Structure Database (LMSD)
Common Name
Genkwanin
Systematic Name
Synonyms
3D model of Genkwanin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Genkwanin is a flavonoid that has been found in T. kirilowii and has diverse biological activities.1,2 It inhibits proliferation of MDA-MB-231 and MCF-7 breast cancer, Eca-109 esophageal carcinoma, and A549 lung adenocarcinoma cells (IC50s = 58.54, 101.4, 98.2, and 120.77 µM, respectively).1 It decreases the levels of PI3Kγ, as well as the levels of phosphorylated Akt, mTOR, p70 ribosomal S6 kinase (p70S6K) and ULK, and induces apoptosis and cell cycle arrest at the G2/M phase in MDA-MB-231 cells. Genkwanin (20-40 µM) reverses increases in apoptosis, lactate dehydrogenase (LDH) release, and reactive oxygen species (ROS) production induced by 1-methyl-4-phenylpyridinium (MPP+) in an in vitro model of Parkinson’s disease inflammation using SH-SY5Y cells.2 It also reduces protein levels of toll-like receptor 4 (TLR4), MyD88, NOD-like receptor protein 3 (NLRP3), and caspase-1 in SH-SY5Y cells.
This information has been provided by Cayman Chemical
References
1. Zhang, H.-W., Hu, J.-J., Fu, R.-Q., et al. Flavonoids inhibit cell proliferation and induce apoptosis and autophagy through downregulation of PI3Kγ mediated PI3K/AKT/mTOR/p70S6K/ULK signaling pathway in human breast cancer cells. Sci. Rep. 8(1), 11255 (2018).
2. Li, Q., Zhang, P., and Cai, Y. Genkwanin suppresses MPP+-induced cytotoxicity by inhibiting TLR4/MyD88/NLRP3 inflammasome pathway in a cellular model of Parkinson’s disease. Neurotoxicology 87, 62-69 (2021).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
JPMYFOBNRRGFNO-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
238.41
Topological Polar Surface Area
79.90
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
3.78
Molar Refractivity
77.91
Admin
Created at
-
Updated at
-