Structure Database (LMSD)

Common Name
Ethyl icosapentate
Systematic Name
ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Synonyms
LM ID
LMFA07010877
Formula
Exact Mass
Calculate m/z
330.25588
Sum Composition
Status
Curated


Classification

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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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

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Created at
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Updated at
6th Jun 2022