PC(20:4(8Z,11Z,14Z,17Z)/22:0) (YMDB02138)

Identification
YMDB IDYMDB02138
NamePC(20:4(8Z,11Z,14Z,17Z)/22:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:4(8Z,11Z,14Z,17Z)/22:0) 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(20:4(8Z,11Z,14Z,17Z)/22:0), in particular, consists of one chain of eicsoatetraenoic acid at the C-1 position and one chain of behenic acid at the C-2 position. The eicsoatetraenoic acid moiety is derived from fish oils, while the behenic acid moiety is derived from groundnut oil. 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-eicsoate
  • 1-eicsoatetraenoyl-2-behenoyl-sn-glycero-3-phosphocholine
  • 1-eicsoic acid
  • GPCho(20:4/22:0)
  • GPCho(20:4n3/22:0)
  • GPCho(20:4w3/22:0)
  • Lecithin
  • PC(20:4/22:0)
  • PC(20:4n3/22:0)
  • PC(20:4w3/22:0)
  • PC(42:4)
  • Phosphatidylcholine(20:4/22:0)
  • Phosphatidylcholine(20:4n3/22:0)
  • Phosphatidylcholine(20:4w3/22:0)
  • Phosphatidylcholine(42:4)
  • GPCho(42:4)
  • Phosphatidylcholine(42:4)
  • PC(20:4/22:0)
  • Phosphatidylcholine(20:4/22:0)
  • 1-Eicsoatetraenoyl-2-behenoyl-sn-glycero-3-phosphocholine
  • Lecithin
  • GPCho(20:4/22:0)
  • PC(42:4)
  • 1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-docosanoyl-sn-glycero-3-phosphocholine
  • PC(20:4(8Z,11Z,14Z,17Z)/22:0)
CAS numberNot Available
WeightAverage: 866.2411
Monoisotopic: 865.656055437
InChI KeyXJLHAZSETMTODV-QSCHNALKSA-N
InChIInChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,28,30,48H,6-8,10,12-14,16,18-20,22,24-27,29,31-47H2,1-5H3/t48-/m1/s1
IUPAC Name(2-{[(2R)-2-(docosanoyloxy)-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC50H92NO8P
SMILESCCCCCCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=CCC=CCC=CCC=CCC)COP([O-])(=O)OCC[N+](C)(C)C
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 Solubility2.7e-05 g/LALOGPS
logP6.61ALOGPS
logP11.11ChemAxon
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 Count46ChemAxon
Refractivity266.34 m³·mol⁻¹ChemAxon
Polarizability106.83 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
0.006 ± 0.0003 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9046041130-139b3926ab0d3b74cc04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0080-5297021010-c16249cea60db5595439JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001a-9077002000-583e84db5a3d64d91ef5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gw0-0049000040-19e3aaac370fd7b0a6b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0059000100-f9594bb27d6cbe4eeb7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-5059100000-11280a34cea1c7c9318bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000009-1791f8bf865a0857471fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003000009-1106ee3d4ff4b91b67d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0009000004-08262e03cf5ef2485552JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-885c0d2b6e3e4f892e2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000090-9125665aeeab92b4ca2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-0900161930-b1ec07edb27e71323b93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-c23bf4396560995f2075JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-7ff854621a9c368ce93bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0100197030-d3a98160891623fbafa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-3aaaad39472490bbd6f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0600000090-d0d848a19ec2a7607a12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041030-5a238d4b4acc48a93de1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-230d27d4bf1e5d1a8a2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-0028003090-dfc3686e5374a2e34f0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-5129300000-279ffdfffae9d28f3188JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID88905
HMDB IDHMDB08479
Pubchem Compound ID53479097
Kegg IDC00157
ChemSpider ID24767140
FOODB IDFDB025669
Wikipedia IDNot Available
BioCyc IDNot Available