CHEBI:68878 - kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside

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ChEBI Name kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside
ChEBI ID CHEBI:68878
ChEBI ASCII Name kaempferol 3-O-alpha-L-arabinopyranosyl-7-O-alpha-L-rhamnopyranoside
Definition A glycosyloxyflavone that is kaempferol attached to a α-L-arabinopyranosyl 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H28O14
Net Charge 0
Average Mass 564.49210
Monoisotopic Mass 564.14791
InChI InChI=1S/C26H28O14/c1-9-17(30)20(33)22(35)26(37-9)38-12-6-13(28)16-15(7-12)39-23(10-2-4-11(27)5-3-10)24(19(16)32)40-25-21(34)18(31)14(29)8-36-25/h2-7,9,14,17-18,20-22,25-31,33-35H,8H2,1H3/t9-,14-,17-,18-,20+,21+,22+,25-,26-/m0/s1
InChIKey DQBVFTJNUYZVQL-CLFUFSEMSA-N
SMILES C[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(-c2ccc(O)cc2)c(O[C@@H]2OC[C@H](O)[C@H](O)[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 branch (BTO:0000148). 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
Roles Classification
Biological Role(s): 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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) has functional parent kaempferol (CHEBI:28499)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) has role metabolite (CHEBI:25212)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) is a α-L-arabinopyranoside (CHEBI:37782)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) is a α-L-rhamnoside (CHEBI:27848)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) is a dihydroxyflavone (CHEBI:38686)
kaempferol 3-O-α-L-arabinopyranosyl-7-O-α-L-rhamnopyranoside (CHEBI:68878) is a glycosyloxyflavone (CHEBI:50018)
IUPAC Name
3-(α-L-arabinopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-α-L-mannopyranoside
Registry Number Type Source
7676935 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22014228 PubMed citation Europe PMC
Last Modified
27 November 2013