quercetin 4'-O-alpha-L-rhamnopyranosyl-3-O-beta-D-allopyranoside (CHEBI:66289)

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

ChEBI ID	CHEBI:66289
ChEBI Name	quercetin 4'-O-α-L-rhamnopyranosyl-3-O-β-D-allopyranoside
Stars
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.
Last Modified	26 November 2013
Downloads	Molfile

Formula	C27H30O16
Net Charge	0
Average Mass	610.521
Monoisotopic Mass	610.15338
SMILES	C[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
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

Species of Metabolite	Component	Source	Comments
Acacia pennata (IPNI:471110-1)	leaf (BTO:0000713)	PubMed (17823873)

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.

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.

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 Numbers	Sources
Reaxys:11296175	Reaxys

Citations