kaempferol 3-O-[alpha-L-rhamnopyranosyl(1->2)-beta-D-glucopyranosyl]-7-O-alpha-L-rhamnopyranoside (CHEBI:68879)

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CHEBI:68879 - kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside

ChEBI ID	CHEBI:68879
ChEBI Name	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside
Stars
ASCII Name	kaempferol 3-O-[alpha-L-rhamnopyranosyl(1->2)-beta-D-glucopyranosyl]-7-O-alpha-L-rhamnopyranoside
Definition	A kaempferol O-glucoside that is kaempferol attached to a α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl residue at position 3 and a α-L-rhamnopyranosyl residue at position 7. Isolated from the aerial parts of Vicia faba and Lotus edulis, it exhibits inhibitory activity against topoisomerase I.
Last Modified	15 February 2016
Downloads	Molfile

Formula	C33H40O19
Net Charge	0
Average Mass	740.664
Monoisotopic Mass	740.21638
SMILES	[H][C@@]1(O[C@H]2[C@H](Oc3c(-c4ccc(O)cc4)oc4cc(O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)cc(O)c4c3=O)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(46-10)48-14-7-15(36)18-16(8-14)49-28(12-3-5-13(35)6-4-12)29(22(18)40)51-33-30(25(43)21(39)17(9-34)50-33)52-32-27(45)24(42)20(38)11(2)47-32/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21+,23+,24+,25-,26+,27+,30+,31-,32-,33-/m0/s1
InChIKey	DDELFAUOHDSZJL-CPGGTDLHSA-N

Species of Metabolite	Component	Source	Comments
Vicia faba (ncbitaxon:3906)
	leaf (BTO:0000713)	PubMed (22014228)	Methanolic extract of leaves and branches
	branch (BTO:0000148)	PubMed (22014228)	Methanolic extract of leaves and branches
Lotus edulis (ncbitaxon:181270)
	branch (BTO:0000148)	PubMed (22014228)	Methanolic extract of leaves and branches
	leaf (BTO:0000713)	PubMed (22014228)	Methanolic extract of leaves and branches

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.

EC 5.99.1.2 (DNA topoisomerase) inhibitor A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

ChEBI Ontology

Outgoing Relation(s)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) has role metabolite (CHEBI:25212)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) has role plant metabolite (CHEBI:76924)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) is a dihydroxyflavone (CHEBI:38686)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) is a kaempferol O-glucoside (CHEBI:64634)
	kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68879) is a α-L-rhamnoside (CHEBI:27848)

IUPAC Name
7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside

Synonym	Source
Kaempferol 3-O-Rha(1-2)Glc 7-O-Rha	ChEBI

Registry Numbers	Sources
Reaxys:7164389	Reaxys

Citations