Showing metabocard for PC(o-22:1(13Z)/20:4(8Z,11Z,14Z,17Z)) (LMDB00618)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:52 UTC
Update Date2016-07-19 23:08:23 UTC
LmdbLMDB00618
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-22:1(13Z)/20:4(8Z,11Z,14Z,17Z))
DescriptionPC(o-22:1(13Z)/20:4(8Z,11Z,14Z,17Z)) 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-22:1(13Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of Erucyl alcohol at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. The Erucyl alcohol moiety is derived from Rapeseed oil, while the eicosatetraenoic acid moiety is derived from fish oils. 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-Erucyl-2-eicsoateHMDB
1-Erucyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholineHMDB
1-Erucyl-2-eicsoic acidHMDB
Gpcho(22:1/20:4)HMDB
Gpcho(22:1n9/20:4n3)HMDB
Gpcho(22:1W9/20:4W3)HMDB
Gpcho(42:5)HMDB
LecithinHMDB
PC Ae C42:5HMDB
PC(22:1/20:4)HMDB
PC(22:1n9/20:4n3)HMDB
PC(22:1W9/20:4W3)HMDB
PC(42:5)HMDB
PC(O-42:5)HMDB
Phosphatidylcholine(22:1/20:4)HMDB
Phosphatidylcholine(22:1n9/20:4n3)HMDB
Phosphatidylcholine(22:1W9/20:4W3)HMDB
Phosphatidylcholine(42:5)HMDB
1-(13Z-Docosenyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-22:1(13Z)/20:4(8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC50H92NO7P
Average Molecular Weight850.2417
Monoisotopic Molecular Weight849.661140815
IUPAC Name(2-{[(2R)-3-[(13Z)-docos-13-en-1-yloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(13Z)-docos-13-en-1-yloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C50H92NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-28-30-32-34-36-38-40-42-45-55-47-49(48-57-59(53,54)56-46-44-51(3,4)5)58-50(52)43-41-39-37-35-33-31-29-27-23-21-19-17-15-13-11-9-7-2/h15,17,20-23,29,31,35,37,49H,6-14,16,18-19,24-28,30,32-34,36,38-48H2,1-5H3/b17-15-,22-20-,23-21-,31-29-,37-35-/t49-/m1/s1
InChI KeyOQRGDDBNUMCNLP-ABEXPZPBSA-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 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
logP6.93ALOGPS
logP11.13ChemAxon
logS-7.5ALOGPS
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
Refractivity267.7 m³·mol⁻¹ChemAxon
Polarizability105.6 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, Negativesplash10-001i-0000000090-e77c619e7de6d9b40531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000090-e77c619e7de6d9b40531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0urr-0006120190-6955d7909b96f1364cebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-b06089deb912f274f139Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0032002390-c98ae2225456174c6aeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi0-6149300000-ad1a499261af6bd2820dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-a90e6cbba1ff17ae54a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-a90e6cbba1ff17ae54a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900061160-2f0a4bc416c501e31bedSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected and Quantified0.6438 +/- 0.0459-0.6665+/-0.0459 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.6660 +/- 0.0443-0.6873+/-0.0443 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.6791 +/- 0.0497-0.5943+/-0.0497 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.7193 +/- 0.0459-0.5447+/-0.0459 uMNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0013451
FooDB IDFDB029451
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 ID53481757
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available