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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
SpectraGC-MS
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.435 +/- 0.010 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2100.0 +/- 990.0 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified11.0 +/- 8.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.09 +/- 0.72 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified11.1 +/- 9.5 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified10.8 +/- 6.2 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified270 +/- 160 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.401 +/- 0.068 uMAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.0 +/- 7.3 uMAdult (>18 years old)Both
Hypertension
details
BloodDetected and Quantified10.6 +/- 7.2 uMAdult (>18 years old)Male
Essential hypertension
details
BloodDetected and Quantified11.9 +/- 7.6 uMAdult (>18 years old)FemaleEssential hypertension details
Associated Disorders and Diseases
Disease References
Essential hypertension
  1. 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
  1. 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

General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses arachidonate and eicosapentaenoate as substrates.
Gene Name:
ACSL4
Uniprot ID:
O60488
Molecular weight:
74435.495
References
  1. Heimli H, Hollung K, Drevon CA: Eicosapentaenoic acid-induced apoptosis depends on acyl CoA-synthetase. Lipids. 2003 Mar;38(3):263-8. Pubmed: 12784866
  2. Covault J, Pettinati H, Moak D, Mueller T, Kranzler HR: Association of a long-chain fatty acid-CoA ligase 4 gene polymorphism with depression and with enhanced niacin-induced dermal erythema. Am J Med Genet B Neuropsychiatr Genet. 2004 May 15;127B(1):42-7. Pubmed: 15108178
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetases (ACSL) activates long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. ACSL3 mediates hepatic lipogenesis (By similarity). Preferentially uses myristate, laurate, arachidonate and eicosapentaenoate as substrates (By similarity). Has mainly an anabolic role in energy metabolism. Required for the incorporation of fatty acids into phosphatidylcholine, the major phospholipid located on the surface of VLDL (very low density lipoproteins).
Gene Name:
ACSL3
Uniprot ID:
O95573
Molecular weight:
80419.415
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: Differential modulation of Toll-like receptors by fatty acids: preferential inhibition by n-3 polyunsaturated fatty acids. J Lipid Res. 2003 Mar;44(3):479-86. Epub 2002 Dec 1. Pubmed: 12562875
  2. Ait-Said F, Elalamy I, Werts C, Gomard MT, Jacquemin C, Couetil JP, Hatmi M: Inhibition by eicosapentaenoic acid of IL-1beta-induced PGHS-2 expression in human microvascular endothelial cells: involvement of lipoxygenase-derived metabolites and p38 MAPK pathway. Biochim Biophys Acta. 2003 Feb 20;1631(1):77-84. Pubmed: 12573452
  3. Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. Pubmed: 16141635
  4. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. Pubmed: 16190133
  5. Chene G, Dubourdeau M, Balard P, Escoubet-Lozach L, Orfila C, Berry A, Bernad J, Aries MF, Charveron M, Pipy B: n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells. Biochim Biophys Acta. 2007 May;1771(5):576-89. Epub 2007 Mar 16. Pubmed: 17459764
  6. Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. Epub 2010 May 12. Pubmed: 20463020
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Malkowski MG, Thuresson ED, Lakkides KM, Rieke CJ, Micielli R, Smith WL, Garavito RM: Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001 Oct 5;276(40):37547-55. Epub 2001 Jul 27. Pubmed: 11477109
  2. Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. Pubmed: 16141635
  3. Das UN: COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit. 2005 Jul;11(7):RA233-7. Epub 2005 Jun 29. Pubmed: 15990700
  4. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. Pubmed: 16190133
  5. Yang P, Chan D, Felix E, Cartwright C, Menter DG, Madden T, Klein RD, Fischer SM, Newman RA: Formation and antiproliferative effect of prostaglandin E(3) from eicosapentaenoic acid in human lung cancer cells. J Lipid Res. 2004 Jun;45(6):1030-9. Epub 2004 Mar 1. Pubmed: 14993240
  6. Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. Epub 2010 May 12. Pubmed: 20463020
  7. Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: Differential modulation of Toll-like receptors by fatty acids: preferential inhibition by n-3 polyunsaturated fatty acids. J Lipid Res. 2003 Mar;44(3):479-86. Epub 2002 Dec 1. Pubmed: 12562875
General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic aciddetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:
FFAR1
Uniprot ID:
O14842
Molecular weight:
31456.6
References
  1. Itoh Y, Hinuma S: GPR40, a free fatty acid receptor on pancreatic beta cells, regulates insulin secretion. Hepatol Res. 2005 Oct;33(2):171-3. Epub 2005 Oct 6. Pubmed: 16214394
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
References
  1. Chambrier C, Bastard JP, Rieusset J, Chevillotte E, Bonnefont-Rousselot D, Therond P, Hainque B, Riou JP, Laville M, Vidal H: Eicosapentaenoic acid induces mRNA expression of peroxisome proliferator-activated receptor gamma. Obes Res. 2002 Jun;10(6):518-25. Pubmed: 12055328
  2. Selvaraj RK, Klasing KC: Lutein and eicosapentaenoic acid interact to modify iNOS mRNA levels through the PPARgamma/RXR pathway in chickens and HD11 cell lines. J Nutr. 2006 Jun;136(6):1610-6. Pubmed: 16702329
  3. Iwata Y, Miyamoto S, Takamura M, Yanagisawa H, Kasuya A: Interaction between peroxisome proliferator-activated receptor gamma and its agonists: docking study of oximes having 5-benzyl-2,4-thiazolidinedione. J Mol Graph Model. 2001;19(6):536-42, 598-600. Pubmed: 11552681
  4. Horia E, Watkins BA: Complementary actions of docosahexaenoic acid and genistein on COX-2, PGE2 and invasiveness in MDA-MB-231 breast cancer cells. Carcinogenesis. 2007 Apr;28(4):809-15. Epub 2006 Oct 19. Pubmed: 17052999
  5. Ramakers JD, Mensink RP, Schaart G, Plat J: Arachidonic acid but not eicosapentaenoic acid (EPA) and oleic acid activates NF-kappaB and elevates ICAM-1 expression in Caco-2 cells. Lipids. 2007 Aug;42(8):687-98. Epub 2007 Jul 3. Pubmed: 17610002
General function:
Involved in ion channel activity
Specific function:
Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular weight:
94955.3
References
  1. Matta JA, Miyares RL, Ahern GP: TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. J Physiol. 2007 Jan 15;578(Pt 2):397-411. Epub 2006 Oct 12. Pubmed: 17038422
General function:
Involved in DNA binding
Specific function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular weight:
49903.0
References
  1. Iwata Y, Miyamoto S, Takamura M, Yanagisawa H, Kasuya A: Interaction between peroxisome proliferator-activated receptor gamma and its agonists: docking study of oximes having 5-benzyl-2,4-thiazolidinedione. J Mol Graph Model. 2001;19(6):536-42, 598-600. Pubmed: 11552681
  2. Xu HE, Lambert MH, Montana VG, Parks DJ, Blanchard SG, Brown PJ, Sternbach DD, Lehmann JM, Wisely GB, Willson TM, Kliewer SA, Milburn MV: Molecular recognition of fatty acids by peroxisome proliferator-activated receptors. Mol Cell. 1999 Mar;3(3):397-403. Pubmed: 10198642
  3. Kondo H, Misaki R, Gelman L, Watabe S: Ligand-dependent transcriptional activities of four torafugu pufferfish Takifugu rubripes peroxisome proliferator-activated receptors. Gen Comp Endocrinol. 2007 Oct-Dec;154(1-3):120-7. Epub 2007 Jun 12. Pubmed: 17632107
  4. Inoue I, Shino K, Noji S, Awata T, Katayama S: Expression of peroxisome proliferator-activated receptor alpha (PPAR alpha) in primary cultures of human vascular endothelial cells. Biochem Biophys Res Commun. 1998 May 19;246(2):370-4. Pubmed: 9610365
  5. Caldari-Torres C, Rodriguez-Sallaberry C, Greene ES, Badinga L: Differential effects of n-3 and n-6 fatty acids on prostaglandin F2alpha production by bovine endometrial cells. J Dairy Sci. 2006 Mar;89(3):971-7. Pubmed: 16507691
General function:
Involved in heme binding
Specific function:
Component of a lipid metabolic pathway that catalyzes biosynthesis of highly unsaturated fatty acids (HUFA) from precursor essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3). Catalyzes the desaturation of dihomo-gamma-linoleic acid (DHGLA) (20:3n-6) and eicosatetraenoic acid (20:4n-3) to generate arachidonic acid (AA) (20:4n-6) and eicosapentaenoic acid (EPA)(20:5n-3) respectively
Gene Name:
FADS1
Uniprot ID:
O60427
Molecular weight:
51963.9
References
  1. Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH: Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans. J Nutr. 2000 Aug;130(8):1925-31. Pubmed: 10917903
  2. Navarro E, Esteve M, Olive A, Klaassen J, Cabre E, Tena X, Fernandez-Banares F, Pastor C, Gassull MA: Abnormal fatty acid pattern in rheumatoid arthritis. A rationale for treatment with marine and botanical lipids. J Rheumatol. 2000 Feb;27(2):298-303. Pubmed: 10685788
  3. Engler MM, Bellenger-Germain SH, Engler MB, Narce MM, Poisson JP: Dietary docosahexaenoic acid affects stearic acid desaturation in spontaneously hypertensive rats. Lipids. 2000 Sep;35(9):1011-5. Pubmed: 11026622
  4. Chavali SR, Zhong WW, Forse RA: Dietary alpha-linolenic acid increases TNF-alpha, and decreases IL-6, IL-10 in response to LPS: effects of sesamin on the delta-5 desaturation of omega6 and omega3 fatty acids in mice. Prostaglandins Leukot Essent Fatty Acids. 1998 Mar;58(3):185-91. Pubmed: 9610840
  5. Watts JL, Browse J: Isolation and characterization of a Delta 5-fatty acid desaturase from Caenorhabditis elegans. Arch Biochem Biophys. 1999 Feb 1;362(1):175-82. Pubmed: 9917342
General function:
Involved in cell communication
Specific function:
Rapidly transports Ca(2+) during excitation-contraction coupling. Ca(2+) is extruded from the cell during relaxation so as to prevent overloading of intracellular stores
Gene Name:
SLC8A1
Uniprot ID:
P32418
Molecular weight:
108546.1
References
  1. Xiao YF, Ke Q, Chen Y, Morgan JP, Leaf A: Inhibitory effect of n-3 fish oil fatty acids on cardiac Na+/Ca2+ exchange currents in HEK293t cells. Biochem Biophys Res Commun. 2004 Aug 13;321(1):116-23. Pubmed: 15358223
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic aciddetails