Showing metabocard for PC(o-22:0/20:1(11Z)) (BMDB0013447)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:40:20 UTC
Update Date2020-06-04 19:12:52 UTC
BMDB IDBMDB0013447
Secondary Accession Numbers
  • BMDB13447
Metabolite Identification
Common NamePC(o-22:0/20:1(11Z))
DescriptionPC(O-22:0/20:1(11Z)), also known as gpcho(22:0/20:1) or gpcho(42:1), belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-22:0/20:1(11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-22:0/20:1(11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Behenyl-2-eicosenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:0/20:1)HMDB
Gpcho(22:0/20:1n9)HMDB
Gpcho(22:0/20:1W9)HMDB
Gpcho(42:1)HMDB
LecithinHMDB
PC Ae C42:1HMDB
PC(22:0/20:1)HMDB
PC(22:0/20:1n9)HMDB
PC(22:0/20:1W9)HMDB
PC(42:1)HMDB
PC(O-42:1)HMDB
Phosphatidylcholine(22:0/20:1)HMDB
Phosphatidylcholine(22:0/20:1n9)HMDB
Phosphatidylcholine(22:0/20:1W9)HMDB
Phosphatidylcholine(42:1)HMDB
1-Docosanyl-2-(11-eicosenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-22:0/20:1(11Z))Lipid Annotator
Chemical FormulaC50H100NO7P
Average Molecular Weight858.3053
Monoisotopic Molecular Weight857.723741071
IUPAC Name(2-{[(2R)-3-(docosyloxy)-2-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(docosyloxy)-2-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C50H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-28-30-32-34-36-38-40-42-45-55-47-49(48-57-59(53,54)56-46-44-51(3,4)5)58-50(52)43-41-39-37-35-33-31-29-27-23-21-19-17-15-13-11-9-7-2/h21,23,49H,6-20,22,24-48H2,1-5H3/b23-21-/t49-/m1/s1
InChI KeyXKPLZICHJPNOFR-WIEGMJJDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • 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
logP6.93ALOGPS
logP12.58ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count49ChemAxon
Refractivity263.24 m³·mol⁻¹ChemAxon
Polarizability111.37 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, Negativesplash10-0006-0000000090-656bc5fb5ee8977d19e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000000090-656bc5fb5ee8977d19e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0006120190-fecfe15aec927569ef78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-0d9c4fe61ea03c749608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000090-0d9c4fe61ea03c749608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-1900061160-6d0664d7d471183576adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-9e6b8f53a60370b7a9f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0051001390-bbda392ad04c0813dc84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4019400000-7a510af11edac9168d4bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.046 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.045 +/- 0.001 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.057 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.017 +/- 0.002 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0013447
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029447
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481749
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.