Showing metabocard for PC(18:3(6Z,9Z,12Z)/P-16:0) (BMDB0008192)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:15:48 UTC
Update Date2020-06-04 19:37:05 UTC
BMDB IDBMDB0008192
Secondary Accession Numbers
  • BMDB08192
Metabolite Identification
Common NamePC(18:3(6Z,9Z,12Z)/P-16:0)
DescriptionPC(18:3(6Z,9Z,12Z)/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(18:3(6Z,9Z,12Z)/P-16:0), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl 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
1-g-Linolenoyl-2-(1-enyl-palmitoyl)-sn-glycero-3-phosphocholineHMDB
1-gamma-Linolenoyl-2-(1-enyl-palmitoyl)-sn-glycero-3-phosphocholineHMDB
Gpcho(18:3/16:0)HMDB
Gpcho(18:3n6/16:0)HMDB
Gpcho(18:3W6/16:0)HMDB
Gpcho(34:3)HMDB
LecithinHMDB
PC Aa C34:3HMDB
PC(18:3/16:0)HMDB
PC(18:3n6/16:0)HMDB
PC(18:3W6/16:0)HMDB
PC(34:3)HMDB
Phosphatidylcholine(18:3/16:0)HMDB
Phosphatidylcholine(18:3n6/16:0)HMDB
Phosphatidylcholine(18:3W6/16:0)HMDB
Phosphatidylcholine(34:3)HMDB
Chemical FormulaC42H78NO7P
Average Molecular Weight740.045
Monoisotopic Molecular Weight739.551590367
IUPAC Name[2-({2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]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/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H78NO7P/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/h14,16,20,22,25,27,34,37,41H,6-13,15,17-19,21,23-24,26,28-33,35-36,38-40H2,1-5H3/b16-14-,22-20-,27-25-,37-34-
InChI KeyXRJDZRCUSSFZDP-LHKYHRLFSA-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
logP5.83ALOGPS
logP8.31ChemAxon
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 Count38ChemAxon
Refractivity228.76 m³·mol⁻¹ChemAxon
Polarizability90.67 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, Positivesplash10-01p9-9060231300-1a370ef51bbf8b73d364View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l9-4291121000-df14af78de585b9a63b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-5090021000-7abbc94c1e4194027f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-0090000300-425d28e623188de0cc62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-c6d7ec234a8f290b49e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3090100000-d29b429d538408c9b636View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-0dd39b4f99d862ce6c4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0050003900-1a4ce8cef4e707a7ddf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-8290100000-cd2fa00f7e0f235f3e98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3100003900-c57ac1d4cf908ac5a71fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3900001100-29358985ea05aefdfbdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-55e25de7b07e7f9ad05fView 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 IDHMDB0008192
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025382
KNApSAcK IDNot Available
Chemspider ID24766854
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478823
PDB IDNot Available
ChEBI ID89523
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available