PE(16:1(9Z)/0:0) (YMDB01201)

Identification
YMDB IDYMDB01201
NamePE(16:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPE(16:1(9Z)) 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
  • (9Z-hexadecenoyl)-lysophosphatidylethanolamine
  • 1-palmitoleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
  • LPE(16:1)
  • LPE(16:1/0:0)
  • LPE(16:1n7/0:0)
  • LPE(16:1w7/0:0)
  • Lyso-PE(16:1)
  • Lyso-PE(16:1/0:0)
  • Lyso-PE(16:1n7/0:0)
  • Lyso-PE(16:1w7/0:0)
  • LysoPE(16:1)
  • LysoPE(16:1/0:0)
  • LysoPE(16:1n7/0:0)
  • LysoPE(16:1w7/0:0)
  • Lysophosphatidylethanolamine(16:1)
  • Lysophosphatidylethanolamine(16:1/0:0)
  • Lysophosphatidylethanolamine(16:1n7/0:0)
  • Lysophosphatidylethanolamine(16:1w7/0:0)
  • 1-(9Z-Hexadecenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamine
  • LysoPE(16:1(9Z)/0:0)
CAS numberNot Available
WeightAverage: 451.5344
Monoisotopic: 451.269889215
InChI KeyDSOWUEHXZJUNID-WHXUGTBJSA-N
InChIInChI=1S/C21H42NO7P/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/h7-8,20,23H,2-6,9-19,22H2,1H3,(H,25,26)/b8-7-/t20-/m1/s1
IUPAC Name(2-aminoethoxy)[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxyphosphinic acid
Chemical FormulaC21H42NO7P
SMILES[H][C@@](O)(COC(=O)CCCCCCC\C=C/CCCCCC)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 Solubility0.0029 g/LALOGPS
logP3.99ALOGPS
logP3.17ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity118.53 m³·mol⁻¹ChemAxon
Polarizability50.65 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(16:1(9Z)/16:1(9Z))PW002785 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:1(9Z)/16:1(9Z))PW002793 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
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, Positivesplash10-0k9x-2920100000-8c2c0054d14411307ccbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02ji-5390200000-4a4d2b8705acec22be32JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121200000-e5e030ac2247473d4bfeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-4afde7e41dde7e379bf9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9220000000-688c27b38b2b5b649882JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1290400000-c3d61005a3168aff7a5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug3-6490000000-ca7585f4e8dc6cb7f945JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-50e7828921698bf2d0d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-5004900000-326e1e4670d78edb6e7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9103100000-bd046a3553de8be50ab1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-5f5b068a7f080cf81bdaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-527770f0a202591b0703JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4980800000-a8d6a1e3a6f4f756fda9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1490000000-4c772eece08c289ea51dJSpectraViewer
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 IDNot Available
HMDB IDHMDB11504
Pubchem Compound ID42607464
Kegg IDNot Available
ChemSpider ID24769383
FOODB IDFDB028220
Wikipedia IDNot Available
BioCyc IDNot Available