Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 05:05:33 UTC
Update Date2024-04-30 20:17:50 UTC
Metabolite IDMMDBc0033842
Metabolite Identification
Common NamePC(18:1(11Z)/22:1(13Z))
DescriptionPC(18:1(11Z)/22:1(13Z)) 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(18:1(11Z)/22:1(13Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of erucic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the erucic acid moiety is derived from seed oils and avocados. 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.
Structure
SynonymsNot Available
Molecular FormulaC48H92NO8P
Average Mass842.2197
Monoisotopic Mass841.656055437
IUPAC Name(2-{[(2R)-2-(docos-13-enoyloxy)-3-(octadec-11-enoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(docos-13-enoyloxy)-3-(octadec-11-enoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCC=CCCCCCCCC
InChI Identifier
InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h17,19-20,22,46H,6-16,18,21,23-45H2,1-5H3/t46-/m1/s1
InChI KeyFMYLRXULDVDXKI-YACUFSJGSA-N