Showing metabocard for PC(20:3(8Z,11Z,14Z)/P-16:0) (BMDB0008422)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:21:01 UTC
Update Date2020-06-04 19:51:36 UTC
BMDB IDBMDB0008422
Secondary Accession Numbers
  • BMDB08422
Metabolite Identification
Common NamePC(20:3(8Z,11Z,14Z)/P-16:0)
DescriptionPC(20:3(8Z,11Z,14Z)/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(20:3(8Z,11Z,14Z)/P-16:0), in particular, consists of one 8Z,11Z,14Z-eicosatrienoyl 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
GlycerophosphocholineHMDB
1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(1Z-hexadecenyl)-sn-glycero-3-phosphocholineHMDB
Glycerophosphocholine(20:3(8Z,11Z,14Z)/p-16:0)HMDB
PC(20:3)HMDB
Gpcho(20:3)HMDB
Phosphatidylcholine(20:3)HMDB
PC(20:3/P-16:0)HMDB
Gpcho(20:3/p-16:0)HMDB
Phosphatidylcholine(20:3/p-16:0)HMDB
Chemical FormulaC44H82NO7P
Average Molecular Weight768.0981
Monoisotopic Molecular Weight767.582890495
IUPAC Name[2-({2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\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/C44H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)50-41-43(42-52-53(47,48)51-40-38-45(3,4)5)49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,36,39,43H,6-13,15,17-19,21,23,26-35,37-38,40-42H2,1-5H3/b16-14-,22-20-,25-24-,39-36-
InChI KeyYNEOKOLTTKSNFT-NXTBAPBJSA-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
Polarizability94.67 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, Positivesplash10-000i-9060231300-42fe3e4d82678d96c0a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-4290011000-933349099abf0a11db53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-5091021000-c1e67fdff32e8341508cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0097001500-43d4d4cdaa51a7cc07bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0079002100-f40923c3de5bd9742f64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-4094200000-253d83393ae3a03a1403View 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-0031000900-2202c90c18a0d806e606View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9236100000-d24d9e49abe388744f1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3100002900-410f8a8d3ca6ccfb7a8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900001200-5266ded0550556c6cc58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-530a0dc09205e64df3adView 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 IDHMDB0008422
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025612
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479025
PDB IDNot Available
ChEBI ID88885
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available