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
LM ID
LMPK12111230
Formula
Exact Mass
Calculate m/z
316.058305
Status
Curated


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