Showing metabocard for LysoPE(0:0/22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0011494)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:27 UTC
Update Date2020-05-11 19:17:41 UTC
BMDB IDBMDB0011494
Secondary Accession Numbers
  • BMDB11494
Metabolite Identification
Common NameLysoPE(0:0/22:5(4Z,7Z,10Z,13Z,16Z))
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(0:0/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z-docosapentaenoyl 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
(4Z,7Z,10Z,13Z,16Z-Docosapentaenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-osbondoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/22:5)HMDB
LPE(0:0/22:5n6)HMDB
LPE(0:0/22:5W6)HMDB
LPE(22:5)HMDB
Lyso-pe(0:0/22:5)HMDB
Lyso-pe(0:0/22:5n6)HMDB
Lyso-pe(0:0/22:5W6)HMDB
Lyso-pe(22:5)HMDB
LysoPE(0:0/22:5)HMDB
LysoPE(0:0/22:5n6)HMDB
LysoPE(0:0/22:5W6)HMDB
LysoPE(22:5)HMDB
Lysophosphatidylethanolamine(0:0/22:5)HMDB
Lysophosphatidylethanolamine(0:0/22:5n6)HMDB
Lysophosphatidylethanolamine(0:0/22:5W6)HMDB
Lysophosphatidylethanolamine(22:5)HMDB
1-Hydroxy-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/22:5(4Z,7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC27H46NO7P
Average Molecular Weight527.6304
Monoisotopic Molecular Weight527.301189343
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C27H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(30)35-26(24-29)25-34-36(31,32)33-23-22-28/h6-7,9-10,12-13,15-16,18-19,26,29H,2-5,8,11,14,17,20-25,28H2,1H3,(H,31,32)/b7-6-,10-9-,13-12-,16-15-,19-18-/t26-/m1/s1
InChI KeyZMHRXVSSWJALGN-GOGKNFEWSA-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
logP5ALOGPS
logP4.39ChemAxon
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
Refractivity150.6 m³·mol⁻¹ChemAxon
Polarizability57.07 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, Positivesplash10-0012-8950400000-96439090369b0d187ad6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mj-6291110000-e4f83a8a3a3f82d22cf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9102020000-e011ad5eb67725d5ebc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9112000000-d2e8b0927e902ea12a8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9011000000-5094775361c6342985d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3937580000-3b01ba8476e04046e05eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9512110000-3bb044cc9b129b301eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-a63eafae4d9713e8c081View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-5206980000-053202fbb8d1c654f9e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-5319510000-1255405a5106fec6c18cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9421000000-1a31667f5dc0b5a0a949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1600590000-fecc6a88d3db751f4f32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9502010000-0f549cbf690f78f6ca90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-ef0cf68a8dbed5553d30View 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 IDHMDB0011494
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028210
KNApSAcK IDNot Available
Chemspider ID24769375
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480943
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available