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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:05:48 UTC
Update Date2022-03-07 02:56:37 UTC
HMDB IDHMDB0040537
Secondary Accession Numbers
  • HMDB40537
Metabolite Identification
Common NameKaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside)
DescriptionKaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) is found in herbs and spices. Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) is isolated from leaves of bog myrtle (Myrica gale). Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) is a natural flavonoid that has been isolated from tea, broccoli, Delphinium, Witch-hazel, grapefruit, brussel sprouts, apples and other plant sources. Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 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
Kaempferol 3-(2'',3''-diacetyl-4''-P-coumarylrhamnosideHMDB
4,5-Bis(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-2-methyloxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC34H30O14
Average Molecular Weight662.5936
Monoisotopic Molecular Weight662.163555668
IUPAC Name4,5-bis(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-2-methyloxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name4,5-bis(acetyloxy)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-2-methyloxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry Number128941-61-7
SMILES
CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(C)=O)C(OC(C)=O)C1OC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C34H30O14/c1-16-29(47-26(41)13-6-19-4-9-21(37)10-5-19)32(44-17(2)35)33(45-18(3)36)34(43-16)48-31-28(42)27-24(40)14-23(39)15-25(27)46-30(31)20-7-11-22(38)12-8-20/h4-16,29,32-34,37-40H,1-3H3/b13-6+
InChI KeyNEYRFFHYUHAXKD-AWNIVKPZSA-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
  • Flavone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Coumaric acid ester
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Glycosyl compound
  • Chromone
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Tricarboxylic acid or derivatives
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Pyranone
  • Monosaccharide
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • 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 Solubility0.017 g/LALOGPS
logP4.4ALOGPS
logP4.82ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area204.58 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity165.6 m³·mol⁻¹ChemAxon
Polarizability65.65 ųChemAxon
Number of Rings5ChemAxon
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]+237.97230932474
DeepCCS[M-H]-236.14730932474
DeepCCS[M-2H]-269.38930932474
DeepCCS[M+Na]+243.57830932474
AllCCS[M+H]+249.832859911
AllCCS[M+H-H2O]+248.832859911
AllCCS[M+NH4]+250.732859911
AllCCS[M+Na]+251.032859911
AllCCS[M-H]-240.732859911
AllCCS[M+Na-2H]-242.932859911
AllCCS[M+HCOO]-245.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside)CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(C)=O)C(OC(C)=O)C1OC(=O)\C=C\C1=CC=C(O)C=C18014.3Standard polar33892256
Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside)CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(C)=O)C(OC(C)=O)C1OC(=O)\C=C\C1=CC=C(O)C=C14930.7Standard non polar33892256
Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside)CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(C)=O)C(OC(C)=O)C1OC(=O)\C=C\C1=CC=C(O)C=C15689.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-2852209000-3448edc43c4df9bd60ea2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 10V, Positive-QTOFsplash10-000j-1480219000-db720707b36a094647c82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 20V, Positive-QTOFsplash10-000i-0390001000-4264ffe429d8eac42bd02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 40V, Positive-QTOFsplash10-052r-1690100000-aa03de1de03e735065fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 10V, Negative-QTOFsplash10-07vr-4140019000-9fc98ce58a961ef5c16f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 20V, Negative-QTOFsplash10-0a4r-7492212000-6bf2fb08213229a89c8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 40V, Negative-QTOFsplash10-0a4i-9740000000-18970869a6a97ac9f74d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 10V, Positive-QTOFsplash10-03di-0000009000-8016e6def809cbe4cec62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 20V, Positive-QTOFsplash10-03di-0000009000-ac05c4356342771aa8fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 40V, Positive-QTOFsplash10-0w29-1900014000-791d6ae4eb7d038c18dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 10V, Negative-QTOFsplash10-03di-0000009000-75a8a0f6ddc9a19462b02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 20V, Negative-QTOFsplash10-03di-0300009000-a1918bf2f2e78fea8d522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferol 3-(2'',3''-diacetyl-4''-p-coumaroylrhamnoside) 40V, Negative-QTOFsplash10-0hh0-1910102000-3b62e50d3fc6f8eb9efd2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB020306
KNApSAcK IDC00005870
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14630678
PDB IDNot Available
ChEBI ID172788
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.. .