PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (YMDB01922)

Identification
YMDB IDYMDB01922
NamePC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. 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-vaccenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine
  • GPCho(18:1/20:5)
  • GPCho(18:1n7/20:5n3)
  • GPCho(18:1w7/20:5w3)
  • GPCho(38:6)
  • Lecithin
  • PC(18:1/20:5)
  • PC(18:1n7/20:5n3)
  • PC(18:1w7/20:5w3)
  • PC(38:6)
  • Phosphatidylcholine(18:1/20:5)
  • Phosphatidylcholine(18:1w7/20:5w3)
  • Phosphatidylcholine(38:6)
  • Phosphatidylcholine(18:1n7/20:5n3)
  • 1-Vaccenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine
  • GPCho(18:1n7/20:5n3)
  • GPCho(18:1W7/20:5W3)
  • PC(18:1n7/20:5n3)
  • PC(18:1W7/20:5W3)
  • Phosphatidylcholine(18:1W7/20:5W3)
  • GPCho(18:1/20:5)
  • PC(18:1/20:5)
  • GPCho(38:6)
  • Phosphatidylcholine(18:1/20:5)
  • Phosphatidylcholine(38:6)
  • Lecithin
  • 1-(11Z-Octadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine
  • PC(38:6)
  • PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))
CAS numberNot Available
WeightAverage: 806.1031
Monoisotopic: 805.562155053
InChI KeyBLXFIBZJVTVAKI-USYZEHPZSA-N
InChIInChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14,16-17,19-20,22,25,27,31,33,44H,6-7,9,11-13,15,18,21,23-24,26,28-30,32,34-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC46H80NO8P
SMILESCCCCCCC=CCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC=CCC=CCC=CCC=CCC=CCC
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 Solubility3.1e-05 g/LALOGPS
logP5.75ALOGPS
logP8.61ChemAxon
logS-7.4ALOGPS
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 Count40ChemAxon
Refractivity250.17 m³·mol⁻¹ChemAxon
Polarizability95.92 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
0.557 ± 0.02785 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, Positivesplash10-000i-8091041220-67f3a9acaa5dd088dcb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3192011100-72082ee2ab7c6411886cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8095002100-39f9c7186583f0e391dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w30-0092000030-9ddf1a858783a3803cf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000100-159187ac6aacc532231bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4091000000-5190bdb2750f4981bbcfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6dad79f01b1173c5421fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0064004390-fa4299cd69252942486dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3191000000-3c534cf655f49f1fdb76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-1e78e28c2730b5262b1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-f42482894aa2a9df4b6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0200498220-1f50f01c17486fa733f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-489803391fb15e1d23f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-e0c7549473f8627cae46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900041210-e217843874811fac0f10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-8b00eebc929d9a9097dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-71d714a518c51ee5a089JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-566b0332f47d6b9f3ac3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-16b357af2387839179b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-a2c506801eba0e6a8b43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uf6-0099000090-27a21c830ff5331bd7a0JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86186
HMDB IDHMDB08083
Pubchem Compound ID24778898
Kegg IDC00157
ChemSpider ID24766747
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available