Showing metabocard for LysoPE(0:0/20:2(11Z,14Z)) (BMDB0011483)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:14 UTC
Update Date2020-05-11 19:17:32 UTC
BMDB IDBMDB0011483
Secondary Accession Numbers
  • BMDB11483
Metabolite Identification
Common NameLysoPE(0:0/20:2(11Z,14Z))
Descriptionis 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.LysoPE(0:0/20:2(11Z,14Z)), in particular, consists of one 11Z,14Z-eicosadienoyl chain. 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z,14Z-Eicosadienoyl)-lysophosphatidylethanolamineChEBI
1-Hydroxy-2-eicosadienoyl-sn-glycero-3-phosphoethanolamineChEBI
2-[(11Z,14Z)-Eicosadienoyl]-sn-glycero-3-phosphoethanolamineChEBI
LPE(0:0/20:2)ChEBI
LPE(0:0/20:2n6)ChEBI
LPE(0:0/20:2W6)ChEBI
LPE(20:2)ChEBI
LysoPE(0:0/20:2)ChEBI
LysoPE(0:0/20:2n6)ChEBI
LysoPE(0:0/20:2W6)ChEBI
LysoPE(20:2)ChEBI
Lysophosphatidylethanolamine(0:0/20:2)ChEBI
Lysophosphatidylethanolamine(0:0/20:2n6)ChEBI
Lysophosphatidylethanolamine(0:0/20:2W6)ChEBI
Lysophosphatidylethanolamine(20:2)ChEBI
Lyso-pe(0:0/20:2)HMDB
Lyso-pe(0:0/20:2n6)HMDB
Lyso-pe(0:0/20:2W6)HMDB
Lyso-pe(20:2)HMDB
1-Hydroxy-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/20:2(11Z,14Z))Lipid Annotator, ChEBI
Chemical FormulaC25H48NO7P
Average Molecular Weight505.6249
Monoisotopic Molecular Weight505.316839407
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C25H48NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)33-24(22-27)23-32-34(29,30)31-21-20-26/h6-7,9-10,24,27H,2-5,8,11-23,26H2,1H3,(H,29,30)/b7-6-,10-9-/t24-/m1/s1
InChI KeyNHBRVTKHMMOYTG-XBJNFHHOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphoethanolamine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct Parent2-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
Substituents
  • 2-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
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.18ALOGPS
logP4.58ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity138.05 m³·mol⁻¹ChemAxon
Polarizability57.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pn-7930400000-06f58da9d1e26746196aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9770030000-e7792f80b38cf149f942View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-0f7935c386a61e67e496View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-4931a6337b10b32b21e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9020000000-c40a3366d4524da0d32dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-114m-3946760000-b606b2893be7a51c5ef8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9521100000-5faa3c5b9d96d7e01c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-b0fa53900432a5f22327View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2600590000-5e1efc4d81d2d3e67f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbc-8923020000-0a64f258d8f185c90dfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-47fd9285de6268e84f96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0cdi-6129870000-cc3b704f9061f073aee5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-8779810000-2d4c4990029dcbee6b15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9310000000-a4336d60330337fac4e1View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011483
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028199
KNApSAcK IDNot Available
Chemspider ID24769364
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480932
PDB IDNot Available
ChEBI ID131692
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available