Kaempferol
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Basic Info
| Common Name | Kaempferol(F05516) |
| 2D Structure | |
| Description | Kaempferol is a natural flavonoid which has been isolated from Delphinium, Witch-hazel, grapefruit, and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 degree centigrade. It is slightly soluble in water, and well soluble in hot ethanol and diethyl ether. |
| FRCD ID | F05516 |
| CAS Number | 520-18-3 |
| PubChem CID | 5280863 |
| Formula | C15H10O6 |
| IUPAC Name | 3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one |
| InChI Key | IYRMWMYZSQPJKC-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O |
| Isomeric SMILES | C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O |
| Wikipedia | Kaempferol |
| Synonyms |
Pelargidenolon
kaempferol
520-18-3
Kempferol
Kaempherol
Populnetin
Rhamnolutein
Robigenin
Trifolitin
Rhamnolutin
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavonols |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as flavonols. These are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 286.239 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 1 |
| Complexity | 451 |
| Monoisotopic Mass | 286.048 |
| Exact Mass | 286.048 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6286 |
| Human Intestinal Absorption | HIA+ | 0.9855 |
| Caco-2 Permeability | Caco2- | 0.7447 |
| P-glycoprotein Substrate | Substrate | 0.5139 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8869 |
| Non-inhibitor | 0.6099 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9145 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6122 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7797 |
| CYP450 2D6 Substrate | Non-substrate | 0.9075 |
| CYP450 3A4 Substrate | Non-substrate | 0.6591 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9108 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8948 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9083 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6434 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7241 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7652 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9795 |
| Non-inhibitor | 0.8734 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9363 |
| Fish Toxicity | High FHMT | 0.8970 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9852 |
| Honey Bee Toxicity | High HBT | 0.6472 |
| Biodegradation | Not ready biodegradable | 0.8854 |
| Acute Oral Toxicity | II | 0.6238 |
| Carcinogenicity (Three-class) | Non-required | 0.6985 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1423 | LogS |
| Caco-2 Permeability | 0.7994 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.0825 | LD50, mol/kg |
| Fish Toxicity | 0.5730 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7783 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Safety assessment of Morus nigra L. leaves: Acute and subacute oral toxicity studies in Wistar rats. | J Ethnopharmacol | 2018 Oct 5 | 29772355 |
| Enrichment and Purification of Total Ginkgo Flavonoid O-Glycosides from GinkgoBiloba Extract with Macroporous Resin and Evaluation of Anti-InflammationActivities In Vitro. | Molecules | 2018 May 13 | 29757247 |
| LC-ESI-Q-TOF-MS/MS profiling and antioxidant activity of phenolics from L.Sativum seedcake. | J Food Sci Technol | 2018 Mar | 29487458 |
| Anti-ulcer and anti-Helicobacter pylori potentials of the ethyl acetate fraction of Physalis alkekengi L. var. franchetii (Solanaceae) in rodent. | J Ethnopharmacol | 2018 Jan 30 | 28964871 |
| Comparison of partial least squares and random forests for evaluatingrelationship between phenolics and bioactivities of Neptunia oleracea. | J Sci Food Agric | 2018 Jan | 28580581 |
| In vitro screening of dual flavonoid combinations for reversingP-glycoprotein-mediated multidrug resistance: Focus on antiepileptic drugs. | Food Chem Toxicol | 2018 Jan | 29122665 |
| Biological effects and chemical characterization of Iris schachtii Markgr.extracts: A new source of bioactive constituents. | Food Chem Toxicol | 2018 Feb | 28797651 |
| Complexation of Bioelements and Toxic Metals by Polyphenolic Compounds - Implications for Health. | Curr Drug Targets | 2018 | 29611487 |
| Antimicrobial Activity of Selected Polyphenols and Capsaicinoids Identified inPepper (Capsicum annuum L.) and Their Possible Mode of Interaction. | Curr Microbiol | 2017 Nov | 28721659 |
| Antibacterial and Antiadhesive Activities of Extracts from Edible Plants against Soft Drink Spoilage by Asaia spp. | J Food Prot | 2017 Jan | 28221885 |
| Antioxidant, anti-inflammatory and anti-septic potential of phenolic acids and flavonoid fractions isolated from Lolium multiflorum. | Pharm Biol | 2017 Dec | 27937124 |
| Kaempferol impedes IL-32-induced monocyte-macrophage differentiation. | Chem Biol Interact | 2017 Aug 25 | 28711657 |
| Modulatory effects of Terminalia arjuna against domoic acid induced toxicity in Caco-2 cell line. | Cytotechnology | 2017 Aug | 28342004 |
| Differential Gene Expression by Lactobacillus plantarum WCFS1 in Response to Phenolic Compounds Reveals New Genes Involved in Tannin Degradation. | Appl Environ Microbiol | 2017 Apr 1 | 28115379 |
| A new approach for the assessment of the toxicity of polyphenol-rich compounds with the use of high content screening analysis. | PLoS One | 2017 | 28662177 |
| Polyphenolic extracts of cherry (Prunus cerasus L.) and blackcurrant (Ribesnigrum L.) leaves as natural preservatives in meat products. | Food Microbiol | 2016 Oct | 27375255 |
| Antimicrobial activities, toxicity and phenolic composition of Asphodeline anatolica E. Tuzlaci leaf extracts from Turkey. | Nat Prod Res | 2016 Nov | 26727992 |
| Protective effects of kaempferol against reactive oxygen species-induced hemolysis and its antiproliferative activity on human cancer cells. | Eur J Med Chem | 2016 May 23 | 26974372 |
| Evaluation of ozonation technique for pesticide residue removal and its effect onascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits. | Environ Monit Assess | 2016 May | 27098519 |
| Intake of selected bioactive compounds from plant food supplements containingfennel (Foeniculum vulgare) among Finnish consumers. | Food Chem | 2016 Mar 1 | 26471600 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular Weight:
- 98979.96 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Udp-glycosyltransferase activity
- Specific Function:
- UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
- Gene Name:
- UGT3A1
- Uniprot ID:
- Q6NUS8
- Molecular Weight:
- 59150.34 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]