Structure Database (LMSD)
Common Name
Methyl-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate
Systematic Name
Methyl-(5Z,8Z,11Z,14Z,17Z)-eicosa-(5,8,11,14,17)-pentaenoate
Synonyms
- (5Z,8Z,11Z,14Z,17Z)-eicosapentanoic acid methyl ester
3D model of Methyl-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Eicosapentaenoic acid (EPA) is an ω-3 fatty acid which can have beneficial effects on vascular and immune physiology.1,2,3 Also, EPA serves as a precursor for resolvins, mediators that help resolve inflammatory processes.4 Eicosapentaenoic acid (EPA) methyl ester is an esterified form of EPA (Item Nos. 90110 | 90110.1 | 21908). It has been used as a reference standard in the quantification of fatty acids in microalgal and fish oils.5
This information has been provided by Cayman Chemical
References
1. Armenta, R.E., Scott, S.D., Burja, A.M., et al. Optimization of fatty acid determination in selected fish and microalgal oils. Chromatographia 70(3), 629–636 (2009).
2. Seki, H., Sasaki, T., Ueda, T., et al. Resolvins as regulators of the immune system. ScientificWorldJournal 10, 818-831 (2010).
3. Pottala, J.V., Garg, S., Cohen, B.E., et al. Blood eicosapentaenoic and docosahexaenoic acids predict all-cause mortality in patients with stable coronary heart disease: The heart and soul study. Circ. Cardiovasc. Qual. Outcomes 3(4), 406-412 (2010).
4. Pestka, J.J. N-3 polyunsaturated fatty acids and autoimmune-mediated glomerulonephritis. Prostaglandins Leukot. Essent. Fatty Acids 82(4-6), 1-17 (2010).
5. Chapkin, R.S., Kim, W., Lupton, J.R., et al. Dietary docosahexaenoic and eicosapentaenoic acid: Emerging mediators of inflammation. Prostaglandins Leukot. Essent. Fatty Acids 81(2-3), 1-10 (2009).
References
String Representations
InChiKey (Click to copy)
QWDCYFDDFPWISL-JEBPEJKESA-N
InChi (Click to copy)
InChI=1S/C21H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23-2/h4-5,7-8,10-11,13-14,16-17H,3,6,9,12,15,18-20H2,1-2H3/b5-4-,8-7-,11-10-,14-13-,17-16-
SMILES (Click to copy)
C(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)OC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
373.60
Topological Polar Surface Area
26.30
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
2
logP
6.08
Molar Refractivity
100.33
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Created at
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Updated at
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