Structure Database (LMSD)
Common Name
Kaempferol
Systematic Name
Synonyms
3D model of Kaempferol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Kaempferol is a flavonoid which is abundant in a variety of plant leaves and fruits. It has diverse physiological activities through both direct and indirect effects.1,2 For example, kaempferol directly binds estrogen receptors α and β, acting as an inverse agonist or agonist.3,4 It also acts as an antioxidant, which presumably contributes to its ability to suppress advanced glycation endproduct-induced NADPH oxidase, NF-κB signaling, and hypoxia-inducible factor-related angiogenesis and VEGF expression.5,6 Kaempferol also suppresses signaling through certain receptor tyrosine kinases, including EGFR and HGF.7,8,2
This information has been provided by Cayman Chemical
References
1. Kumamoto, T., Fujii, M., and Hou, D.X. Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett. 275(1), 17-26 (2009).
2. Aiyer, H.S., Warri, A.M., Woode, D.R., et al. Influence of berry polyphenols on receptor signaling and cell-death pathways: Implications for breast cancer prevention. J. Agric. Food Chem. 60(23), 5693-5708 (2012).
3. Wang, J., Fang, F., Huang, Z., et al. Kaempferol is an estrogen-related receptor α and γ inverse agonist. FEBS Lett. 583(4), 643-647 (2009).
6. Kim, J.M., Lee, E.K., Kim, D.H., et al. Kaempferol modulates pro-inflammatory NF-κB activation by suppressing advanced glycation endproducts-induced NADPH oxidase. Age (Dordr) 32(2), 197-208 (2010).
8. Luo, H., Rankin, G.O., Liu, L., et al. Kaempferol inhibits angiogenesis and VEGF expression through both HIF dependent and independent pathways in human ovarian cancer cells. Nutr. Cancer 61(4), 554-563 (2009).
String Representations
InChiKey (Click to copy)
IYRMWMYZSQPJKC-UHFFFAOYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1(O)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C(O)C=1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
229.90
Topological Polar Surface Area
111.13
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
6
logP
3.18
Molar Refractivity
74.69
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Updated at
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