Showing metabocard for PC(o-24:0/18:3(6Z,9Z,12Z)) (LMDB00621)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:56 UTC
Update Date2016-07-19 23:33:23 UTC
LmdbLMDB00621
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-24:0/18:3(6Z,9Z,12Z))
DescriptionPC(o-24:0/18:3(6Z,9Z,12Z)) 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-24:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of Lignoceryl alcohol at the C-1 position and one chain of g-linolenic acid at the C-2 position. The Lignoceryl alcohol moiety is derived from plant waxes and beeswax, while the g-linolenic 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(o-24:0/18:3(6Z,9Z,12Z))Lipid Annotator
Phosphatidylcholine(42:3)Lipid Annotator, HMDB
GPCho(24:0/18:3)Lipid Annotator, HMDB
GPCho(42:3)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(24:0/18:3)Lipid Annotator, HMDB
PC(42:3)Lipid Annotator, HMDB
1-Lignoceryl-2-g-linolenoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
1-Tetracosanyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(24:0/18:3)Lipid Annotator, HMDB
1-Lignoceryl-2-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
gpcho(24:0/18:3n6)HMDB
gpcho(24:0/18:3W6)HMDB
PC Ae C42:3HMDB
PC(24:0/18:3n6)HMDB
PC(24:0/18:3W6)HMDB
PC(O-42:3)HMDB
Phosphatidylcholine(24:0/18:3n6)HMDB
Phosphatidylcholine(24:0/18:3W6)HMDB
Chemical FormulaC50H96NO7P
Average Molecular Weight854.2735
Monoisotopic Molecular Weight853.692440943
IUPAC Nametrimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(tetracosyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(tetracosyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C50H96NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-28-30-32-34-36-38-40-42-45-55-47-49(48-57-59(53,54)56-46-44-51(3,4)5)58-50(52)43-41-39-37-35-33-31-29-21-19-17-15-13-11-9-7-2/h15,17,21,29,33,35,49H,6-14,16,18-20,22-28,30-32,34,36-48H2,1-5H3/b17-15-,29-21-,35-33-/t49-/m1/s1
InChI KeyLDFITNYTODJQBW-AQBSXLNYSA-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
logP6.97ALOGPS
logP11.85ChemAxon
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 Count47ChemAxon
Refractivity265.47 m³·mol⁻¹ChemAxon
Polarizability108.59 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, Negativesplash10-0udi-0000000090-e853a3638bcff17c07eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0051002290-584fdae28a15beac4491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5094210000-f8c7c876b9f28bc23addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-fa683c998cacc001940fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000090-fa683c998cacc001940fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0060120190-88d6de679a2bb0f44d1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-3e6a9355af2acd596ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-3e6a9355af2acd596ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900061160-669733c4b1d44c4b1b5dSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified0.008 +/- 0.001 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected and Quantified0.1 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.11 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.08 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.12 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013458
FooDB IDFDB029458
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032640
ChEBI ID86451
PubChem Compound ID53481771
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available