CHEBI:68877 - kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside

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ChEBI Name kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside
ChEBI ID CHEBI:68877
ChEBI ASCII Name kaempferol 3-O-(5-O-acetyl-alpha-D-apiofuranosyl)-7-O-alpha-L-rhamnopyranoside
Definition A glycosyloxyflavone that is kaempferol attached to a 5-O-acetyl-α-D-apiofuranosyl 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 topoisomerse I and II.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H30O15
Net Charge 0
Average Mass 606.52880
Monoisotopic Mass 606.15847
InChI InChI=1S/C28H30O15/c1-11-19(32)21(34)22(35)26(40-11)41-15-7-16(31)18-17(8-15)42-23(13-3-5-14(30)6-4-13)24(20(18)33)43-27-25(36)28(37,10-39-27)9-38-12(2)29/h3-8,11,19,21-22,25-27,30-32,34-37H,9-10H2,1-2H3/t11-,19-,21+,22+,25+,26-,27+,28+/m0/s1
InChIKey XOUMRQRJVFZBHB-JMCDDRANSA-N
SMILES C[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(-c2ccc(O)cc2)c(O[C@H]2OC[C@](O)(COC(C)=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 leaf (BTO:0000713). Methanolic extract of leaves and branches See: PubMed
Lotus edulis (NCBI:txid181270) 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
Vicia faba (NCBI:txid3906) Found in branch (BTO:0000148). 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) has functional parent kaempferol (CHEBI:28499)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) has role antineoplastic agent (CHEBI:35610)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) is a α-L-rhamnoside (CHEBI:27848)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) is a acetate ester (CHEBI:47622)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) is a dihydroxyflavone (CHEBI:38686)
kaempferol 3-O-(5-O-acetyl-α-D-apiofuranosyl)-7-O-α-L-rhamnopyranoside (CHEBI:68877) is a glycosyloxyflavone (CHEBI:50018)
IUPAC Name
[(3S,4S,5R)-5-({7-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl}oxy)-3,4-dihydroxytetrahydrofuran-3-yl]methyl acetate
Registry Number Type Source
20310874 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22014228 PubMed citation Europe PMC
Last Modified
09 January 2014