Showing metabocard for PC(16:0/18:3(6Z,9Z,12Z)) (BMDB0007974)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:48:13 UTC
Update Date2020-06-04 20:41:42 UTC
BMDB IDBMDB0007974
Secondary Accession Numbers
  • BMDB07974
Metabolite Identification
Common NamePC(16:0/18:3(6Z,9Z,12Z))
DescriptionPC(16:0/18:3(6Z,9Z,12Z)), also known as PC(16:0/18:3) or PC(34:3), 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(16:0/18:3(6Z,9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:3(6Z,9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:3(6Z,9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:3(6Z,9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:3(6Z,9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:3(6Z,9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:3(6Z,9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:3(6Z,9Z,12Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:3(6Z,9Z,12Z)) and L-serine can be converted into choline and PS(16:0/18:3(6Z,9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:3(6Z,9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:3(6Z,9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:3(6Z,9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-(gamma-linolenoyl)-sn-glycero-3-phosphocholineChEBI
PC(16:0/18:3)ChEBI
1-Palmitoyl-2-(g-linolenoyl)-sn-glycero-3-phosphocholineGenerator
1-Palmitoyl-2-(γ-linolenoyl)-sn-glycero-3-phosphocholineGenerator
PC(34:3)HMDB
LecithinHMDB
GPCho(16:0/18:3)HMDB
Phosphatidylcholine(34:3)HMDB
GPCho(34:3)HMDB
Phosphatidylcholine(16:0/18:3)HMDB
1-Palmitoyl-2-g-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-gamma-linolenoyl-GPCHMDB
1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-linolenoyl-GPCHMDB
GPC(16:0/18:3(6Z,9Z,12Z))HMDB
GPC(16:0/18:3)HMDB
GPC(16:0/18:3n6)HMDB
GPC(16:0/18:3W6)HMDB
GPC(34:3)HMDB
GPCho(16:0/18:3(6Z,9Z,12Z))HMDB
GPCho(16:0/18:3n6)HMDB
GPCho(16:0/18:3W6)HMDB
PC(16:0/18:3n6)HMDB
PC(16:0/18:3W6)HMDB
Phosphatidylcholine(16:0/18:3(6Z,9Z,12Z))HMDB
Phosphatidylcholine(16:0/18:3n6)HMDB
Phosphatidylcholine(16:0/18:3W6)HMDB
PC(16:0/18:3(6Z,9Z,12Z))Lipid Annotator
Chemical FormulaC42H78NO8P
Average Molecular Weight756.0444
Monoisotopic Molecular Weight755.546504989
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H78NO8P/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/h14,16,20-21,25,27,40H,6-13,15,17-19,22-24,26,28-39H2,1-5H3/b16-14-,21-20-,27-25-/t40-/m1/s1
InChI KeyCNNSEHUKQJCGTE-UPPWDXJYSA-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
logP5.47ALOGPS
logP7.92ChemAxon
logS-7.4ALOGPS
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 Count39ChemAxon
Refractivity228.42 m³·mol⁻¹ChemAxon
Polarizability91.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-deb054ff1e14f68ef680View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-0998358a1aca7036ae80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-395dbf80736d8da3f685View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-0090000200-8e8eed2ebe14fe28f08bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090001000-d1e424f1a4bd3396d09cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3090000000-d9691d727f275fdd99bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-3cb602c3acfc6a68ce4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0090032600-596102ff08627c62ff24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4290000000-ed336d5d9c486a34dae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-7d3df73fbaa9dffe7d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-785a8f601a463a4cb653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-1de475ad6e9d4945dbafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-b5946ddd213bca84cd6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-8697b097e89237a32dd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100390200-8c94611232ab673975aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-178043a88be6f491ac6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-13496904f0fd4fc1981eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0500190100-969d191b5a0b12f47eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-7438791c506b384c79b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-871f854ac2854ad8d30bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0090000400-006075ca20ec6574d3e4View 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.84 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.98 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.74 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.019 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.015 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.006 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.026 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.009 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.01 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.06 +/- 0.003 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.038 +/- 0.021 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007974
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778699
PDB IDNot Available
ChEBI ID84786
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.