Showing metabocard for PC(15:0/20:0) (BMDB0007944)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:47:38 UTC
Update Date2020-06-04 19:35:11 UTC
BMDB IDBMDB0007944
Secondary Accession Numbers
  • BMDB07944
Metabolite Identification
Common NamePC(15:0/20:0)
DescriptionPC(15:0/20:0), also known as lecithin or gpcho(35:0), 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(15:0/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/20:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/20:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/20:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/20:0) can be biosynthesized from CDP-choline and DG(15:0/20:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/20:0) and L-serine can be converted into choline and PS(15:0/20:0) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(15:0/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/20:0) pathway and phosphatidylethanolamine biosynthesis pe(15:0/20:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Pentadecanoyl-2-arachidonyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
GPCho(35:0)HMDB
Phosphatidylcholine(15:0/20:0)HMDB
Phosphatidylcholine(35:0)HMDB
PC(35:0)HMDB
1-Pentadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineHMDB
GPCho(15:0/20:0)HMDB
PC(15:0/20:0)Lipid Annotator
Chemical FormulaC43H86NO8P
Average Molecular Weight776.1186
Monoisotopic Molecular Weight775.609105245
IUPAC Name(2-{[(2R)-2-(icosanoyloxy)-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H86NO8P/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/h41H,6-40H2,1-5H3/t41-/m1/s1
InChI KeyOUQNLKQTFDIKCN-VQJSHJPSSA-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
logP5.78ALOGPS
logP9.45ChemAxon
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 Count43ChemAxon
Refractivity229.67 m³·mol⁻¹ChemAxon
Polarizability97.72 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, Positivesplash10-004i-0000000900-bc383b154a6203ea7df2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-7e4a442ba394cc1765a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-1521bafd03cd85bef05bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e46a7d29f47e96cb7248View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-0864e00ee142428242daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-2d7a897ce62c4a0479aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-48cd21ce307fe049ff10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000090-f61c69993c3e264af887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-0099000090-aff90e063c6bc7a685fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-b1f95a0e718a13f5e5e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0063010900-6f138af8cb7c95e9c2bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3197000000-91c0e1b107fe422fa5e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-1da76a8c224e917f4cc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-a82a8a74d88fa3e27839View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0900449300-a4fa887bf3600ed6c88aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-21a54198374898e25ad6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-8a0f2e73f3f1f1c37430View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007k-0100690300-7bc95bc791a0a13ccdc3View 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 Quantified0.229 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.63 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.88 +/- 0.07 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.20 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007944
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025136
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922322
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.