Showing metabocard for LysoPE(0:0/18:4(6Z,9Z,12Z,15Z)) (BMDB0011480)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:11 UTC
Update Date2020-05-11 19:17:29 UTC
BMDB IDBMDB0011480
Secondary Accession Numbers
  • BMDB11480
Metabolite Identification
Common NameLysoPE(0:0/18:4(6Z,9Z,12Z,15Z))
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(0:0/18:4(6Z,9Z,12Z,15Z)), in particular, consists of one 6Z,9Z,12Z,15Z-octadecatetraenoyl 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
(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-stearidonoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/18:4)HMDB
LPE(0:0/18:4n3)HMDB
LPE(0:0/18:4W3)HMDB
LPE(18:4)HMDB
Lyso-pe(0:0/18:4)HMDB
Lyso-pe(0:0/18:4n3)HMDB
Lyso-pe(0:0/18:4W3)HMDB
Lyso-pe(18:4)HMDB
LysoPE(0:0/18:4)HMDB
LysoPE(0:0/18:4n3)HMDB
LysoPE(0:0/18:4W3)HMDB
LysoPE(18:4)HMDB
Lysophosphatidylethanolamine(0:0/18:4)HMDB
Lysophosphatidylethanolamine(0:0/18:4n3)HMDB
Lysophosphatidylethanolamine(0:0/18:4W3)HMDB
Lysophosphatidylethanolamine(18:4)HMDB
1-Hydroxy-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/18:4(6Z,9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC23H40NO7P
Average Molecular Weight473.54
Monoisotopic Molecular Weight473.254239151
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C23H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)31-22(20-25)21-30-32(27,28)29-19-18-24/h3-4,6-7,9-10,12-13,22,25H,2,5,8,11,14-21,24H2,1H3,(H,27,28)/b4-3-,7-6-,10-9-,13-12-/t22-/m1/s1
InChI KeySYKRNJVTCMUCGF-JVBHARQXSA-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
logP3.93ALOGPS
logP2.97ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity131.08 m³·mol⁻¹ChemAxon
Polarizability50.88 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, Positivesplash10-001m-6940200000-a6002d3ec0534ca03e2eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9680120000-7311e5f2e676a97bf9c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9120200000-baa0ed5130e6dbebe03bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-0b8413d3331d1ab258cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9020000000-4091fba48705100a7e7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-2570900000-27dae011445efc2190bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9530200000-5c2f4dd93992a96fd930View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-dd6f0ec56b510e6c39d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-3006900000-e7a9e5f455a1cc69e6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053u-9327500000-02645f9260915c8739ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9310000000-b92fca052de68a7cc4eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1300900000-ba1060d42791979bea01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9620100000-23521cd0869947a2ad2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9310000000-c773734eb27db001ebbfView 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 IDHMDB0011480
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028196
KNApSAcK IDNot Available
Chemspider ID24769361
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480929
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available