General Information of MET (ID: META00575)
Name PE(18:0/20:4(5Z,8Z,11Z,14Z))
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine; 1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphoethanolamine zwitterion; 1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine; 1-Stearoyl-2-arachidonoyl phosphatidylethanolamine; 1-Stearoyl-2-arachidonoyl-gpe; 1-Stearoyl-2-arachidonoyl-gpe (18:0/20:4); 1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine; 1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylethanolamine; 1-Stearoyl-2-arachidonoyl-sn-glycero-phosphatidylethanolamine; GPE(18:0/20:4(5Z,8Z,11Z,14Z)); GPE(18:0/20:4); GPE(18:0/20:4n6); GPE(18:0/20:4w6); GPE(38:4); GPEtn(18:0/20:4(5Z,8Z,11Z,14Z)); GPEtn(18:0/20:4); GPEtn(18:0/20:4n6); GPEtn(18:0/20:4w6); GPEtn(38:4); PE(18:0/20:4(5Z,8Z,11Z,14Z)); PE(18:0/20:4); PE(18:0/20:4n6); PE(18:0/20:4w6); PE(38:4); Phophatidylethanolamine(18:0/20:4); Phophatidylethanolamine(38:4); Phosphatidylethanolamine(18:0/20:4(5Z,8Z,11Z,14Z)); Phosphatidylethanolamine(18:0/20:4); Phosphatidylethanolamine(18:0/20:4n6); Phosphatidylethanolamine(18:0/20:4w6); Phosphatidylethanolamine(38:4); SAPE
Source Endogenous;Glycerophospholipids;Food;Microbial
Structure Type   Glycerophosphoethanolamines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Glycerophospholipids
Glycerophosphoethanolamines
PubChem CID
5289133
HMDB ID
HMDB0009003
Formula
C43H78NO8P
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
78268
Physicochemical Properties Molecular Weight 768.1 Topological Polar Surface Area 134
XlogP 10.5 Complexity 1010
Heavy Atom Count 53 Rotatable Bond Count 41
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Function
PE(18:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 [1]
                      Introduced Variation Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change PE(18:0/20:4(5Z,8Z,11Z,14Z)) concentration: increase (FC = 1.64)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the increase of PE(18:0/20:4(5Z,8Z,11Z,14Z)) levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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