PC(22:1(13Z)/20:1(11Z)) (YMDB02164)

Identification
YMDB IDYMDB02164
NamePC(22:1(13Z)/20:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(22:1(13Z)/20:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:1(13Z)/20:1(11Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of eicosenoic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the eicosenoic acid moiety is derived from vegetable oils and cod oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-erucoyl-2-eicosenoyl-sn-glycero-3-phosphocholine
  • GPCho(22:1/20:1)
  • GPCho(22:1n9/20:1n9)
  • GPCho(42:2)
  • Lecithin
  • PC(22:1/20:1)
  • PC(22:1n9/20:1n9)
  • PC(22:1w9/20:1w9)
  • PC(42:2)
  • Phosphatidylcholine(22:1/20:1)
  • Phosphatidylcholine(22:1n9/20:1n9)
  • Phosphatidylcholine(22:1w9/20:1w9)
  • Phosphatidylcholine(42:2)
  • GPCho(22:1w9/20:1w9)
  • 1-Erucoyl-2-eicosenoyl-sn-glycero-3-phosphocholine
  • GPCho(22:1/20:1)
  • PC(22:1/20:1)
  • Phosphatidylcholine(42:2)
  • Lecithin
  • Phosphatidylcholine(22:1/20:1)
  • GPCho(42:2)
  • PC(42:2)
  • 1-(13Z-Docosenoyl)-2-(11-eicosenoyl)-sn-glycero-3-phosphocholine
  • PC(22:1(13Z)/20:1(11Z))
CAS numberNot Available
WeightAverage: 870.2729
Monoisotopic: 869.687355565
InChI KeyRDVFINNZTUFVCO-QSCHNALKSA-N
InChIInChI=1S/C50H96NO8P/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/h20-23,48H,6-19,24-47H2,1-5H3/t48-/m1/s1
IUPAC Name(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC50H96NO8P
SMILESCCCCCCCCC=CCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCC=CCCCCCCCC
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.1e-05 g/LALOGPS
logP6.6ALOGPS
logP11.84ChemAxon
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 Count48ChemAxon
Refractivity264.11 m³·mol⁻¹ChemAxon
Polarizability109.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.01 ± 0.0005 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9055041140-2b2ca98d6f58cbf0b9b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00a6-6398021110-13c174d2ea731bc269d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00cc-9067005310-1ba71772933183f24b9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0019000020-2ecb262d18ca9695f9d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0019000100-0774a8092e5b55b729d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-5059100000-e5715fe6b1549dded9d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-68ac673f23e394c3c146JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0600000090-d18782d551cf189f549cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-2c127122230282b71315JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-1a99a84a66e8fb9335ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000090-3c6b6ad511895debb4a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05po-0100197030-4a26fdc7556d2499b713JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-c336174e69b9e1796bbaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0015003090-408c9bce1a4d2d9865b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1009100000-a2e7f385e057c7399c1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-e605ed621546773b38cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000090-1f36656371040c902947JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-0900161930-41b7373a89d744e82b69JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000009-7cbfab51475788a607c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000009-20e5fa6d981bdd1ff387JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-14ii-0009000004-758d049828c8ce39ef9eJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID88726
HMDB IDHMDB08570
Pubchem Compound ID53479189
Kegg IDC00157
ChemSpider ID24767231
FOODB IDFDB025760
Wikipedia IDNot Available
BioCyc IDNot Available