucosideKEGG COMPOUND
FellavineChemIDplus
3,5,7,4'-tetrahydroxy-8-(3-methylbut-2-enyl)flavanone-7-O-β-glucosideChEBI
Manual XrefsDatabases
C09808KEGG COMPOUND
PhellamurinWikipedia
C00000989KNApSAcK
Registry NumbersSources
Reaxys:9458481Reaxys
CAS:52589-11-4KEGG COMPOUND
CAS:52589-11-4ChemIDplus
Citations