Showing metabocard for LysoPE(20:0/0:0) (LMDB00559)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:32 UTC
Update Date2016-07-20 21:04:14 UTC
LmdbLMDB00559
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPE(20:0/0:0)
DescriptionLysoPE(20:0/0:0) 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
ValueSource
1-Arachidonyl-2-hydroxy-sn-glycero-3-phosphoethanolamineChEBI
1-Arachidoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Eicosanoyl-glycero-3-phosphoethanolamineChEBI
1-Eicosanoyl-sn-glycero-3-phosphoethanolamineChEBI
Eicosanoyl-lysophosphatidylethanolamineChEBI
LPE(20:0)ChEBI
LPE(20:0/0:0)ChEBI
Lyso-pe(20:0)ChEBI
Lyso-pe(20:0/0:0)ChEBI
LysoPE(20:0)ChEBI
Lysophosphatidylethanolamine(20:0)ChEBI
Lysophosphatidylethanolamine(20:0/0:0)ChEBI
PE(20:0/0:0)ChEBI
1-Eicosanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(20:0/0:0)Lipid Annotator
1-ArachidoylglycerophosphoethanolamineHMDB
1-EicosanoylglycerophosphoethanolamineHMDB
Chemical FormulaC25H52NO7P
Average Molecular Weight509.6566
Monoisotopic Molecular Weight509.348139535
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-(icosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-hydroxy-3-(icosanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H52NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1
InChI KeyHEQMDGOBDIGJOC-XMMPIXPASA-N
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.47ALOGPS
logP5.31ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity135.82 m³·mol⁻¹ChemAxon
Polarizability60.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-3920200000-0efc847bf5001cdfad4bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0329-4190200000-89f10b5cb2675325d2aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9111010000-069aa0725da01d787102Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-cd2b0817372d87a2355eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9130000000-666de551a7fd28da0703Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06r6-2489550000-be9fc03087bf42ca1d35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-9657100000-e61378182869ee0ed889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-eb380163bfa7f2f0ba11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3003090000-c13188261dabdfec0410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9104200000-5d1a70f68aa386e775efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-92a9f11483cee2b5cd75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000490000-f1ea2cdea550e326a305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2539240000-133a041f021264a70bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1309000000-9cb5913bfb8193d93150Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Sergio Polakof, D...
 details
DrugBank IDNot Available
HMDB IDHMDB0011511
FooDB IDFDB028227
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24769389
ChEBI ID131690
PubChem Compound ID52925131
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available