Details of Metabolite

General Information of MET (ID: META00463)
Name Eicosapentaenoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoate; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoate; (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoate; (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid; (all-Z)-5,8,11,14,17-Eicosapentaenoate; (all-Z)-5,8,11,14,17-Eicosapentaenoic acid; (all-cis)-5,8,11,14,17-Eicosapentaenoic acid; 5,8,11,14,17-EICOSAPENTAENOIC ACID; 5,8,11,14,17-EICOSAPENTAENOate; 5,8,11,14,17-Icosapentaenoate; 5,8,11,14,17-Icosapentaenoic acid; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid; Acid, eicosapentanoic; EPA; Eicosapentaenoate; Eicosapentaenoic acid; Eicosapentanoic acid; FA(20:5(5Z,8Z,11Z,14Z,17Z)); FA(20:5n3); Icosapent; Icosapentaenoate; Icosapentaenoic acid; Icosapento; Icosapentum; Omega 3 eicosapentaenoic acid; Omega-3-eicosapentaenoic acid; Timnodonate; Timnodonic acid; all-cis-5,8,11,14,17-Eicosapentaenoate; all-cis-5,8,11,14,17-Eicosapentaenoic acid; all-cis-Icosa-5,8,11,14,17-pentaenoate; all-cis-Icosa-5,8,11,14,17-pentaenoic acid; all-cis-Icosapentaenoate; all-cis-Icosapentaenoic acid; cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoate; cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid; cis-5,8,11,14,17-EPA; cis-5,8,11,14,17-Eicosapentaenoate; cis-5,8,11,14,17-Eicosapentaenoic acid; cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid
Source Endogenous;Drug Metabolite;Fatty acyls;Food;Drug;Cosmetic;TCM Ingredients
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
446284
HMDB ID
HMDB0001999
Formula
C20H30O2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C06428
DrugBank ID
DB00159
ChEBI ID
28364
FooDB ID
FDB030126
ChemSpider ID
393682
METLIN ID
6423
Physicochemical Properties Molecular Weight 302.5 Topological Polar Surface Area 37.3
XlogP 5.6 Complexity 398
Heavy Atom Count 22 Rotatable Bond Count 13
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Group 10 secretory phospholipase A2 (PLA2G10) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Pla2g10
                      Induced Change Eicosapentaenoic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that knockout of Pla2g10 leads to the decrease of eicosapentaenoic acid levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of Pla2g10
                      Induced Change Eicosapentaenoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that overexpression of Pla2g10 leads to the increase of eicosapentaenoic acid levels compared with control group.
            Group 3 secretory phospholipase A2 (PLA2G3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change Eicosapentaenoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of Pla2g3 leads to the increase of eicosapentaenoic acid levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Eicosapentaenoic acid concentration: increase (FC = 2.25 / 3.62)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of eicosapentaenoic acid levels compared with control group.
      Transferases (EC 2)
            Carnitine O-palmitoyltransferase 1 (CPT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout of Cpt1c
                      Induced Change Eicosapentaenoic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Cpt1c leads to the decrease of eicosapentaenoic acid levels compared with control group.
References
1 Group X Secreted Phospholipase A2 Releases 3 Polyunsaturated Fatty Acids, Suppresses Colitis, and Promotes Sperm Fertility. J Biol Chem. 2016 Mar 25;291(13):6895-911.
2 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.
3 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
4 Metabolomic profiling reveals a role for CPT1c in neuronal oxidative metabolism. BMC Biochem. 2012 Oct 25;13:23.

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