Showing metabocard for LysoPE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0011496)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:30 UTC
Update Date2020-05-11 19:17:43 UTC
BMDB IDBMDB0011496
Secondary Accession Numbers
  • BMDB11496
Metabolite Identification
Common NameLysoPE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
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(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), 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 0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)ChEBI
LPE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))ChEBI
Lyso-pe(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))ChEBI
PE 0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)ChEBI
PE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))ChEBI
(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/22:6)HMDB
LPE(0:0/22:6n3)HMDB
LPE(0:0/22:6W3)HMDB
LPE(22:6)HMDB
Lyso-pe(0:0/22:6)HMDB
Lyso-pe(0:0/22:6n3)HMDB
Lyso-pe(0:0/22:6W3)HMDB
Lyso-pe(22:6)HMDB
LysoPE(0:0/22:6)HMDB
LysoPE(0:0/22:6n3)HMDB
LysoPE(0:0/22:6W3)HMDB
LysoPE(22:6)HMDB
Lysophosphatidylethanolamine(0:0/22:6)HMDB
Lysophosphatidylethanolamine(0:0/22:6n3)HMDB
Lysophosphatidylethanolamine(0:0/22:6W3)HMDB
Lysophosphatidylethanolamine(22:6)HMDB
1-Hydroxy-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator, ChEBI
Chemical FormulaC27H44NO7P
Average Molecular Weight525.6145
Monoisotopic Molecular Weight525.285539279
IUPAC Name(2-aminoethoxy)[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-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/C\C=C/CC
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)35-26(24-29)25-34-36(31,32)33-23-22-28/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 KeyTWBVHOYVCUOMJY-PAUXXPOVSA-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 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
logP4.79ALOGPS
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
Polarizability55.67 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, Positivesplash10-001j-7951200000-0c28e55fd06d9f61a89bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9671030000-5c5548c3034c9d7d5d63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9102020000-a70484399e2533514d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9112000000-638907270a9d5a83f364View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9021000000-4ef76072442dc5266ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-3937580000-067930dff2397a1ef579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9512110000-4bf75e392d5518d4a61bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-5621a9bd4f97ac271991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-1500590000-9d16ab710816c1b0b238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9501010000-b757a0c7cf74c32fdf6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9301000000-11ff26249d3cd6d60ce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-005i-4004970000-f3d9661dd8d70e339ec1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01px-6219410000-671092ad09a8c93130ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9341000000-972c23ccae76bc3e47b9View 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 IDHMDB0011496
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028212
KNApSAcK IDNot Available
Chemspider ID24769377
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480945
PDB IDNot Available
ChEBI ID72749
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available