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

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ChEBI Name quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside
ChEBI ID CHEBI:66289
ChEBI ASCII Name quercetin 4'-O-alpha-L-rhamnopyranosyl-3-O-beta-D-allopyranoside
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H30O16
Net Charge 0
Average Mass 610.51750
Monoisotopic Mass 610.15338
InChI InChI=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
InChIKey RKMUSTNOWMLGOU-ZRLZMVRZSA-N
SMILES C[C@@H]1O[C@@H](Oc2ccc(cc2O)-c2oc3cc(O)cc(O)c3c(=O)c2O[C@@H]2O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Acacia pennata (IPNI:471110-1) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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 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 α-L-rhamnoside (CHEBI:27848)
quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside (CHEBI:66289) is a quercetin O-glycoside (CHEBI:76424)
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 Number Type Source
11296175 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17823873 PubMed citation Europe PMC
Last Modified
26 November 2013