Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-27 17:03:12 UTC
Primary IDFDB000633
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol
DescriptionVery widespread in the plant world, e.g. in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae, Leguminosae, etc. Found especies in broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon [CCD] Kaempferol is a natural flavonol, a type of flavonoid. Many glycosides of kaempferol, such as kaempferitrin and astragalin, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. [Wikipedia]. Kaempferol is a biomarker for the consumption of dried and cooked beans. Kaempferol is found in many foods, some of which are peppermint, mexican groundcherry, green zucchini, and wax gourd.
CAS Number520-18-3
Structure
Thumb
Synonyms
SynonymSource
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
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)chromen-4-onebiospider
3,5,7,4'-Tetrahydroxyflavonebiospider
4',5,7-Trihydroxyflavonoldb_source
Kaemferolbiospider
Kaempferoldb_source
Kampcetinbiospider
Pelargidenonbiospider
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O6
IUPAC name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
Classification
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:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 62.94%; H 3.52%; O 33.54%DFC
    Melting PointMp 276-278°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data365 () (EtOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    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
    ChemSpider ID4444395
    ChEMBL IDCHEMBL150
    KEGG Compound IDC05903
    Pubchem Compound ID5280863
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID290
    DrugBank IDDB01852
    HMDB IDHMDB05801
    CRC / DFC (Dictionary of Food Compounds) IDBFG98-E:BFG98-E
    EAFUS IDNot Available
    Dr. Duke ID3,5,7,4'-TETRAHYDROXYFLAVONE|KAEMPFEROL
    BIGG IDNot Available
    KNApSAcK IDC00004565
    HET IDKMP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDKaempferol
    Phenol-Explorer Metabolite ID290
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    11beta-hydroxysteroid-dehydrogenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    5-lipoxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
    anti aggregantDUKE
    anti allergic50857 A drug used to treat allergic reactions.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti fertilityDUKE
    anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
    anti implantationDUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti lymphocyticDUKE
    anti mutagenicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti periodonticDUKE
    anti plaqueDUKE
    anti radicularDUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti serotonin48278 DUKE
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    apoptoticDUKE
    aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
    cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    cholereticDUKE
    copper chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
    cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
    cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
    cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    diaphoreticDUKE
    diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
    estrogenicDUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
    HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    hypotensiveDUKE
    ICAM-1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    iNOS inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    inotropicDUKE
    iodothyronine-deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    JNK inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
    monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    mutagenicDUKE
    natriureticDUKE
    neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.DUKE
    nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    platelet aggregation factor inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    protisticideDUKE
    quinone-reductase inducerDUKE
    teratologicDUKE
    TNF-alpha inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
    topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
    tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
    utero trophic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    bitter
    1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.