Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:42:17 UTC
Update Date2024-04-30 20:04:20 UTC
Metabolite IDMMDBc0033281
Metabolite Identification
Common NamePC(18:1(9Z)/18:1(9Z))
DescriptionPC(18:1(9Z)/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(18:1(9Z)/18:1(9Z)), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are 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. Dioleoylphosphatidylcholine is found in human platelets and red blood cells, in mitochondria from skeletal muscle, lung, umbilical artery and vein endothelial cells (PMID: 15351277 , 7138900 , 2351875 , 4046747 , 2755318 ).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
(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxideChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1,2-Dioleoyl-L-alpha-lecithinChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholineChEBI
Dioleoyl lecithinChEBI
Dioleoyl phosphatidylcholineChEBI
PC 18:1ChEBI
PC(18:1(9Z)/18:1(9Z))ChEBI
PC(18:1/18:1)ChEBI
Phosphatidylcholine 18:1ChEBI
1,2-Dioleoyl-L-a-lecithinGenerator
1,2-Dioleoyl-L-α-lecithinGenerator
1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineHMDB
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholineMeSH
DioleylphosphatidylcholineMeSH
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomerMeSH
DielaidoylphosphatidylcholineMeSH
DioleoylphosphatidylcholineMeSH
1,2-DioleoylglycerophosphocholineMeSH
1,2-Oleoyl-sn-glycero-3-phosphocholineMeSH
DOPCMeSH
Dielaidinoyl lecithinMeSH
1,2-DOCPCMeSH
1,2-Dioleoyl glycerophosphocholineMeSH
1,2-Dioleoyl-sn-glycero-3-phosphocholineMeSH
1,2-OleoylphosphatidylcholineMeSH
1,2-Dioleoyl-GPCHMDB
1,2-Dioleoyl-sn-glycero-phosphatidylcholineHMDB
GPC(18:1(9Z)/18:1(9Z))HMDB
GPC(18:1/18:1)HMDB
GPC(18:1n9/18:1n9)HMDB
GPC(18:1w9/18:1w9)HMDB
GPC(36:2)HMDB
GPCho(18:1(9Z)/18:1(9Z))HMDB
GPCho(18:1/18:1)HMDB
GPCho(18:1n9/18:1n9)HMDB
GPCho(18:1w9/18:1w9)HMDB
GPCho(36:2)HMDB
PC(18:1n9/18:1n9)HMDB
PC(18:1w9/18:1w9)HMDB
PC(36:2)HMDB
Phosphatidylcholine(18:1(9Z)/18:1(9Z))HMDB
Phosphatidylcholine(18:1/18:1)HMDB
Phosphatidylcholine(18:1n9/18:1n9)HMDB
Phosphatidylcholine(18:1w9/18:1w9)HMDB
Phosphatidylcholine(36:2)HMDB
1,2-Dioleoyl-3-sn-phosphatidylcholineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphochlineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphorylcholineHMDB
1,2-Dioleoyl-sn-phosphatidylcholineHMDB
1,2-DioleoylphosphatidylcholineHMDB
1,2-Dioleyl-L-lecithinHMDB
Dioleoyl L-alpha-lecithinHMDB
Dioleoyl L-α-lecithinHMDB
Dioleoyl-3-sn-phosphatidylcholineHMDB
Dioleoyl-L-alpha-glycerophosphocholineHMDB
Dioleoyl-L-alpha-glycerophosphorylcholineHMDB
Dioleoyl-L-alpha-phosphatidylcholineHMDB
Dioleoyl-L-α-glycerophosphocholineHMDB
Dioleoyl-L-α-glycerophosphorylcholineHMDB
Dioleoyl-L-α-phosphatidylcholineHMDB
DioleoyllecithinHMDB
L-Dioleoyl lecithinHMDB
L-DioleoylphosphatidylcholineHMDB
L-alpha-Di(cis-9-octadecanoyl) lecithinHMDB
L-alpha-Dioleoyl phosphatidylcholineHMDB
L-alpha-DioleoyllecithinHMDB
L-alpha-DioleylphosphatidylcholineHMDB
L-α-Di(cis-9-octadecanoyl) lecithinHMDB
L-α-Dioleoyl phosphatidylcholineHMDB
L-α-DioleoyllecithinHMDB
L-α-DioleylphosphatidylcholineHMDB
sn-3-DioleoyllecithinHMDB
1,2-Dioleoylglycerol-3-phosphorylcholineHMDB
1,2-Dioleoylglyceryl-3-phosphorylcholineHMDB
1,2-DioleoyllecithinHMDB
DioleoylglycerophosphocholineHMDB
DioleoylglycerophosphorylcholineHMDB
DioleoylglycerylphosphorylcholineHMDB
Dioleyl lecithinHMDB
Dioleyl phosphatidylcholineHMDB
Molecular FormulaC44H84NO8P
Average Mass786.1134
Monoisotopic Mass785.593455181
IUPAC Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number68737-67-7
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H84NO8P/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/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1
InChI KeySNKAWJBJQDLSFF-NVKMUCNASA-N