PC(18:1(9Z)/18:1(11Z)) (YMDB01936)

Identification
YMDB IDYMDB01936
NamePC(18:1(9Z)/18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:1(9Z)/18:1(11Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(18:1(9Z)/18:1(11Z)), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one 11Z-octadecenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-oleoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
  • GPCho(18:1/18:1)
  • GPCho(18:1n9/18:1n7)
  • GPCho(18:1w9/18:1w7)
  • GPCho(36:2)
  • Lecithin
  • PC(18:1n9/18:1n7)
  • PC(18:1w9/18:1w7)
  • PC(36:2)
  • Phosphatidylcholine(18:1/18:1)
  • Phosphatidylcholine(18:1n9/18:1n7)
  • Phosphatidylcholine(18:1w9/18:1w7)
  • Phosphatidylcholine(36:2)
  • PC(18:1/18:1)
  • GPCho(36:2)
  • PC(36:2)
  • Phosphatidylcholine(36:2)
  • GPCho(18:1/18:1)
  • Lecithin
  • 1-Oleoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(18:1/18:1)
  • 1-(9Z-Octadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • PC(18:1(9Z)/18:1(11Z))
CAS numberNot Available
WeightAverage: 786.1134
Monoisotopic: 785.593455181
InChI KeyGMCZAOACLPIWHN-VZDDXLEPSA-N
InChIInChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h17,19-20,22,42H,6-16,18,21,23-41H2,1-5H3/b19-17-,22-20-/t42-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Namelecithin
Chemical FormulaC44H84NO8P
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCC
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 Solubility2.2e-05 g/LALOGPS
logP5.77ALOGPS
logP9.17ChemAxon
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 Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability95.35 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 Pathways
Phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(11Z))PW002942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.755 ± 0.03775 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, Positivesplash10-0ut9-0000072900-aea3d44cdb094a7885d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000400-e1cb49a597c3d9e80074JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090001000-ba90c433d971adc4f750JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-4090100000-dd6959c7e189396fa448JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-64c382f846ba04194d31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6c06686879d9f7790e62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200249400-1ae2411ef15a63cb3b2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-23df8d3c4971511f3b91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0050030900-b121f3ff4b078b5df33eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1090200000-673c166236d767f9289eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-683d2aaf9f12a9d08614JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010000090-37042360a3899f1fdc23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00f0-0090000090-06eeedb644af6eeff7ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-53a8e01f33b2af13f226JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-64f46bdfe255d6a5b5e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0900139110-7365097ffb2d5d55b434JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-e54f4b7d729e27672b37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-3a2440aaca7e87ec13a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-24d60344b49a468b0469JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89604
HMDB IDHMDB08103
Pubchem Compound ID53478765
Kegg IDC00157
ChemSpider ID24766766
FOODB IDFDB025294
Wikipedia IDNot Available
BioCyc IDNot Available