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PC(18:0/18:1(9Z)) (YMDB01189)

Identification
YMDB IDYMDB01189
NamePC(18:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:0/18:1(9Z)) 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(18:0/18:1(9Z)), in particular, consists of one octadecanoyl chain to the C-1 atom, and one 9Z-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-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine
  • 1,2-Diacyl-sn-glycero-3-phosphocholine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-Phosphatidylcholine
  • Choline phosphatide
  • GPCho(18:0/18:1)
  • GPCho(18:0/18:1n9)
  • GPCho(18:0/18:1w9)
  • GPCho(36:1)
  • Lecithin
  • Lecithins
  • O3-Phosphatidyl-L-serine
  • PC(18:0/18:1)
  • PC(18:0/18:1n9)
  • PC(18:0/18:1w9)
  • PC(36:1)
  • Phosphatidyl-L-serine
  • phosphatidyl-L-serines
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(18:0/18:1)
  • Phosphatidylcholine(18:0/18:1n9)
  • Phosphatidylcholine(18:0/18:1w9)
  • Phosphatidylcholine(36:1)
  • (2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphate
  • 1-18:0-2-18:1-Phosphatidylcholine
  • 1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine
  • 1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • 1-Stearoyl-2-oleoyl-GPC
  • 1-Stearoyl-2-oleoyl-GPC (18:0/18:1)
  • 1-Steroyl-2-oleoylphosphatidylcholine
  • 18:0-18:1-PC
  • GPC(18:0/18:1)
  • GPCho 18:0/18:1(9Z)
  • L-alpha-1-Stearoyl-2-oleoyl lecithin
  • PC 18:0/18:1(9Z)
  • PC(18:0/18:1omega9)
  • Phosphatidylcholine(18:0/18:1(9Z))
  • Phosphatidylcholine(18:0/18:1omega9)
  • SOPC
  • (2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acid
  • L-a-1-Stearoyl-2-oleoyl lecithin
  • L-Α-1-stearoyl-2-oleoyl lecithin
  • PC(18:0/18:1(9Z))
  • 1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (e)-isomer
  • 1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (S-(Z))-isomer
  • 1-Stearoyl-2-oleoyl lecithin
  • 1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (R-(Z))-isomer
  • 1-SOPC
  • 1-Stearoyl-2-oleoyl-sn-3-glycerophosphocholine
  • 1-Stearoyl-2-oleoyl glycerylphosphorylcholine
  • 1-Stearoyl-2-oleoyl-sn-glycero-phosphatidylcholine
  • 1-Stearoyl-2-oleoyllecithin
  • 1-Stearoyl-2-oleoylphosphatidylcholine
  • 1-Stearyl-2-oleoyl-3-sn-glycerophosphatidylcholine
  • GPC(18:0/18:1(9Z))
  • GPC(18:0/18:1n9)
  • GPC(18:0/18:1w9)
  • GPC(36:1)
  • GPCho(18:0/18:1(9Z))
  • L-alpha-1-Stearoyl-2-oleoylphosphatidylcholine
  • L-α-1-Stearoyl-2-oleoylphosphatidylcholine
CAS number8002-43-5
WeightAverage: 788.1293
Monoisotopic: 787.609105245
InChI KeyATHVAWFAEPLPPQ-VRDBWYNSSA-N
InChIInChI=1S/C44H86NO8P/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/h21,23,42H,6-20,22,24-41H2,1-5H3/b23-21-/t42-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
Traditional IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
Chemical FormulaC44H86NO8P
SMILESCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
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
logP5.89ALOGPS
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
Polarizability97.79 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
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(18:0/18:1(9Z))PW002945 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arachidonic acid metabolismec00590 Map00590
Glycerophospholipid metabolismec00564 Map00564
Linoleic acid metabolismec00591 Map00591
alpha-Linolenic acid metabolismec00592 Map00592
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
37250 ± 9675 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
325250 ± 1925 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-b859f2c3b3c1a8178429JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-740e271e86363b8b605aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041300-22e6346bd3881ccf6ad0JSpectraViewer
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, Positivesplash10-004j-0900369110-8d8283d716b8945882e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-c7d2a706ee4c08cac004JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0030000090-9becebc4c350016d45deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-0090000040-58b0dfd010ce87ff0a8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-11c57723ac725e930e50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0071010900-5a423108e9ed5868292aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2092200000-f53135f214f9fe93df45JSpectraViewer
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, Positivesplash10-0089-1900041300-20b479e3bfdf095f4186JSpectraViewer
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, Positivesplash10-03di-0200498400-d8a93635e28c18a04dd4JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
  • Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). "Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry." Proc Natl Acad Sci U S A 104:2193-2198.17287358
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Gruhler, A., Olsen, J. V., Mohammed, S., Mortensen, P., Faergeman, N. J., Mann, M., Jensen, O. N. (2005). "Quantitative phosphoproteomics applied to the yeast pheromone signaling pathway." Mol Cell Proteomics 4:310-327.15665377
  • Smolka, M. B., Albuquerque, C. P., Chen, S. H., Zhou, H. (2007). "Proteome-wide identification of in vivo targets of DNA damage checkpoint kinases." Proc Natl Acad Sci U S A 104:10364-10369.17563356
  • Li, X., Gerber, S. A., Rudner, A. D., Beausoleil, S. A., Haas, W., Villen, J., Elias, J. E., Gygi, S. P. (2007). "Large-scale phosphorylation analysis of alpha-factor-arrested Saccharomyces cerevisiae." J Proteome Res 6:1190-1197.17330950
  • Yamashita, S., Nikawa, J. (1997). "Phosphatidylserine synthase from yeast." Biochim Biophys Acta 1348:228-235.9370337
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18303
HMDB IDHMDB08038
Pubchem Compound ID6323481
Kegg IDC00157
ChemSpider ID24766704
FOODB IDNot Available
WikipediaLecithin
BioCyc IDPHOSPHATIDYLCHOLINE