Showing metabocard for PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (BMDB0008177)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:15:29 UTC
Update Date2020-06-04 19:35:20 UTC
BMDB IDBMDB0008177
Secondary Accession Numbers
  • BMDB08177
Metabolite Identification
Common NamePC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))
DescriptionPC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)), also known as PC(38:5) or phosphatidylcholine(18:3/20:2), 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(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) can be biosynthesized from CDP-choline and DG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) and L-serine can be converted into choline and PS(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(38:5)HMDB
Phosphatidylcholine(18:3/20:2)HMDB
Phosphatidylcholine(38:5)HMDB
PC(18:3/20:2)HMDB
GPCho(38:5)HMDB
LecithinHMDB
GPCho(18:3/20:2)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholineHMDB
1-g-Linolenoyl-2-eicosadienoyl-sn-glycero-3-phosphocholineHMDB
PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))Lipid Annotator
Chemical FormulaC46H82NO8P
Average Molecular Weight808.1189
Monoisotopic Molecular Weight807.577805117
IUPAC Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H82NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14-17,20-22,24,28,30,44H,6-13,18-19,23,25-27,29,31-43H2,1-5H3/b16-14-,17-15-,22-20-,24-21-,30-28-/t44-/m1/s1
InChI KeyJEEMMQUVRFTVSG-AZITXYQXSA-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
logP5.9ALOGPS
logP8.97ChemAxon
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 Count41ChemAxon
Refractivity249.05 m³·mol⁻¹ChemAxon
Polarizability96.5 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053l-9082041220-7ccdec43ea3f4ba52858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-4292021100-0d73938150c344136b6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8095004200-ea2153cae2265d58d2eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0092000030-83299b39671aaee8ebb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090000100-3e3d3461e770c7265dd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4092000000-ad4dfc0b58abb162f2bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-2ed1617616dcbd8a27a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-fafb872dd2abe717c7e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000090-c9e58bdcdeb4d2078e19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-982a5de1a95b33baa9fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-700b9d4c4e1a88e5359eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-e5926c92ba467e2dc4afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-f63d7860e3264d19dfbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-9706f6071dcd0d9077fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0200498220-38f94e5160ef0e57419bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-176beaa64b72d3c99c1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-c545a38bbe96927ef016View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-51b6a03a1fbe3a48cc54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-09c683f4e3532312072eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0075005390-6da38abde549c887f5ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7295400000-8c3df0260fcb5c4f8d21View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.45 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.537 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.73 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.419 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.015 +/- 0.007 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008177
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 Compound52922801
PDB IDNot Available
ChEBI ID89564
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.