Showing metabocard for PC(16:0/18:2(9Z,12Z)) (BMDB0007973)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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Record Information
Version1.0
Creation Date2016-09-30 23:48:12 UTC
Update Date2020-06-04 20:44:54 UTC
BMDB IDBMDB0007973
Secondary Accession Numbers
  • BMDB07973
Metabolite Identification
Common NamePC(16:0/18:2(9Z,12Z))
DescriptionPC(16:0/18:2(9Z,12Z)), also known as GPC(16:0/18:2) or gpcho 16:0/18:2(9Z,12Z), 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(16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:2(9Z,12Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(16:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC42H80NO8P
Average Molecular Weight758.0603
Monoisotopic Molecular Weight757.562155053
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number6931-84-6
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H80NO8P/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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1
InChI KeyJLPULHDHAOZNQI-ZTIMHPMXSA-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
logP5.48ALOGPS
logP8.28ChemAxon
logS-7.5ALOGPS
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 Count40ChemAxon
Refractivity227.3 m³·mol⁻¹ChemAxon
Polarizability92.66 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, negativesplash10-0udl-0000000490-b7304b809294dbb2ea74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0006-0000000940-6acae25b185d1a864052View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-537e946aca08f069e72bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-002f-0090000700-ecca901df00a9bff124cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-0090000200-fa34aef5028ed4787c4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-0090000000-d9440bc0e6a9f6cdaf65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-004i-0090000000-a5231d807bde53ae849aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, negativesplash10-056r-0090000000-23038428933dc1fcc66dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-056r-0090000000-ccce70356f7c7b18cbbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-056r-1090000000-32df8fc00b6e170aa02aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-004i-7190000000-811ed3f1fe9d51baf806View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 193V, negativesplash10-004i-9000000000-4bd8d3812cfdbafe42c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-aed1ee56f1886685cef5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-f70fecaaa4c193d6952dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-40ddf52a50eed646c5c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-79413b6bfab2c2699ebbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-0006-0020000900-30d6507c6252bceda2abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, negativesplash10-002f-0090000800-e35e5d8e6ef65358f1d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-004i-0090000200-d82c61ca09093ce2f75aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, negativesplash10-004i-0090000000-a788f61f6153073cc513View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-056r-0090000000-5242b45696e3aa936e70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 89V, negativesplash10-056r-0090000000-23038428933dc1fcc66dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-73b8731f1bdde398585fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-37c5a628d36a084e1386View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900231200-522c9f77a95c208b08bcView 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 IDHMDB0007973
DrugBank IDDB02306
Phenol Explorer Compound IDNot Available
FooDB IDFDB030253
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5287971
PDB IDCPL
ChEBI ID73002
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(16:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(16:0/18:2(9Z,12Z))details