Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:45:09 UTC
Update Date2022-08-31 17:34:31 UTC
Metabolite IDMMDBc0029875
Metabolite Identification
Common NamePE(14:0/14:0)
DescriptionPE(14:0/14:0) is a phosphatidylethanolamine. 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 to the C-1 and C-2 positions. PE(14:0/14:0), in particular, consists of two tetradecanoyl chains at positions C-1 and C-2. 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.
Structure
Synonyms
ValueSource
1,2-DimyristoylphosphatidylethanolamineHMDB
DMPEHMDB
PE(28:0)HMDB
GPEtn(28:0)HMDB
GPEtn(14:0/14:0)HMDB
Phophatidylethanolamine(28:0)HMDB
1,2-Dimyristoyl-rac-glycero-3-phosphoethanolamineHMDB
1,2-Ditetradecanoyl-rac-glycero-3-phosphoethanolamineHMDB
Phophatidylethanolamine(14:0/14:0)HMDB
1,2-Dimyristoyl-sn-glycero-3-phosphoethanolamineHMDB
1,2-Ditetradecanoyl-sn-glycero-3-phosphoethanolamineHMDB
Dimyristoyl cephalinHMDB
Tetradecanoic acid, (1R)-1-((((2-aminoethoxy)hydroxyphosphinyl)oxy)methyl)-1,2-ethanediyl esterHMDB
PE(14:0/14:0)Lipid Annotator
Molecular FormulaC33H66NO8P
Average Mass635.864
Monoisotopic Mass635.452605087
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2,3-bis(tetradecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C33H66NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(35)39-29-31(30-41-43(37,38)40-28-27-34)42-33(36)26-24-22-20-18-16-14-12-10-8-6-4-2/h31H,3-30,34H2,1-2H3,(H,37,38)/t31-/m1/s1
InChI KeyNEZDNQCXEZDCBI-WJOKGBTCSA-N