Structure Database (LMSD)

Common Name
Kaempferol
Systematic Name
Synonyms
LM ID
LMPK12110003
Formula
C15H10O6
Exact Mass
Calculate m/z
286.04774
Status
Curated
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Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

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).
4. Calderón-Montaño, J.M., Burgos-Morón, E., Pérez-Guerrero, C., et al. A review on the dietary flavonoid kaempferol. Mini Rev. Med. Chem. 11, 298-344 (2011).
5. Guo, A.J., Choi, R.C., Zheng, K.Y., et al. Kaempferol as a flavonoid induces osteoblastic differentiation via estrogen receptor signaling. Chin.Med. 7, 1-7 (2012).
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).
7. Labbé, D., Provençal, M., Lamy, S., et al. The flavonols quercetin, kaempferol, and myricetin inhibit hepatocyte growth factor-induced medulloblastoma cell migration. J. Nutr. 139(4), 646-652 (2009).
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
kaempferol
KEGG ID
C05903
HMDB ID
HMDB0005801
CHEBI ID
28499
PubChem CID
5280863
Cayman ID
11852
PDB ID
KMP
GuidePharm ID
11052

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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