Showing metabocard for PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(9Z)) (BMDB0008754)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:28:24 UTC
Update Date2020-05-11 18:50:12 UTC
BMDB IDBMDB0008754
Secondary Accession Numbers
  • BMDB08754
Metabolite Identification
Common NamePC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(9Z))
DescriptionPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(9Z)) 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(9Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl chain to the C-1 atom, and one 1Z,9Z-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
1-Docosahexaenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphocholineHMDB
Gpcho(22:6/18:1)HMDB
Gpcho(22:6n3/18:1n9)HMDB
Gpcho(22:6W3/18:1W9)HMDB
Gpcho(40:7)HMDB
LecithinHMDB
PC(22:6/18:1)HMDB
PC(22:6n3/18:1n9)HMDB
PC(22:6W3/18:1W9)HMDB
PC(40:7)HMDB
Phosphatidylcholine(22:6/18:1)HMDB
Phosphatidylcholine(22:6n3/18:1n9)HMDB
Phosphatidylcholine(22:6W3/18:1W9)HMDB
Phosphatidylcholine(40:7)HMDB
Chemical FormulaC48H82NO7P
Average Molecular Weight816.1409
Monoisotopic Molecular Weight815.582890495
IUPAC Name[2-({3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCC\C=C/OC(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C48H82NO7P/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/h8,10,14,16,20-23,25-26,29,31,35,37,40,43,47H,6-7,9,11-13,15,17-19,24,27-28,30,32-34,36,38-39,41-42,44-46H2,1-5H3/b10-8-,16-14-,22-20-,23-21-,26-25-,31-29-,37-35-,43-40-
InChI KeyBETFSIOJEATXGY-WOCLASLBSA-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
logP6.25ALOGPS
logP9.53ChemAxon
logS-7.4ALOGPS
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 Count40ChemAxon
Refractivity260.83 m³·mol⁻¹ChemAxon
Polarizability96.72 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-9034212220-3f35a012ca510a648b23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pt-7398113300-c127b00257ad4999db3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0012-9086013100-e6e707984fbf42b200eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vi-0029000030-1292729224edde76c1f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0029000100-33f84bb5ee6cdf20e886View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5069200000-3a135c46c19331f24c2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3100001390-cd2ea384b10ac4de13ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900000200-70866115846845cea2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0911000000-36770d2818ad655204c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-9148496ef4a74060fdcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0013000390-c17c6393f49ac15d64c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6479000000-88a2afd4f84d93d69964View 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 IDHMDB0008754
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025944
KNApSAcK IDNot Available
Chemspider ID24767415
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479429
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available