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PC(18:0/0:0) (YMDB01187)

Identification
YMDB IDYMDB01187
NamePC(18:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(18:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:0), in particular, consists of one chain of stearic acid at the C-1 position. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-acyl-2-lyso-phosphatidylcholine
  • 1-Acyl-sn-glycero-3-phosphocholine
  • 1-acyl-sn-glycero-3-phosphocholines
  • 1-Acyl-sn-glycerol-3-phosphocholine
  • 1-Acylglycerophosphocholine
  • 1-stearoyl-glycero-3-phosphocholine
  • 2-Lysolecithin
  • 2-Lysophosphatidylcholine
  • alpha-Acylglycerophosphocholine
  • LPC
  • LPC(18:0)
  • LPC(18:0/0:0)
  • LyPC(18:0)
  • LyPC(18:0/0:0)
  • LysoPC(18:0)
  • LysoPC(18:0/0:0)
  • Lysophosphatidylcholine(18:0)
  • Lysophosphatidylcholine(18:0/0:0)
  • (2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
  • 1-O-Stearoyl-sn-glycero-3-phosphocholine
  • 1-Octadecanoyl-sn-glycero-3-phosphocholine
  • 1-Stearoylglycerophosphocholine (18:0)
  • 1-Stearoylglycerophosphocholine(18:0)
  • 18:0 LYSO-PC
  • GPCho 18:0/0:0
  • GPCho(18:0/0:0)
  • LPC 18:0/0:0
  • LysoPC 18:0/0:0
  • Lysophosphatidylcholine (18:0/0:0)
  • PC 18:0/0:0
  • PC(18:0/0:0)
  • (2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid
  • LysoPC a C18:0
  • Stearoyl alpha-lysolecithin
  • Stearoyllysophosphatidylcholine
  • 1-Octadecyl-glycero-3-phosphocholine
  • 1-Stearoyl-sn-glycero-3-phosphorylcholine
  • Stearoyl L-alpha-lysolecithin
  • 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholine
  • Stearoyl alpha-lysolecithin, (+-)-isomer
  • Stearoyl alpha-lysolecithin, (R)-isomer
  • 1-Octadecanoyl-glycero-3-phosphocholine
  • 1-Octadecanoylglycerophosphocholine
  • 1-Octadecylglycerophosphocholine
  • 1-Stearoylglycerophosphocholine
  • 1-O-Stearoyl-2-lyso-sn-glycero-3-phosphocholine
  • 1-Octadecanoyl-3-glycerophosphorylcholine
  • 1-Octadecanoyl-sn-glycerol-3-phosphorylcholine
  • 1-Octadecanoyllysolecithin
  • 1-Stearoyl-2-lysophosphatidylcholine
  • 1-Stearoyl-3-glycerylphosphorylcholine
  • 1-Stearoyl-GPC
  • 1-Stearoyl-lysophosphatidylcholine
  • 1-Stearoyl-sn-glycero-3-phosphocholine
  • 1-Stearoyl-sn-glycerol-3-phosphatidylcholine
  • 1-Stearoyl-sn-glycerol-3-phosphorylcholine
  • 1-Stearoylglycero-3-phosphorylcholine
  • 1-Stearoyllysophosphatidylcholine
  • GPC(18:0)
  • GPC(18:0/0:0)
  • Lysophosphatidylcholine C18:0
  • Stearoyl L-α-lysolecithin
  • Stearoyl lysolecithin
  • Stearoyl lysophosphatidylcholine
CAS numberNot Available
WeightAverage: 523.6832
Monoisotopic: 523.363789599
InChI KeyIHNKQIMGVNPMTC-RUZDIDTESA-N
InChIInChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC26H54NO7P
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • 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 Solubility0.00023 g/LALOGPS
logP2.53ALOGPS
logP2.08ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.48 m³·mol⁻¹ChemAxon
Polarizability61.71 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
Lysolipid incorporation into ER PC(18:0/18:0)PW002787 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:0/18:0)PW002795 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
PC(18:0/0:0) + water → Glycerophosphocholine + a carboxylate
PC(18:0/0:0) → PC(18:0/18:0)
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.135 ± 0.00675 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 (1 TMS) - 70eV, Positivesplash10-024u-9321010000-7c4db1d8f50345253e5eJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900000000-4587eca1f40127997f9aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-8c56fcd29df2d9fc9c2bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0200090000-3a51011c95929ab98d63JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000190000-41c73cffe2f1aaf160f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0001960000-94fcb8b8814d186b45b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609710000-ae76bfe8f474291dc445JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030090000-f659985c9cbbaf332a78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090010000-01d93fd13edb0afa2e7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-ca0fc5a9d32fa941ad45JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-3069bae6fba637487e2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090070000-1397c10d116d343edd9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090020000-274c1e62706a1695b7b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000090000-0d83963fc8d256300785JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-23beae7a997640f05765JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-0910040000-b24aadea134c86d41382JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000190000-db2c4daf832d5e722111JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00f0-0002990000-f2b5b69d9cc9121b1dc6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdp-0309400000-f08bc6aa7b631fbc521eJSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17504
HMDB IDHMDB10384
Pubchem Compound ID14420997
Kegg IDC04230
ChemSpider ID435389
FOODB IDFDB027535
WikipediaLecithin
BioCyc IDPHOSPHATIDYLCHOLINE

Enzymes

Protein Details
1. Lysophospholipase NTE1
General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.