Showing metabocard for PC(22:2(13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0008609)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:25:20 UTC
Update Date2020-05-11 18:48:12 UTC
BMDB IDBMDB0008609
Secondary Accession Numbers
  • BMDB08609
Metabolite Identification
Common NamePC(22:2(13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPC(22:2(13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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(22:2(13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one 13Z,16Z-docosadienoyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl 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-Docosadienoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:2/20:5)HMDB
Gpcho(22:2n6/20:5n3)HMDB
Gpcho(22:2W6/20:5W3)HMDB
Gpcho(42:7)HMDB
LecithinHMDB
PC(22:2/20:5)HMDB
PC(22:2n6/20:5n3)HMDB
PC(22:2W6/20:5W3)HMDB
PC(42:7)HMDB
Phosphatidylcholine(22:2/20:5)HMDB
Phosphatidylcholine(22:2n6/20:5n3)HMDB
Phosphatidylcholine(22:2W6/20:5W3)HMDB
Phosphatidylcholine(42:7)HMDB
1-(13Z,16Z-Docosadienoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(22:2(13Z,16Z)/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC50H86NO8P
Average Molecular Weight860.1935
Monoisotopic Molecular Weight859.609105245
IUPAC Name(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C50H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h9,11,14-17,20-23,29,31,35,37,48H,6-8,10,12-13,18-19,24-28,30,32-34,36,38-47H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,31-29-,37-35-/t48-/m1/s1
InChI KeyLQGLSURTFNDIMU-JXUGAEHWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP6.2ALOGPS
logP10.03ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity269.69 m³·mol⁻¹ChemAxon
Polarizability102.47 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, Positivesplash10-03di-0000000090-15b1c1efeca130176d72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-1bf9301d22c51cce565fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900041030-b357ee52e06a86acf687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-df576825f79d2a98cfa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-4bcfbb1cefe522c6780bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900179030-2c2c15cf3dc0f35939daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-781e4cb18f413ae935feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000090-5c2c43b8a7f892a0e17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue6-0009000040-63827e30dc9151cb51feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-313e864a8a4543f87d7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-21723311ec5e149bb2f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-f3c3d3de849a58f04c18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-175d4e9cdcb782cbd5e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0018004390-233eaf246d7cd6ccd10fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4049100000-6b37ee3973ce8a3f28e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-f962fc94dcc7517ba6beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-026be09b385c4028e7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100197030-e0672faa81c13455ac4aView 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 IDHMDB0008609
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025799
KNApSAcK IDNot Available
Chemspider ID24767270
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52923595
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available