Showing metabocard for LysoPE(22:1(13Z)/0:0) (BMDB0011521)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:20:00 UTC
Update Date2020-05-11 19:18:03 UTC
BMDB IDBMDB0011521
Secondary Accession Numbers
  • BMDB11521
Metabolite Identification
Common NameLysoPE(22:1(13Z)/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(22:1(13Z)/0:0), in particular, consists of one 13Z-docosenoyl 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
(13Z-Docosenoyl)-lysophosphatidylethanolamineHMDB
1-Erucoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(22:1)HMDB
LPE(22:1/0:0)HMDB
LPE(22:1n9/0:0)HMDB
LPE(22:1W9/0:0)HMDB
Lyso-pe(22:1)HMDB
Lyso-pe(22:1/0:0)HMDB
Lyso-pe(22:1n9/0:0)HMDB
Lyso-pe(22:1W9/0:0)HMDB
LysoPE(22:1)HMDB
LysoPE(22:1/0:0)HMDB
LysoPE(22:1n9/0:0)HMDB
LysoPE(22:1W9/0:0)HMDB
Lysophosphatidylethanolamine(22:1)HMDB
Lysophosphatidylethanolamine(22:1/0:0)HMDB
Lysophosphatidylethanolamine(22:1n9/0:0)HMDB
Lysophosphatidylethanolamine(22:1W9/0:0)HMDB
1-(13Z-Docosenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(22:1(13Z)/0:0)Lipid Annotator
Chemical FormulaC27H54NO7P
Average Molecular Weight535.6939
Monoisotopic Molecular Weight535.363789599
IUPAC Name(2-aminoethoxy)[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C27H54NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(30)33-24-26(29)25-35-36(31,32)34-23-22-28/h9-10,26,29H,2-8,11-25,28H2,1H3,(H,31,32)/b10-9-/t26-/m1/s1
InChI KeyXHNHVLOJRORARF-RASRKNKNSA-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 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
logP6.05ALOGPS
logP5.84ChemAxon
logS-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 Count28ChemAxon
Refractivity146.14 m³·mol⁻¹ChemAxon
Polarizability63.5 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-2911200000-83160f1d6b9b49200afeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01xx-4291210000-0e85e43fb8d5c62795f0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPE(22:1(13Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9103020000-0d73609c01c3931a7e81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9102000000-f62e3553149190d9e0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9022000000-4898aeb50d9c05740de4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00li-1209230000-8eeb8d82989830778b91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00n3-6519000000-c61e8f4a948be059ac3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-8b38c8d1633394868842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000490000-908e7cdd0db5ba7aeac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001u-4917260000-213ee8fe45151d7c85a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1409100000-e5c583e6abaa6059482eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4005090000-2e13227dd0dc62fcf3aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9104200000-48ce2fd3e7ff0dfed597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9402000000-c9cb32b5b5b36a6dd79dView 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 IDHMDB0011521
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028237
KNApSAcK IDNot Available
Chemspider ID24769398
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480953
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available