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

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:48:08 UTC
Update Date2020-06-04 19:51:04 UTC
MCDB ID BMDB0007970
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-13View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0a4i-0000000490-d88f2a12c72c6e16b54c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-052b-0000000950-8d9dfe7e55c52dab1c772020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0002-0020000910-01911c1e0f87c8e49b152020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000t-0090000800-80590273ac2914fa2bac2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-9b2292a7f9bcea1dc8c92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000100-330d9a7ac1ed8c7dddf52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-053r-0090000000-ee0d4df936e8eb46d2242020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-4130545053cd0c87703f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-375f7f0bcf027901b6ab2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 134V, negativesplash10-053r-0090000000-1061c43309feed3824662020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-057i-5090000000-e95f748355aa842e15db2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 196V, negativesplash10-004i-9000000000-1a84ff016029161234df2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0002-0000000900-6e195caba9da71e7c3742020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03di-0500000900-95b01663df695379be1f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-0300000900-62c4e365b0fafe8efec92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-03dl-0008900000-be1d0d6b38f1002d172b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-01ox-0109500000-392db28d858abd8bb3152020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, positivesplash10-054k-0000970100-8d9eb2bbec5f813ae4a72020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kkb-0000690700-eaeb1022d870966c83732016-09-19View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu9-0090000200-7f7015fd1f2dab1557082017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090001000-0fb9ba9bcef10544408b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-3090000000-a3206c8150970740995d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9125bd0d43e31222ebc92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0030000900-a6c60e32bbd2feacba2d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0090000400-36b22ac20ecd43e2bd0e2021-09-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified2.45 +/- 0.04 uM details
Detected and Quantified4.7 +/- 0.1 uM details
Detected and Quantified5.2 +/- 0.1 uM details
Detected and Quantified2.26 +/- 0.03 uM details
HMDB IDHMDB0007970
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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.