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CHEBI:68882 - kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside

ChEBI IDCHEBI:68882
ChEBI Namekaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside
Stars
ASCII Namekaempferol 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside
DefinitionA kaempferol O-glucoside that is kaempferol attached to a β-D-glucopyranosyl 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 and II.
Last Modified17 July 2018
DownloadsMolfile
FormulaC27H30O15
Net Charge0
Average Mass594.522
Monoisotopic Mass594.15847
SMILESC[C@@H]1O[C@@H](Oc2cc(O)c3c(=O)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(-c4ccc(O)cc4)oc3c2)[C@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1
InChIKeyJYXSWDCPHRTYGU-RVCYDTIBSA-N
Species of MetaboliteComponentSourceComments
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)
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 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
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-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) is a dihydroxyflavone (CHEBI:38686)
kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) is a kaempferol O-glucoside (CHEBI:64634)
kaempferol 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68882) is a α-L-rhamnoside (CHEBI:27848)
Synonyms  Source
7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl β-D-glucopyranosideChEBI
kaempferol 3-O-glucoside 7-O-rhamnosideChEBI
Registry NumbersSources
Reaxys:74580Reaxys
Citations