Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2018-05-28 22:35:55 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
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
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
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
Files
MSDSshow
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.