Showing metabocard for LysoPE(20:1(11Z)/0:0) (BMDB0011512)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:49 UTC
Update Date2020-05-11 19:17:56 UTC
BMDB IDBMDB0011512
Secondary Accession Numbers
  • BMDB11512
Metabolite Identification
Common NameLysoPE(20:1(11Z)/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(20:1(11Z)/0:0), in particular, consists of one 11Z-eicosenoyl 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
(11-Eicosenoyl)-lysophosphatidylethanolamineHMDB
1-Eicosenoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(20:1)HMDB
LPE(20:1/0:0)HMDB
LPE(20:1n9/0:0)HMDB
LPE(20:1W9/0:0)HMDB
Lyso-pe(20:1)HMDB
Lyso-pe(20:1/0:0)HMDB
Lyso-pe(20:1n9/0:0)HMDB
Lyso-pe(20:1W9/0:0)HMDB
LysoPE(20:1)HMDB
LysoPE(20:1/0:0)HMDB
LysoPE(20:1n9/0:0)HMDB
LysoPE(20:1W9/0:0)HMDB
Lysophosphatidylethanolamine(20:1)HMDB
Lysophosphatidylethanolamine(20:1/0:0)HMDB
Lysophosphatidylethanolamine(20:1n9/0:0)HMDB
Lysophosphatidylethanolamine(20:1W9/0:0)HMDB
1-(11-Eicosenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(20:1(11Z)/0:0)Lipid Annotator
Chemical FormulaC25H50NO7P
Average Molecular Weight507.6408
Monoisotopic Molecular Weight507.332489471
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H50NO7P/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/h9-10,24,27H,2-8,11-23,26H2,1H3,(H,29,30)/b10-9-/t24-/m1/s1
InChI KeyJEAGLCKGAKACCE-OPSAWKISSA-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
logP5.37ALOGPS
logP4.95ChemAxon
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 Count26ChemAxon
Refractivity136.93 m³·mol⁻¹ChemAxon
Polarizability59.18 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, Positivesplash10-0f6x-2920200000-331c37cd0b9a4476b269View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02nj-8590050000-1ca9163b432ea5dfe5a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9111010000-b7c1ae1533167310db6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-61bcec085ea841766fd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-749d968e9ba7b39260ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-2489550000-b4700d811c9969509cfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054o-9657100000-d7858ab52eb0ea2e0696View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-90cdb1615c93a8c167adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000490000-aa00c8ee6c25f6dc4254View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4935360000-9c2ee88aff94327f2b7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1409000000-8dd469d56ab084196695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5106190000-e7d872fbc8265ce9878fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9103200000-f11e086147ba178e420dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9401000000-5a76d1b1aa797878159fView 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 IDHMDB0011512
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028228
KNApSAcK IDNot Available
Chemspider ID24769390
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925139
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available