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Record Information
Version4.0
Creation Date2006-05-22 14:17:31 UTC
Update Date2017-09-27 08:24:10 UTC
HMDB IDHMDB0001999
Secondary Accession Numbers
  • HMDB01999
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. EPA is a biomarker for the consumption of salt-water fish.
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACIDChEBI
5,8,11,14,17-Icosapentaenoic acidChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acidChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acidChEBI
cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
cis-5,8,11,14,17-EPAChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acidChEBI
EPAChEBI
IcosapentChEBI
Icosapentaenoic acidChEBI
IcosapentoChEBI
IcosapentumChEBI
Timnodonic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EicosapentaenoateGenerator
EicosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-IcosapentaenoateGenerator
(all-Z)-5,8,11,14,17-EicosapentaenoateGenerator
5,8,11,14,17-EICOSAPENTAENOateGenerator
5,8,11,14,17-IcosapentaenoateGenerator
all-cis-5,8,11,14,17-EicosapentaenoateGenerator
all-cis-Icosa-5,8,11,14,17-pentaenoateGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoateGenerator
cis-5,8,11,14,17-EicosapentaenoateGenerator
cis-delta(5,8,11,14,17)-EicosapentaenoateGenerator
cis-δ(5,8,11,14,17)-eicosapentaenoateGenerator
cis-δ(5,8,11,14,17)-eicosapentaenoic acidGenerator
IcosapentaenoateGenerator
TimnodonateGenerator
5Z,8Z,11Z,14Z,17Z-EicosapentaenoateHMDB
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acidHMDB
all-cis-IcosapentaenoateHMDB
all-cis-Icosapentaenoic acidHMDB
Acid, eicosapentanoicMeSH
Omega-3-eicosapentaenoic acidMeSH
Eicosapentanoic acidMeSH
Omega 3 eicosapentaenoic acidMeSH
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 Nameeicosapentaenoic acid
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
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Vascular disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

  Cell and elements:

    Cell:

    Element:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 Solubility0.00029 g/LALOGPS
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m³·mol⁻¹ChemAxon
Polarizability35.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9700000000-09ea61ed836b88205028View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-9700000000-09ea61ed836b88205028View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5490000000-ee15446245c5d0190ca2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adr-9462000000-6310373b498d395ee4b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0029000000-02c67e3601df249d2476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1196000000-2fd0631ba34b61c02823View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-5891000000-6b514ce76e6321b59f49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8950000000-5f7ac71eb4fd77059c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-63f4108595227b77b5f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-c196324eb61e1a26da90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-844643f720715a477b35View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05ox-9400000000-567226e93d65502352cdView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Sweat
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Liver
  • Neutrophil
  • Platelet
  • Skeletal Muscle
Pathways
NameSMPDB/PathwhizKEGG
Alpha Linolenic Acid and Linoleic Acid MetabolismPw000006Pw000006 greyscalePw000006 simpleMap00592
Displaying 1 entry
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)BothNormal 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 but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified270 +/- 160 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified36.370 +/- 16.532 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified33.0632 +/- 9.919 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified23.144 +/- 9.919 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.00039 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00058 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00052 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00073 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified19.838 +/- 9.919 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified37.890 +/- 24.764 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified66.457 +/- 42.321 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified70.425 +/- 48.603 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified260 +/- 110 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified79.649 +/- 51.182 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified200 +/- 110 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.401 +/- 0.068 uMAdult (>18 years old)BothNormal details
SweatDetected but not Quantified Adult BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    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
    BloodDetected and Quantified63.151 +/- 36.700 uMAdult (>18 years old)BothDepression details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer 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. doi: 10.1291/hypres.31.623. [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. doi: 10.1291/hypres.31.623. [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
    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. doi: 10.1074/jbc.M110.119867. 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. doi: 10.1074/jbc.M110.119867. 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