Showing metabocard for LysoPE(18:3(9Z,12Z,15Z)/0:0) (BMDB0011509)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:45 UTC
Update Date2020-05-11 19:17:53 UTC
BMDB IDBMDB0011509
Secondary Accession Numbers
  • BMDB11509
Metabolite Identification
Common NameLysoPE(18:3(9Z,12Z,15Z)/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(18:3(9Z,12Z,15Z)/0:0), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl 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,15Z-Octadeatrienoyl)-lysophosphatidylethanolamineHMDB
1-a-Linolenoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
1-alpha-Linolenoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(18:3)HMDB
LPE(18:3/0:0)HMDB
LPE(18:3n3/0:0)HMDB
LPE(18:3W3/0:0)HMDB
Lyso-pe(18:3)HMDB
Lyso-pe(18:3/0:0)HMDB
Lyso-pe(18:3n3/0:0)HMDB
Lyso-pe(18:3W3/0:0)HMDB
LysoPE(18:3)HMDB
LysoPE(18:3/0:0)HMDB
LysoPE(18:3n3/0:0)HMDB
LysoPE(18:3W3/0:0)HMDB
Lysophosphatidylethanolamine(18:3)HMDB
Lysophosphatidylethanolamine(18:3/0:0)HMDB
Lysophosphatidylethanolamine(18:3n3/0:0)HMDB
Lysophosphatidylethanolamine(18:3W3/0:0)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC23H42NO7P
Average Molecular Weight475.5558
Monoisotopic Molecular Weight475.269889215
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-hydroxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C23H42NO7P/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/h3-4,6-7,9-10,22,25H,2,5,8,11-21,24H2,1H3,(H,27,28)/b4-3-,7-6-,10-9-/t22-/m1/s1
InChI KeyNTBBASCGALPTDC-WOBXFXBNSA-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
logP4.39ALOGPS
logP3.33ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity129.96 m³·mol⁻¹ChemAxon
Polarizability52.04 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-1920200000-b21ff0f830de784793beView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0iu0-4290020000-f76e9ce26b04aa446ab0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121200000-26a4ead7194ff4d90222View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121000000-ef4fee9db2fc2390e4aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-314cfad9871ee1586c0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-1290500000-e5859ec08595eea47158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6490100000-2406723ed65a755ae935View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-fd70ebbb8a7b6576d16fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4009500000-4ef5b506385314f6acd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9004100000-111d8fdef22aec5e7fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9510000000-9b506cf67cf9f04f4b10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-6afc23dae96a6dd6d2acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-5980800000-a2cb5149c0fdf6354fedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2590000000-169b2b40a1de49d95bf4View 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 IDHMDB0011509
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028225
KNApSAcK IDNot Available
Chemspider ID24769387
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925148
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available