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
SMILES
OC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O2)C=C(O)C=C3O
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
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.2363 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26419945 |
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Target ID: CHEMBL2345 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24994661 |
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Target ID: CHEMBL4237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24994661 |
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Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10813558 |
0.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). | 2002-04-10 |
|
| Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries. | 2002-04-10 |
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| Selective responses of three Ginkgo biloba leaf-derived constituents on human intestinal bacteria. | 2002-03-27 |
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| Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols. | 2002-03-15 |
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| Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L. | 2002-03-06 |
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| Flavonoids from the flowers of Prunus spinosa L. | 2002-03-06 |
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| Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. | 2002-03-01 |
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| Antioxidant activity of flavonoids from Licania licaniaeflora. | 2002-03 |
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| Hepatoprotective principles from the flowers of Tilia argentea (linden): structure requirements of tiliroside and mechanisms of action. | 2002-03 |
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| Phytochemical and pharmacological analysis of Bauhinia microstachya (Raddi) Macbr. (Leguminosae). | 2002-02-12 |
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| The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds. | 2002-02 |
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| Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9. | 2002-02 |
|
| Isolation and characterization of stelladerol, a new antioxidant naphthalene glycoside, and other antioxidant glycosides from edible daylily (hemerocallis) flowers. | 2002-01-02 |
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| Flavonoid gene expression and UV photoprotection in transgenic and mutant Petunia leaves. | 2002-01 |
|
| A pharmacophore for human pregnane X receptor ligands. | 2002-01 |
|
| Inhibition of nitric oxide synthase expression by a methanolic extract of Crescentia alata and its derived flavonols. | 2001-12-21 |
|
| Ethyl m-digallate from red maple, Acer rubrum L., as the major resistance factor to forest tent caterpillar, Malacosoma disstria Hbn. | 2001-12 |
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| Proposed active constituents of Dipladenia martiana. | 2001-12 |
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| Coumaroyl flavonol glycosides from the leaves of Ginkgo biloba. | 2001-12 |
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| A new C-methylated flavonoid glycoside from Pinus densiflora. | 2001-12 |
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| Flavonoids and UV photoprotection in Arabidopsis mutants. | 2001-11-29 |
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| Kaempferol and its glycosides in the seeds hair of Asclepias syriaca L. | 2001-11-20 |
|
| Direct extraction of specific pharmacophoric flavonoids from gingko leaves using a molecularly imprinted polymer for quercetin. | 2001-11-16 |
|
| Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L. | 2001-11-06 |
|
| Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils. | 2001-11-01 |
|
| In vitro anti-inflammatory effects of quercetin 3-O-methyl ether and other constituents from Rhamnus species. | 2001-11 |
|
| A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation. | 2001-11 |
|
| Flavonol glycosides from the flowers of Bellis perennis. | 2001-11 |
|
| Phenolic compounds in seven South American Ilex species. | 2001-11 |
|
| Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. | 2001-10 |
|
| Antioxidative components from the aerial parts of Lactuca scariola L. | 2001-10 |
|
| Effect of plant growth temperature on antioxidant capacity in strawberry. | 2001-10 |
|
| Indolopyridoquinazoline alkaloid from Leptothyrsa sprucei. | 2001-10 |
|
| Flavonol glycosides from the stems of Trigonella foenum-graecum. | 2001-10 |
|
| Flavonoids protect neurons from oxidized low-density-lipoprotein-induced apoptosis involving c-Jun N-terminal kinase (JNK), c-Jun and caspase-3. | 2001-09-15 |
|
| Alkaline phosphatase from rat liver and kidney is differentially modulated. | 2001-09 |
|
| Determination of flavonoids and stilbenes in red wine and related biological products by HPLC and HPLC-ESI-MS-MS. | 2001-09 |
|
| Polyphenolic compounds: interactions with the gut and implications for human health. | 2001-09 |
|
| Antipruritic and antidermatitic effect of extract and compounds of Impatiens balsamina L. in atopic dermatitis model NC mice. | 2001-09 |
|
| Electrochemical behaviors of quercetin and kaempferol in neutral buffer solution. | 2001-08 |
|
| Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat. | 2001-08 |
|
| Four new isoflavone triglycosides from Sophora japonica. | 2001-08 |
|
| Medicinal foodstuffs. XXV. Hepatoprotective principle and structures of ionone glucoside, phenethyl glycoside, and flavonol oligoglycosides from young seedpods of garden peas, Pisum sativum L. | 2001-08 |
|
| Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams. | 2001-08 |
|
| Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids. | 2001-08 |
|
| Inhibitory activity for chitin synthase II from Saccharomyces cerevisiae by tannins and related compounds. | 2001-08 |
|
| [Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC]. | 2001-06 |
|
| Flavonoids and urate antioxidant interplay in plasma oxidative stress. | 2001-05 |
|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
| Induction of glutathione synthesis in human keratinocytes by Ginkgo biloba extract (EGb761). | 2001 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27175782
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
| Substance Class |
Chemical
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1221 (Number of products:6)
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KAEMPFEROL
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DTXSID7020768
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 89.7 uM.
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