Showing metabocard for PC(20:3(8Z,11Z,14Z)/P-18:0) (BMDB0008423)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:21:02 UTC
Update Date2020-06-04 19:31:45 UTC
BMDB IDBMDB0008423
Secondary Accession Numbers
  • BMDB08423
Metabolite Identification
Common NamePC(20:3(8Z,11Z,14Z)/P-18:0)
DescriptionPC(20:3(8Z,11Z,14Z)/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(20:3(8Z,11Z,14Z)/P-18:0), in particular, consists of one 8Z,11Z,14Z-eicosatrienoyl 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-(8Z,11Z,14Z-Eicosatrienoyl)-2-(1Z-octadecenyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(20:3(8Z,11Z,14Z)/p-18:0)HMDB
PC(20:3)HMDB
Gpcho(20:3)HMDB
Phosphatidylcholine(20:3)HMDB
PC(20:3/P-18:0)HMDB
Gpcho(20:3/p-18:0)HMDB
Phosphatidylcholine(20:3/p-18:0)HMDB
Chemical FormulaC46H86NO7P
Average Molecular Weight796.1513
Monoisotopic Molecular Weight795.614190623
IUPAC Name[2-({3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(1Z)-octadec-1-en-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC\C=C/OC(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C46H86NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)52-43-45(44-54-55(49,50)53-42-40-47(3,4)5)51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,38,41,45H,6-13,15,17-19,21,23-24,26,28-37,39-40,42-44H2,1-5H3/b16-14-,22-20-,27-25-,41-38-
InChI KeyIMISCMOUPRVKCY-JCOVWSEZSA-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
logP6.44ALOGPS
logP10.09ChemAxon
logS-7.5ALOGPS
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 Count42ChemAxon
Refractivity247.16 m³·mol⁻¹ChemAxon
Polarizability98.96 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-9051212400-accddee1d77c4e19c2ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5293012100-82db63b249522bde3338View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-8095012100-19b8b5ee54b5d1d89e39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4u-0097000600-b64b0bcbb8a5f3e9220dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0079001200-d10348e20ee35a94ab3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-4094200000-44cc1d3f5b3b8ec66fc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3100002900-51d56242a460136cb5e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900001200-ba6308987c7d3339bcc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-6f26e800cc6e1a3f6141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-396b53711a21a76df333View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0021000900-af993f84b47fe4383d94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9236100000-52c7fa0d3711fbd84e78View 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 IDHMDB0008423
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479027
PDB IDNot Available
ChEBI ID88886
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available