PC(14:0/22:1(13Z)) (YMDB01821)

Identification
YMDB IDYMDB01821
NamePC(14:0/22:1(13Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(14:0/22:1(13Z)) 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(14:0/22:1(13Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of erucic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the erucic acid moiety is derived from seed oils and avocados. 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-myristoyl-2-erucoyl-sn-glycero-3-phosphocholine
  • GPCho(14:0/22:1)
  • GPCho(14:0/22:1n9)
  • GPCho(14:0/22:1w9)
  • Lecithin
  • PC(14:0/22:1)
  • PC(14:0/22:1n9)
  • PC(14:0/22:1w9)
  • PC(36:1)
  • Phosphatidylcholine(14:0/22:1)
  • Phosphatidylcholine(14:0/22:1n9)
  • Phosphatidylcholine(14:0/22:1w9)
  • Phosphatidylcholine(36:1)
  • GPCho(36:1)
  • 1-Myristoyl-2-erucoyl-sn-glycero-3-phosphocholine
  • Gpcho(14:0/22:1)
  • Gpcho(14:0/22:1n9)
  • Gpcho(14:0/22:1W9)
  • Lecithin
  • PC Aa C36:1
  • PC(14:0/22:1)
  • PC(14:0/22:1n9)
  • PC(14:0/22:1W9)
  • PC(36:1)
  • Phosphatidylcholine(14:0/22:1)
  • Phosphatidylcholine(14:0/22:1n9)
  • Phosphatidylcholine(14:0/22:1W9)
  • Phosphatidylcholine(36:1)
  • 1-Tetradecanoyl-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholine
  • PC(14:0/22:1(13Z))
CAS numberNot Available
WeightAverage: 788.1293
Monoisotopic: 787.609105245
InChI KeyLOVKBDFNFACEND-HUESYALOSA-N
InChIInChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h19-20,42H,6-18,21-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC44H86NO8P
SMILESCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCC=CCCCCCCCC
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 Solubility2.0e-05 g/LALOGPS
logP5.88ALOGPS
logP9.53ChemAxon
logS-7.6ALOGPS
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 Count43ChemAxon
Refractivity235.39 m³·mol⁻¹ChemAxon
Polarizability98.1 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
0.762 ± 0.0381 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-9155311500-d1fd1d3a92225a64caebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022i-6696112100-8c664001155129bdf138JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-9383012200-dbd8b8d6f35683fe52eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-0093000300-7df6ff11b9e8d3845c61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0192001100-66f413d77a1d7341ffe9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6397000000-abef2689896f7b3104fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-973b6e2c5af7633f95b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-7a868a8ad9eb6f9e7bbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-0202469400-7585447a1d6e7bbc06d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-c7d2a706ee4c08cac004JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011000090-4eb1120dbd3d5f1e89baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ii-0099000090-575770130bdd3e9145f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-5649a580e0942e999145JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-fad619901ff8ea0e25d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0700329110-0b17e89841d3afefd672JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-11c57723ac725e930e50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0015030900-b190aa168cc072208377JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2095100000-7598cb40a7fa645d8eadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-575f764ae3b8a734c007JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-1e34e2e526af2e3adedaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900221300-98da8e058c426c30fd32JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89516
HMDB IDHMDB07887
Pubchem Compound ID53478609
Kegg IDC00157
ChemSpider ID24766563
FOODB IDFDB025079
Wikipedia IDNot Available
BioCyc IDNot Available