PC(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(9Z)) (YMDB02146)

Identification
YMDB IDYMDB02146
NamePC(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(9Z)) 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(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(9Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of plasmalogen 18:1n9 at the C-2 position. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the plasmalogen 18:1n9 moiety is derived from animal fats, 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-eicosapentaenoyl-2-(1-enyl-oleoyl)-sn-glycero-3-phosphocholine
  • GPCho(20:5/18:1)
  • GPCho(20:5n3/18:1n9)
  • GPCho(20:5w3/18:1w9)
  • GPCho(38:6)
  • Lecithin
  • PC(20:5/18:1)
  • PC(20:5n3/18:1n9)
  • PC(20:5w3/18:1w9)
  • PC(38:6)
  • Phosphatidylcholine(20:5n3/18:1n9)
  • Phosphatidylcholine(20:5w3/18:1w9)
  • Phosphatidylcholine(38:6)
  • Phosphatidylcholine(20:5/18:1)
  • Glycerophosphocholine
  • 1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(1Z,9Z-octadecadienyl)-sn-glycero-3-phosphocholine
  • Glycerophosphocholine(20:5(5Z,8Z,11Z,14Z,17Z)/p-18:1(9Z))
  • PC(20:6)
  • Gpcho(20:6)
  • Phosphatidylcholine(20:6)
  • PC(20:5/P-18:1)
  • Gpcho(20:5/p-18:1)
  • Phosphatidylcholine(20:5/p-18:1)
CAS numberNot Available
WeightAverage: 790.1037
Monoisotopic: 789.567240431
InChI KeyUSPBFZFHJPVLST-UHFFFAOYSA-N
InChIInChI=1S/C46H80NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)52-43-45(44-54-55(49,50)53-42-40-47(3,4)5)51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20-23,25,27,31,33,38,41,45H,6-7,9,11-13,15,17-19,24,26,28-30,32,34-37,39-40,42-44H2,1-5H3
IUPAC Name[2-({3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-2-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC46H80NO7P
SMILESCCCCCCCCC=CCCCCCCC=COC(COC(=O)CCCC=CCC=CCC=CCC=CCC=CCC)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl,2-(1Z-alkenyl)-glycerophosphocholines
Alternative Parents
Substituents
  • 1-acyl,2-(1z-alkenyl)-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.9e-05 g/LALOGPS
logP6.12ALOGPS
logP9ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity250.51 m³·mol⁻¹ChemAxon
Polarizability94.4 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-9051212500-defc984e9c3cbd96fa2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5393013200-0f44bad92ed938326ca9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-8094021100-67a0f63bae4468ccde07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f80-0097000600-0140577b2a8df950b1b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0089001200-2513e839660dd0a3d96eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ugi-4093200000-b4d98976701a99b8f0e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2000001900-a4dee4d5f17551a1193dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900001300-39b5057f633570165ec8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0910000000-f2fe5d9a39385582cd2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-ccee64249dd340e638d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-28ce90d24e341cca8510JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-7394100000-dac704c0f41df8592754JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89064
HMDB IDHMDB08524
Pubchem Compound ID53479145
Kegg IDC00157
ChemSpider ID24767185
FOODB IDFDB025714
Wikipedia IDNot Available
BioCyc IDNot Available