PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (YMDB02126)

Identification
YMDB IDYMDB02126
NamePC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:4(5Z,8Z,11Z,14Z)/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(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The arachidonic acid moiety is derived from animal fats and eggs, 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-arachidonoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • GPCho(20:4/18:2)
  • GPCho(20:4n6/18:2n6)
  • GPCho(20:4w6/18:2w6)
  • GPCho(38:6)
  • Lecithin
  • PC(20:4/18:2)
  • PC(20:4n6/18:2n6)
  • PC(20:4w6/18:2w6)
  • PC(38:6)
  • Phosphatidylcholine(20:4n6/18:2n6)
  • Phosphatidylcholine(20:4w6/18:2w6)
  • Phosphatidylcholine(38:6)
  • Phosphatidylcholine(20:4/18:2)
  • 1-Arachidonoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • GPCho(20:4n6/18:2n6)
  • GPCho(20:4W6/18:2W6)
  • PC(20:4n6/18:2n6)
  • PC(20:4W6/18:2W6)
  • Phosphatidylcholine(20:4n6/18:2n6)
  • Phosphatidylcholine(20:4W6/18:2W6)
  • PC(38:6)
  • GPCho(38:6)
  • GPCho(20:4/18:2)
  • Phosphatidylcholine(38:6)
  • Lecithin
  • PC(20:4/18:2)
  • 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
  • PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))
CAS numberNot Available
WeightAverage: 806.1031
Monoisotopic: 805.562155053
InChI KeyPLZBTDKJYHXIEW-USYZEHPZSA-N
InChIInChI=1S/C46H80NO8P/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/h14-17,20-22,24-26,30,32,44H,6-13,18-19,23,27-29,31,33-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC46H80NO8P
SMILESCCCCCC=CCC=CCCCCCCCC(=O)O[C@H](COC(=O)CCCC=CCC=CCC=CCC=CCCCCC)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 Solubility3.1e-05 g/LALOGPS
logP5.73ALOGPS
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
Polarizability95.46 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8091041220-fb991c2a90125c461409JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3191011100-ae2a98737af7f6857e05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-7094003100-da05e52d953323e13b62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0095000040-5ff89925eb6ab8451c71JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0098000200-63ec058f202d88d5ec81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fbi-4092000000-f84f2b117914ab5d1c04JSpectraViewer
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-b70a47abc65e2e98867cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-16b357af2387839179b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-3c2d12da68314bd9861cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ui6-0099000090-659059b54ab6c0df71cfJSpectraViewer
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, Positivesplash10-0089-1900041210-6a88b3160e1dd26f3b53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6dad79f01b1173c5421fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0075004390-456b6ba7ddfd3867248eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9288500000-49fbdf684ba4d9283912JSpectraViewer
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-0200498220-882e69f0546935966511JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86184
HMDB IDHMDB08434
Pubchem Compound ID52923295
Kegg IDC00157
ChemSpider ID24822657
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available