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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-07 20:53:58 UTC
HMDB IDHMDB0000593
Secondary Accession Numbers
  • HMDB0008104
  • HMDB00593
  • HMDB0062690
  • HMDB08104
  • HMDB62690
Metabolite Identification
Common NamePC(36:2)
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
Data?1582752142
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
Chemical FormulaC44H84NO8P
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
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 Number4235-95-4
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationSource
Process
Naturally occurring process