Showing metabocard for PC(o-18:1(9Z)/20:0) (LMDB00602)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:30 UTC
Update Date2016-07-19 23:32:48 UTC
LmdbLMDB00602
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-18:1(9Z)/20:0)
DescriptionPC(o-18:1(9Z)/20:0) 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)/20:0), in particular, consists of one chain of Oleyl alcohol at the C-1 position and one chain of arachidic acid at the C-2 position. The Oleyl alcohol moiety is derived from beef fat, fish oil, while the arachidic acid moiety is derived from peanut 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Oleyl-2-arachidonyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(38:1)Lipid Annotator, HMDB
PC(18:1/20:0)Lipid Annotator, HMDB
PC(38:1)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(o-18:1(9Z)/20:0)Lipid Annotator
GPCho(18:1/20:0)Lipid Annotator, HMDB
GPCho(38:1)Lipid Annotator, HMDB
1-(9Z-octadecenyl)-2-eicosanoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(18:1/20:0)Lipid Annotator, HMDB
gpcho(18:1n9/20:0)HMDB
gpcho(18:1W9/20:0)HMDB
PC Ae C38:1HMDB
PC(18:1n9/20:0)HMDB
PC(18:1W9/20:0)HMDB
PC(O-38:1)HMDB
Phosphatidylcholine(18:1n9/20:0)HMDB
Phosphatidylcholine(18:1W9/20:0)HMDB
Chemical FormulaC46H92NO7P
Average Molecular Weight802.1989
Monoisotopic Molecular Weight801.661140815
IUPAC Name(2-{[(2R)-2-(icosanoyloxy)-3-[(9Z)-octadec-9-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(icosanoyloxy)-3-[(9Z)-octadec-9-en-1-yloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H92NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h21,23,45H,6-20,22,24-44H2,1-5H3/b23-21-/t45-/m1/s1
InChI KeyXKGBWHAITCMFLI-MWGCQCNTSA-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
logP6.44ALOGPS
logP10.8ChemAxon
logS-7.6ALOGPS
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 Count45ChemAxon
Refractivity244.83 m³·mol⁻¹ChemAxon
Polarizability101.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-1ca8923c03ec589a6f8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-1ca8923c03ec589a6f8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900141160-1100a1dbcf899e4b4c5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-189726d11493dee43612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000090-189726d11493dee43612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03i0-0006300910-5a687a8cf112cc8ed1b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-4cf1dda8bdd56dd830cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0021002290-26989e93ad9eeaa854f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-5039800000-59d4f6505cb504598bb4Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected and Quantified0.6834 +/- 0.0915-0.6972+/-0.0915 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.9486 +/- 0.0976-0.6565+/-0.0976 uMNot AvailablePorcine details
Ruminal FluidDetected and Quantified0.022 +/- 0.03 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected and Quantified1.2 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified1.4 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.6 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified1 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013430
FooDB IDFDB029430
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 ID53481727
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available