Showing metabocard for PC(14:0/20:2(11Z,14Z)) (BMDB0007880)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:46:17 UTC
Update Date2020-06-04 20:44:53 UTC
BMDB IDBMDB0007880
Secondary Accession Numbers
  • BMDB07880
Metabolite Identification
Common NamePC(14:0/20:2(11Z,14Z))
DescriptionPC(14:0/20:2(11Z,14Z)), also known as gpcho(14:0/20:2) or gpcho(34:2), 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(14:0/20:2(11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/20:2(11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/20:2(11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:0/20:2(11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/20:2(11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/20:2(11Z,14Z)) can be biosynthesized from CDP-choline and DG(14:0/20:2(11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/20:2(11Z,14Z)) and L-serine can be converted into choline and PS(14:0/20:2(11Z,14Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(14:0/20:2(11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/20:2(11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/20:2(11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoyl-2-eicosadienoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(14:0/20:2)HMDB
Gpcho(14:0/20:2n6)HMDB
Gpcho(14:0/20:2W6)HMDB
Gpcho(34:2)HMDB
LecithinHMDB
PC Aa C34:2HMDB
PC(14:0/20:2)HMDB
PC(14:0/20:2n6)HMDB
PC(14:0/20:2W6)HMDB
PC(34:2)HMDB
Phosphatidylcholine(14:0/20:2)HMDB
Phosphatidylcholine(14:0/20:2n6)HMDB
Phosphatidylcholine(14:0/20:2W6)HMDB
Phosphatidylcholine(34:2)HMDB
1-Tetradecanoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholineHMDB
PC(14:0/20:2(11Z,14Z))Lipid Annotator
Chemical FormulaC42H80NO8P
Average Molecular Weight758.0603
Monoisotopic Molecular Weight757.562155053
IUPAC Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H80NO8P/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/h14,16,19-20,40H,6-13,15,17-18,21-39H2,1-5H3/b16-14-,20-19-/t40-/m1/s1
InChI KeyIRYMXEVDAKMFIF-YBLKGUNISA-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
logP5.47ALOGPS
logP8.28ChemAxon
logS-7.5ALOGPS
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 Count40ChemAxon
Refractivity227.3 m³·mol⁻¹ChemAxon
Polarizability92.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053l-8191331400-383c29e45b5c5f171ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3490010000-7e6efed16da28349663dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-7290010000-03963361b186435a5495View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0092000300-51c232c4f6385e19dd57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0191001000-90baf5e8ace009bda661View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5293000000-e3267550799f209c4ea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-8ecd56b42b9f6b271e5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-ab98c2d6a7f897263cd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0600490200-b1d0377f3eb23dc639f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-02ab676d31620f046e54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-80f99b213a3cb752bf9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0101490300-29669763601eb7d267baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-b382b9772ae071121f32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-e509931f6dd2f1ba96fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-40b321385b5a4db35813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000900-4f45d46462d3badb869eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0064043900-117c709afa6a95105e94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3192100000-e7229eddd2eeb1039d88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-e3f5d1861df776418aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000900-0312567647eb94448865View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000900-7606b2439ad0eb33fb24View 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 Quantified11.0 +/- 0.4 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.7 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified9.5 +/- 0.5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.9 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.041 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.028 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.038 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.73 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.535 +/- 0.32 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.431 +/- 0.41 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.345 +/- 0.22 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.781 +/- 0.66 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007880
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025072
KNApSAcK IDNot Available
Chemspider ID24766556
KEGG Compound IDC00157
BioCyc IDPhosphatidylcholines-34-2
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922228
PDB IDNot Available
ChEBI ID89518
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.