PC(24:1(15Z)/P-18:1(11Z)) (YMDB02208)

Identification
YMDB IDYMDB02208
NamePC(24:1(15Z)/P-18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(24:1(15Z)/P-18:1(11Z)) 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(24:1(15Z)/P-18:1(11Z)), in particular, consists of one chain of nervonic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The nervonic acid moiety is derived from fish oils, while the plasmalogen 18:1n7 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-nervonoyl-2-(1-enyl-vaccenoyl)-sn-glycero-3-phosphocholine
  • GPCho(24:1/18:1)
  • GPCho(24:1n9/18:1n7)
  • GPCho(24:1w9/18:1w7)
  • GPCho(42:2)
  • Lecithin
  • PC(24:1n9/18:1n7)
  • PC(24:1w9/18:1w7)
  • PC(42:2)
  • Phosphatidylcholine(24:1/18:1)
  • Phosphatidylcholine(24:1n9/18:1n7)
  • Phosphatidylcholine(24:1w9/18:1w7)
  • Phosphatidylcholine(42:2)
  • PC(24:1/18:1)
  • Glycerophosphocholine
  • 1-(15Z-Tetracosenoyl)-2-(1Z,11Z-octadecadienyl)-sn-glycero-3-phosphocholine
  • Glycerophosphocholine(24:1(15Z)/p-18:1(11Z))
  • PC(24:2)
  • Gpcho(24:2)
  • Phosphatidylcholine(24:2)
  • PC(24:1/P-18:1)
  • Gpcho(24:1/p-18:1)
  • Phosphatidylcholine(24:1/p-18:1)
CAS numberNot Available
WeightAverage: 854.2735
Monoisotopic: 853.692440943
InChI KeyXUCRMKOOPPYQFN-UHFFFAOYSA-N
InChIInChI=1S/C50H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-28-29-31-33-35-37-39-41-43-50(52)56-47-49(48-58-59(53,54)57-46-44-51(3,4)5)55-45-42-40-38-36-34-32-30-23-21-19-17-15-13-11-9-7-2/h17,19-20,22,42,45,49H,6-16,18,21,23-41,43-44,46-48H2,1-5H3
IUPAC Nametrimethyl[2-({2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-[(15Z)-tetracos-15-enoyloxy]propyl phosphonato}oxy)ethyl]azanium
Traditional IUPAC Namelecithin
Chemical FormulaC50H96NO7P
SMILESCCCCCCCCC=CCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC=CCCCCCCCCC=CCCCCCC
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 Solubility2.3e-05 g/LALOGPS
logP6.99ALOGPS
logP12.23ChemAxon
logS-7.6ALOGPS
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 Count47ChemAxon
Refractivity264.45 m³·mol⁻¹ChemAxon
Polarizability108.71 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
0.01 ± 0.0005 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-9005212130-e9812e6efd33937ffe42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-6329103110-debe3b40235a4bf7a632JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053j-9028106200-64327188934f6b652019JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gba-0019000030-91aae3b878bbf73dba99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009000100-8f5fe563a69c438507d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-4039020000-72c101bd1b8497d7e9faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1100000190-a6454f4c9190457f1373JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900000110-b2cca630128233249fd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-1adcc40364e034d34dc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-e853a3638bcff17c07eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0010000390-5aff2b329b2f1ba9eb73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-7009100000-6b5c2997cbb970ab983aJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89427
HMDB IDHMDB08819
Pubchem Compound ID53479547
Kegg IDC00157
ChemSpider ID24767477
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available