Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:51:17 UTC
Update Date2022-08-31 06:10:29 UTC
Metabolite IDMMDBc0000620
Metabolite Identification
Common NamePC(16:0/18:3(6Z,9Z,12Z))
DescriptionPC(16:0/18:3(6Z,9Z,12Z)) 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(16:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the g-linolenic acid moiety is derived from animal fats. 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
Synonyms
ValueSource
1-Hexadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-(gamma-linolenoyl)-sn-glycero-3-phosphocholineChEBI
PC(16:0/18:3)ChEBI
1-Palmitoyl-2-(g-linolenoyl)-sn-glycero-3-phosphocholineGenerator
1-Palmitoyl-2-(γ-linolenoyl)-sn-glycero-3-phosphocholineGenerator
PC(34:3)HMDB
LecithinHMDB
GPCho(16:0/18:3)HMDB
Phosphatidylcholine(34:3)HMDB
GPCho(34:3)HMDB
Phosphatidylcholine(16:0/18:3)HMDB
1-Palmitoyl-2-g-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-gamma-linolenoyl-GPCHMDB
1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-linolenoyl-GPCHMDB
GPC(16:0/18:3(6Z,9Z,12Z))HMDB
GPC(16:0/18:3)HMDB
GPC(16:0/18:3n6)HMDB
GPC(16:0/18:3W6)HMDB
GPC(34:3)HMDB
GPCho(16:0/18:3(6Z,9Z,12Z))HMDB
GPCho(16:0/18:3n6)HMDB
GPCho(16:0/18:3W6)HMDB
PC(16:0/18:3n6)HMDB
PC(16:0/18:3W6)HMDB
Phosphatidylcholine(16:0/18:3(6Z,9Z,12Z))HMDB
Phosphatidylcholine(16:0/18:3n6)HMDB
Phosphatidylcholine(16:0/18:3W6)HMDB
PC(16:0/18:3(6Z,9Z,12Z))Lipid Annotator
Molecular FormulaC42H78NO8P
Average Mass756.0444
Monoisotopic Mass755.546504989
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,25,27,40H,6-13,15,17-19,22-24,26,28-39H2,1-5H3/b16-14-,21-20-,27-25-/t40-/m1/s1
InChI KeyCNNSEHUKQJCGTE-UPPWDXJYSA-N