KAEMPFEROL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O6
Molecular Weight	286.2363
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=IYRMWMYZSQPJKC-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21428901 | https://www.ncbi.nlm.nih.gov/pubmed/25982933 | https://www.ncbi.nlm.nih.gov/pubmed/24578792

Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26419945	Inhibitor 8297
Ribosomal protein S6 kinase alpha 3 5 Target ID: CHEMBL2345 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24994661	Inhibitor 8297
Ribosomal protein S6 kinase alpha 5 4 Target ID: CHEMBL4237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24994661	Inhibitor 8297
Monoamine oxidase A 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10813558	Inhibitor 8297	0.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24578792 https://www.ncbi.nlm.nih.gov/pubmed/26323894 https://www.ncbi.nlm.nih.gov/pubmed/26878784 https://www.ncbi.nlm.nih.gov/pubmed/26883800	Primary	Preclinical	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22110339	Primary	Preclinical	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27330526	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
0.46 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
3.84 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
1.43 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640	6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1.51 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
7.17 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
17.72 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640	6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
3.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
3.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255	25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
5.11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640	6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	KAEMPFEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003A28	https://www.1pchem.com/search?query=1P003A28
A2B Chem	AB52208	http://a2bchem.com/prod/AB52208
AK Scientific	C554	https://aksci.com/item_detail.php?cat=C554
AK Scientific	J10449	https://aksci.com/item_detail.php?cat=J10449
AK Scientific	W1682	https://aksci.com/item_detail.php?cat=W1682
Accela ChemBio Inc	SY023424	http://accelachem.com/cn/search.html?keyword=SY023424&attname=0
Achemo Scientific Limited	AC-106690	http://www.achemo.com/search/?Keyword=AC-106690
Ambeed	A272671	http://www.ambeed.com/search/Search.html?keyword=A272671
Angene	AGN-PC-088NKM	http://www.angenechemical.com/productshow/AGN-PC-088NKM.html
ApexBio Technology	N1719	https://www.apexbt.com/catalogsearch/result/?q=N1719
AstaTech	H10428	http://astatechinc.com/CPSResult.php?CRNO=H10428
BOC Sciences	520-18-3	http://www.bocsci.com/description.asp?cas=520-18-3
BioSynth	Q-100584	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100584
Biopurify Phytochemicals	BP0820	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0820&searchhtmp=simplesearch&t=1
Cayman Chemical	11852	http://www.caymanchem.com/app/template/Product.vm/catalog/11852
Chem Scene	CS-1273	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1273
ChemShuttle	141536	https://www.chemshuttle.com/catalogsearch/result/?q=141536
Combi-Blocks	QA-0803	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-0803
Combi-Blocks	QC-5720	http://www.combi-blocks.com/cgi-bin/find.cgi?QC-5720
Enamine	EN300-205764	https://www.enaminestore.com/catalog/EN300-205764
Enamine	EN300-206857	https://www.enaminestore.com/catalog/EN300-206857
Frontier Scientific Services	501003636	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=501003636&type=hts
Hairui	HR122347	http://www.hairuichem.com/en/product/search.do?q=HR122347
Indofine	021123S	https://indofinechemical.com/details.aspx?Sku=021123S
Indofine	021124S	https://indofinechemical.com/details.aspx?Sku=021124S
Indofine	021243S	https://indofinechemical.com/details.aspx?Sku=021243S
Indofine	K-102	https://indofinechemical.com/details.aspx?Sku=K-102
KeyOrganics	GS-3570	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=GS-3570
Lab Network	LN00008740	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00008740
Lab Seeker	SC-17291	http://www.labseeker.com/search.php?keywords=SC-17291&category=0
LabSeeker	SC-17291	http://www.labseeker.com/search.php?keywords=SC-17291&category=0
MedChem Express	HY-14590	https://www.medchemexpress.com/search.html?q=HY-14590&ft=&fa=&fp=
MolPort	MolPort-001-741-568	https://www.molport.com/shop/molecule-link/MolPort-001-741-568
Molnova	M14822	https://www.molnova.com/en/serch-list.html?keywords=M14822
PI Chemicals	PI-14733	http://www.pipharm.com/catalog_products/PI-14733.html
Selleck Chemicals	S2314	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2314
ShangHai Biochempartner	BCP20472	http://www.biochempartner.com/search_BCP20472
TargetMol	BBP00243	https://www.targetmol.com/search?keyword=BBP00243
TargetMol	T2177	https://www.targetmol.com/search?keyword=T2177
Tetrahedron	TS77144	http://www.thsci.com/search.do?q=TS77144
TimTec	SBB066091	http://www.echemstore.com/catalogsearch/result/?q=SBB066091
TimTec	ST030560	http://www.echemstore.com/catalogsearch/result/?q=ST030560
Tocris	3603	https://www.tocris.com/search.php?Type=QuickSearch&Value=3603
Toronto Research Chemicals	B692910	https://www.trc-canada.com/product-detail/?CatNum=B692910
Toronto Research Chemicals	K100000	https://www.trc-canada.com/product-detail/?CatNum=K100000
W&J PharmaChem	50A258643	http://wjpharmachem.com/new/searcht.php?keyword=50A258643
eMolecules	50377688	https://orderbb.emolecules.com/search/#?query=50377688
eMolecules	524531	https://orderbb.emolecules.com/search/#?query=524531
eNovation Chemicals	D693235	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D693235&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-8965218413	https://mcule.com/MCULE-8965218413/

PubMed

Title	Date	PubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880
Induction of glutathione synthesis in human keratinocytes by Ginkgo biloba extract (EGb761).	2001	11673643
New flavonol glycosides from the flowers of Aconitum napellus ssp. tauricum.	2001 Apr	11345707
Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis.	2001 Apr	11310664
Measurement of copper-binding sites on low density lipoprotein.	2001 Apr	11304478
Effect of five flavonoid compounds isolated from Quercus dentata Thunb on superoxide generation in human neutrophils and phosphorylation of neutrophil proteins.	2001 Apr	11282099
Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat.	2001 Aug	11545625
Inhibitory activity for chitin synthase II from Saccharomyces cerevisiae by tannins and related compounds.	2001 Aug	11509967
The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp1a1 expression.	2001 Aug	11454723
Ethyl m-digallate from red maple, Acer rubrum L., as the major resistance factor to forest tent caterpillar, Malacosoma disstria Hbn.	2001 Dec	11789956
Inhibition of nitric oxide synthase expression by a methanolic extract of Crescentia alata and its derived flavonols.	2001 Dec 21	11811897
[Identification of seeds of Cuscuta australis and C. chinensis by TLC and HPLC].	2001 Feb	11402739
Preferential induction of a 9-lipoxygenase by salt in salt-tolerant cells of Citrus sinensis L. Osbeck.	2001 Feb	11289601
Flavonoids as cycline-dependent kinase inhibitors: inhibition of cdc 25 phosphatase activity by flavonoids belonging to the quercetin and kaempferol series.	2001 Jul	11488465
Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments.	2001 Jul	11457914
Flavonol content varies among black currant cultivars.	2001 Jul	11453762
Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L.	2001 Jul-Aug	11693731
Isolation and antioxidant activity of galloyl flavonol glycosides from the seashore plant, Pemphis acidula.	2001 Jun	11471728
Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants.	2001 Jun	11410016
Flavonoid accumulation patterns of transparent testa mutants of arabidopsis.	2001 Jun	11402185
Flavonoids from Aconitum napellus subsp. neomontanum.	2001 Jun	11394854
Flavonoids and phenylpropanoid derivatives from Campanula barbata.	2001 Mar	11281141
Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae).	2001 Mar-Apr	11501790
A novel acetylated 3-deoxyanthocyanidin laminaribioside from the fern Blechnum novae-zelandiae.	2001 Mar-Apr	11371005
Flavonoids and urate antioxidant interplay in plasma oxidative stress.	2001 May	11506190
Kaempferol acetylrhamnosides from the rhizome of Dryopteris crassirhizoma and their inhibitory effects on three different activities of human immunodeficiency virus-1 reverse transcriptase.	2001 May	11383604
Two new glycosides from Astragalus caprinus.	2001 May	11374969
Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids.	2001 May	11306701
Kaempferol and its glycosides in the seeds hair of Asclepias syriaca L.	2001 May-Jun	11712739
A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation.	2001 Nov	11725550
Flavonol glycosides from the flowers of Bellis perennis.	2001 Nov	11677029
Phenolic compounds in seven South American Ilex species.	2001 Nov	11677016
Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils.	2001 Nov 1	11673865
Phytochemical and pharmacological analysis of Bauhinia microstachya (Raddi) Macbr. (Leguminosae).	2001 Nov-Dec	11837679
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.	2001 Oct	11814152
Antioxidative components from the aerial parts of Lactuca scariola L.	2001 Oct	11693545
Flavonol glycosides from the stems of Trigonella foenum-graecum.	2001 Oct	11576601
Alkaline phosphatase from rat liver and kidney is differentially modulated.	2001 Sep	11676975
Antimicrobial activity of Argentine plants used in the treatment of infectious diseases. Isolation of active compounds from Sebastiania brasiliensis.	2001 Sep	11483376
Flavonoids protect neurons from oxidized low-density-lipoprotein-induced apoptosis involving c-Jun N-terminal kinase (JNK), c-Jun and caspase-3.	2001 Sep 15	11535118
Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L.	2001 Sep-Oct	11876448
Flavonoids from the flowers of Prunus spinosa L.	2001 Sep-Oct	11876444
Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch).	2002 Apr 10	11929314
Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries.	2002 Apr 10	11929309
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.	2002 Feb	11849977
A pharmacophore for human pregnane X receptor ligands.	2002 Jan	11744617
Hepatoprotective principles from the flowers of Tilia argentea (linden): structure requirements of tiliroside and mechanisms of action.	2002 Mar	11814859
Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter.	2002 Mar 1	11864778
Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols.	2002 Mar 15	11931850
Selective responses of three Ginkgo biloba leaf-derived constituents on human intestinal bacteria.	2002 Mar 27	11902921

Patents

Sample Use Guides

In Vivo Use Guide

humans: orally as a component of plant (e.g. Elaeagnus Angustifolia or Ginkgo Biloba) extracts. mice: 100 mg/kg/d, p. o. for 6 weeks. rats: 20 mg/kg; i.p. daily for a period of 28 days.

Route of Administration: Other

In Vitro Use Guide

50 μM of kaempferol specifically inhibited the cell viability by approximately 40% in Miapaca-2 cells, 15% in Panc-1 cells, and 10% in SNU-213 cells

Name

Type

Language

KAEMPFEROL

Official Name

English

CI 75640

Common Name

English

KAEMPFEROL [INCI]

Common Name

English

KAEMPFEROL [IARC]

Common Name

English

SWARTZIOL

Common Name

English

NIMBECETIN

Common Name

English

NSC-656277

Code

English

3'-DEOXYQUERCETIN

Common Name

English

3,4',5,7-TETRAHYDROXYFLAVONE

Systematic Name

English

KAEMPFEROL (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

PELARGIDENON

Common Name

English

KAEMPHEROL

Common Name

English

PELARGIDENOLON 1497

Brand Name

English

RHAMNOLUTEIN

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 3,5,7-TRIHYDROXY-2-(4-HYDROXYPHENYL)-

Systematic Name

English

3,5,7-TRIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

5,7,4'-TRIHYDROXYFLAVONOL

Systematic Name

English

POPULNETIN

Common Name

English

FLAVONE, 3,4',5,7-TETRAHYDROXY-

Systematic Name

English

KAMPCETIN

Common Name

English

ROBIGENIN

Common Name

English

C.I. 75640

Common Name

English

KAEMPFEROL [USP-RS]

Common Name

English

KAEMPFEROL [HSDB]

Common Name

English

KAEMPFEROL [MI]

Common Name

English

INDIGO YELLOW

Common Name

English

NSC-407289

Code

English

TRIFOLITIN

Common Name

English

Classification Tree Code System Code

DSLD

1221 (Number of products:6)