CHEBI:8048 - phellamurin

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ChEBI Name phellamurin
ChEBI ID CHEBI:8048
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66743
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Formula C26H30O11
Net Charge 0
Average Mass 518.50980
InChI InChI=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
InChIKey GRDZTDZJQRPNCN-YIANMRPHSA-N
SMILES CC(C)=CCc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c2C(=O)[C@H](O)[C@H](Oc12)c1ccc(O)cc1
Metabolite of Species Details
Phellodendron wilsonii (IPNI:774789-1) Found in leaf (BTO:0000713). See: PubMed
Commiphora africana (NCBI:181237) Found in stem wood (BTO:0001469). See: PubMed
Phellodendron amurense (NCBI:68554) See: DOI
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phellamurin (CHEBI:8048) has functional parent (+)-dihydrokaempferol (CHEBI:15401)
phellamurin (CHEBI:8048) has role metabolite (CHEBI:25212)
phellamurin (CHEBI:8048) is a β-D-glucoside (CHEBI:22798)
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)
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 Sources
3,5,7,4'-tetrahydroxy-8-(3-methylbut-2-enyl)flavanone-7-O-β-glucoside ChEBI
8-Prenyldihydrokaempferol 7-glucoside KEGG COMPOUND
Fellavine ChemIDplus
Phellamurin KEGG COMPOUND
Database Links Databases
C00000989 KNApSAcK
C09808 KEGG COMPOUND
Phellamurin Wikipedia
View more database links
Registry Numbers Types Sources
52589-11-4 CAS Registry Number ChemIDplus
9458481 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11859464 PubMed citation CiteXplore
15679332 PubMed citation CiteXplore
16141579 PubMed citation CiteXplore
1810962 PubMed citation CiteXplore
20814754 PubMed citation CiteXplore
21573758 PubMed citation CiteXplore
412468 PubMed citation CiteXplore
Last Modified
28 July 2014