Showing metabocard for PC(22:2(13Z,16Z)/18:2(9Z,12Z)) (BMDB0008598)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:25:05 UTC
Update Date2020-06-04 19:13:55 UTC
BMDB IDBMDB0008598
Secondary Accession Numbers
  • BMDB08598
Metabolite Identification
Common NamePC(22:2(13Z,16Z)/18:2(9Z,12Z))
DescriptionPC(22:2(13Z,16Z)/18:2(9Z,12Z)) 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)/18:2(9Z,12Z)), in particular, consists of one 13Z,16Z-docosadienoyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl 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
PC(22:2(13Z,16Z)/18:2(9Z,12Z))Lipid Annotator
1-docosadienoyl-2-linoleoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(22:2/18:2)Lipid Annotator, HMDB
Phosphatidylcholine(40:4)Lipid Annotator, HMDB
GPCho(22:2/18:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
GPCho(40:4)Lipid Annotator, HMDB
Phosphatidylcholine(22:2/18:2)Lipid Annotator, HMDB
1-(13Z,16Z-docosadienoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(40:4)Lipid Annotator, HMDB
Chemical FormulaC48H88NO8P
Average Molecular Weight838.188
Monoisotopic Molecular Weight837.624755309
IUPAC Name(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C48H88NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-26-21-19-17-15-13-11-9-7-2/h14-17,20-22,26,46H,6-13,18-19,23-25,27-45H2,1-5H3/b16-14-,17-15-,22-20-,26-21-/t46-/m1/s1
InChI KeyQQIYXJBHMDYXHH-NMUBDWGHSA-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
logP6.29ALOGPS
logP10.22ChemAxon
logS-7.5ALOGPS
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 Count44ChemAxon
Refractivity257.14 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, Positivesplash10-000i-0000000090-aef124e8ea5cbd2733f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-d55488a375c07bd7b12aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900041120-a337105a697375af8e55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-60376684b4ec5b1d67c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000190-959c52fa4c6f7919722fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0100197110-154d1bf50899f1e9c867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-385623721ad6580e192fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000090-4444b7f17662755da0b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ii-0099000090-f28949da08ff1f5cacccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-05e3eed79d70b8943852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-3d3ed3cbb1c8d0f3ab7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0900179030-47d811fac12ba3a4739cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-d1b04c31274557ab9f7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0064004390-afeb2cb273919f9c3b2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3039100000-fccbeee67943fbdba60dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-230b965f595c2bec9d63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-9f4137f40d638028ea32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-77ebfff2909758bc553dView 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 IDHMDB0008598
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24767259
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available