Showing metabocard for PC(16:0/18:0) (BMDB0007970)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:48:08 UTC
Update Date2020-06-04 19:51:04 UTC
BMDB IDBMDB0007970
Secondary Accession Numbers
  • BMDB07970
Metabolite Identification
Common NamePC(16:0/18:0)
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.
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 Weight762.092
Monoisotopic Molecular Weight761.593455181
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
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=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
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
logP5.62ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0a4i-0000000490-d88f2a12c72c6e16b54cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-052b-0000000950-8d9dfe7e55c52dab1c77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0002-0020000910-01911c1e0f87c8e49b15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000t-0090000800-80590273ac2914fa2bacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-9b2292a7f9bcea1dc8c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000100-330d9a7ac1ed8c7dddf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-053r-0090000000-ee0d4df936e8eb46d224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-4130545053cd0c87703fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-375f7f0bcf027901b6abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 134V, negativesplash10-053r-0090000000-1061c43309feed382466View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-057i-5090000000-e95f748355aa842e15dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 196V, negativesplash10-004i-9000000000-1a84ff016029161234dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0002-0000000900-6e195caba9da71e7c374View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03di-0500000900-95b01663df695379be1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-0300000900-62c4e365b0fafe8efec9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-03dl-0008900000-be1d0d6b38f1002d172bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-01ox-0109500000-392db28d858abd8bb315View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, positivesplash10-054k-0000970100-8d9eb2bbec5f813ae4a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kkb-0000690700-eaeb1022d870966c8373View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu9-0090000200-7f7015fd1f2dab155708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090001000-0fb9ba9bcef10544408bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-3090000000-a3206c8150970740995dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9125bd0d43e31222ebc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0030000900-a6c60e32bbd2feacba2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0090000400-36b22ac20ecd43e2bd0eView 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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified2.45 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.7 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.2 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.26 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007970
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025161
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778686
PDB IDNot Available
ChEBI ID73000
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

Enzyme Details
1. Phosphatidylserine synthase 1
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(16:0/18:0) + L-Serine → Choline + PS(16:0/18:0)details