Showing metabocard for PC(22:2(13Z,16Z)/P-16:0) (BMDB0008619)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:25:33 UTC
Update Date2020-05-11 18:48:20 UTC
BMDB IDBMDB0008619
Secondary Accession Numbers
  • BMDB08619
Metabolite Identification
Common NamePC(22:2(13Z,16Z)/P-16:0)
DescriptionPC(22:2(13Z,16Z)/P-16:0) 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(22:2(13Z,16Z)/P-16:0), in particular, consists of one 13Z,16Z-docosadienoyl chain to the C-1 atom, and one 1Z-hexadecenyl 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,16Z-Docosadienoyl)-2-(1Z-hexadecenyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(22:2(13Z,16Z)/p-16:0)HMDB
PC(22:2)HMDB
Gpcho(22:2)HMDB
Phosphatidylcholine(22:2)HMDB
PC(22:2/P-16:0)HMDB
Gpcho(22:2/p-16:0)HMDB
Phosphatidylcholine(22:2/p-16:0)HMDB
Chemical FormulaC46H88NO7P
Average Molecular Weight798.1672
Monoisotopic Molecular Weight797.629840687
IUPAC Name[2-({3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(1Z)-hexadec-1-en-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC(COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H88NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-46(48)52-43-45(44-54-55(49,50)53-42-40-47(3,4)5)51-41-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h14,16,20,22,38,41,45H,6-13,15,17-19,21,23-37,39-40,42-44H2,1-5H3/b16-14-,22-20-,41-38-
InChI KeyOSDASXIAONDOLJ-RIFWRQLLSA-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
logP6.49ALOGPS
logP10.45ChemAxon
logS-7.5ALOGPS
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 Count43ChemAxon
Refractivity246.04 m³·mol⁻¹ChemAxon
Polarizability100.4 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, Positivesplash10-00kr-9033212400-b84500ae2750d8edbccbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01c9-6395103100-48538e8a62e65f41e6e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-6092012100-007340f1169b27176455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ks-0029000400-94cd5e4df4be3b2cc34dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0029000100-7b4c1a5f07cc00b18eb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-5069200000-227b6c96cf92b5d7a9cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2000001900-f34edf05e9ad7f4c7988View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000200-4d6a217b3253864eff5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-f4b03d82fab0b2135540View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-e880c2b27fa01dea7aebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0004000900-3c81d15dc7a122a9f017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-9118200000-fdc98f14995884987961View 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 IDHMDB0008619
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 Compound53479243
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available