Showing metabocard for LysoPE(20:4(5Z,8Z,11Z,14Z)/0:0) (LMDB00561)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:34 UTC
Update Date2016-07-20 21:04:15 UTC
LmdbLMDB00561
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPE(20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionLysoPE(20:4(5Z,8Z,11Z,14Z)/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
(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-lysophosphatidylethanolamineChEBI
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-Arachidonyl-sn-glycero-3-phosphoethanolamineChEBI
1-O-Arachidonoyl-sn-glycero-3-phosphoethanolamineChEBI
1-O-Arachidonyl-sn-glycero-3-phosphoethanolamineChEBI
LPE(20:4)ChEBI
LPE(20:4/0:0)ChEBI
LPE(20:4omega6/0:0)ChEBI
LysoPE(20:4)ChEBI
LysoPE(20:4/0:0)ChEBI
LysoPE(20:4omega6/0:0)ChEBI
Lysophosphatidylethanolamine(20:4)ChEBI
Lysophosphatidylethanolamine(20:4/0:0)ChEBI
PE(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
PE(20:4/0:0)ChEBI
1-Arachidonoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(20:4n6/0:0)HMDB
LPE(20:4W6/0:0)HMDB
Lyso-pe(20:4)HMDB
Lyso-pe(20:4/0:0)HMDB
Lyso-pe(20:4n6/0:0)HMDB
Lyso-pe(20:4W6/0:0)HMDB
LysoPE(20:4n6/0:0)HMDB
LysoPE(20:4W6/0:0)HMDB
Lysophosphatidylethanolamine(20:4n6/0:0)HMDB
Lysophosphatidylethanolamine(20:4W6/0:0)HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
1-ArachidonylglycerophosphoethanolamineHMDB
1-Arachidonoyl-gpeHMDB
1-Arachidonoyl-lysophosphatidylethanolamineHMDB
1-Arachidonoyl-sn-glycero-3-phosphoethanolamineHMDB
GPE(20:4(5Z,8Z,11Z,14Z))HMDB
GPE(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
GPE(20:4)HMDB
GPE(20:4n6)HMDB
GPE(20:4n6/0:0)HMDB
GPE(20:4W6)HMDB
GPE(20:4W6/0:0)HMDB
LPE(20:4(5Z,8Z,11Z,14Z))HMDB
LPE(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
LPE(20:4n6)HMDB
LPE(20:4W6)HMDB
LysoPE(20:4(5Z,8Z,11Z,14Z))HMDB
LysoPE(20:4n6)HMDB
LysoPE(20:4W6)HMDB
Lysophosphatidylethanolamine(20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylethanolamine(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
Lysophosphatidylethanolamine(20:4n6)HMDB
Lysophosphatidylethanolamine(20:4W6)HMDB
1-Arachidonoyl-2-hydroxy-sn-glycerol-3-phosphatidyl ethanolamineHMDB
LysoPE(20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC25H44NO7P
Average Molecular Weight501.5931
Monoisotopic Molecular Weight501.285539279
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H44NO7P/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/h6-7,9-10,12-13,15-16,24,27H,2-5,8,11,14,17-23,26H2,1H3,(H,29,30)/b7-6-,10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyROPRRXYVXLDXQO-XSQXPFHXSA-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
logP4.65ALOGPS
logP3.86ChemAxon
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 Count23ChemAxon
Refractivity140.28 m³·mol⁻¹ChemAxon
Polarizability55.07 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, Positivesplash10-0zgl-1930300000-2236e87d5bc1f07e55ecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-076r-3190200000-6b2b65ae182b013dd767Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121110000-e69332874b8a3b68bd71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121100000-13f14d49046b78c51f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-3045cfbacfc8a3c6f5f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-2479550000-df3affc60626c6eb7095Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-9868100000-86e9978369a5724d8747Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-6197c3cb09d1f6d23c7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000490000-512277d77bd947786568Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-6936360000-a46cb26f4874c9691536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2509000000-b8c6bce5a152c6fa2ec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8006390000-5c4cb029cbc83b391eaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9004100000-8c8fd668e29a3cde45bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9721000000-30c5f93c87ae45524672Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0011517
FooDB IDFDB028233
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21403171
ChEBI ID64395
PubChem Compound ID42607465
Kegg Compound IDNot Available
YMDB IDYMDB16218
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available