Structure Database (LMSD)
Common Name
Nepetin
Systematic Name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
Synonyms
- Eupafolin
- 6-Methoxyluteolin
3D model of Nepetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Eupafolin is a flavonoid that has been found in E. adenophorum and has diverse biological activities.1,2,3,4 It inhibits iron-dependent lipid peroxidation in a cell-free assay (IC50 = 7.9 µM).1 Eupafolin (50-150 µM) inhibits prion protein 106-126 (PrP106-126) aggregation in a cell-free assay and reduces PrP106-126-induced cell death in SH-SY5Y cells.2 It inhibits the production of hemolysin and leukocidin by methicillin-susceptible S. aureus (MSSA) and methicillin-resistant S. aureus (MRSA) and reduces S. aureus-induced hemolysis of erythrocytes in isolated rabbit whole blood when used at a concentration of 100 µM.3 In vivo, eupafolin (100 mg/kg) reduces the number of lung colony-forming units (CFUs) and increases survival in a mouse model of MRSA infection. It also reduces angiogenesis and tumor volume in a Hep3B hepatocellular carcinoma (HCC) mouse xenograft model when administered at a dose of 60 mg/kg.4
This information has been provided by Cayman Chemical
References
1. Sanz, M.J., Ferrandiz, M.L., Cejudo, M., et al. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica 24(7), 689-699 (1994).
2. Huo, Y., Wang, Y., Wang, S., et al. Roles of apigenin and nepetin in the assembly behavior and cytotoxicity of prion neuropeptide PrP106-126. ACS Chem. Neurosci. 15(2), 245-257 (2024).
3. Jing, S., Ren, X., Wang, L., et al. Nepetin reduces virulence factors expression by targeting ClpP against MRSA-induced pneumonia infection. Virulence 13(1), 578-588 (2022).
4. Jiang, H., Wu, D., Xu, D., et al. Eupafolin exhibits potent anti-angiogenic and antitumor activity in hepatocellular carcinoma. Int. J. Biol. Sci. 13(6), 701-711 (2017).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
FHHSEFRSDKWJKJ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(O)=CC=3)=CC(=O)C=2C(O)=C1OC
Other Databases
Wikipedia
METABOLOMICS ID
PubChem CID
Cayman ID
NP-MRD ID(NMR)
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
255.99
Topological Polar Surface Area
120.36
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
7
logP
3.19
Molar Refractivity
81.24
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Created at
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Updated at
6th Oct 2023