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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-22 22:44:31 UTC
Update Date2018-05-20 20:42:09 UTC
HMDB IDHMDB0005801
Secondary Accession Numbers
  • HMDB05801
Metabolite Identification
Common NameKaempferol
DescriptionKaempferol is a natural flavonoid which has been isolated from Delphinium, Witch-hazel, grapefruit, and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 degree centigrade. It is slightly soluble in water, and well soluble in hot ethanol and diethyl ether. Kaempferol is a biomarker for the consumption of dried and cooked beans.
Structure
Thumb
Synonyms
ValueSource
3,4',5,7-TetrahydroxyflavoneChEBI
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4'-trihydroxyflavonolChEBI
5,7,4'-TrihydroxyflavonolChEBI
C.I. 75640ChEBI
CampherolChEBI
indigo YellowChEBI
KaempherolChEBI
KampherolChEBI
KempferolChEBI
NimbecetinChEBI
PelargidenolonChEBI
PopulnetinChEBI
RhamnoluteinChEBI
RhamnolutinChEBI
RobigeninChEBI
SwartziolChEBI
TrifolitinChEBI
3,4',5,7-Tetrahydroxy-flavone (7ci,8ci)HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB
KampferolHMDB
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namekaempferol
CAS Registry Number520-18-3
SMILES
OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
InChI KeyIYRMWMYZSQPJKC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 - 287 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP1.99ALOGPS
logP2.46ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.88 m³·mol⁻¹ChemAxon
Polarizability27.59 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0bt9-0000290000-4a7068686e907a319864View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4290000000-ccb984ce16e32c25d878View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000290000-4a7068686e907a319864View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0590000000-3bfd778520b9c39bc4baView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0mc0-2150190000-3a2826fb2ce8460675bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-f0101bac1cb6491794f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0690000000-3afcadc746823bc03ebdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0v4i-5900000000-6a870572cf8a486dd6b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positivesplash10-000i-4290000000-75bfe61cc0a42797e86aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-000i-0090000000-ead9f201b8c5b6b6e46eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0190000000-2bc892de84e0225a49cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052u-1930000000-08779ff26cd586d78e41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udr-0920000000-97d144af795812440c46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0290000000-5573e7fd91cf25805a11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014s-2920000000-397e01f2d2cf07025409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-1920000000-891ca58b63b857f31594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090040000-5111d04af3f3d3e053c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0091000000-295f056c177e6e49fb6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-0d8eaf63d3860cdc1cbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-3969010f013a967001daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-6790000000-5668e7d87a859b519804View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4cba2efdae1d7d094e17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-489c309b159fce3df0d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4950000000-9d8aab7149b59126c14aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0106 +/- 0.00789 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0579 +/- 0.0609 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0908 +/- 0.0742 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
BloodDetected and Quantified0.010 +/- 0.0078 uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.00184 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0400 +/- 0.100 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0533 +/- 0.133 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified40 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified40 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
UrineDetected and Quantified0.008 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00980 +/- 0.0100 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01852
Phenol Explorer Compound ID290
FoodDB IDFDB000633
KNApSAcK IDC00004565
Chemspider ID4444395
KEGG Compound IDC05903
BioCyc IDCPD1F-90
BiGG IDNot Available
Wikipedia Linkkaempferol
METLIN IDNot Available
PubChem Compound5280863
PDB IDKMP
ChEBI ID28499
References
Synthesis ReferenceWuth, B. Indigo Yellow. Faerber-Zeitung (1912), 22 343-5. CODEN: FAZTAZ CAN 6:966 AN 1912:966
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Kaempferol → 3,4,5-trihydroxy-6-[4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails
Kaempferol → 6-{[3,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Kaempferol → 6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Kaempferol → Kaempferol 3-glucuronidedetails