Showing metabocard for PC(18:3(6Z,9Z,12Z)/24:1(15Z)) (BMDB0008191)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:15:47 UTC
Update Date2020-06-04 19:01:36 UTC
BMDB IDBMDB0008191
Secondary Accession Numbers
  • BMDB08191
Metabolite Identification
Common NamePC(18:3(6Z,9Z,12Z)/24:1(15Z))
DescriptionPC(18:3(6Z,9Z,12Z)/24:1(15Z)), also known as pc(18:3(6z,9z,12z)/24:1(15z)) or pc(18:3(6z,9z,12z)/24:1(15z)), 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)/24:1(15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/24:1(15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/24:1(15Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(6Z,9Z,12Z)/24:1(15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(6Z,9Z,12Z)/24:1(15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(6Z,9Z,12Z)/24:1(15Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(6Z,9Z,12Z)/24:1(15Z)) can be biosynthesized from CDP-choline and DG(18:3(6Z,9Z,12Z)/24:1(15Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(6Z,9Z,12Z)/24:1(15Z)) and L-serine can be converted into choline and PS(18:3(6Z,9Z,12Z)/24:1(15Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:3(6Z,9Z,12Z)/24:1(15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/24:1(15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-gamma-Linolenoyl-2-nervonoyl-sn-glycero-3-phosphocholineChEBI
GPCho(18:3n6/24:1n9)ChEBI
GPCho(18:3W6/24:1W9)ChEBI
PC(18:3n6/24:1n9)ChEBI
PC(18:3W6/24:1W9)ChEBI
Phosphatidylcholine(18:3n6/24:1n9)ChEBI
Phosphatidylcholine(18:3W6/24:1W9)ChEBI
1-g-Linolenoyl-2-nervonoyl-sn-glycero-3-phosphocholineGenerator
1-Γ-linolenoyl-2-nervonoyl-sn-glycero-3-phosphocholineGenerator
Gpcho(18:3/24:1)HMDB
Gpcho(42:4)HMDB
LecithinHMDB
PC Aa C42:4HMDB
PC(18:3/24:1)HMDB
PC(42:4)HMDB
Phosphatidylcholine(18:3/24:1)HMDB
Phosphatidylcholine(42:4)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(15Z-tetracosanoyl)-sn-glycero-3-phosphocholineHMDB
PC(18:3(6Z,9Z,12Z)/24:1(15Z))Lipid Annotator
Chemical FormulaC50H92NO8P
Average Molecular Weight866.2411
Monoisotopic Molecular Weight865.656055437
IUPAC Nametrimethyl(2-{[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-[(15Z)-tetracos-15-enoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCCCC(=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/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h15,17,20-22,28,32,34,48H,6-14,16,18-19,23-27,29-31,33,35-47H2,1-5H3/b17-15-,22-20-,28-21-,34-32-/t48-/m1/s1
InChI KeyLQQRQYIGEYFSIG-UWESVXFQSA-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
logP6.58ALOGPS
logP11.11ChemAxon
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 Count46ChemAxon
Refractivity266.34 m³·mol⁻¹ChemAxon
Polarizability106.48 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, Negativesplash10-07fr-0094000030-7b897c99f4563dafe00fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0091000100-2c095125ce9419264961View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6097100000-14bf360cdeadb160b514View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000009-1791f8bf865a0857471fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0011000009-4c1c332648212dcb1fceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0vmi-0099000009-2de8eeb152365a2f83e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-8e865372fc15a66c7bf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0035003090-5341c7b05bb55e7458f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7294500000-c3d2604c8291555fa952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-9045041130-4709019f2a479e9e8fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pt-5259022110-dd4721820fad7c7b36f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-8039001100-d11605591e3c32851796View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-c23bf4396560995f2075View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-7ff854621a9c368ce93bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0100179030-e7954d34f2d8d7a00e4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-885c0d2b6e3e4f892e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000090-9125665aeeab92b4ca2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4k-0900143930-a08e465298a0b77138cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-3aaaad39472490bbd6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0600000090-d0d848a19ec2a7607a12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900032030-47edec1b0f8abed94bdbView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.008 +/- 0.004 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008191
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025381
KNApSAcK IDNot Available
Chemspider ID24766853
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478821
PDB IDNot Available
ChEBI ID86422
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available