Showing metabocard for PC(18:4(6Z,9Z,12Z,15Z)/P-18:1(9Z)) (BMDB0008261)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:17:20 UTC
Update Date2020-06-04 19:27:21 UTC
BMDB IDBMDB0008261
Secondary Accession Numbers
  • BMDB08261
Metabolite Identification
Common NamePC(18:4(6Z,9Z,12Z,15Z)/P-18:1(9Z))
DescriptionPC(18:4(6Z,9Z,12Z,15Z)/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(18:4(6Z,9Z,12Z,15Z)/P-18:1(9Z)), in particular, consists of one 6Z,9Z,12Z,15Z-octadecatetraenoyl 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
GlycerophosphocholineHMDB
1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-(1Z,9Z-octadecadienyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(18:4(6Z,9Z,12Z,15Z)/p-18:1(9Z))HMDB
PC(18:5)HMDB
Gpcho(18:5)HMDB
Phosphatidylcholine(18:5)HMDB
PC(18:4/P-18:1)HMDB
Gpcho(18:4/p-18:1)HMDB
Phosphatidylcholine(18:4/p-18:1)HMDB
Chemical FormulaC44H78NO7P
Average Molecular Weight764.0664
Monoisotopic Molecular Weight763.551590367
IUPAC Nametrimethyl[2-({2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato}oxy)ethyl]azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCC\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/C44H78NO7P/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/h9,11,15,17,20-23,27,29,36,39,43H,6-8,10,12-14,16,18-19,24-26,28,30-35,37-38,40-42H2,1-5H3/b11-9-,17-15-,22-20-,23-21-,29-27-,39-36-
InChI KeyKRKGEBPORBUETM-JJJJCJMPSA-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
logP5.96ALOGPS
logP8.48ChemAxon
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 Count38ChemAxon
Refractivity240.19 m³·mol⁻¹ChemAxon
Polarizability91.77 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-9060331300-235fa50e4bd9db1a6630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5j-4293021100-ae14809b6e1c0ab505feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053b-7093030000-db701a69bf217d7bb07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0090001400-559b93a5f466448ab399View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090001000-2f7ea4bfa3f418027be0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2090100000-3212cfaf6bb0d8f4c958View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3100004900-4ac575c23f8e75d90e76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3900002100-21b3da28d19aacd69d40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0920000000-21da2d4e3f8b2de28716View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-5e879d0a64a34ebf5084View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0050000900-c8fdfaf96e8edc83405eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6390000000-92299a1dd7825e9ebadaView 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 IDHMDB0008261
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025451
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478877
PDB IDNot Available
ChEBI ID89356
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available