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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:06:02 UTC
Update Date2022-03-07 02:56:38 UTC
HMDB IDHMDB0040540
Secondary Accession Numbers
  • HMDB40540
Metabolite Identification
Common NameKaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside]
DescriptionKaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] is found in fats and oils. Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] is isolated from Ginkgo biloba (ginkgo). Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] is a natural flavonoid that has been isolated from tea, broccoli, Delphinium, Witch-hazel, grapefruit, brussel sprouts, apples and other plant sources. Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] is a yellow crystalline solid with a melting point of 276-278 °C. It is slightly soluble in water but soluble in hot ethanol and diethyl ether.
Structure
Data?1563863561
Synonyms
ValueSource
{6-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC36H36O17
Average Molecular Weight740.6608
Monoisotopic Molecular Weight740.195249726
IUPAC Name{6-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name{6-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry Number102231-39-0
SMILES
CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1OC1OC(COC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C36H36O17/c1-15-32(52-36-30(46)28(44)26(42)23(51-36)14-48-24(41)11-4-16-2-7-18(37)8-3-16)29(45)31(47)35(49-15)53-34-27(43)25-21(40)12-20(39)13-22(25)50-33(34)17-5-9-19(38)10-6-17/h2-13,15,23,26,28-32,35-40,42,44-47H,14H2,1H3/b11-4+
InChI KeyVZCQGYCHGJQNAD-NYYWCZLTSA-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
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Coumaric acid ester
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Chromone
  • Disaccharide
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Pyranone
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Oxane
  • Fatty acyl
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point337 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP2.26ALOGPS
logP2.17ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area271.59 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity179.71 m³·mol⁻¹ChemAxon
Polarizability73 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]+251.14730932474
DeepCCS[M-H]-249.25130932474
DeepCCS[M-2H]-282.66730932474
DeepCCS[M+Na]+256.81630932474
AllCCS[M+H]+255.732859911
AllCCS[M+H-H2O]+255.332859911
AllCCS[M+NH4]+256.032859911
AllCCS[M+Na]+256.032859911
AllCCS[M-H]-248.032859911
AllCCS[M+Na-2H]-251.732859911
AllCCS[M+HCOO]-255.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside]CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1OC1OC(COC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O8302.3Standard polar33892256
Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside]CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1OC1OC(COC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O5777.6Standard non polar33892256
Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside]CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1OC1OC(COC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C(O)C1O6949.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fs-5429730600-4effb6699ce3908891512017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 10V, Positive-QTOFsplash10-000i-0490710500-18e3b6b9f094b9ef8d082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 20V, Positive-QTOFsplash10-000i-0290300000-05173a386a695f5169b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 40V, Positive-QTOFsplash10-052r-0790100000-1ec71b64cbf4cec31ae02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 10V, Negative-QTOFsplash10-01pa-0941200300-6a747561e6e0bfe1df3e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 20V, Negative-QTOFsplash10-01p9-0970200100-19157d4c1002eb32ce3e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 40V, Negative-QTOFsplash10-01p9-0970000000-3ffda111c2bb575b78842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 10V, Positive-QTOFsplash10-0006-0000000900-750f2b00bcb4b59c3e7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 20V, Positive-QTOFsplash10-0006-0000000900-5c164a9e1ca36c37f5ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 40V, Positive-QTOFsplash10-0udl-1900001400-afff188885a4f4b90a312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 10V, Negative-QTOFsplash10-000i-0000000900-abdeb3a4263fcb5111a32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 20V, Negative-QTOFsplash10-000i-0300000900-d48c6a873303c60e844d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-[4''-(p-coumaroylglucosyl)rhamnoside] 40V, Negative-QTOFsplash10-0mii-1910010200-777572937d0ccd7888072021-09-25Wishart 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 IDFDB020309
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752848
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.. .