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PE(16:0/0:0) (YMDB01197)

Identification
YMDB IDYMDB01197
NamePE(16:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPE(16:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
  • hexadecanoyl-lysophosphatidylethanolamine
  • LPE(16:0)
  • LPE(16:0/0:0)
  • Lyso-PE(16:0)
  • Lyso-PE(16:0/0:0)
  • LysoPE(16:0)
  • LysoPE(16:0/0:0)
  • Lysophosphatidylethanolamine(16:0)
  • Lysophosphatidylethanolamine(16:0/0:0)
  • 1-Hexadecanoyl-sn-glycero-3-phosphoethanolamine
  • 1-Palmitoyl-gpe
  • 1-Palmitoyl-gpe (16:0)
  • 1-Palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion
  • 2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphate
  • GPE(16:0)
  • GPE(16:0/0:0)
  • PE(16:0/0:0)
  • 2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphoric acid
  • 1-Hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
  • 1-Hexadecanoylglycerophosphoethanolamine
  • 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamine
  • 1-Palmitoyl-3-glycerylphosphorylethanolamine
  • 1-Palmitoyl-sn-glycero-3-phosphoethanolamine
  • 1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamine
  • 1-Palmitoyl-sn-glycerol-3-L-α-phosphorylethanolamine
  • 1-Palmitoyl-sn-glycerol-3-phosphylethanolamine
  • 1-Palmitoyl-sn-glycerophosphatidylethanolamine
  • 1-Palmitoylglycero-3-phosphorylethanolamine
  • 1-Palmitoylglycerophosphoethanolamine
  • 3-Palmitoyl-DL-glycerol-1-phosphorylethanolamine
  • Palmitoyl lysophosphatidylethanolamine
  • 1-Palmitoyl-lysophosphatidylethanolamine
CAS number19805-23-3
WeightAverage: 453.5503
Monoisotopic: 453.285539279
InChI KeyYVYMBNSKXOXSKW-HXUWFJFHSA-N
InChIInChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxyphosphinic acid
Chemical FormulaC21H44NO7P
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCN
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent1-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 1-monoacyl-sn-glycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Primary amine
  • 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 Solubility0.0024 g/LALOGPS
logP4.1ALOGPS
logP3.53ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity117.41 m³·mol⁻¹ChemAxon
Polarizability52.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ER PC(16:0/16:0)PW002784 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:0/16:0)PW002753 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PE(16:0/0:0) PE(14:0/14:0)
PE(16:0/0:0) PE(16:0/16:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvo-3920100000-42e56a40b9f2f651e243JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-4290100000-9d4961833a31a61505d2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-97d2ee81d43b3bd577a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009200000-f0bf5c950a6907bcfdb2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-7029000000-95a7a790a5eea029d0c3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9110200000-adac1ea4ba52b6c32a6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-9cc034fa9a4c6eeac716JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-1e7e20f5d5acdebdbeadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-1290500000-c144e6d1cc68b4901cb6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-6490000000-d52a88743171a228301cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-93d9fa86c2fd00af0101JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-22a78e3986af43ab255eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1390400000-c75746e1322e5add0887JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1390000000-ead0e380f07431d54e75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3003900000-aa1d7b02acdc1b34723eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9104100000-e9614e19f5cf4a3f6310JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-707e02754187fe4a66c7JSpectraViewer
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 ID73004
HMDB IDHMDB11503
Pubchem Compound ID89229
Kegg IDNot Available
ChemSpider ID7826019
FOODB IDFDB028219
Wikipedia IDNot Available
BioCyc IDNot Available