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Record Information
Version1.0
Creation Date2016-09-30 23:48:10 UTC
Update Date2020-06-04 20:44:21 UTC
BMDB IDBMDB0007972
Secondary Accession Numbers
  • BMDB07972
Metabolite Identification
Common NamePC(16:0/18:1(9Z))
DescriptionPC(16:0/18:1(9Z)), also known as PC(16:0/18:1) or 1-POPC, 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(16:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(16:0/18:1(9Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:1(9Z)) and L-serine can be converted into choline and PS(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:1(9Z)) pathway.
Structure
Thumb
Synonyms
Chemical FormulaC42H82NO8P
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number6753-55-5
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H82NO8P/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/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1
InChI KeyWTJKGGKOPKCXLL-VYOBOKEXSA-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
logP5.59ALOGPS
logP8.64ChemAxon
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 Count41ChemAxon
Refractivity226.18 m³·mol⁻¹ChemAxon
Polarizability94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-000t-0090200800-c8db3c4042d858672ebdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-0006-0020000900-603012fb0ce5ff46f1eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-0udi-0000000190-afc4cd2ac0e64fa39623View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-09171592a6955e57e163View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0f6x-0000000940-3b9edba3cc0cdfff4945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-e80b4b8f6690eea16c9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000x-0090000700-527aadfe756a5f2ad9a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-e27632edecd3a83538a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000000-875a5d38cc2b636df4a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-053r-0090000000-6bdad7ea857755dad8dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-a0160ca0a20b8ca408deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-d2bc446076d9d86bbadfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-053r-1090000000-a94d8052959d35d3d25eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-057i-5190000000-12de950663c450d5ad7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 194V, negativesplash10-004i-9000000000-906a0ebc0dd0220ac288View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-0bfd0ce87b7b119d82fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-88f30608c9fd0df934c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-fb159b53855796db7d35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-084480cec1d6930fa834View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0006-0020000900-103adeac53f876868122View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-000x-0090000800-a9198efdf2f4fe5ec5daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-053r-0090000200-9df170809bae304c6bc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-64875131a83d4fda43e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-dfb450caf9537c97446eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-1900230300-31ec54e207b217422a2eView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0007972
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030200
KNApSAcK IDNot Available
Chemspider ID4593686
KEGG Compound IDNot Available
BioCyc IDCPD-8157
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5497103
PDB IDNot Available
ChEBI ID73001
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.

Enzymes

General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q7YRH6
Molecular weight:
22018.0
Reactions
S-Adenosylmethionine + PE-NMe2(16:0/18:1(9Z)) → S-Adenosylhomocysteine + PC(16:0/18:1(9Z))details
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(16:0/18:1(9Z)) + L-Serine → Choline + PS(16:0/18:1(9Z))details