Showing metabocard for PC(22:1(13Z)/P-18:1(11Z)) (BMDB0008588)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:24:52 UTC
Update Date2020-06-04 19:09:42 UTC
BMDB IDBMDB0008588
Secondary Accession Numbers
  • BMDB08588
Metabolite Identification
Common NamePC(22:1(13Z)/P-18:1(11Z))
DescriptionPC(22:1(13Z)/P-18:1(11Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(22:1(13Z)/P-18:1(11Z)), in particular, consists of one 13Z-docosenoyl chain to the C-1 atom, and one 1Z,11Z-octadecadienyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GlycerophosphocholineHMDB
1-(13Z-Docosenoyl)-2-(1Z,11Z-octadecadienyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(22:1(13Z)/p-18:1(11Z))HMDB
PC(22:2)HMDB
Gpcho(22:2)HMDB
Phosphatidylcholine(22:2)HMDB
PC(22:1/P-18:1)HMDB
Gpcho(22:1/p-18:1)HMDB
Phosphatidylcholine(22:1/p-18:1)HMDB
Chemical FormulaC48H92NO7P
Average Molecular Weight826.2203
Monoisotopic Molecular Weight825.661140815
IUPAC Name[2-({3-[(13Z)-docos-13-enoyloxy]-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C48H92NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-48(50)54-45-47(46-56-57(51,52)55-44-42-49(3,4)5)53-43-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h17,19-20,22,40,43,47H,6-16,18,21,23-39,41-42,44-46H2,1-5H3/b19-17-,22-20-,43-40-
InChI KeyVJMHNWXIJKHKHT-GYTYNKKYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl,2-(1Z-alkenyl)-glycerophosphocholines
Alternative Parents
Substituents
  • 1-acyl,2-(1z-alkenyl)-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not 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
logP6.75ALOGPS
logP11.34ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity255.24 m³·mol⁻¹ChemAxon
Polarizability104.44 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-9014212130-3c2bd32a096c0adc5b03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-7359113110-b9eedbd4662c4a94af96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9056016100-61908a303f533f530b55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ri-0029000030-d53329d8935d3cbb114fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0019000100-c90168989a4bb0fd0389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-5069200000-2f158233573296b41b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-24336b3dd18126a5fabbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010000390-4eac90b014d1b1922bb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-7009100000-3299acc72b883a4fcfecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1100000190-6153a378a2e952d61feaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900000110-acad6951a753dd0b0b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-5f0a06f1d9ff9a529f33View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008588
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025778
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479223
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available