AFCDB: Kaempferol (FDB000633)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:39 UTC

Update date

2020-09-17 15:33:11 UTC

Primary ID

FDB000633

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Kaempferol

Description

Kaempferol, 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 a flavonoid lipid molecule. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol is a bitter tasting compound. It is very widespread in the plant world and is found in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae and Leguminosae. It is detected in apples, tomatoes, green tea, potatoes, onions, brussels sprouts, squash, cucumbers, lettuce, green beans, peaches, blackberries, raspberries, spinach, grapes, broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon (PMID: 21428901). Kaempferol is a biomarker for the consumption of dried and cooked beans. 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. Kaempferol has numerous protective properties and has been used to treat intervertebral disc degeneration and colitis, post-menopausal bone loss, acute lung injury and has beneficial effects against cancer, liver injury, obesity and diabetes, and inhibits vascular endothelial inflammation. These treatments and protective properties of kaempferol and the potential mechanisms that kaempferol exerts these effects are part of this review ( PMID: 31572524).

CAS Number

520-18-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	1.99	ALOGPS
logP	2.46	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.88 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O6

IUPAC name

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

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 Key

IYRMWMYZSQPJKC-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:28499 )
flavonols (CHEBI:28499 )
7-hydroxyflavonol (CHEBI:28499 )
flavonols (C05903 )
Flavones and Flavonols (C05903 )
Flavones and Flavonols (LMPK12110003 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 62.94%; H 3.52%; O 33.54%	DFC
Melting Point	Mp 276-278°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	365 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0079-1963700000-1d3775db7c536f63b70c	Spectrum
GC-MS	Kaempferol, 5 TMS, GC-MS Spectrum	splash10-0bt9-0000290000-4a7068686e907a319864	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-000i-4290000000-ccb984ce16e32c25d878	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0079-1963700000-1d3775db7c536f63b70c	Spectrum
GC-MS	Kaempferol, non-derivatized, GC-MS Spectrum	splash10-0bt9-0000290000-4a7068686e907a319864	Spectrum
Predicted GC-MS	Kaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-0590000000-3bfd778520b9c39bc4ba	Spectrum
Predicted GC-MS	Kaempferol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0mc0-2150190000-3a2826fb2ce8460675bc	Spectrum
Predicted GC-MS	Kaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-f0101bac1cb6491794f5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-0690000000-3afcadc746823bc03ebd	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0v4i-5900000000-6a870572cf8a486dd6b7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positive	splash10-000i-4290000000-75bfe61cc0a42797e86a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-000i-0090000000-ead9f201b8c5b6b6e46e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0190000000-2bc892de84e0225a49cf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052u-1930000000-08779ff26cd586d78e41	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udr-0920000000-97d144af795812440c46	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0290000000-5573e7fd91cf25805a11	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014s-2920000000-397e01f2d2cf07025409	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-1920000000-891ca58b63b857f31594	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0079-0090040000-5111d04af3f3d3e053c7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0950000000-580cab3c0e471a3f4e00	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0091000000-295f056c177e6e49fb6b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-066r-0930000000-f40d69c592d60004cae0	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-0d8eaf63d3860cdc1cbf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-3969010f013a967001da	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-6790000000-5668e7d87a859b519804	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-4cba2efdae1d7d094e17	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-489c309b159fce3df0d6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4950000000-9d8aab7149b59126c14a	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

290

DrugBank ID

DB01852

HMDB ID

HMDB05801

CRC / DFC (Dictionary of Food Compounds) ID

BFG98-E:BFG98-E

EAFUS ID

Not Available

Dr. Duke ID

3,5,7,4'-TETRAHYDROXYFLAVONE|KAEMPFEROL

BIGG ID

Not Available

KNApSAcK ID

C00004565

HET ID

KMP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Kaempferol

Phenol-Explorer Metabolite ID

290

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
11beta-hydroxysteroid-dehydrogenase inhibitor	23924	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 inhibitor	23924	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 inhibitor	48550	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 aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti aggregant			DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti fertility			DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti histaminic	37956	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 implantation			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti lymphocytic			DUKE
anti mutagenic			DUKE
antioxidant	22586	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 periodontic			DUKE
anti plaque			DUKE
anti radicular			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti serotonin	48278		DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	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 viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
apoptotic			DUKE
aromatase inhibitor	50790	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 inhibitor	23924	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 preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carcinogenic	50903	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
choleretic			DUKE
copper chelator	38161	A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cyclooxygenase inhibitor	35544	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
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
diaphoretic			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
HIV-reverse-transcriptase inhibitor	23924	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
hypotensive			DUKE
ICAM-1 inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
iNOS inhibitor	23924	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
inotropic			DUKE
iodothyronine-deiodinase inhibitor	23924	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 inhibitor	23924	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 inhibitor	35856	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 inhibitor	23924	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
mutagenic			DUKE
natriuretic			DUKE
neuroprotective	63726	Any compound that can be used for the treatment of neurodegenerative disorders.	DUKE
nitric-oxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
platelet aggregation factor inhibitor	50427	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
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
protisticide			DUKE
quinone-reductase inducer			DUKE
teratologic			DUKE
TNF-alpha inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
topoisomerase-II inhibitor	50750	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 inhibitor	50276	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 inhibitor	59997	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 trophic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	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

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Kaempferol (FDB000633)

Structure for FDB000633 (Kaempferol)