Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 05:09:52 UTC
Update Date2024-04-30 20:18:55 UTC
Metabolite IDMMDBc0033950
Metabolite Identification
Common NamePC(18:4(6Z,9Z,12Z,15Z)/dm18:0)
DescriptionPC(18:4(6Z,9Z,12Z,15Z)/dm18:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines 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. PC(18:4(6Z,9Z,12Z,15Z)/dm18:0), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of plasmalogen 18:0 at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. 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. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.↵↵Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives.
Structure
SynonymsNot Available
Molecular FormulaC44H80NO7P
Average Mass766.0823
Monoisotopic Mass765.567240431
IUPAC Nametrimethyl(2-{[2-(octadec-1-en-1-yloxy)-3-(octadeca-6,9,12,15-tetraenoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[2-(octadec-1-en-1-yloxy)-3-(octadeca-6,9,12,15-tetraenoyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCC=COC(COC(=O)CCCCC=CCC=CCC=CCC=CCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C44H80NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-49-43(42-52-53(47,48)51-40-38-45(3,4)5)41-50-44(46)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,36,39,43H,6-8,10,12-14,16,18-20,22,24-26,28,30-35,37-38,40-42H2,1-5H3
InChI KeyFHDLSCQITSAFFT-UHFFFAOYSA-N