General Information of Metabolite (ID: MT109)
  Meta Name
eicosapentaenoic acid (EPA)
  Unify Name
Eicosapentaenoic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid;(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate;(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid;(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid;(all-Z)-5,8,11,14,17-Eicosapentaenoic acid;5,8,11,14,17-EICOSAPENTAENOIC ACID;5,8,11,14,17-Icosapentaenoic acid;all-cis-5,8,11,14,17-Eicosapentaenoic acid;all-cis-Icosa-5,8,11,14,17-pentaenoic acid;cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid;cis-5,8,11,14,17-Eicosapentaenoic acid;cis-5,8,11,14,17-EPA;cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid;EPA;Icosapent;Icosapentaenoic acid;Icosapento;Icosapentum;Timnodonic acid;Eicosapentaenoate;Omega-3-eicosapentaenoic acid;Acid, eicosapentanoic;Eicosapentanoic acid;Omega 3 eicosapentaenoic acid;all-cis-Icosapentaenoate;all-cis-Icosapentaenoic acid;(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acid;(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid;(all-Z)-delta-5,8,11,14,17-Eicosapentaenoic acid;(all-cis)-5,8,11,14,17-Eicosapentaenoic acid;Eicosapentaenoic acid;FA(20:5(5Z,8Z,11Z,14Z,17Z));FA(20:5n3)
  Molecule Type
Fatty acids
  Formula
C20H29O2
  Inchi Key
JAZBEHYOTPTENJ-JLNKQSITSA-M
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): Eicosapentaenoic 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.
  External Links   HMDB ID   HMDB0001999
  VMH ID   tmndnc
  KEGG ID   C06428
  Metlin ID   6423

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
Histone Trimethylation H3 EM Info Breast cancer cells lysine 27 Breast cancer [1], [2]

The microbes that produce this metabolite
      Yarrowia lipolytica
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Yarrowia lipolytica is one of the most extensively studied ''non-conventional'' yeasts, being a strictly aerobic microorganism capable of producing important metabolites.

References
1 Impact of dietary gut microbial metabolites on the epigenome. Philos Trans R Soc Lond B Biol Sci. 2018 Jun 5;373(1748):20170359. doi: 10.1098/rstb.2017.0359.
2 Production of High-Value Polyunsaturated Fatty Acids Using Microbial Cultures. Methods Mol Biol. 2019;1995:229-248. doi: 10.1007/978-1-4939-9484-7_15.

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