Record Information
Version3.6
Creation Date2006-05-22 14:17:31 UTC
Update Date2013-03-25 21:39:38 UTC
HMDB IDHMDB01999
Secondary Accession NumbersNone
Metabolite Identification
Common NameEicosapentaenoic acid
DescriptionEicosapentaenoic acid (EPA or also icosapentaenoic acid) is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3 and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in human breast milk. -- Wikipedia.
Structure
Thumb
Synonyms
  1. (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate
  2. (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
  3. 5,8,11,14,17-Eicosapentaenoate
  4. 5,8,11,14,17-Eicosapentaenoic acid
  5. 5,8,11,14,17-Icosapentaenoate
  6. 5,8,11,14,17-Icosapentaenoic acid
  7. 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate
  8. 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid
  9. All-cis-icosapentaenoate
  10. All-cis-icosapentaenoic acid
  11. cis-5,8,11,14,17-Eicosapentaenoate
  12. cis-5,8,11,14,17-Eicosapentaenoic acid
  13. Eicosapentaenoate
  14. Eicosapentaenoic acid
  15. EPA
  16. Icosapent
  17. Icosapentaenoate
  18. Icosapentaenoic acid
  19. Icosapento
  20. Icosapentum
  21. Timnodonate
  22. Timnodonic acid
Chemical FormulaC20H30O2
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional IUPAC Nameicosapent
CAS Registry Number10417-94-4
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyJAZBEHYOTPTENJ-JLNKQSITSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassUnsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct ParentUnsaturated Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility2.890E-04 g/LALOGPS
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (strongest acidic)4.82ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count13ChemAxon
refractivity101.07ChemAxon
polarizability36.13ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Liver
  • Neutrophil
  • Platelet
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.435 +/- 0.010 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified2100.0 +/- 990.0 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified11.0 +/- 8.3 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified1.09 +/- 0.72 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified11.1 +/- 9.5 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified10.8 +/- 6.2 uMAdult (>18 years old)FemaleCommentNormal
BloodDetected and Quantified270 +/- 160 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.401 +/- 0.068 uMAdult (>18 years old)BothNormal
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified11.0 +/- 7.3 uMAdult (>18 years old)BothCommentHypertension
BloodDetected and Quantified10.6 +/- 7.2 uMAdult (>18 years old)MaleCommentEssential hypertension
BloodDetected and Quantified11.9 +/- 7.6 uMAdult (>18 years old)FemaleEssential hypertension
Associated Disorders and Diseases
Disease References
Essential hypertension
  • Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. Pubmed: 18633173
Hypertension
  • Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. Pubmed: 18633173
Associated OMIM IDs
DrugBank IDDB00159
DrugBank Metabolite IDDBMET00546
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003102
KNApSAcK IDC00000408
Chemspider ID393682
KEGG Compound IDC06428
BioCyc IDCPD-6941
BiGG ID2218016
Wikipedia LinkEicosapentaenoic acid
NuGOwiki LinkHMDB01999
Metagene LinkHMDB01999
METLIN ID6423
PubChem Compound446284
PDB IDEPA
ChEBI ID28364
References
Synthesis ReferenceSandri, Jacqueline; Viala, Jacques. Syntheses of all-(Z)-5,8,11,14,17-Eicosapentaenoic Acid and all-(Z)-4,7,10,13,16,19-Docosahexaenoic Acid from (Z)-1,1,6,6-tetraisopropoxy-3-hexene. Journal of Organic Chemistry (1995), 60(20), 6627-30.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. Pubmed: 16872308
  2. Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33. Pubmed: 12499346
  3. Hafstrom I, Ringertz B, Gyllenhammar H, Palmblad J, Harms-Ringdahl M: Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis. Arthritis Rheum. 1988 May;31(5):585-92. Pubmed: 2837251
  4. Woodman RJ, Mori TA, Burke V, Puddey IB, Barden A, Watts GF, Beilin LJ: Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. Atherosclerosis. 2003 Jan;166(1):85-93. Pubmed: 12482554
  5. Sipka S, Dey I, Buda C, Csongor J, Szegedi G, Farkas T: The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes. Clin Immunol Immunopathol. 1996 Jun;79(3):224-8. Pubmed: 8635279
  6. Miwa H, Yamamoto M, Futata T, Kan K, Asano T: Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration. J Chromatogr B Biomed Appl. 1996 Mar 3;677(2):217-23. Pubmed: 8704924
  7. Kim HH, Shin CM, Park CH, Kim KH, Cho KH, Eun HC, Chung JH: Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts. J Lipid Res. 2005 Aug;46(8):1712-20. Epub 2005 Jun 1. Pubmed: 15930517
  8. Gillis RC, Daley BJ, Enderson BL, Karlstad MD: Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells. J Surg Res. 2002 Sep;107(1):145-53. Pubmed: 12384078
  9. Takenaga M, Hirai A, Terano T, Tamura Y, Kitagawa H, Yoshida S: Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid. Thromb Res. 1986 Feb 1;41(3):373-84. Pubmed: 3010490
  10. Hereliuk VI: [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis] Fiziol Zh. 2000;46(6):112-5. Pubmed: 11424554
  11. Aas V, Rokling-Andersen MH, Kase ET, Thoresen GH, Rustan AC: Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells. J Lipid Res. 2006 Feb;47(2):366-74. Epub 2005 Nov 21. Pubmed: 16301737
  12. Kim HH, Cho S, Lee S, Kim KH, Cho KH, Eun HC, Chung JH: Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo. J Lipid Res. 2006 May;47(5):921-30. Epub 2006 Feb 7. Pubmed: 16467281
  13. Herrmann W, Beitz J: [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet] Z Gesamte Inn Med. 1987 Mar 1;42(5):117-22. Pubmed: 3035811
  14. Ide T, Okamura T, Kumashiro R, Koga Y, Hino T, Hisamochi A, Ogata K, Tanaka K, Kuwahara R, Seki R, Sata M: A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C. Int J Mol Med. 2003 Jun;11(6):729-32. Pubmed: 12736713
  15. Dunstan JA, Roper J, Mitoulas L, Hartmann PE, Simmer K, Prescott SL: The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition. Clin Exp Allergy. 2004 Aug;34(8):1237-42. Pubmed: 15298564
  16. Luostarinen R, Saldeen T: Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release. Prostaglandins Leukot Essent Fatty Acids. 1996 Sep;55(3):167-72. Pubmed: 8931114
  17. Calzada C, Vericel E, Lagarde M: Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid. Biochim Biophys Acta. 1992 Jul 29;1127(2):147-52. Pubmed: 1643099
  18. Lagarde M, Croset M, Vericel E, Calzada C: Effects of small concentrations of eicosapentaenoic acid on platelets. J Intern Med Suppl. 1989;731:177-9. Pubmed: 2539831
  19. Bays HE, Ballantyne CM, Kastelein JJ, Isaacsohn JL, Braeckman RA, Soni PN: Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). Am J Cardiol. 2011 Sep 1;108(5):682-90. doi: 10.1016/j.amjcard.2011.04.015. Epub 2011 Jun 16. Pubmed: 21683321

Enzymes

Gene Name:
ACSL4
Uniprot ID:
O60488
Gene Name:
ACSL3
Uniprot ID:
O95573
Gene Name:
PTGS2
Uniprot ID:
P35354
Gene Name:
PTGS1
Uniprot ID:
P23219
Gene Name:
ACOT7
Uniprot ID:
O00154
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water unknown Coenzyme A + Eicosapentaenoic aciddetails
Gene Name:
ACOT2
Uniprot ID:
P49753
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water unknown Coenzyme A + Eicosapentaenoic aciddetails
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water unknown Coenzyme A + Eicosapentaenoic aciddetails
Gene Name:
ACOT8
Uniprot ID:
O14734
Gene Name:
FFAR1
Uniprot ID:
O14842
Gene Name:
FADS1
Uniprot ID:
O60427
Gene Name:
SLC8A1
Uniprot ID:
P32418
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water unknown Coenzyme A + Eicosapentaenoic aciddetails