PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (YMDB01842)

Identification
YMDB IDYMDB01842
NamePC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 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(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the docosapentaenoic acid moiety is derived from fish 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-myristoleoyl-2-docosapentaenoyl-sn-glycero-3-phosphocholine
  • GPCho(14:1/22:5)
  • GPCho(14:1n5/22:5n3)
  • GPCho(14:1w5/22:5w3)
  • GPCho(36:6)
  • Lecithin
  • PC(14:1/22:5)
  • PC(14:1n5/22:5n3)
  • PC(14:1w5/22:5w3)
  • PC(36:6)
  • Phosphatidylcholine(14:1/22:5)
  • Phosphatidylcholine(14:1w5/22:5w3)
  • Phosphatidylcholine(36:6)
  • Phosphatidylcholine(14:1n5/22:5n3)
  • Phosphatidylcholine(36:6)
  • GPCho(36:6)
  • PC(14:1/22:5)
  • 1-Myristoleoyl-2-docosapentaenoyl-sn-glycero-3-phosphocholine
  • Lecithin
  • GPCho(14:1/22:5)
  • PC(36:6)
  • 1-(9Z-Tetradecenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(14:1/22:5)
  • PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))
CAS numberNot Available
WeightAverage: 778.0499
Monoisotopic: 777.530854925
InChI KeyQXPGEDBVJUZDLW-HUESYALOSA-N
InChIInChI=1S/C44H76NO8P/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/h8,10,13-16,19-20,22-23,25,27,42H,6-7,9,11-12,17-18,21,24,26,28-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H76NO8P
SMILESCCCCC=CCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC=CCC=CCC=CCC=CCC=CCC
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
logP5.36ALOGPS
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
Polarizability91.29 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, Positivesplash10-01q0-9154331300-e9e724081883980dfa0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gr-5594120100-3cb75366514bae39f224JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-7292010000-957280fefe836cae69afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0093000300-8cb5ca9237acf3829351JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0191001000-96cba87c5ed8ec42c006JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7297000000-babf82050352bc1fb93eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-5a1f7e5d648203ccaa08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0034030900-6964268f153e615c8b8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4492000000-196dce28730535b6a8a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-87e491c712a61c58fe72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000090-7f9dda42b2a9366e09f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0099000090-9cc2aa4c0558ae928a0aJSpectraViewer
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, Positivesplash10-001i-1900230300-d2c342e9454bd44eaf38JSpectraViewer
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, Positivesplash10-014j-0900449110-2cfb44f3de81e4422695JSpectraViewer
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, Positivesplash10-0udi-0202649400-935bfeae2aa67aadbb2aJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID88929
HMDB IDHMDB07924
Pubchem Compound ID53478633
Kegg IDC00157
ChemSpider ID24766600
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available