Showing metabocard for LysoPE(0:0/20:0) (BMDB0011481)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:12 UTC
Update Date2020-05-11 19:17:30 UTC
BMDB IDBMDB0011481
Secondary Accession Numbers
  • BMDB11481
Metabolite Identification
Common NameLysoPE(0:0/20:0)
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(0:0/20:0), 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
(2-Aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinic acidChEBI
1-Hydroxy-2-arachidonyl-sn-glycero-3-phosphoethanolamineChEBI
2-Arachidoyl-sn-glycero-3-phosphoethanolamineChEBI
2-Eicosanoyl-sn-glycero-3-phosphoethanolamineChEBI
Eicosanoyl-lysophosphatidylethanolamineChEBI
LPE(0:0/20:0)ChEBI
LPE(20:0)ChEBI
Lyso-pe(0:0/20:0)ChEBI
Lyso-pe(20:0)ChEBI
LysoPE(20:0)ChEBI
Lysophosphatidylethanolamine(0:0/20:0)ChEBI
Lysophosphatidylethanolamine(20:0)ChEBI
(2-Aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinateGenerator
LysoPE(0:0/20:0)Lipid Annotator
1-hydroxy-2-eicosanoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
2-ArachidoylglycerophosphoethanolamineHMDB
2-EicosanoylglycerophosphoethanolamineHMDB
Chemical FormulaC25H52NO7P
Average Molecular Weight509.6566
Monoisotopic Molecular Weight509.348139535
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-(icosanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-(icosanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCCCC
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)33-24(22-27)23-32-34(29,30)31-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1
InChI KeyQEQAJJJSRGAOOG-XMMPIXPASA-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
logP5.43ALOGPS
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
Polarizability60.8 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, Positivesplash10-00l5-9840200000-29216a8373f6d4ef7751View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00sj-9580030000-e835a8c95da2996f6af6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-c42f4819c295ce972cd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-9dda2ee2e63d37d2c11aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-52dc8a6f626408eb31dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fv-3946660000-a63e224a3935c224ce53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tc-9521100000-aadf3e5ed57c3d4dee69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-f9b70d38b4722a270ee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-4039870000-ac78f0694881b103017cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3219300000-ef674c8bb64e78b5e587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9401000000-dc73bd44c8697b2ba8a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1200290000-86df1dc6d258df78a238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3429010000-aadd65d03ab57b6c3857View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-e0916c7ecf3244017e41View 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 IDHMDB0011481
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028197
KNApSAcK IDNot Available
Chemspider ID24769362
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480930
PDB IDNot Available
ChEBI ID131691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available