PC(16:0/18:0) (CHEM037292)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 09:43:22 UTC
Update Date2016-11-09 01:21:39 UTC
Accession NumberCHEM037292
Identification
Common NamePC(16:0/18:0)
ClassSmall Molecule
DescriptionPC(16:0/18:0), 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(16:0/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:0); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:0) can be biosynthesized from CDP-choline and DG(16:0/18:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:0) and L-serine can be converted into choline and PS(16:0/18:0) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:0) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:0) pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-3-(Palmitoyloxy)-2-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphateChEBI
1-Palmitoyl-2-stearoyl-GPCChEBI
1-Palmitoyl-2-stearoyl-GPC (16:0/18:0)ChEBI
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphorylcholineChEBI
1-Palmitoyl-2-stearoylphosphatidylcholineChEBI
GPC(16:0/18:0)ChEBI
GPCho(16:0/18:0)ChEBI
GPCho(34:0)ChEBI
PC(34:0)ChEBI
Phosphatidylcholine(16:0/18:0)ChEBI
Phosphatidylcholine(34:0)ChEBI
(2R)-3-(Palmitoyloxy)-2-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
LecithinHMDB
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-stearoyl-sn-glycero-phosphatidylcholineHMDB
GPC(34:0)HMDB
PSPCHMDB
PC(16:0/18:0)Lipid Annotator
Chemical FormulaC42H84NO8P
Average Molecular Mass762.092 g/mol
Monoisotopic Mass761.593 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
InChI IdentifierInChI=1S/C42H84NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h40H,6-39H2,1-5H3/t40-/m1/s1
InChI KeyPZNPLUBHRSSFHT-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
logP5.62ALOGPS
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
Polarizability95.56 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
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0a4i-0000000490-d88f2a12c72c6e16b54cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-052b-0000000950-8d9dfe7e55c52dab1c77Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0002-0020000910-01911c1e0f87c8e49b15Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000t-0090000800-80590273ac2914fa2bacSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-9b2292a7f9bcea1dc8c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000100-330d9a7ac1ed8c7dddf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-053r-0090000000-ee0d4df936e8eb46d224Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-4130545053cd0c87703fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-375f7f0bcf027901b6abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 134V, negativesplash10-053r-0090000000-1061c43309feed382466Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-057i-5090000000-e95f748355aa842e15dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 196V, negativesplash10-004i-9000000000-1a84ff016029161234dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0002-0000000900-6e195caba9da71e7c374Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03di-0500000900-95b01663df695379be1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-0300000900-62c4e365b0fafe8efec9Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-03dl-0008900000-be1d0d6b38f1002d172bSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-01ox-0109500000-392db28d858abd8bb315Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, positivesplash10-054k-0000970100-8d9eb2bbec5f813ae4a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kkb-0000690700-eaeb1022d870966c8373Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu9-0090000200-7f7015fd1f2dab155708Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090001000-0fb9ba9bcef10544408bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-3090000000-a3206c8150970740995dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9125bd0d43e31222ebc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0030000900-a6c60e32bbd2feacba2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0090000400-36b22ac20ecd43e2bd0eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0007970
FooDB IDFDB025161
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 ID73000
PubChem Compound ID24778686
Kegg Compound IDNot Available
YMDB IDYMDB01182
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)
2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.