Common Name1-tetradecanoyl-2-(9z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
DescriptionPE(14:0/18:1(9Z)) 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(14:0/18:1(9Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of oleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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.
Structure
Molecular FormulaC37H72NO8P
Average Mass689.95600
Monoisotopic Mass689.49956
IUPAC Name(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2r)-2-[(9z)-octadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILESCCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)([O-])OCC[NH3+]
InChI IdentifierInChI=1S/C37H72NO8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38)33-43-36(39)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,35H,3-15,18-34,38H2,1-2H3,(H,41,42)/b17-16-/t35-/m1/s1
InChI KeyQZGYPUQNTDWNBR-XHYHITGYSA-N
CHEBI IDCHEBI:84300
HMDB IDHMDB0008828
Pathways
NameSMPDB/PathBank
Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))
Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))
StateSolid
Water Solubility9.92e-05 g/l
logP8.01
logS-6.84
pKa (Strongest Acidic)1.87
pKa (Strongest Basic)10.00
Hydrogen Acceptor Count5
Hydrogen Donor Count2
Polar Surface Area134.38 Ų
Rotatable Bond Count38
Physiological Charge0
Formal Charge0
Refractivity192.12 m³·mol⁻¹
Polarizability83.48

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