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Record Information
Version1.0
Creation Date2016-07-13 19:53:33 UTC
Update Date2016-07-19 23:33:05 UTC
LmdbLMDB00604
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-18:1(9Z)/22:0)
DescriptionPC(o-18:1(9Z)/22:0) 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(o-18:1(9Z)/22:0), in particular, consists of one chain of Oleyl alcohol at the C-1 position and one chain of behenic acid at the C-2 position. The Oleyl alcohol moiety is derived from beef fat, fish oil, while the behenic acid moiety is derived from groundnut 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
Thumb
Synonyms
ValueSource
1-Oleyl-2-behenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(18:1/22:0)HMDB
Gpcho(18:1n9/22:0)HMDB
Gpcho(18:1W9/22:0)HMDB
Gpcho(40:1)HMDB
LecithinHMDB
PC Ae C40:1HMDB
PC(18:1/22:0)HMDB
PC(18:1n9/22:0)HMDB
PC(18:1W9/22:0)HMDB
PC(40:1)HMDB
PC(O-40:1)HMDB
Phosphatidylcholine(18:1/22:0)HMDB
Phosphatidylcholine(18:1n9/22:0)HMDB
Phosphatidylcholine(18:1W9/22:0)HMDB
Phosphatidylcholine(40:1)HMDB
1-(9Z-Octadecenyl)-2-docosanoyl-sn-glycero-3-phosphocholineHMDB
PC(o-18:1(9Z)/22:0)Lipid Annotator
Chemical FormulaC48H96NO7P
Average Molecular Weight830.2521
Monoisotopic Molecular Weight829.692440943
IUPAC Name(2-{[(2R)-2-(docosanoyloxy)-3-[(9Z)-octadec-9-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(docosanoyloxy)-3-[(9Z)-octadec-9-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C48H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-48(50)56-47(46-55-57(51,52)54-44-42-49(3,4)5)45-53-43-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h21,23,47H,6-20,22,24-46H2,1-5H3/b23-21-/t47-/m1/s1
InChI KeyVTSFZGCXFALJSV-FYAZAUILSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.7ALOGPS
logP11.69ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity254.04 m³·mol⁻¹ChemAxon
Polarizability106.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-54c43337d7f5e6d2b9f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0003002290-dc8384b90269a1cda398Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-4029800000-0670ba3135afc8533b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-2999ef61b45d0dcda51bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000090-2999ef61b45d0dcda51bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0006300190-4fcb82a43b5adf055229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-637ace8ab9ffcf7834d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-637ace8ab9ffcf7834d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900141160-f8ccbfdc78dac21dd3a5Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.32 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.35 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.28 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.46 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
DrugBank IDNot Available
HMDB IDHMDB0013433
FooDB IDFDB029433
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 ID53481731
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available