Showing metabocard for PC(18:1(9Z)/22:1(13Z)) (BMDB0008118)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:14:06 UTC
Update Date2020-06-04 19:29:31 UTC
BMDB IDBMDB0008118
Secondary Accession Numbers
  • BMDB08118
Metabolite Identification
Common NamePC(18:1(9Z)/22:1(13Z))
DescriptionPC(18:1(9Z)/22:1(13Z)), also known as PC(40:2) or gpcho(18:1/22:1), 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(18:1(9Z)/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/22:1(13Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(9Z)/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/22:1(13Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/22:1(13Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/22:1(13Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/22:1(13Z)) and L-serine can be converted into choline and PS(18:1(9Z)/22:1(13Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(40:2)HMDB
Phosphatidylcholine(18:1/22:1)HMDB
GPCho(18:1/22:1)HMDB
1-Oleoyl-2-erucoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
PC(18:1/22:1)HMDB
GPCho(40:2)HMDB
1-(9Z-Octadecenoyl)-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(40:2)HMDB
PC(18:1(9Z)/22:1(13Z))Lipid Annotator
Chemical FormulaC48H92NO8P
Average Molecular Weight842.2197
Monoisotopic Molecular Weight841.656055437
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C48H92NO8P/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/h20-22,26,46H,6-19,23-25,27-45H2,1-5H3/b22-20-,26-21-/t46-/m1/s1
InChI KeyMOAVQOSWWXXGJQ-ACZCORRTSA-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
logP6.37ALOGPS
logP10.95ChemAxon
logS-7.6ALOGPS
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
Refractivity254.91 m³·mol⁻¹ChemAxon
Polarizability103.73 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, Positivesplash10-0006-0000000090-d5d4a7344dd9b429532cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-12f1e6ed1f67b0bf6f7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-164ee5a9f5e28fa42d82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-334ce021df69056ff46bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-b86490a18567af168853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0700159020-f0a7d7d0e10531ded0b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-7798f4de22a79938254aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0011000090-69d774e968327e33ee65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006i-0099000090-560a493d4d309bd5114eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-22c680cb0cae12530752View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-2ed5ce7d2651aa92b053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-a77806ba9056772b030cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-4b489c53edd2019c68bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-0045004390-08387468a337765dc289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-5096600000-458f6942df75cf0f9a56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-22004a077e65cf532e85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000190-063b8600b5379c7321f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0100197110-e110a7ee942e5c37c5a2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected and Quantified0.4 +/- 0.1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified0.7 +/- 0.2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.017 +/- 0.004 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified0.026 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.032 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.038 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.025 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
Semimembranosus MuscleDetected and Quantified0.02 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.12 +/- 0.02 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008118
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 Compound53478769
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.