Showing metabocard for PC(18:3(6Z,9Z,12Z)/22:1(13Z)) (BMDB0008184)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:15:38 UTC
Update Date2020-06-04 19:13:50 UTC
BMDB IDBMDB0008184
Secondary Accession Numbers
  • BMDB08184
Metabolite Identification
Common NamePC(18:3(6Z,9Z,12Z)/22:1(13Z))
DescriptionPC(18:3(6Z,9Z,12Z)/22:1(13Z)), also known as PC(18:3/22:1) or phosphatidylcholine(18:3/22:1), 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(18:3(6Z,9Z,12Z)/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/22:1(13Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(6Z,9Z,12Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(6Z,9Z,12Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(6Z,9Z,12Z)/22:1(13Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(6Z,9Z,12Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(18:3(6Z,9Z,12Z)/22:1(13Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(6Z,9Z,12Z)/22:1(13Z)) and L-serine can be converted into choline and PS(18:3(6Z,9Z,12Z)/22:1(13Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:3(6Z,9Z,12Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(18:3/22:1)HMDB
Phosphatidylcholine(18:3/22:1)HMDB
Phosphatidylcholine(40:4)HMDB
LecithinHMDB
1-g-Linolenoyl-2-erucoyl-sn-glycero-3-phosphocholineHMDB
GPCho(40:4)HMDB
GPCho(18:3/22:1)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineHMDB
PC(40:4)HMDB
PC(18:3(6Z,9Z,12Z)/22:1(13Z))Lipid Annotator
Chemical FormulaC48H88NO8P
Average Molecular Weight838.188
Monoisotopic Molecular Weight837.624755309
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=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/C48H88NO8P/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/h15,17,20-22,26,30,32,46H,6-14,16,18-19,23-25,27-29,31,33-45H2,1-5H3/b17-15-,22-20-,26-21-,32-30-/t46-/m1/s1
InChI KeyKRZVEGHGJRMPEH-SXHNUEEOSA-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
logP6.33ALOGPS
logP10.22ChemAxon
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 Count44ChemAxon
Refractivity257.14 m³·mol⁻¹ChemAxon
Polarizability102.23 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, Positivesplash10-000i-0000000090-aef124e8ea5cbd2733f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-d55488a375c07bd7b12aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900041120-9d0ec7aa8d2da432e1a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-230b965f595c2bec9d63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-9f4137f40d638028ea32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-c3e8f7326c9de3c12279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-60376684b4ec5b1d67c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000190-959c52fa4c6f7919722fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-0100197110-b94db6381c20d29892eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-d1b04c31274557ab9f7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0057004390-5263765f4a3221b130fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7295500000-51a67dc512044d6b7fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-385623721ad6580e192fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000090-d1c750142f24429788adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ii-0099000090-bcf364753cb6124d692bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-05e3eed79d70b8943852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-3d3ed3cbb1c8d0f3ab7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0700159020-86002fb66d993cf344c3View 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 Quantified0.044 +/- 0.001 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.056 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008184
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 Compound53478813
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.