Showing metabocard for PC(22:1(13Z)/22:2(13Z,16Z)) (BMDB0008579)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:24:41 UTC
Update Date2020-05-11 18:47:47 UTC
BMDB IDBMDB0008579
Secondary Accession Numbers
  • BMDB08579
Metabolite Identification
Common NamePC(22:1(13Z)/22:2(13Z,16Z))
DescriptionPC(22:1(13Z)/22:2(13Z,16Z)), also known as pc(22:1(13z)/22:2(13z,16z)) or PC(44:3), 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. PC(22:1(13Z)/22:2(13Z,16Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PC(22:1(13Z)/22:2(13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(22:1(13Z)/22:2(13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(22:1(13Z)/22:2(13Z,16Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(22:1(13Z)/22:2(13Z,16Z)) can be biosynthesized from CDP-choline and DG(22:1(13Z)/22:2(13Z,16Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(22:1(13Z)/22:2(13Z,16Z)) and L-serine can be converted into choline and PS(22:1(13Z)/22:2(13Z,16Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(22:1(13Z)/22:2(13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:1(13Z)/22:2(13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(22:1(13Z)/22:2(13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphatidylcholine(44:3)HMDB
PC(44:3)HMDB
Phosphatidylcholine(22:1/22:2)HMDB
1-Erucoyl-2-docosadienoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
GPCho(22:1/22:2)HMDB
PC(22:1/22:2)HMDB
1-(13Z-Docosenoyl)-2-(13Z,16Z-docosadienoyl)-sn-glycero-3-phosphocholineHMDB
GPCho(44:3)HMDB
PC(22:1(13Z)/22:2(13Z,16Z))Lipid Annotator
Chemical FormulaC52H98NO8P
Average Molecular Weight896.3102
Monoisotopic Molecular Weight895.703005629
IUPAC Name(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C52H98NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,20-23,50H,6-14,16,18-19,24-49H2,1-5H3/b17-15-,22-20-,23-21-/t50-/m1/s1
InChI KeyPSZSIHHWRNZDLC-OSGOGHEWSA-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 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
logP6.81ALOGPS
logP12.36ChemAxon
logS-7.6ALOGPS
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 Count49ChemAxon
Refractivity274.43 m³·mol⁻¹ChemAxon
Polarizability112.2 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, Positivesplash10-0002-0000000090-3626f7df7a8c39e527d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0600000090-d3e7148b737d333b245eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900040130-376496bd1a9f507792c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-7f5ee98e6ae6407eb2a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000019-bcec7f55e91ce6fa62ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-0100090511-2fcf5ecb8244c0d7045fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-24aa829d2808b0a361b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0600000090-48a07bfe92c40f7996abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900040130-efc8c1d77bba39d4e9ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000009-5f1d0f85cd35e26fdb51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0003000009-ce35dee5f58bb1087e47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0009000004-47f43524987177aae026View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000009-4216f7fc9501632ac426View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000019-fa3ed0c4319d1cb61661View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0900071911-245fb3d3e593b700e16eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-c9f405d10c1e78216db6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0009002070-739227794ca55404193aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2009100000-c9e6f5ac132901a9c16cView 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 IDHMDB0008579
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 Compound53479205
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available