Showing metabocard for PC(o-18:0/20:4(8Z,11Z,14Z,17Z)) (LMDB00598)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:24 UTC
Update Date2016-07-20 20:46:05 UTC
LmdbLMDB00598
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-18:0/20:4(8Z,11Z,14Z,17Z))
DescriptionPC(o-18:0/20:4(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-18:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of Stearyl alcohol at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. The Stearyl alcohol moiety is derived from beef fat, fish 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-O-Octadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-phosphatidylcholineChEBI
1-Octadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Octadecyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Stearyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholineChEBI
PC(O-18:0/20:4(5Z,8Z,11Z,14Z))ChEBI
PC(O-18:0/20:4)ChEBI
1-Stearyl-2-eicsoateHMDB
1-Stearyl-2-eicsoic acidHMDB
Gpcho(18:0/20:4)HMDB
Gpcho(18:0/20:4n3)HMDB
Gpcho(18:0/20:4W3)HMDB
Gpcho(38:4)HMDB
LecithinHMDB
PC Ae C38:4HMDB
PC(18:0/20:4)HMDB
PC(18:0/20:4n3)HMDB
PC(18:0/20:4W3)HMDB
PC(38:4)HMDB
PC(O-38:4)HMDB
Phosphatidylcholine(18:0/20:4)HMDB
Phosphatidylcholine(18:0/20:4n3)HMDB
Phosphatidylcholine(18:0/20:4W3)HMDB
Phosphatidylcholine(38:4)HMDB
1-Octadecanyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-18:0/20:4(8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC46H86NO7P
Average Molecular Weight796.1513
Monoisotopic Molecular Weight795.614190623
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOC[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/C46H86NO7P/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/h14,16,20,22,25,27,31,33,45H,6-13,15,17-19,21,23-24,26,28-30,32,34-44H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t45-/m1/s1
InChI KeyGBNPCIWXLWZJGA-IGBSIYCFSA-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
logP6.39ALOGPS
logP9.71ChemAxon
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 Count42ChemAxon
Refractivity248.18 m³·mol⁻¹ChemAxon
Polarizability98.74 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, Positivesplash10-000i-9152211400-8370d318fc2953751ef6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw0-4292002100-2f6cbef42ce9e3607e36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9085003100-ea7aabc04029a789a066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0034000900-70f18db23e1ca106d72fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0frf-2093203600-0d4be29b4830823a0cabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-6094200000-b8e2919f82587bc81b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-a8777a162743af0cfcd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000090-a8777a162743af0cfcd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0vi0-0006300910-7a5f39eea6d9e38d6589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-6787195d11ad42096df1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-6787195d11ad42096df1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900141700-9845a38ebea24d73c905Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-396b53711a21a76df333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0022011900-1656d87f9cc3d7ecb3a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5169100000-fb8ae0602aa1569e58d0Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified0.034 +/- 0.026 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified11.7 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified12.4 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified6.5 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified10 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013420
FooDB IDFDB029420
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4947105
ChEBI ID75245
PubChem Compound ID6443065
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available