Showing metabocard for PC(22:1(13Z)/20:0) (BMDB0008569)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:24:27 UTC
Update Date2020-06-04 19:08:54 UTC
BMDB IDBMDB0008569
Secondary Accession Numbers
  • BMDB08569
Metabolite Identification
Common NamePC(22:1(13Z)/20:0)
DescriptionPC(22:1(13Z)/20:0) 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(22:1(13Z)/20:0), in particular, consists of one 13Z-docosenoyl chain to the C-1 atom, and one eicosanoyl 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-Erucoyl-2-arachidonyl-sn-glycero-3-phosphocholineHMDB
GPCho(22:1/20:0)HMDB
Phosphatidylcholine(22:1/20:0)HMDB
GPCho(42:1)HMDB
PC(22:1/20:0)HMDB
Phosphatidylcholine(42:1)HMDB
LecithinHMDB
PC(42:1)HMDB
1-(13Z-Docosenoyl)-2-eicosanoyl-sn-glycero-3-phosphocholineHMDB
PC(22:1(13Z)/20:0)Lipid Annotator
Chemical FormulaC50H98NO8P
Average Molecular Weight872.2888
Monoisotopic Molecular Weight871.703005629
IUPAC Name(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C50H98NO8P/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/h20,22,48H,6-19,21,23-47H2,1-5H3/b22-20-/t48-/m1/s1
InChI KeyGHUGFCZMTRWVKH-RURDTVAGSA-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
StatusDetected and 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
logP6.6ALOGPS
logP12.2ChemAxon
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
Refractivity262.99 m³·mol⁻¹ChemAxon
Polarizability110.91 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, Positivesplash10-0079-9055041140-144b9c8db2490f75fa57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fh1-5296021010-4e28d2ea7107397a7fc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fa2-9087002110-2262c17d44b3ab33e14bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02g9-0019000030-3bd252004ded1f7c2fecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0019000100-92961729c264c226559fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-029f-5059100000-f2a31e5e4a32d7c4e870View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-342307a5f81e24ba838bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0600000090-edd5a97757345b36a380View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-6391a36f3418f1386f0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-f5a92f86761149fa229dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-0016003090-63f81b132bc92905587aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4009400000-bec4ab2147967905743cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-006e98cedb5140920851View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-35af76fdb6837b18196aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nb-0100197030-079c0376788cc4099095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-fedb0c557e96d742004fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000090-f2c7c389d57105341225View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-0900161930-f2e99e60a72152c52557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000009-aa7976ed120b850370e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0003000009-b22b25f73157fbc97e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0dii-0009000004-90ec856fe3b4787222b0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.009 +/- 0.005 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008569
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 Compound53479187
PDB IDNot Available
ChEBI ID88737
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available