Showing metabocard for LysoPE(0:0/20:4(5Z,8Z,11Z,14Z)) (BMDB0011487)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:19 UTC
Update Date2020-05-11 19:17:35 UTC
BMDB IDBMDB0011487
Secondary Accession Numbers
  • BMDB11487
Metabolite Identification
Common NameLysoPE(0:0/20:4(5Z,8Z,11Z,14Z))
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(5Z,8Z,11Z,14Z)), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl 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-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoethanolamineChEBI
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoethanolamineChEBI
2-ArachidonoyllysophosphatidylethanolamineChEBI
LPE 0:0/20:4(5Z,8Z,11Z,14Z)ChEBI
LPE(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
Lyso-pe(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
Lysophosphatidylethanolamine 0:0/20:4(5Z,8Z,11Z,14Z)ChEBI
PE 0:0/20:4(5Z,8Z,11Z,14Z)ChEBI
PE(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-arachidonoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/20:4)HMDB
LPE(0:0/20:4n6)HMDB
LPE(0:0/20:4W6)HMDB
LPE(20:4)HMDB
Lyso-pe(0:0/20:4)HMDB
Lyso-pe(0:0/20:4n6)HMDB
Lyso-pe(0:0/20:4W6)HMDB
Lyso-pe(20:4)HMDB
LysoPE(0:0/20:4)HMDB
LysoPE(0:0/20:4n6)HMDB
LysoPE(0:0/20:4W6)HMDB
LysoPE(20:4)HMDB
Lysophosphatidylethanolamine(0:0/20:4)HMDB
Lysophosphatidylethanolamine(0:0/20:4n6)HMDB
Lysophosphatidylethanolamine(0:0/20:4W6)HMDB
Lysophosphatidylethanolamine(20:4)HMDB
1-Hydroxy-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator, ChEBI
Chemical FormulaC25H44NO7P
Average Molecular Weight501.5931
Monoisotopic Molecular Weight501.285539279
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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/h6-7,9-10,12-13,15-16,24,27H,2-5,8,11,14,17-23,26H2,1H3,(H,29,30)/b7-6-,10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyYWOCITMXHHTBAW-XSQXPFHXSA-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
logP4.64ALOGPS
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
Polarizability54.93 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, Positivesplash10-053v-9850400000-735751bd5062987db5d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-8590040000-d53b2807b6920fa18acbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-13328b2bb438d100f252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-c20ccb5fa31455881778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9020000000-f9c147af74952470c16eView 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, Negativesplash10-0udr-1600590000-0bd4ab5b8f7b3caf440aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9611010000-43fce7486741970c57d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-9b3bc3cee971f1e7da97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-6218980000-49007b00b22f72c6dec5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-7339600000-06a9736a8e0356ceb25eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9311000000-e0dafc3f8c4c144892e4View 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 IDHMDB0011487
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028203
KNApSAcK IDNot Available
Chemspider ID24769368
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480936
PDB IDNot Available
ChEBI ID72741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available