Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:42:12 UTC
Update Date2024-04-30 20:04:15 UTC
Metabolite IDMMDBc0033279
Metabolite Identification
Common NamePC(18:0/18:1(9Z))
DescriptionPC(18:0/18:1(9Z)) 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(18:0/18:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of oleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, 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. 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
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphateChEBI
1-18:0-2-18:1-PhosphatidylcholineChEBI
1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-2-oleoyl-GPCChEBI
1-Stearoyl-2-oleoyl-GPC (18:0/18:1)ChEBI
1-Steroyl-2-oleoylphosphatidylcholineChEBI
18:0-18:1-PCChEBI
GPC(18:0/18:1)ChEBI
GPCho 18:0/18:1(9Z)ChEBI
L-alpha-1-Stearoyl-2-oleoyl lecithinChEBI
PC 18:0/18:1(9Z)ChEBI
PC(18:0/18:1n9)ChEBI
PC(18:0/18:1omega9)ChEBI
PC(18:0/18:1W9)ChEBI
Phosphatidylcholine(18:0/18:1(9Z))ChEBI
Phosphatidylcholine(18:0/18:1)ChEBI
Phosphatidylcholine(18:0/18:1n9)ChEBI
Phosphatidylcholine(18:0/18:1omega9)ChEBI
Phosphatidylcholine(18:0/18:1W9)ChEBI
Phosphatidylcholine(36:1)ChEBI
SOPCChEBI
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
L-a-1-Stearoyl-2-oleoyl lecithinGenerator
L-Α-1-stearoyl-2-oleoyl lecithinGenerator
GPCho(36:1)Lipid Annotator, HMDB
PC(36:1)Lipid Annotator, HMDB
1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholineLipid Annotator, MeSH, HMDB
PC(18:0/18:1)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(18:0/18:1(9Z))Lipid Annotator
GPCho(18:0/18:1)Lipid Annotator, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (e)-isomerMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (S-(Z))-isomerMeSH, HMDB
1-Stearoyl-2-oleoyl lecithinMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (R-(Z))-isomerMeSH, HMDB
1-SOPCMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-3-glycerophosphocholineMeSH, HMDB
1-Stearoyl-2-oleoyl glycerylphosphorylcholineHMDB
1-Stearoyl-2-oleoyl-sn-glycero-phosphatidylcholineHMDB
1-Stearoyl-2-oleoyllecithinHMDB
1-Stearoyl-2-oleoylphosphatidylcholineHMDB
1-Stearyl-2-oleoyl-3-sn-glycerophosphatidylcholineHMDB
GPC(18:0/18:1(9Z))HMDB
GPC(18:0/18:1n9)HMDB
GPC(18:0/18:1w9)HMDB
GPC(36:1)HMDB
GPCho(18:0/18:1(9Z))HMDB
GPCho(18:0/18:1n9)HMDB
GPCho(18:0/18:1w9)HMDB
L-alpha-1-Stearoyl-2-oleoylphosphatidylcholineHMDB
L-α-1-Stearoyl-2-oleoylphosphatidylcholineHMDB
Molecular FormulaC44H86NO8P
Average Mass788.1293
Monoisotopic Mass787.609105245
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
CAS Registry Number8002-43-5
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,42H,6-20,22,24-41H2,1-5H3/b23-21-/t42-/m1/s1
InChI KeyATHVAWFAEPLPPQ-VRDBWYNSSA-N