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CHEBI:66289 - quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside

Default Structure
ChEBI IDCHEBI:66289
ChEBI Namequercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside
Stars
ASCII Namequercetin 4'-O-alpha-L-rhamnopyranosyl-3-O-beta-D-allopyranoside
DefinitionA quercetin O-glycoside that consists of quercetin attached to a α-L-rhamnopyranosyl moiety at position 4' and a β-D-allopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Acacia pennata, it exhibits inhibitory activity against cyclooxygenase 1 and 2.
Last Modified26 November 2013
DownloadsMolfile
FormulaC27H30O16
Net Charge0
Average Mass610.521
Monoisotopic Mass610.15338
SMILESC[C@@H]1O[C@@H](Oc2ccc(-c3oc4cc(O)cc(O)c4c(=O)c3O[C@@H]3O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]3O)cc2O)[C@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)41-13-3-2-9(4-11(13)30)24-25(19(34)16-12(31)5-10(29)6-14(16)40-24)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21+,22+,23+,26-,27-/m0/s1
InChIKeyRKMUSTNOWMLGOU-ZRLZMVRZSA-N
Species of MetaboliteComponentSourceComments
Acacia pennata (IPNI:471110-1) leaf (BTO:0000713) PubMed (17823873)
Roles Classification
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
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)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) has functional parent β-D-allose (CHEBI:40656)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) has role metabolite (CHEBI:25212)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) is a quercetin O-glycoside (CHEBI:76424)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) is a α-L-rhamnoside (CHEBI:27848)
IUPAC Name 
2-{4-[(6-deoxy-α-L-mannopyranosyl)oxy]-3-hydroxyphenyl}-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-allopyranoside
Registry NumbersSources
Reaxys:11296175Reaxys
Citations