Showing metabocard for LysoPE(0:0/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0011489)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:21 UTC
Update Date2020-05-11 19:17:37 UTC
BMDB IDBMDB0011489
Secondary Accession Numbers
  • BMDB11489
Metabolite Identification
Common NameLysoPE(0:0/20:5(5Z,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(0:0/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one 5Z,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
(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-eicosapentaenoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/20:5)HMDB
LPE(0:0/20:5n3)HMDB
LPE(0:0/20:5W3)HMDB
LPE(20:5)HMDB
Lyso-pe(0:0/20:5)HMDB
Lyso-pe(0:0/20:5n3)HMDB
Lyso-pe(0:0/20:5W3)HMDB
Lyso-pe(20:5)HMDB
LysoPE(0:0/20:5)HMDB
LysoPE(0:0/20:5n3)HMDB
LysoPE(0:0/20:5W3)HMDB
LysoPE(20:5)HMDB
Lysophosphatidylethanolamine(0:0/20:5)HMDB
Lysophosphatidylethanolamine(0:0/20:5n3)HMDB
Lysophosphatidylethanolamine(0:0/20:5W3)HMDB
Lysophosphatidylethanolamine(20:5)HMDB
1-Hydroxy-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC25H42NO7P
Average Molecular Weight499.5772
Monoisotopic Molecular Weight499.269889215
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]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/C\C=C/CC
InChI Identifier
InChI=1S/C25H42NO7P/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/h3-4,6-7,9-10,12-13,15-16,24,27H,2,5,8,11,14,17-23,26H2,1H3,(H,29,30)/b4-3-,7-6-,10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyMMHCCHGAKPRCIO-KOYQJJOGSA-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
logP4.26ALOGPS
logP3.5ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity141.4 m³·mol⁻¹ChemAxon
Polarizability54.01 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, Positivesplash10-06s5-7950200000-4ef00c129e6ed4ee0c7aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ur-9580030000-542d92343c2f2e1e0d4eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121010000-6b0eb75f9b0dae6da656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-44b90371fea49418de73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9020000000-59e34f46f8e5d627078eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2533900000-3b0bb93de5a24cd1ad5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9521200000-13c73ee068bcb202f5b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-5c3f1bbdfd64b9dc0ee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-4006960000-e036f6393e4c78b3c587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9448600000-057fd6bcb1f117bc091fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9421000000-182d7d5662e90e9a5585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1300900000-1c03eea9a326c7360c71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-9502100000-e0bafe6264f4ffd6f028View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-2c71ae5862996eac270bView 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 IDHMDB0011489
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028205
KNApSAcK IDNot Available
Chemspider ID24769370
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480938
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available