Showing metabocard for LysoPE(22:4(7Z,10Z,13Z,16Z)/0:0) (LMDB00563)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:37 UTC
Update Date2016-07-20 21:04:16 UTC
LmdbLMDB00563
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPE(22:4(7Z,10Z,13Z,16Z)/0:0)
DescriptionLysoPE(22:4(7Z,10Z,13Z,16Z)/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
(7Z,10Z,13Z,16Z-Docosatetraenoyl)-lysophosphatidylethanolamineHMDB
1-Adrenoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(22:4)HMDB
LPE(22:4/0:0)HMDB
LPE(22:4n6/0:0)HMDB
LPE(22:4W6/0:0)HMDB
Lyso-pe(22:4)HMDB
Lyso-pe(22:4/0:0)HMDB
Lyso-pe(22:4n6/0:0)HMDB
Lyso-pe(22:4W6/0:0)HMDB
LysoPE(22:4)HMDB
LysoPE(22:4/0:0)HMDB
LysoPE(22:4n6/0:0)HMDB
LysoPE(22:4W6/0:0)HMDB
Lysophosphatidylethanolamine(22:4)HMDB
Lysophosphatidylethanolamine(22:4/0:0)HMDB
Lysophosphatidylethanolamine(22:4n6/0:0)HMDB
Lysophosphatidylethanolamine(22:4W6/0:0)HMDB
1-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(22:4(7Z,10Z,13Z,16Z)/0:0)Lipid Annotator
Chemical FormulaC27H48NO7P
Average Molecular Weight529.6463
Monoisotopic Molecular Weight529.316839407
IUPAC Name(2-aminoethoxy)[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C27H48NO7P/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/h6-7,9-10,12-13,15-16,26,29H,2-5,8,11,14,17-25,28H2,1H3,(H,31,32)/b7-6-,10-9-,13-12-,16-15-/t26-/m1/s1
InChI KeyNJHKGJJIKOCCMZ-YMIVKDKMSA-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
logP5.3ALOGPS
logP4.75ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity149.48 m³·mol⁻¹ChemAxon
Polarizability59.24 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, Positivesplash10-0udu-2921200000-e8999fb8eb5d65925147Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0f7c-8972070000-879e9cf188fd4b56e78dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPE(22:4(7Z,10Z,13Z,16Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9102020000-25723142f84ffaf45400Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9112000000-c862653feee612a6d351Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9022000000-af8226a0a7bdae35f6a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01si-1209230000-f510d484dfb23f847aa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sl-6519000000-2f70c2d850c8e7f4b1ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9101000000-2279a0046b4a478c21d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-6005190000-df91a3799e919c1b6809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9005200000-22262a6dbca13c990b0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9622000000-28affc5b28eccbe87863Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000490000-c39c4e281e7556a2a79bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6927270000-9a9f7588ba19d5fdfa88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2509000000-5248f2259cda5a7da180Spectrum
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 IDHMDB0011523
FooDB IDFDB028239
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24769400
ChEBI IDNot Available
PubChem Compound ID52925133
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available