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CHEBI:68884 - kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside

ChEBI IDCHEBI:68884
ChEBI Namekaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside
Stars
ASCII Namekaempferol 3-O-beta-D-apiofuranosyl-7-O-alpha-L-rhamnopyranoside
DefinitionA glycosyloxyflavone that is kaempferol attached to a β-D-apiofuranosyl group at position 3 and a α-L-rhamnopyranosyl residue at position 7 via a glycosidic linkage. Isolated from the aerial parts of Vicia faba and Lotus edulis, it exhibits inhibitory activity against topoisomerase II.
Last Modified27 November 2013
DownloadsMolfile
FormulaC26H28O14
Net Charge0
Average Mass564.496
Monoisotopic Mass564.14791
SMILESC[C@@H]1O[C@@H](Oc2cc(O)c3c(=O)c(O[C@@H]4OC[C@](O)(CO)[C@H]4O)c(-c4ccc(O)cc4)oc3c2)[C@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C26H28O14/c1-10-17(30)19(32)20(33)24(37-10)38-13-6-14(29)16-15(7-13)39-21(11-2-4-12(28)5-3-11)22(18(16)31)40-25-23(34)26(35,8-27)9-36-25/h2-7,10,17,19-20,23-25,27-30,32-35H,8-9H2,1H3/t10-,17-,19+,20+,23-,24-,25-,26+/m0/s1
InChIKeySVQKJHRWPYLYKM-BRPMHDARSA-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)
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:
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.
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-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) has functional parent kaempferol (CHEBI:28499)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) has role metabolite (CHEBI:25212)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) is a dihydroxyflavone (CHEBI:38686)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) is a glycosyloxyflavone (CHEBI:50018)
kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68884) is a α-L-rhamnoside (CHEBI:27848)
IUPAC Name 
3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-α-L-mannopyranoside
Citations