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

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ChEBI Name kaempferol 3-O-β-D-apiofuranosyl-7-O-α-L-rhamnopyranoside
ChEBI ID CHEBI:68884
ChEBI ASCII Name kaempferol 3-O-beta-D-apiofuranosyl-7-O-alpha-L-rhamnopyranoside
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H28O14
Net Charge 0
Average Mass 564.49210
Monoisotopic Mass 564.14791
InChI InChI=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
InChIKey SVQKJHRWPYLYKM-BRPMHDARSA-N
SMILES C[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(-c2ccc(O)cc2)c(O[C@@H]2OC[C@](O)(CO)[C@H]2O)c3=O)[C@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Lotus edulis (NCBI:txid181270) Found in branch (BTO:0000148). Methanolic extract of leaves and branches See: PubMed
Lotus edulis (NCBI:txid181270) Found in leaf (BTO:0000713). Methanolic extract of leaves and branches See: PubMed
Vicia faba (NCBI:txid3906) Found in leaf (BTO:0000713). Methanolic extract of leaves and branches See: PubMed
Vicia faba (NCBI:txid3906) Found in branch (BTO:0000148). Methanolic extract of leaves and branches See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α-L-rhamnoside (CHEBI:27848)
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)
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
Citation Waiting for Citations Type Source
22014228 PubMed citation Europe PMC
Last Modified
27 November 2013