Showing metabocard for LysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) (LMDB00565)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:39 UTC
Update Date2016-07-20 21:04:16 UTC
LmdbLMDB00565
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
DescriptionLysoPE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a lysophosphatidylethanolamine or 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. 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. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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 KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8c-1931200000-7f3fbb311421dae20ba4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03n9-4191200000-1c2283427274b0332f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9102020000-ca00c0a4dcef061e56b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9112100000-e32a9c8765aeed05f439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9022000000-f9df2d08dbb4cd721788Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-1209240000-05dfa1755f99b786a15cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6519000000-ca44381047efa71f6348Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-6b0c9b9c70eb1ebfbe30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6008790000-0cb1fecf83bee4e7d299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9104100000-8ac8dae348bddc372d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9682000000-42a9ed90b3777e3f7a2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000490000-196c704e021cd61f99abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-7937380000-b68471a66f83ec37c237Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3907100000-cd4805fcee490c907e17Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Sergio Polakof, D...
 details
DrugBank IDNot Available
HMDB IDHMDB0011526
FooDB IDFDB028242
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24769403
ChEBI ID72747
PubChem Compound ID52925132
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available