Structure Database (LMSD)

Common Name
Genkwanin
Systematic Name
Synonyms
LM ID
LMPK12111018
Formula
Exact Mass
Calculate m/z
284.068475
Status
Curated



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

Wikipedia
KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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

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Updated at
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