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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:06:45 UTC
Update Date2022-03-07 02:55:54 UTC
HMDB IDHMDB0038768
Secondary Accession Numbers
  • HMDB38768
Metabolite Identification
Common NameKaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside]
DescriptionKaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside], also known as kaempferol 3-(3R-glucosylrutinoside), belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), green tea, and black tea. This could make kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside].
Structure
Data?1563863254
Synonyms
ValueSource
Kaempferol 3-(3R-glucosylrutinoside)HMDB
Kaempferol 3-(3Rha-glucosylrutinoside)HMDB
Chemical FormulaC33H40O20
Average Molecular Weight756.6587
Monoisotopic Molecular Weight756.21129372
IUPAC Name3-{[(2S,3R,4S,5R,6R)-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Name3-{[(2S,3R,4S,5R,6R)-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
CAS Registry Number136449-09-7
SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O
InChI Identifier
InChI=1S/C33H40O20/c1-10-19(38)29(52-32-25(44)23(42)20(39)16(8-34)50-32)27(46)31(48-10)47-9-17-21(40)24(43)26(45)33(51-17)53-30-22(41)18-14(37)6-13(36)7-15(18)49-28(30)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-27,29,31-40,42-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21-,23-,24-,25+,26+,27+,29+,31+,32-,33-/m0/s1
InChI KeyMFIXKYXSBNIMPX-CHLFRWFTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavone
  • O-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Oxane
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.88 g/LALOGPS
logP-0.59ALOGPS
logP-2.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area324.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity170.58 m³·mol⁻¹ChemAxon
Polarizability71.34 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+246.3130932474
DeepCCS[M-H]-244.65730932474
DeepCCS[M-2H]-278.69130932474
DeepCCS[M+Na]+252.46730932474
AllCCS[M+H]+252.732859911
AllCCS[M+H-H2O]+252.432859911
AllCCS[M+NH4]+252.932859911
AllCCS[M+Na]+252.932859911
AllCCS[M-H]-249.432859911
AllCCS[M+Na-2H]-253.232859911
AllCCS[M+HCOO]-257.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside]C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O5878.9Standard polar33892256
Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside]C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O5770.8Standard non polar33892256
Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside]C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O6796.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] GC-MS (TBDMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 10V, Positive-QTOFsplash10-000i-0190270700-c311130c0cf6660967612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 20V, Positive-QTOFsplash10-000i-0190220000-75dd8d5cc7bda08d85cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 40V, Positive-QTOFsplash10-000i-0591010000-99a36c3a3df8bab0a21d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 10V, Negative-QTOFsplash10-052r-1393330700-83b0fe40881987c89b4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 20V, Negative-QTOFsplash10-000i-1391020100-7d4454270fa65bfe277e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 40V, Negative-QTOFsplash10-000i-2490000000-448551d141e949989bad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 10V, Positive-QTOFsplash10-000i-0090000200-0d30ef8e9000187bccb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 20V, Positive-QTOFsplash10-0a50-0090000900-c78a14fc1602f417660f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 40V, Positive-QTOFsplash10-000i-0090000000-03ec6f5113b2bb58d5cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 10V, Negative-QTOFsplash10-0a4i-0000000900-986f422c56923aeed7c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 20V, Negative-QTOFsplash10-0a4i-0050000900-d1fc55a7493e514528352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside] 40V, Negative-QTOFsplash10-001i-0090000000-ac05e4cfe665d4c44d042021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000164
KNApSAcK IDC00005201
Chemspider ID16737880
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20055968
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .