PC(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)) (YMDB02094)

Identification
YMDB IDYMDB02094
NamePC(20:3(5Z,8Z,11Z)/18:2(9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)) 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(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)), in particular, consists of one chain of mead acid at the C-1 position and one chain of linoleic acid at the C-2 position. The mead acid moiety is derived from fish oils, liver and kidney, while the linoleic acid moiety is derived from seed 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-meadoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • GPCho(20:3/18:2)
  • GPCho(20:3n9/18:2n6)
  • GPCho(20:3w9/18:2w6)
  • GPCho(38:5)
  • Lecithin
  • PC(20:3/18:2)
  • PC(20:3n9/18:2n6)
  • PC(20:3w9/18:2w6)
  • PC(38:5)
  • Phosphatidylcholine(20:3/18:2)
  • Phosphatidylcholine(20:3w9/18:2w6)
  • Phosphatidylcholine(38:5)
  • Phosphatidylcholine(20:3n9/18:2n6)
  • GPCho(20:3/18:2)
  • PC(38:5)
  • Phosphatidylcholine(20:3/18:2)
  • GPCho(38:5)
  • Lecithin
  • Phosphatidylcholine(38:5)
  • 1-Meadoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • 1-(5Z,8Z,11Z-Eicosatrienoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
  • PC(20:3/18:2)
  • PC(20:3(5Z,8Z,11Z)/18:2(9Z,12Z))
CAS numberNot Available
WeightAverage: 808.1189
Monoisotopic: 807.577805117
InChI KeySKQBFCOATFWTGJ-USYZEHPZSA-N
InChIInChI=1S/C46H82NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h15,17,20-22,24-26,30,32,44H,6-14,16,18-19,23,27-29,31,33-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC46H82NO8P
SMILESCCCCCCCCC=CCC=CCC=CCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=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 Solubility2.8e-05 g/LALOGPS
logP5.91ALOGPS
logP8.97ChemAxon
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 Count41ChemAxon
Refractivity249.05 m³·mol⁻¹ChemAxon
Polarizability97.28 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
0.772 ± 0.0386 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-8091041220-9d35a249e9bcb9c7ce4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-3191011100-08b25f6dadf42106021aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-8095003100-35d962b4e85af7af4ef3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0095000040-7cd8e47a22562c68d544JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0097000200-92d4603f01b46eddaa41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vr-4092000000-ca676c00563d3ae4a31eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-176beaa64b72d3c99c1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-c545a38bbe96927ef016JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-a860a7c869b40d9f287eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-982a5de1a95b33baa9fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-700b9d4c4e1a88e5359eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-d2581b10aea3e557015bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-2ed1617616dcbd8a27a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-13a0a6850f2cb883fbc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000090-bf6d80c90bb05954192dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-09c683f4e3532312072eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0064004390-ba134c8daf2cf68478e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4049100000-71f2c1dafd3a2f1848c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-f63d7860e3264d19dfbcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-9706f6071dcd0d9077fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0200498220-a090990bb49cd826e8a6JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89113
HMDB IDHMDB08369
Pubchem Compound ID53478959
Kegg IDC00157
ChemSpider ID24767029
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available