Kaempferol 3-O-(2''-rhamnosyl-galactoside) 7-O-rhamnoside (CHEM022929)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:44:30 UTC
Update Date2016-11-09 01:17:36 UTC
Accession NumberCHEM022929
Identification
Common NameKaempferol 3-O-(2''-rhamnosyl-galactoside) 7-O-rhamnoside
ClassSmall Molecule
DescriptionA glycosyloxyflavone that is kaempferol attached to a alpha-L-rhamnopyranosyl(1->2)-beta-D-galactopyranosyl residue at position 3 and a alpha-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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Kaempferol 3-O-[a-L-rhamnopyranosyl(1->2)-b-D-galactopyranosyl]-7-O-a-L-rhamnopyranosideGenerator
Kaempferol 3-O-[α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl]-7-O-α-L-rhamnopyranosideGenerator
Chemical FormulaC33H40O19
Average Molecular Mass740.659 g/mol
Monoisotopic Mass740.216 g/mol
CAS Registry NumberNot Available
IUPAC Name3-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name3-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one
SMILESC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2OC2=C(OC3=CC(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(46-10)48-14-7-15(36)18-16(8-14)49-28(12-3-5-13(35)6-4-12)29(22(18)40)51-33-30(25(43)21(39)17(9-34)50-33)52-32-27(45)24(42)20(38)11(2)47-32/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,30+,31-,32-,33-/m0/s1
InChI KeyDDELFAUOHDSZJL-KINVIYQBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.09 g/LALOGPS
logP-0.26ALOGPS
logP-1.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area304.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity168.76 m³·mol⁻¹ChemAxon
Polarizability71.73 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009t-0120980400-21cfc1dd3f64dad74052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0012-0160940000-73173c89eda472335c04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-0480921100-291b9764a34b4486256cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ac-1102593600-1ece18e37548f905d13eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u0-0421960100-a8a9c2362763da3b3013Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qa-2961801000-77f2a706d0185158fcd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900200-996ab5f48cf12018467eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0000900900-e1324d510b24aaa4cfe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000900000-fa0a1381502338409394Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-f0058e4130bf776e99d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0000500900-2ec4b4ddb6316e3d0fc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0000900000-ac239bcf92abd2356870Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301698
FooDB IDFDB000210
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID28492088
ChEBI ID68880
PubChem Compound ID57397583
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22014228