Showing metabocard for PC(18:2(9Z,12Z)/22:1(13Z)) (BMDB0008151)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:14:52 UTC
Update Date2020-06-04 19:11:26 UTC
BMDB IDBMDB0008151
Secondary Accession Numbers
  • BMDB08151
Metabolite Identification
Common NamePC(18:2(9Z,12Z)/22:1(13Z))
DescriptionPC(18:2(9Z,12Z)/22:1(13Z)), also known as PC(40:3) or gpcho(18:2/22:1), 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(18:2(9Z,12Z)/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:2(9Z,12Z)/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/22:1(13Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:2(9Z,12Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:2(9Z,12Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/22:1(13Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:2(9Z,12Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/22:1(13Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:2(9Z,12Z)/22:1(13Z)) and L-serine can be converted into choline and PS(18:2(9Z,12Z)/22:1(13Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(18:2(9Z,12Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(40:3)HMDB
GPCho(18:2/22:1)HMDB
1-Linoleoyl-2-erucoyl-sn-glycero-3-phosphocholineHMDB
PC(18:2/22:1)HMDB
Phosphatidylcholine(18:2/22:1)HMDB
LecithinHMDB
GPCho(40:3)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(40:3)HMDB
PC(18:2(9Z,12Z)/22:1(13Z))Lipid Annotator
Chemical FormulaC48H90NO8P
Average Molecular Weight840.2039
Monoisotopic Molecular Weight839.640405373
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C48H90NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h15,17,20-22,26,46H,6-14,16,18-19,23-25,27-45H2,1-5H3/b17-15-,22-20-,26-21-/t46-/m1/s1
InChI KeyJJWICPUXGFOAPG-PUXNAPJVSA-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
logP6.3ALOGPS
logP10.58ChemAxon
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 Count45ChemAxon
Refractivity256.02 m³·mol⁻¹ChemAxon
Polarizability102.49 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, Positivesplash10-01w0-9055041140-7ae9e832d33e9cf00ba8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-6389031110-bc6d17550056e8414c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9058002200-c4157f36fb9c322bfa0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ri-0093000030-f1b371488bf8fc626885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0091000100-6c1e6d1cef4571381525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-5095000000-fb41d6054dcec51f4cfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-a0a28947ac0361512993View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000190-d03890e36ea5447534aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gj-0100197110-5c6f8437a5a86304b99eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-7d26e455c245b2eccf0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-073d352de9ed7cf4ffbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-e7e4b417dee8fb8d9eb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-61a369759c619288f5c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0056004390-b421b5cfde2fea400fdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-7196500000-8e2d6d962eb98f62ea13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-070cc75312afe664feecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000090-43a003841c9cabaaf894View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ii-0099000090-a64d32239b1a571893bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-9fdbf0263bab6953525aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-c20a8da7b81bea8ffe7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0700159020-0bea7e0995223784cbf9View 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 Quantified0.043 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.008 +/- 0.002 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008151
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025341
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478791
PDB IDNot Available
ChEBI ID89585
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.