Showing metabocard for LysoPE(18:2(9Z,12Z)/0:0) (BMDB0011507)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:43 UTC
Update Date2020-05-11 20:42:25 UTC
BMDB IDBMDB0011507
Secondary Accession Numbers
  • BMDB11507
Metabolite Identification
Common NameLysoPE(18:2(9Z,12Z)/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(18:2(9Z,12Z)/0:0), in particular, consists of one 9Z,12Z-octadecadienoyl 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
(9Z,12Z-Octadecadienoyl)-lysophosphatidylethanolamineChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphoethanolamineChEBI
1-Linoleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineChEBI
Lyso-pe(18:2n6/0:0)ChEBI
LysoPE(18:2W6/0:0)ChEBI
PE(18:2(9Z,12Z)/0:0)ChEBI
LPE(18:2)HMDB
LPE(18:2/0:0)HMDB
Lyso-pe(18:2)HMDB
Lysophosphatidylethanolamine(18:2/0:0)HMDB
Lysophosphatidylethanolamine(18:2)HMDB
Lyso-pe(18:2/0:0)HMDB
LysoPE(18:2)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(18:2/0:0)HMDB
LPE(18:2n6/0:0)HMDB
LPE(18:2W6/0:0)HMDB
Lyso-pe(18:2W6/0:0)HMDB
LysoPE(18:2n6/0:0)HMDB
Lysophosphatidylethanolamine(18:2n6/0:0)HMDB
Lysophosphatidylethanolamine(18:2W6/0:0)HMDB
1-Linoleoyl-gpeHMDB
1-Linoleoyl-lysophosphatidylethanolamineHMDB
1-Linoleoyl-sn-glycero-3-phosphoethanolamineHMDB
GPE(18:2(9Z,12Z))HMDB
GPE(18:2(9Z,12Z)/0:0)HMDB
GPE(18:2)HMDB
GPE(18:2n6)HMDB
GPE(18:2n6/0:0)HMDB
GPE(18:2W6)HMDB
GPE(18:2W6/0:0)HMDB
LPE(18:2(9Z,12Z))HMDB
LPE(18:2(9Z,12Z)/0:0)HMDB
LPE(18:2n6)HMDB
LPE(18:2W6)HMDB
LysoPE(18:2(9Z,12Z))HMDB
LysoPE(18:2n6)HMDB
LysoPE(18:2W6)HMDB
Lysophosphatidylethanolamine(18:2(9Z,12Z))HMDB
Lysophosphatidylethanolamine(18:2(9Z,12Z)/0:0)HMDB
Lysophosphatidylethanolamine(18:2n6)HMDB
Lysophosphatidylethanolamine(18:2W6)HMDB
LysoPE(18:2(9Z,12Z)/0:0)Lipid Annotator, ChEBI
Chemical FormulaC23H44NO7P
Average Molecular Weight477.5717
Monoisotopic Molecular Weight477.285539279
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid
CAS Registry Number85046-18-0
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h6-7,9-10,22,25H,2-5,8,11-21,24H2,1H3,(H,27,28)/b7-6-,10-9-/t22-/m1/s1
InChI KeyDBHKHNGBVGWQJE-USWSLJGRSA-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
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
logP4.66ALOGPS
logP3.7ChemAxon
logS-5.3ALOGPS
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
Refractivity128.85 m³·mol⁻¹ChemAxon
Polarizability53.23 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, Positivesplash10-0uec-1920200000-2736c34b2b299311ef9aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03n9-3290200000-a7ee0d1a6bdee1339f7dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 36V, Positivesplash10-004i-0090000000-dfd6d89a9c0498ca5510View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121200000-1df6e76d25b4656375d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121100000-78baf2504825977759d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-5220828b50893ed6c6ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1290500000-5f409c7f21e2a4e8afc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6490100000-dc8606018ec83a480ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-0d24bd97678298d1846dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-bd22f4716d37e92e667dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4890800000-eacd4ac5ea754f72a894View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2590000000-295a55250c1d49d7e48cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-7008900000-78327ddd9081fe72f5bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9103100000-8b4444fdc1418813cbcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-b63cc618a1bd0c58d57dView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011507
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028223
KNApSAcK IDNot Available
Chemspider ID24769385
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925130
PDB IDNot Available
ChEBI ID83058
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available