Showing metabocard for PC(20:3(5Z,8Z,11Z)/22:1(13Z)) (BMDB0008382)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:20:09 UTC
Update Date2020-06-04 19:01:38 UTC
BMDB IDBMDB0008382
Secondary Accession Numbers
  • BMDB08382
Metabolite Identification
Common NamePC(20:3(5Z,8Z,11Z)/22:1(13Z))
DescriptionPC(20:3(5Z,8Z,11Z)/22:1(13Z)), also known as pc(20:3(5z,8z,11z)/22:1(13z)) or PC(20:3/22:1), 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(20:3(5Z,8Z,11Z)/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:3(5Z,8Z,11Z)/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:3(5Z,8Z,11Z)/22:1(13Z)) exists in all eukaryotes, ranging from yeast to humans. PC(20:3(5Z,8Z,11Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:3(5Z,8Z,11Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:3(5Z,8Z,11Z)/22:1(13Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:3(5Z,8Z,11Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(20:3(5Z,8Z,11Z)/22:1(13Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:3(5Z,8Z,11Z)/22:1(13Z)) and L-serine can be converted into choline and PS(20:3(5Z,8Z,11Z)/22:1(13Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(20:3(5Z,8Z,11Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:3(5Z,8Z,11Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphatidylcholine(42:4)HMDB
PC(20:3/22:1)HMDB
Phosphatidylcholine(20:3/22:1)HMDB
1-Meadoyl-2-erucoyl-sn-glycero-3-phosphocholineHMDB
GPCho(20:3/22:1)HMDB
LecithinHMDB
PC(42:4)HMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineHMDB
GPCho(42:4)HMDB
PC(20:3(5Z,8Z,11Z)/22:1(13Z))Lipid Annotator
Chemical FormulaC50H92NO8P
Average Molecular Weight866.2411
Monoisotopic Molecular Weight865.656055437
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h20-23,28,30,34,36,48H,6-19,24-27,29,31-33,35,37-47H2,1-5H3/b22-20-,23-21-,30-28-,36-34-/t48-/m1/s1
InChI KeyQLUBHBLHAFOGNI-FLBVHRRTSA-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
logP6.59ALOGPS
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
Polarizability107.23 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, Positivesplash10-000i-9046041130-e4b393de9316117c7c90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0080-6389032110-58bf072f64ad079cbc39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9067002310-155baad55b7aa83d6402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06ri-0049000030-457856facd5290d24b8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0059000100-97b9bcdb6c62ab00f6baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-6059100000-745889f811d7909cfeccView 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-0900161930-d995e747f42b6a59d5bfView 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-0003000009-c662cf122ce7f6117c8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-14ii-0009000004-b6e3b1d14ce5397890b5View 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-1900041030-515f21e71c3c29bd2c32View 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, Negativesplash10-0900-0017003090-8b5758ea923b7a7243baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5119300000-db1dc6fbc2dc9790de1cView 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, Positivesplash10-0019-0100197030-d8420a94a299bee75aa4View 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 IDHMDB0008382
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 Compound53478985
PDB IDNot Available
ChEBI ID89196
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available