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CHEBI:68880 - kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside

ChEBI IDCHEBI:68880
ChEBI Namekaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside
Stars
ASCII Namekaempferol 3-O-[alpha-L-rhamnopyranosyl(1->2)-beta-D-galactopyranosyl]-7-O-alpha-L-rhamnopyranoside
DefinitionA glycosyloxyflavone that is kaempferol attached to a α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl residue at position 3 and a α-L-rhamnopyranosyl residue at position 7 via glycosidic linkages. Isolated from the aerial parts of Vicia faba and Lotus edulis, it exhibits inhibitory activity against topoisomerase I.
Last Modified27 November 2013
DownloadsMolfile
FormulaC33H40O19
Net Charge0
Average Mass740.664
Monoisotopic Mass740.21638
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
InChIInChI=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
InChIKeyDDELFAUOHDSZJL-KINVIYQBSA-N
Species of MetaboliteComponentSourceComments
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
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
Roles Classification
Biological Roles:
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.
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)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) has functional parent kaempferol (CHEBI:28499)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) has role metabolite (CHEBI:25212)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) is a dihydroxyflavone (CHEBI:38686)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) is a glycosyloxyflavone (CHEBI:50018)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) is a α-L-rhamnoside (CHEBI:27848)
kaempferol 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranoside (CHEBI:68880) is a β-D-galactoside (CHEBI:28034)
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-galactopyranoside
Registry NumbersSources
Reaxys:6995749Reaxys
Citations