Showing metabocard for PC(18:4(6Z,9Z,12Z,15Z)/P-16:0) (BMDB0008258)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:17:17 UTC
Update Date2020-06-04 19:20:12 UTC
BMDB IDBMDB0008258
Secondary Accession Numbers
  • BMDB08258
Metabolite Identification
Common NamePC(18:4(6Z,9Z,12Z,15Z)/P-16:0)
DescriptionPC(18:4(6Z,9Z,12Z,15Z)/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(18:4(6Z,9Z,12Z,15Z)/P-16:0), in particular, consists of one 6Z,9Z,12Z,15Z-octadecatetraenoyl 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
GlycerophosphocholineMetBuilder, HMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-(1Z-hexadecenyl)-sn-glycero-3-phosphocholineMetBuilder, HMDB
Glycerophosphocholine(18:4(6Z,9Z,12Z,15Z)/p-16:0)MetBuilder, HMDB
PC(18:4)MetBuilder, HMDB
gpcho(18:4)MetBuilder, HMDB
Phosphatidylcholine(18:4)MetBuilder, HMDB
PC(18:4/P-16:0)MetBuilder, HMDB
gpcho(18:4/P-16:0)MetBuilder, HMDB
Phosphatidylcholine(18:4/p-16:0)MetBuilder, HMDB
Chemical FormulaC42H76NO7P
Average Molecular Weight738.0291
Monoisotopic Molecular Weight737.535940303
IUPAC Name[2-({2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC(COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H76NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)48-39-41(40-50-51(45,46)49-38-36-43(3,4)5)47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25,27,34,37,41H,6-7,9,11-13,15,17-19,21,23-24,26,28-33,35-36,38-40H2,1-5H3/b10-8-,16-14-,22-20-,27-25-,37-34-
InChI KeyCLSCXJAQDUXCBA-DWIAYCKOSA-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
logP5.72ALOGPS
logP7.95ChemAxon
logS-7.3ALOGPS
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 Count37ChemAxon
Refractivity229.87 m³·mol⁻¹ChemAxon
Polarizability89.19 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-9060321300-4eeff530cb7666b1ea89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac9-4291121000-6a835d32eaaa0e7970a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-5090021000-331238b52485a85a6730View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-0090000300-97c649454d50ba478cb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-1d95d9b88c99ebc2f354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3090100000-d08b1a10c696d385a272View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-f383c452164ec608dc1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0050003900-8e0c7a0d36b7c78a9130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7290000000-6ee5d36fad16086e213cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2100004900-eb2e542ff795c6e2acdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3900002100-5fb143e207090375bbd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0920000000-3708a93519433f2ff90cView 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 IDHMDB0008258
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478871
PDB IDNot Available
ChEBI ID89428
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available