PC(14:0/20:0) (CHEM037212)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 09:31:23 UTC
Update Date2016-11-09 01:21:38 UTC
Accession NumberCHEM037212
Identification
Common NamePC(14:0/20:0)
ClassSmall Molecule
DescriptionPC(14:0/20:0), also known as gpcho(34:0) or lecithin, 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(14:0/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/20:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/20:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/20:0) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/20:0) can be biosynthesized from CDP-choline and DG(14:0/20:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/20:0) and L-serine can be converted into choline and PS(14:0/20:0) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(14:0/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/20:0) pathway and phosphatidylethanolamine biosynthesis pe(14:0/20:0) pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoyl-2-arachidonyl-sn-glycero-3-phosphocholineHMDB
Gpcho(14:0/20:0)HMDB
Gpcho(34:0)HMDB
LecithinHMDB
PC(34:0)HMDB
Phosphatidylcholine(14:0/20:0)HMDB
Phosphatidylcholine(34:0)HMDB
1-Tetradecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineHMDB
PC(14:0/20:0)Lipid Annotator
Chemical FormulaC42H84NO8P
Average Molecular Mass762.092 g/mol
Monoisotopic Mass761.593 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-2-(icosanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C42H84NO8P/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/h40H,6-39H2,1-5H3/t40-/m1/s1
InChI KeyVELOKQJUJJVGMB-RRHRGVEJSA-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 Solubility2.2e-05 g/LALOGPS
logP5.63ALOGPS
logP9ChemAxon
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
Refractivity225.07 m³·mol⁻¹ChemAxon
Polarizability95.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-22b6ff3f4d5466401c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-4bd30bb1a8a4ca9730a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900230300-55bc0840789eb9efea4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9125bd0d43e31222ebc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0011000900-e9bc261013c1c49b3a65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03i2-0099000900-d587f859e180b73accb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-8d1c8fc9cea1cc051076Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-a4eee925f9874fb4ba4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0900639300-66809f4142941ccb93e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-f3925cc9b9687a1d1fecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-02016a73ba6909880995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-0101490300-d619fc248a89e44503e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-20019ba3db4313c31bc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0063010900-34f277f5bd27dd758217Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-3197000000-1b1af334e58d85475b2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-56bf2f4be9d4ae62ae59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-ff25f3a4d72aa5491d62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900230300-2a876da163951d8f9c6aSpectrum
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 IDHMDB0007878
FooDB IDFDB025070
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID PHOSPHATIDYLCHOLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766554
ChEBI IDNot Available
PubChem Compound ID24778633
Kegg Compound IDC00157
YMDB IDNot Available
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)