PC(14:0/20:4(5Z,8Z,11Z,14Z)) (CHEM022393)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:31:01 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022393
Identification
Common NamePC(14:0/20:4(5Z,8Z,11Z,14Z))
ClassSmall Molecule
DescriptionPC(14:0/20:4(5Z,8Z,11Z,14Z)), also known as phosphatidylcholine(14:0/20:4) or gpcho(14:0/20:4), 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(14:0/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/20:4(5Z,8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:0/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/20:4(5Z,8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(14:0/20:4(5Z,8Z,11Z,14Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/20:4(5Z,8Z,11Z,14Z)) and L-serine can be converted into choline and PS(14:0/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Tetradecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
GPCho(14:0/20:4)ChEBI
GPCho(14:0/20:4n6)ChEBI
GPCho(14:0/20:4W6)ChEBI
PC(14:0/20:4)ChEBI
PC(14:0/20:4n6)ChEBI
PC(14:0/20:4W6)ChEBI
Phosphatidylcholine(14:0/20:4)ChEBI
Phosphatidylcholine(14:0/20:4n6)ChEBI
Phosphatidylcholine(14:0/20:4W6)ChEBI
GPCho(34:4)HMDB
PC(34:4)HMDB
LecithinHMDB
Phosphatidylcholine(34:4)HMDB
PC(14:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC42H76NO8P
Average Molecular Mass754.029 g/mol
Monoisotopic Mass753.531 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
SMILESCCCCCCCCCCCCCC(=O)OC[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 IdentifierInChI=1S/C42H76NO8P/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/h14,16,19-20,22-23,27,29,40H,6-13,15,17-18,21,24-26,28,30-39H2,1-5H3/b16-14-,20-19-,23-22-,29-27-/t40-/m1/s1
InChI KeySRQSAJRUMDQMMS-NLDJLLEISA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.2e-05 g/LALOGPS
logP5.36ALOGPS
logP7.56ChemAxon
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 Count38ChemAxon
Refractivity229.53 m³·mol⁻¹ChemAxon
Polarizability89.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi0-0092000300-fb8e5f8e6cf0caa4c67eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0191001000-5ad30a59a3f2abd37194Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-5293000000-20b4c6327140f214686aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-fd248ad900d1f4236853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-5dd296d2b9d56fc4c0f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uii-0099000900-def7911c65c8a1611846Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-58a43ac72477d144a720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0074042900-7223d1d2cf28133c0b93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5492100000-004519068a9f4226a17aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8191331300-e09b2465ca6875a71d90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3390010000-0639ab49a1263cdee172Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7290011000-8bec9f02630c5adc0da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-117f3fc6982fc425d794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-e0182f758af441932884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0008-0600490200-9ff7dff4fe3789e17d14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-b98e9d2d756a1104b321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-d92091f9cf400c110537Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-f0a2e10786ef89689e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-fb17bd89e0dbf4476c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-d42a6dc7b67679b57a97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fir-0101490300-6b9d45f785fcfcbac104Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0007883
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID86102
PubChem Compound ID24778634
Kegg Compound IDNot Available
YMDB IDYMDB01819
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)