1-18:1-2-18:1-sn-glycerol-3-phosphocholine (CHEM041807)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:42:27 UTC
Update Date2016-11-09 01:22:32 UTC
Accession NumberCHEM041807
Identification
Common Name1-18:1-2-18:1-sn-glycerol-3-phosphocholine
ClassSmall Molecule
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. [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(36:2)Lipid Annotator, HMDB
1,2-dioleoyl-rac-glycero-3-phosphocholineLipid Annotator, HMDB
PC(36:2)Lipid Annotator, HMDB
PC(18:1(9Z)/18:1(9Z))Lipid Annotator, HMDB
Phosphatidylcholine(36:2)Lipid Annotator, HMDB
GPCho(18:1/18:1)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(18:1/18:1)Lipid Annotator, HMDB
1,2-di(9Z-octadecenoyl)-rac-glycero-3-phosphocholineLipid Annotator, HMDB
PC(18:1/18:1)Lipid Annotator, HMDB
(Z,Z)-(1)-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxideHMDB
(Z,Z)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-3,5,9-trioxa-4-phosphaheptacos-18-en-1-aminium 4-oxide hydroxide inner saltHMDB
1,2-Dioleoylglycerol-3-phosphorylcholineHMDB
1,2-Dioleoylglyceryl-3-phosphorylcholineHMDB
1,2-DioleoyllecHMDB
DioleoylphosphatidylcholineHMDB, MeSH
gpcho(18:1n9/18:1n9)HMDB
gpcho(18:1W9/18:1W9)HMDB
PC Aa C36:2HMDB
PC(18:1n9/18:1n9)HMDB
PC(18:1W9/18:1W9)HMDB
Phosphatidylcholine(18:1n9/18:1n9)HMDB
Phosphatidylcholine(18:1W9/18:1W9)HMDB
1,2-DOCPCMeSH, HMDB
1,2-Dioleoyl glycerophosphocholineMeSH, HMDB
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholineMeSH, HMDB
1,2-DioleoylglycerophosphocholineMeSH, HMDB
1,2-Oleoyl-sn-glycero-3-phosphocholineMeSH, HMDB
1,2-OleoylphosphatidylcholineMeSH, HMDB
1,2-Oleoylphosphatidylcholine, (e,e)-isomerMeSH, HMDB
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomerMeSH, HMDB
1,2-Oleoylphosphatidylcholine, (R-(e,e))-isomerMeSH, HMDB
1,2-Oleoylphosphatidylcholine, (Z,Z)-(+-)-isomerMeSH, HMDB
1,2-Oleoylphosphatidylcholine, 14C-labeled, (R-(Z,Z))-isomerMeSH, HMDB
DOPCMeSH, HMDB
Dielaidinoyl lecithinMeSH, HMDB
DielaidoylphosphatidylcholineMeSH, HMDB
Dioleoyl lecithinMeSH, HMDB
Dioleoyl phosphatidylcholineMeSH, HMDB
DioleylphosphatidylcholineMeSH, HMDB
1,2-Dioleoyl-sn-glycero-3-phosphocholineMeSH, HMDB
Chemical FormulaC44H84NO8P
Average Molecular Mass786.113 g/mol
Monoisotopic Mass785.593 g/mol
CAS Registry NumberNot Available
IUPAC Name[2-({2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono}oxy)ethyl]trimethylazanium
Traditional Name[2-({2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono}oxy)ethyl]trimethylazanium
SMILESCCCCCCCCC=CCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
InChI IdentifierInChI=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
InChI KeySNKAWJBJQDLSFF-UHFFFAOYSA-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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP9.17ChemAxon
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability96.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0100000900-8d76152294364173953dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-db47a3894ce23f083a99Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-ac1e031a7d236f329ed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-36f689a3cf8b031c9ce5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-4df68b8e85813f4b5ad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-f15a88b3adc3a38193cbSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB022133
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6437081
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available