Showing metabocard for LysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0011526)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:20:06 UTC
Update Date2020-05-11 19:18:08 UTC
BMDB IDBMDB0011526
Secondary Accession Numbers
  • BMDB11526
Metabolite Identification
Common NameLysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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
LPE 22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0ChEBI
LPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
Lyso-pe(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
PE 22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0ChEBI
PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-lysophosphatidylethanolamineHMDB
1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(22:6)HMDB
LPE(22:6/0:0)HMDB
LPE(22:6n3/0:0)HMDB
LPE(22:6W3/0:0)HMDB
Lyso-pe(22:6)HMDB
Lyso-pe(22:6/0:0)HMDB
Lyso-pe(22:6n3/0:0)HMDB
Lyso-pe(22:6W3/0:0)HMDB
LysoPE(22:6)HMDB
LysoPE(22:6/0:0)HMDB
LysoPE(22:6n3/0:0)HMDB
LysoPE(22:6W3/0:0)HMDB
Lysophosphatidylethanolamine(22:6)HMDB
Lysophosphatidylethanolamine(22:6/0:0)HMDB
Lysophosphatidylethanolamine(22:6n3/0:0)HMDB
Lysophosphatidylethanolamine(22:6W3/0:0)HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)Lipid Annotator, ChEBI
Chemical FormulaC27H44NO7P
Average Molecular Weight525.6145
Monoisotopic Molecular Weight525.285539279
IUPAC Name(2-aminoethoxy)[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C27H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(30)33-24-26(29)25-35-36(31,32)34-23-22-28/h3-4,6-7,9-10,12-13,15-16,18-19,26,29H,2,5,8,11,14,17,20-25,28H2,1H3,(H,31,32)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-/t26-/m1/s1
InChI KeyXEVRBOQZSXWGQO-PAUXXPOVSA-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 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
logP4.83ALOGPS
logP4.03ChemAxon
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
Refractivity151.72 m³·mol⁻¹ChemAxon
Polarizability56.55 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, Positivesplash10-0f8c-1931200000-7f3fbb311421dae20ba4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03n9-4191200000-1c2283427274b0332f6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9102020000-ca00c0a4dcef061e56b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9112100000-e32a9c8765aeed05f439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9022000000-f9df2d08dbb4cd721788View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-1209240000-05dfa1755f99b786a15cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6519000000-ca44381047efa71f6348View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-6b0c9b9c70eb1ebfbe30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6008790000-0cb1fecf83bee4e7d299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9104100000-8ac8dae348bddc372d70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9682000000-42a9ed90b3777e3f7a2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000490000-196c704e021cd61f99abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-7937380000-b68471a66f83ec37c237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3907100000-cd4805fcee490c907e17View 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 IDHMDB0011526
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028242
KNApSAcK IDNot Available
Chemspider ID24769403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925132
PDB IDNot Available
ChEBI ID72747
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available