Structure Database (LMSD)

Common Name
Eupatilin
Systematic Name
Synonyms
LM ID
LMPK12111228
Formula
Exact Mass
Calculate m/z
344.089605
Status
Curated



Classification

Biological Context

Eupatilin is a flavonoid that has been found in Artemisia and has diverse biological activities.1,2,3,4,5 It inhibits cell growth in A375 melanoma cells when used at concentrations ranging from 25 to 800 µM.1 Eupatilin binds to peroxisome proliferator-activated receptor α (PPARα; IC50 = 1.18 µM) and induces reporter gene expression in CV-1 cells expressing human PPARα, but not PPARγ, when used at concentrations ranging from 10 to 300 µM.2 It prevents hydrogen peroxide-induced disruption of the F-actin cytoskeleton and inhibition of cell migration in AGS gastric epithelial cells.6 Eupatilin also inhibits 5-lipoxygenase (5-LO) activity in cultured mastocytoma cells (IC50 = 14 µM).3 In vivo, eupatilin (5, 10, and 15 mg/kg) reduces pulmonary edema and levels of the lung injury markers surfactant protein A (SPA) and SPD in a rat model of LPS-induced acute lung injury.4 It reduces serum levels of histamine and increases survival in a mouse model of allergic anaphylactic shock induced by compound 48/80 .5

This information has been provided by Cayman Chemical

References

1. Choi, Y., Jung, Y., and Kim, S.N. Identification of eupatilin from Artemisia argyi as a selective PPARα agonist using affinity selection ultrafiltration LC-MS. Molecules 20(8), 13753-13763 (2015).
4. Shawi, A.A., Rasul, A., Khan, M., et al. Eupatilin: A flavonoid compound isolated from the artemisia plant, induces apoptosis and G2/M phase cell cycle arrest in human melanoma A375 cells. Afr. J. Pharm. Pharmacol. 5(5), 582-588 (2011).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
DRRWBCNQOKKKOL-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(OC)C(OC)=CC=3)=CC(=O)C=2C(O)=C1OC

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 3
Aromatic Rings 3
Rotatable Bonds 4
Van der Waals Molecular Volume 290.59
Topological Polar Surface Area 98.36
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 3.80
Molar Refractivity 91.01

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