Showing metabocard for LysoPE(20:3(5Z,8Z,11Z)/0:0) (BMDB0011515)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:52 UTC
Update Date2020-05-11 19:17:58 UTC
BMDB IDBMDB0011515
Secondary Accession Numbers
  • BMDB11515
Metabolite Identification
Common NameLysoPE(20:3(5Z,8Z,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(20:3(5Z,8Z,11Z)/0:0), in particular, consists of one 5Z,8Z,11Z-eicosatrienoyl 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-Eicosatrienoyl)-lysophosphatidylethanolamineHMDB
1-Meadoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(20:3)HMDB
LPE(20:3/0:0)HMDB
LPE(20:3n9/0:0)HMDB
LPE(20:3W9/0:0)HMDB
Lyso-pe(20:3)HMDB
Lyso-pe(20:3/0:0)HMDB
Lyso-pe(20:3n9/0:0)HMDB
Lyso-pe(20:3W9/0:0)HMDB
LysoPE(20:3)HMDB
LysoPE(20:3/0:0)HMDB
LysoPE(20:3n9/0:0)HMDB
LysoPE(20:3W9/0:0)HMDB
Lysophosphatidylethanolamine(20:3)HMDB
Lysophosphatidylethanolamine(20:3/0:0)HMDB
Lysophosphatidylethanolamine(20:3n9/0:0)HMDB
Lysophosphatidylethanolamine(20:3W9/0:0)HMDB
1-(5Z,8Z,11Z-Eicosatrienoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC25H46NO7P
Average Molecular Weight503.609
Monoisotopic Molecular Weight503.301189343
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H46NO7P/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/h9-10,12-13,15-16,24,27H,2-8,11,14,17-23,26H2,1H3,(H,29,30)/b10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyYBDFPZJQBYCWBA-WMTBOZPISA-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
logP5.12ALOGPS
logP4.22ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity139.17 m³·mol⁻¹ChemAxon
Polarizability56.87 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, Positivesplash10-0uec-2930200000-93904c545b68448d0bb1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-3190200000-00a953fe0514964260b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-2489450000-2082d2eb181960e749b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-9657100000-3f77b284ae6fd75ffbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-2a5012ca171d327049b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000490000-786daf9c93de8a3f30f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-5935250000-153a6516fc02401b52fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2509000000-4b30132f4a43b58b1866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9111110000-bc45d84709ec65fa80b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-0845078a607d233c8ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-05f761f8b7ec7385a465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-5005190000-4f62ef5462326151991aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9004200000-fe5db9ac894a71a641ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9611000000-ab2793f569f34e953f74View 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 IDHMDB0011515
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028231
KNApSAcK IDNot Available
Chemspider ID24769393
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480951
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available