Showing metabocard for LysoPE(20:0/0:0) (BMDB0011511)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:48 UTC
Update Date2020-05-11 19:17:55 UTC
BMDB IDBMDB0011511
Secondary Accession Numbers
  • BMDB11511
Metabolite Identification
Common NameLysoPE(20:0/0:0)
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(20:0/0:0), in particular, consists of one eicosanoyl 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
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 Number899445-69-3
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
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
logP5.47ALOGPS
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-3920200000-0efc847bf5001cdfad4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0329-4190200000-89f10b5cb2675325d2aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9111010000-069aa0725da01d787102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-cd2b0817372d87a2355eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9130000000-666de551a7fd28da0703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06r6-2489550000-be9fc03087bf42ca1d35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-9657100000-e61378182869ee0ed889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-eb380163bfa7f2f0ba11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3003090000-c13188261dabdfec0410View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9104200000-5d1a70f68aa386e775efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-92a9f11483cee2b5cd75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000490000-f1ea2cdea550e326a305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2539240000-133a041f021264a70bb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1309000000-9cb5913bfb8193d93150View 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 IDHMDB0011511
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028227
KNApSAcK IDNot Available
Chemspider ID24769389
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925131
PDB IDNot Available
ChEBI ID131690
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available