PC(20:0/20:2(11Z,14Z)) (YMDB02041)

Identification
YMDB IDYMDB02041
NamePC(20:0/20:2(11Z,14Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:0/20:2(11Z,14Z)) 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(20:0/20:2(11Z,14Z)), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The arachidic acid moiety is derived from peanut oil, while the eicosadienoic acid moiety is derived from fish oils and liver. 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-arachidonyl-2-eicosadienoyl-sn-glycero-3-phosphocholine
  • GPCho(20:0/20:2)
  • GPCho(20:0/20:2n6)
  • GPCho(40:2)
  • Lecithin
  • PC(20:0/20:2)
  • PC(20:0/20:2n6)
  • PC(20:0/20:2w6)
  • PC(40:2)
  • Phosphatidylcholine(20:0/20:2)
  • Phosphatidylcholine(20:0/20:2n6)
  • Phosphatidylcholine(20:0/20:2w6)
  • Phosphatidylcholine(40:2)
  • GPCho(20:0/20:2w6)
  • 1-Arachidonyl-2-eicosadienoyl-sn-glycero-3-phosphocholine
  • GPCho(20:0/20:2n6)
  • PC(20:0/20:2n6)
  • PC(20:0/20:2W6)
  • Phosphatidylcholine(20:0/20:2n6)
  • Phosphatidylcholine(20:0/20:2W6)
  • PC(40:2)
  • PC(20:0/20:2(11Z,14Z))
  • Phosphatidylcholine(20:0/20:2)
  • Lecithin
  • GPCho(20:0/20:2)
  • GPCho(40:2)
  • PC(20:0/20:2)
  • 1-eicosanoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(40:2)
CAS numberNot Available
WeightAverage: 842.2197
Monoisotopic: 841.656055437
InChI KeyDGKXFLANAYRYMU-YACUFSJGSA-N
InChIInChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,46H,6-14,16,18-20,22,24-45H2,1-5H3/t46-/m1/s1
IUPAC Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC48H92NO8P
SMILESCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCC=CCC=CCCCCC
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 Solubility2.4e-05 g/LALOGPS
logP6.39ALOGPS
logP10.95ChemAxon
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 Count46ChemAxon
Refractivity254.91 m³·mol⁻¹ChemAxon
Polarizability105.34 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
0.043 ± 0.00215 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, Positivesplash10-001c-9072051140-6b7a9c380a8711f668c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0017-4292021110-1576f7a16028a36b718cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lj-9076012200-cb594edb4df5b503349cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-0079000170-8b797278ffa5a6ef0334JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0069000200-daf088494364c4630027JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i3-6189200000-22fc5fa79e7e97af4355JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000090-22004a077e65cf532e85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000190-063b8600b5379c7321f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-0200498220-2cc7aefa3188edcab2eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-4b489c53edd2019c68bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0029003270-5b643e3121c2913c9b82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-3029100000-38a71f952961f4e4d8b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-7798f4de22a79938254aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0003000090-62fa809d3b6eeebba9edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0dmi-0009000040-cd452ba6375d3b33b4c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-22c680cb0cae12530752JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000090-2ed5ce7d2651aa92b053JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-f16115d6508eff7686bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-334ce021df69056ff46bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-b86490a18567af168853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-0900369030-70a5b10e63e2ee0fe7d7JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86199
HMDB IDHMDB08276
Pubchem Compound ID24779046
Kegg IDC00157
ChemSpider ID24766937
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available