Showing metabocard for PC(14:1(9Z)/22:1(13Z)) (BMDB0007920)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:47:08 UTC
Update Date2020-06-04 20:44:41 UTC
BMDB IDBMDB0007920
Secondary Accession Numbers
  • BMDB07920
Metabolite Identification
Common NamePC(14:1(9Z)/22:1(13Z))
DescriptionPC(14:1(9Z)/22:1(13Z)), also known as gpcho(14:1/22:1) or PC(36:2), belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(14:1(9Z)/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/22:1(13Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/22:1(13Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(14:1(9Z)/22:1(13Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/22:1(13Z)) and L-serine can be converted into choline and PS(14:1(9Z)/22:1(13Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(14:1/22:1)Lipid Annotator, HMDB
PC(14:1/22:1)Lipid Annotator, HMDB
PC(36:2)Lipid Annotator, HMDB
Phosphatidylcholine(14:1/22:1)Lipid Annotator, HMDB
1-myristoleoyl-2-erucoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(36:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(14:1(9Z)/22:1(13Z))Lipid Annotator
1-(9Z-tetradecenoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(36:2)Lipid Annotator, HMDB
Chemical FormulaC44H84NO8P
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h13,15,19-20,42H,6-12,14,16-18,21-41H2,1-5H3/b15-13-,20-19-/t42-/m1/s1
InChI KeyCGXBWJDAGMQUFG-MHJIJCEHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.78ALOGPS
logP9.17ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability96.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9155312400-4ac484a5b234e71e2ef2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l7r-6496112200-c162dd75481f3e497789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-8193011100-4e8f52a9f1ee2a6a6774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-057r-0093000300-59d3a67cd95a402f2abeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0192001000-b7eba0453933074f2b15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7297000000-a37a54597f2ca52418c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-64c382f846ba04194d31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6c06686879d9f7790e62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0202469400-08602756fdb5bb814ce1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-23df8d3c4971511f3b91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0040-0043030900-89c5b599d62d2f898018View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-3259000000-ee04583620e20bfc88eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-683d2aaf9f12a9d08614View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000090-06338fba3431f5598089View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ii-0099000090-f6ade794dc5f49ce5904View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-e54f4b7d729e27672b37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-3a2440aaca7e87ec13a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900221300-a38751f4c325dd7c0ac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-53a8e01f33b2af13f226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-64f46bdfe255d6a5b5e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0700329110-97efa49e8e50e1a32606View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified5.82 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.0 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified9.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.48 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.564 +/- 0.381 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.501 +/- 0.341 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.531 +/- 0.436 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.601 +/- 0.735 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.263 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.104 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.019 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.642 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007920
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766596
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478629
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.