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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-22 22:44:31 UTC
Update Date2021-09-07 17:05:25 UTC
HMDB IDHMDB0005801
Secondary Accession Numbers
  • HMDB05801
Metabolite Identification
Common NameKaempferol
DescriptionKaempferol, also known as rhamnolutein or c.i. 75640, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4'. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound.
Structure
Data?1601235360
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
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneKegg
3,4',5,7-Tetrahydroxy-flavone (7ci,8ci)HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB
KampferolHMDB
3,4’,5,7-TetrahydroxyflavonePhytoBank
3,5,7,4'-TetrahydroxyflavonePhytoBank
3,5,7,4’-TetrahydroxyflavonePhytoBank
3'-DeoxyquercetinPhytoBank
3’-DeoxyquercetinPhytoBank
5,7,4’-TrihydroxyflavonolPhytoBank
KaemferolPhytoBank
KaempferolPhytoBank
KampcetinPhytoBank
PelargidenonPhytoBank
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(O)C=C(O)C=C2O1
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
Description Belongs to the class of organic compounds known as flavonols. Flavonols 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 Molecular Properties
PropertyValueReference
Melting Point285 - 287 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP1.99ALOGPS
logP2.46ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalBaker165.9230932474
DeepCCS[M-H]-ExperimentalMetCCS_train_neg160.32330932474
DeepCCS[M+H]+ExperimentalBaker165.98730932474
DeepCCS[M+H]+ExperimentalMetCCS_train_pos162.85730932474
AllCCS[M-H]-ExperimentalNot Available163.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000439
AllCCS[M+H]+ExperimentalNot Available164.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000439

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Kaempferol,1TMS,#13141.7556https://arxiv.org/abs/1905.12712
Kaempferol,1TMS,#23064.8252https://arxiv.org/abs/1905.12712
Kaempferol,1TMS,#33086.8936https://arxiv.org/abs/1905.12712
Kaempferol,1TMS,#43148.8293https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#13141.5671https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#23091.111https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#33050.4233https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#43086.896https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#53045.8218https://arxiv.org/abs/1905.12712
Kaempferol,2TMS,#63124.6511https://arxiv.org/abs/1905.12712
Kaempferol,3TMS,#13077.2122https://arxiv.org/abs/1905.12712
Kaempferol,3TMS,#22979.905https://arxiv.org/abs/1905.12712
Kaempferol,3TMS,#32957.559https://arxiv.org/abs/1905.12712
Kaempferol,3TMS,#43003.2305https://arxiv.org/abs/1905.12712
Kaempferol,4TMS,#13065.891https://arxiv.org/abs/1905.12712
Kaempferol,1TBDMS,#13390.44https://arxiv.org/abs/1905.12712
Kaempferol,1TBDMS,#23346.5767https://arxiv.org/abs/1905.12712
Kaempferol,1TBDMS,#33333.885https://arxiv.org/abs/1905.12712
Kaempferol,1TBDMS,#43390.7827https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#13664.345https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#23631.0881https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#33608.9148https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#43625.97https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#53582.8186https://arxiv.org/abs/1905.12712
Kaempferol,2TBDMS,#63651.0688https://arxiv.org/abs/1905.12712
Kaempferol,3TBDMS,#13889.814https://arxiv.org/abs/1905.12712
Kaempferol,3TBDMS,#23781.3005https://arxiv.org/abs/1905.12712
Kaempferol,3TBDMS,#33746.418https://arxiv.org/abs/1905.12712
Kaempferol,3TBDMS,#43781.2134https://arxiv.org/abs/1905.12712
Kaempferol,4TBDMS,#13985.0254https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0bt9-0000290000-4a7068686e907a3198642014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4290000000-ccb984ce16e32c25d8782017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000290000-4a7068686e907a3198642017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0590000000-3bfd778520b9c39bc4ba2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0mc0-2150190000-3a2826fb2ce8460675bc2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-f0101bac1cb6491794f52012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0690000000-3afcadc746823bc03ebd2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0v4i-5900000000-6a870572cf8a486dd6b72012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positivesplash10-000i-4290000000-75bfe61cc0a42797e86a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-000i-0090000000-ead9f201b8c5b6b6e46e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0190000000-2bc892de84e0225a49cf2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052u-1930000000-08779ff26cd586d78e412012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udr-0920000000-97d144af795812440c462012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0290000000-5573e7fd91cf25805a112012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014s-2920000000-397e01f2d2cf070254092012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-1920000000-891ca58b63b857f315942012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090040000-5111d04af3f3d3e053c72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e002017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0950000000-580cab3c0e471a3f4e002017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae02017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-066r-0930000000-f40d69c592d60004cae02017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e002017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0091000000-295f056c177e6e49fb6b2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae02017-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-0d8eaf63d3860cdc1cbf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-3969010f013a967001da2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-6790000000-5668e7d87a859b5198042016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4cba2efdae1d7d094e172016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-489c309b159fce3df0d62016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4950000000-9d8aab7149b59126c14a2016-09-12View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)2014-09-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, predicted)2012-12-05View Spectrum
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 QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 290 details
UrineExpected but not QuantifiedNot QuantifiedNot 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 QuantifiedNot QuantifiedAdult (>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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000473
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