Showing metabocard for PC(15:0/20:3(8Z,11Z,14Z)) (BMDB0007948)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:47:42 UTC
Update Date2020-06-04 19:25:02 UTC
BMDB IDBMDB0007948
Secondary Accession Numbers
  • BMDB07948
Metabolite Identification
Common NamePC(15:0/20:3(8Z,11Z,14Z))
DescriptionPC(15:0/20:3(8Z,11Z,14Z)), also known as gpcho(15:0/20:3) or gpcho(35:3), 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(15:0/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/20:3(8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/20:3(8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(15:0/20:3(8Z,11Z,14Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/20:3(8Z,11Z,14Z)) and L-serine can be converted into choline and PS(15:0/20:3(8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(15:0/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/20:3(8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(15:0/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(15:0/20:3)HMDB
GPCho(35:3)HMDB
1-Pentadecanoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
PC(35:3)HMDB
PC(15:0/20:3)HMDB
Phosphatidylcholine(15:0/20:3)HMDB
Phosphatidylcholine(35:3)HMDB
1-Pentadecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholineHMDB
PC(15:0/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC43H80NO8P
Average Molecular Weight770.071
Monoisotopic Molecular Weight769.562155053
IUPAC Name(2-{[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44(3,4)5)39-49-42(45)35-33-31-29-27-25-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,41H,6-13,15,17-19,22,25-40H2,1-5H3/b16-14-,21-20-,24-23-/t41-/m1/s1
InChI KeyILVRORZGIYNHIC-XWIBIVISSA-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
logP5.61ALOGPS
logP8.36ChemAxon
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 Count40ChemAxon
Refractivity233.02 m³·mol⁻¹ChemAxon
Polarizability93.46 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, Positivesplash10-00di-0000000900-90c6ff22c045c746c189View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0600000900-f442e1848089fc8f3d98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-9e8029429ef1886b4d2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-c86690b13603a81edc9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0011000090-640ab5b2d4c061d457baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-14i6-0099000090-a04244ce64aca4683f8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-8c52570f13e738ff0d94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-ae1e6dd471a8d66842a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-0100690300-5ff83c9db1edba5a1e9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-9b688f51cdba4f1a9a76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0600000900-576f3f84d06548265365View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-7b50a052c64dcea8e723View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-dc599a9f6ca21fb1abd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0053030900-aff29ae9ec24e8690986View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5492100000-b68af11bdd23f8436305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-f15329e8346b7ddc68f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6b737e22cf4d1b5d3fc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4k-0900449300-fe65466df2c6c860f5b7View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.10 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.18 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.29 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.067 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007948
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025140
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922328
PDB IDNot Available
ChEBI IDNot Available
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.