Structure Database (LMSD)
Common Name
Ethyl icosapentate
Systematic Name
ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Synonyms
3D model of Ethyl icosapentate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Eicosapentaenoic acid (EPA) ethyl ester is an esterified form of the ω-3 fatty acid EPA . Dietary administration of EPA ethyl ester (41.4 g/100 g of total dietary fatty acids) increases the ex vivo activity of hepatic β-oxidation enzymes.1,2 It also reduces total hepatic triglyceride levels and increases the ω-3 fatty acid content of hepatic triglycerides and phospholipids, as well as increases the total levels of ω-3 fatty acids in rats. EPA ethyl ester (1 g/kg) reverses increases in plasma cholesterol levels and reduces circulating triglyceride levels in rats fed a high-fat diet.3 Formulations containing eicosapentaenoic acid ethyl ester have been used as adjuncts in the treatment of hypertriglyceridemia.
This information has been provided by Cayman Chemical
References
1. Pérez-Echarri, N., Pérez-Matute, P., Marcos-Gómez, B., et al. Down-regulation in muscle and liver lipogenic genes: EPA ethyl ester treatment in lean and overweight (high-fat-fed) rats. J. Nutr. Biochem. 20(9), 705-714 (2008).
2. Arachchige, P.G., Takahashi, Y., and Ide, T. Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats. Metabolism 55(3), 381-390 (2006).
String Representations
InChiKey (Click to copy)
SSQPWTVBQMWLSZ-AAQCHOMXSA-N
InChi (Click to copy)
InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-
SMILES (Click to copy)
O(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)CC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
390.90
Topological Polar Surface Area
26.30
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
2
logP
6.76
Molar Refractivity
105.43
Admin
Created at
-
Updated at
6th Jun 2022