Structure Database (LMSD)

Common Name
Ermanin
Systematic Name
5,7-Dihydroxy-3,4'-dimethoxyflavone
Synonyms
  • Kaempferol 3,4'-di-O-methyl ether
LM ID
LMPK12112697
Formula
C17H14O6
Exact Mass
Calculate m/z
314.07904
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Ermanin is a methoxylated flavone that has been found in bee glue and has diverse biological activities.1,2,3 It increases the levels of intracellular reactive oxygen species (ROS) and decreases the levels of glutathione (GSH) in B16/F10 mouse melanoma cells and primary mouse melanocytes when used at concentrations of 8 and 16 µM.1 Ermanin reduces LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 levels in RAW 264.7 mouse macrophages (IC50s = 6.7 and 1.68 µM, respectively).2 It inhibits viral replication of poliovirus type 1 in Vero cells (ED99 = 5 µg/ml).3 Ermanin (8 and 16 µM) induces melanogenesis in zebrafish larvae.1

This information has been provided by Cayman Chemical

References

1. De Meyer, N., Haemers, A., Mishra, L., et al. 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity. J. Med. Chem. 34(2), 736-746 (1991).
2. Ding, Q., Luo, L., Yu, L., et al. The critical role of glutathione redox homeostasis towards oxidation in ermanin-induced melanogenesis. Free Radic. Biol. Med. 176, 392-405 (2021).
3. Guerra, J.A., Molina, M.F., Abad, M.J., et al. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids isolated from Tanacetum microphyllum. Int. Immunopharmacol. 6(11), 1723-1728 (2006).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
RJCJVIFSIXKSAH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H14O6/c1-21-11-5-3-9(4-6-11)16-17(22-2)15(20)14-12(19)7-10(18)8-13(14)23-16/h3-8,18-19H,1-2H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(OC)=CC=3)=C(OC)C(=O)C=2C(O)=C1

Other Databases

Wikipedia
Ermanin
CHEBI ID
146142
METABOLOMICS ID
FL5FDBNS0001
PubChem CID
5352001
Cayman ID
37535

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 3
Aromatic Rings 3
Rotatable Bonds 3
Van der Waals Molecular Volume 264.50
Topological Polar Surface Area 89.13
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 6
logP 3.79
Molar Refractivity 84.46

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Updated at
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