Showing metabocard for LysoPE(0:0/20:4(8Z,11Z,14Z,17Z)) (BMDB0011488)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:20 UTC
Update Date2020-05-11 19:17:36 UTC
BMDB IDBMDB0011488
Secondary Accession Numbers
  • BMDB11488
Metabolite Identification
Common NameLysoPE(0:0/20:4(8Z,11Z,14Z,17Z))
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(0:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one 8Z,11Z,14Z,17Z-eicosapentaenoyl 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
LPE 0:0/20:4(8Z,11Z,14Z,17Z)ChEBI
LPE(0:0/20:4(8Z,11Z,14Z,17Z))ChEBI
Lyso-pe(0:0/20:4(8Z,11Z,14Z,17Z))ChEBI
PE 0:0/20:4(8Z,11Z,14Z,17Z)ChEBI
PE(0:0/20:4(8Z,11Z,14Z,17Z))ChEBI
(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-eicsoateHMDB
1-Hydroxy-2-eicsoatetraenoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Hydroxy-2-eicsoic acidHMDB
LPE(0:0/20:4)HMDB
LPE(0:0/20:4n3)HMDB
LPE(0:0/20:4W3)HMDB
LPE(20:4)HMDB
Lyso-pe(0:0/20:4)HMDB
Lyso-pe(0:0/20:4n3)HMDB
Lyso-pe(0:0/20:4W3)HMDB
Lyso-pe(20:4)HMDB
LysoPE(0:0/20:4)HMDB
LysoPE(0:0/20:4n3)HMDB
LysoPE(0:0/20:4W3)HMDB
LysoPE(20:4)HMDB
Lysophosphatidylethanolamine(0:0/20:4)HMDB
Lysophosphatidylethanolamine(0:0/20:4n3)HMDB
Lysophosphatidylethanolamine(0:0/20:4W3)HMDB
Lysophosphatidylethanolamine(20:4)HMDB
1-Hydroxy-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/20:4(8Z,11Z,14Z,17Z))Lipid Annotator, ChEBI
Chemical FormulaC25H44NO7P
Average Molecular Weight501.5931
Monoisotopic Molecular Weight501.285539279
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C25H44NO7P/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/h3-4,6-7,9-10,12-13,24,27H,2,5,8,11,14-23,26H2,1H3,(H,29,30)/b4-3-,7-6-,10-9-,13-12-/t24-/m1/s1
InChI KeyBAKUYTLDCVITBO-YSKCIPFOSA-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 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
logP4.49ALOGPS
logP3.86ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity140.28 m³·mol⁻¹ChemAxon
Polarizability55.3 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, Positivesplash10-0535-7930300000-36bc379995505593cec0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9770030000-6b05c17df58e99c472daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-a56308dcd6eb2da78742View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-bc8af4b08612efc7b20fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-0586012a64698032fd67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3946760000-0c063fbdf2af0562ea36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9521100000-d90cc1c8972c7feae754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-681a1c9b637f3e3e117fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-5016970000-7042b03bec44fd8a8d20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-9338600000-3c72cea07a077667d00dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9321000000-4cfc6edeae29464779e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1600590000-5642f83458123249ce21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9611010000-30854e49cd542c08ef0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-9b3bc3cee971f1e7da97View 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 IDHMDB0011488
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028204
KNApSAcK IDNot Available
Chemspider ID24769369
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480937
PDB IDNot Available
ChEBI ID72746
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available