PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0) (YMDB02194)

Identification
YMDB IDYMDB02194
NamePC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0) 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of myristic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the myristic acid moiety is derived from nutmeg and butter. 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-docosahexaenoyl-2-myristoyl-sn-glycero-3-phosphocholine
  • GPCho(22:6/14:0)
  • GPCho(22:6w3/14:0)
  • GPCho(36:6)
  • Lecithin
  • PC(22:6/14:0)
  • PC(22:6n3/14:0)
  • PC(22:6w3/14:0)
  • PC(36:6)
  • Phosphatidylcholine(22:6/14:0)
  • Phosphatidylcholine(22:6n3/14:0)
  • Phosphatidylcholine(22:6w3/14:0)
  • Phosphatidylcholine(36:6)
  • GPCho(22:6n3/14:0)
  • PC(36:6)
  • Phosphatidylcholine(36:6)
  • GPCho(36:6)
  • 1-docosahexaenoyl-2-myristoyl-sn-glycero-3-phosphocholine
  • Lecithin
  • GPCho(22:6/14:0)
  • PC(22:6/14:0)
  • Phosphatidylcholine(22:6/14:0)
  • 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine
  • PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0)
CAS numberNot Available
WeightAverage: 778.0499
Monoisotopic: 777.530854925
InChI KeyWJBQZCVRYZHPRT-HUESYALOSA-N
InChIInChI=1S/C44H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-26-17-15-13-11-9-7-2/h8,10,14,16,19-20,22-23,25,27,30,32,42H,6-7,9,11-13,15,17-18,21,24,26,28-29,31,33-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H76NO8P
SMILESCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCC=CCC=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 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 Solubility3.3e-05 g/LALOGPS
logP5.46ALOGPS
logP7.72ChemAxon
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 Count38ChemAxon
Refractivity240.97 m³·mol⁻¹ChemAxon
Polarizability90.7 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
0.021 ± 0.00105 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, Positivesplash10-03g0-9164141300-67f6469042df816fc3b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-6696030100-2c54b238b923c535421fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-9356020100-25aa9a2b2d68e6e1c144JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0049000300-5edb567a29ef1c9d7f5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0029001000-dc1730c1fbc4517b4feaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7297100000-6747f2fd7de1a1d501c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-87e491c712a61c58fe72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000090-351874ded63d21fcfe26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0099000090-11148a6f2d98c6a66a46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-e97180150486da753e49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-cd910875d8659ad53678JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014n-0900449110-b33460e818988ebcbbd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e158c1e70dedba30b57eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-259bce635b325b3b4835JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-1900230300-ffb8eac176958d50fc47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-41c33084af9f783c847dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-dd151cc7bd543b751825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zna-0202649400-7549c6574aa617059714JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-8a1373a75c2e5dc70822JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0034030900-2ed0c674196b99afad77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3296400000-cd50c0995818bace609bJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB08722
Pubchem Compound ID52923675
Kegg IDC00157
ChemSpider ID24767383
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available