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Record Information
Version1.0
Creation Date2016-07-13 19:52:23 UTC
Update Date2016-07-20 20:45:14 UTC
LmdbLMDB00552
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(P-18:1(11Z)/22:2(13Z,16Z))
DescriptionPC(P-18:1(11Z)/22:2(13Z,16Z)) 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(P-18:1(11Z)/22:2(13Z,16Z)), in particular, consists of one chain of plasmalogen 18:1n7 at the C-1 position and one chain of docosadienoic acid at the C-2 position. The plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney, while the docosadienoic acid moiety is derived from animal fats. 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
Structure
Thumb
Synonyms
ValueSource
1-(1-Enyl-vaccenoyl)-2-docosadienoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(18:1/22:2)HMDB
Gpcho(18:1n7/22:2n6)HMDB
Gpcho(18:1W7/22:2W6)HMDB
Gpcho(40:3)HMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-GPCHMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-sn-glycero-3-phosphocholineHMDB
1-(1Z,11Z-Octadecadienyl)-2-docosadienoyl-sn-glycero-phosphatidylcholineHMDB
GPC(18:2/22:2)HMDB
GPC(40:4)HMDB
GPC(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
GPC(O-18:2(1Z,11Z)/22:2n6)HMDB
GPC(O-18:2(1Z,11Z)/22:2W6)HMDB
GPC(p-18:1(11Z)/22:2(13Z,16Z))HMDB
GPC(p-18:1(11Z)/22:2n6)HMDB
GPC(p-18:1(11Z)/22:2W6)HMDB
GPCho(18:2/22:2)HMDB
GPCho(40:4)HMDB
GPCho(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
GPCho(O-18:2(1Z,11Z)/22:2n6)HMDB
GPCho(O-18:2(1Z,11Z)/22:2W6)HMDB
GPCho(p-18:1(11Z)/22:2(13Z,16Z))HMDB
GPCho(p-18:1(11Z)/22:2n6)HMDB
GPCho(p-18:1(11Z)/22:2W6)HMDB
PC(18:2/22:2)HMDB
PC(40:4)HMDB
PC(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
PC(O-18:2(1Z,11Z)/22:2n6)HMDB
PC(O-18:2(1Z,11Z)/22:2W6)HMDB
PC(p-18:1(11Z)/22:2n6)HMDB
PC(p-18:1(11Z)/22:2W6)HMDB
Phosphatidylcholine(18:2/22:2)HMDB
Phosphatidylcholine(40:4)HMDB
Phosphatidylcholine(O-18:2(1Z,11Z)/22:2(13Z,16Z))HMDB
Phosphatidylcholine(O-18:2(1Z,11Z)/22:2n6)HMDB
Phosphatidylcholine(O-18:2(1Z,11Z)/22:2W6)HMDB
Phosphatidylcholine(p-18:1(11Z)/22:2(13Z,16Z))HMDB
Phosphatidylcholine(p-18:1(11Z)/22:2n6)HMDB
Phosphatidylcholine(p-18:1(11Z)/22:2W6)HMDB
Chemical FormulaC48H90NO7P
Average Molecular Weight824.2045
Monoisotopic Molecular Weight823.645490751
IUPAC Name[2-({2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Name[2-({2-[(13Z,16Z)-docosa-13,16-dienoyloxy]-3-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/CCCCCCCC\C=C/OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C48H90NO7P/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/h14,16-17,19-20,22,40,43,47H,6-13,15,18,21,23-39,41-42,44-46H2,1-5H3/b16-14-,19-17-,22-20-,43-40-
InChI KeyGCJYMGXKZROELS-ARPDTERPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-(1Z-alkenyl),2-acyl-glycerophosphocholines
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acyl-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP6.65ALOGPS
logP10.98ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity256.36 m³·mol⁻¹ChemAxon
Polarizability102.42 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, Positivesplash10-000i-9026212130-000668749e11e49eae5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nn-5269112010-750058af9ceb104cd183Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0081-9068003200-fb55aa5bd65775e0e28dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00y0-0078000290-25a217c7d4c08de711a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1094100510-2df22bdd10dabd0ac512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-6098200000-7a3c3833680ca01afed7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-de220e58893f382072b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900000050-93303d1f354afebe5cbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00z9-1900331690-9811bbed7ac5943db687Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-86cf1871415afecc1f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0007002390-c0da90652d6529db62b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-5019400000-69f747cbde88073be78dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-35b0cc58318f5250b758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000090-35b0cc58318f5250b758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abl-0004920170-95156985ea2684425ff6Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified0.008 +/- 0.002 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified0.39 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.43 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.3 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified0.41 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0011291
FooDB IDFDB028038
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24767566
ChEBI ID89914
PubChem Compound ID53480773
Kegg Compound IDNot Available
YMDB IDYMDB02247
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available