Showing metabocard for LysoPE(0:0/20:3(5Z,8Z,11Z)) (BMDB0011485)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:17 UTC
Update Date2020-05-11 19:17:33 UTC
BMDB IDBMDB0011485
Secondary Accession Numbers
  • BMDB11485
Metabolite Identification
Common NameLysoPE(0:0/20:3(5Z,8Z,11Z))
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(0:0/20:3(5Z,8Z,11Z)), in particular, consists of one 5Z,8Z,11Z-eicosatrienoyl 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
(5Z,8Z,11Z-Eicosatrienoyl)-lysophosphatidylethanolamineChEBI
2-[(5Z,8Z,11Z)-Eicosatrienoyl]-sn-glycero-3-phosphoethanolamineChEBI
LPE(0:0/20:3)ChEBI
LPE(0:0/20:3n9)ChEBI
LPE(0:0/20:3W9)ChEBI
LPE(20:3)ChEBI
Lyso-pe(0:0/20:3)ChEBI
Lyso-pe(0:0/20:3n9)ChEBI
Lyso-pe(0:0/20:3W9)ChEBI
Lyso-pe(20:3)ChEBI
LysoPE(0:0/20:3)ChEBI
LysoPE(0:0/20:3n9)ChEBI
LysoPE(0:0/20:3W9)ChEBI
LysoPE(20:3)ChEBI
Lysophosphatidylethanolamine(0:0/20:3)ChEBI
Lysophosphatidylethanolamine(0:0/20:3n9)ChEBI
Lysophosphatidylethanolamine(0:0/20:3W9)ChEBI
Lysophosphatidylethanolamine(20:3)ChEBI
1-Hydroxy-2-meadoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Hydroxy-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/20:3(5Z,8Z,11Z))Lipid Annotator, ChEBI
Chemical FormulaC25H46NO7P
Average Molecular Weight503.609
Monoisotopic Molecular Weight503.301189343
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C25H46NO7P/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/h9-10,12-13,15-16,24,27H,2-8,11,14,17-23,26H2,1H3,(H,29,30)/b10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyFJDVENKXPUIXRG-WMTBOZPISA-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
logP5.07ALOGPS
logP4.22ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity139.17 m³·mol⁻¹ChemAxon
Polarizability57 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, Positivesplash10-03ed-9850400000-797e358b304a443175adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-8590030000-8fdf157ad1f5baaa0b29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-6eb009f8d90ca9cb7c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-ece2b63e1d764678cc22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9020000000-5ac4edf41a8830ca435dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-3946760000-3689ff4b172ea201b649View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9521100000-34c25af50f708348df3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-25c70d43a63104323701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-3219770000-753877cbe21342b027e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-6349700000-8917d62c55c4a2f0a928View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9421000000-ef2f2b6b769149cf50e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1600590000-abb9916a5196bb504805View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9711010000-de06ff774f7d64d685cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-f7629530bf4bc4bb6b6eView 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 IDHMDB0011485
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028201
KNApSAcK IDNot Available
Chemspider ID24769366
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480934
PDB IDNot Available
ChEBI ID90579
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available