Showing metabocard for PC(14:1(9Z)/20:2(11Z,14Z)) (BMDB0007913)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:46:57 UTC
Update Date2020-06-04 20:41:42 UTC
BMDB IDBMDB0007913
Secondary Accession Numbers
  • BMDB07913
Metabolite Identification
Common NamePC(14:1(9Z)/20:2(11Z,14Z))
DescriptionPC(14:1(9Z)/20:2(11Z,14Z)), also known as gpcho(14:1/20:2) or gpcho(34:3), 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)/20:2(11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/20:2(11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/20:2(11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/20:2(11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/20:2(11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/20:2(11Z,14Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/20:2(11Z,14Z)) can be biosynthesized from CDP-choline and DG(14:1(9Z)/20:2(11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/20:2(11Z,14Z)) and L-serine can be converted into choline and PS(14:1(9Z)/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/20:2(11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/20:2(11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:2(11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(14:1/20:2)Lipid Annotator, HMDB
PC(14:1(9Z)/20:2(11Z,14Z))Lipid Annotator
1-myristoleoyl-2-eicosadienoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(14:1/20:2)Lipid Annotator, HMDB
Phosphatidylcholine(14:1/20:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(34:3)Lipid Annotator, HMDB
GPCho(34:3)Lipid Annotator, HMDB
1-(9Z-tetradecenoyl)-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(34:3)Lipid Annotator, HMDB
gpcho(14:1n5/20:2n6)HMDB
gpcho(14:1W5/20:2W6)HMDB
PC Aa C34:3HMDB
PC(14:1n5/20:2n6)HMDB
PC(14:1W5/20:2W6)HMDB
Phosphatidylcholine(14:1n5/20:2n6)HMDB
Phosphatidylcholine(14:1W5/20:2W6)HMDB
Chemical FormulaC42H78NO8P
Average Molecular Weight756.0444
Monoisotopic Molecular Weight755.546504989
IUPAC Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13-16,19-20,40H,6-12,17-18,21-39H2,1-5H3/b15-13-,16-14-,20-19-/t40-/m1/s1
InChI KeyKBHCBANQRIOXLD-FRPVHTQQSA-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
logP5.4ALOGPS
logP7.92ChemAxon
logS-7.4ALOGPS
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 Count39ChemAxon
Refractivity228.42 m³·mol⁻¹ChemAxon
Polarizability90.91 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, Positivesplash10-052r-8191331300-c2608f2603c909632e63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053f-3390010000-913a5700c1d4d47b8975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-6190011000-d4b2bac5c9521800829eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pdi-0092000300-624e072f98a4de69752aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0191001000-257abb92ce7b2f699f6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5293000000-6783e4771c0179efdcdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-3cb602c3acfc6a68ce4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0072043900-2d068071ab3324cead56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3259000000-24866f7b01baf8b173fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-178043a88be6f491ac6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-13496904f0fd4fc1981eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0600490200-32af949b4751236f3330View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-7438791c506b384c79b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-1df045f96b3bdfe483c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000900-5a43268407f42943a4adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-7d3df73fbaa9dffe7d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-785a8f601a463a4cb653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-5118aeb3d203ab60c481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-b5946ddd213bca84cd6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-8697b097e89237a32dd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0101490300-eae8b5db1a4bde3bb214View 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 Quantified0.84 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.98 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.74 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.019 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.015 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.006 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.009 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.01 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.06 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.038 +/- 0.021 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.026 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007913
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766589
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922280
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.