Showing metabocard for PC(18:3(9Z,12Z,15Z)/P-18:0) (BMDB0008226)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:16:37 UTC
Update Date2020-06-04 19:51:34 UTC
BMDB IDBMDB0008226
Secondary Accession Numbers
  • BMDB08226
Metabolite Identification
Common NamePC(18:3(9Z,12Z,15Z)/P-18:0)
DescriptionPC(18:3(9Z,12Z,15Z)/P-18:0) 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(9Z,12Z,15Z)/P-18:0), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl chain to the C-1 atom, and one 1Z-octadecenyl 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-(9Z,12Z,15Z-Octadecatrienoyl)-2-(1Z-octadecenyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(18:3(9Z,12Z,15Z)/p-18:0)HMDB
PC(18:3)HMDB
Gpcho(18:3)HMDB
Phosphatidylcholine(18:3)HMDB
PC(18:3/P-18:0)HMDB
Gpcho(18:3/p-18:0)HMDB
Phosphatidylcholine(18:3/p-18:0)HMDB
Chemical FormulaC44H82NO7P
Average Molecular Weight768.0981
Monoisotopic Molecular Weight767.582890495
IUPAC Nametrimethyl[2-({2-[(1Z)-octadec-1-en-1-yloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato}oxy)ethyl]azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC\C=C/OC(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C44H82NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-49-43(42-52-53(47,48)51-40-38-45(3,4)5)41-50-44(46)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,36,39,43H,6-8,10,12-14,16,18-20,22,24-35,37-38,40-42H2,1-5H3/b11-9-,17-15-,23-21-,39-36-
InChI KeySVYSTFPSOJUEFY-FINMKEMFSA-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
logP6.13ALOGPS
logP9.2ChemAxon
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
Refractivity237.96 m³·mol⁻¹ChemAxon
Polarizability94.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9060231300-53484d8437b110087912View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw0-5293021100-a2f5fc9de985d36a5d3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgr-7093030000-7deeec0d81bf79337055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0090001400-995e2ee2ec0c40a698f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090001000-ead2b5273fe76b0b201cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2090100000-4e1b1d409d8540ac5eb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-4debbea5304ca280bf65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0040000900-6fd18248b2b1a36f998bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7190100000-3f076dee5b287d9fbd67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2000004900-eef5378a0de7ba209ca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3900002200-56e196a35824bde8de33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0910000000-322e2701713fc64e0da8View 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 IDHMDB0008226
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025416
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478849
PDB IDNot Available
ChEBI ID89415
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available