Structure Database (LMSD)
Common Name
Apigenin
Systematic Name
Synonyms
3D model of Apigenin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Apigenin is a flavonoid compound found in many fruits and vegetables that selectively inhibits casein kinase 2 (CK2). Apigenin inhibits CK2 activity in the renal cortex with an IC50 value of 30 µM to improve renal function in a rat model of glomerulonephritis.1 CK2 inhibition by 20 µM apigenin decreases the degradation of IκBα and down-regulates NF-κB levels in WEHI-231 cells.2 Apigenin at 5 µM is a potent inhibitor of the synthesis of the inflammatory mediators nitric oxide and prostaglandin E2, reducing inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression by 56% and 64%, respectively, in the macrophage cell line J774A.1.3
This information has been provided by Cayman Chemical
References
1. Shen, J., Channavajhala, P., Seldin, D.C., et al. Phosphorylation by the protein kinase CK2 promotes calpain-mediated degradation of IκBα1. J. Immunol. 167(9), 4919-4925 (2001).
2. Raso, G.M., Meli, R., Di Carlo, G., et al. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1. Life Sci. 68(8), 921-931 (2001).
String Representations
InChiKey (Click to copy)
KZNIFHPLKGYRTM-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
SMILES (Click to copy)
C1(O)C=C2OC(C3=CC=C(O)C=C3)=CC(=O)C2=C(O)C=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
221.11
Topological Polar Surface Area
90.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.48
Molar Refractivity
73.02
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Updated at
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