Showing metabocard for LysoPE(20:3(11Z,14Z,17Z)/0:0) (BMDB0011514)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:51 UTC
Update Date2020-05-11 19:17:58 UTC
BMDB IDBMDB0011514
Secondary Accession Numbers
  • BMDB11514
Metabolite Identification
Common NameLysoPE(20:3(11Z,14Z,17Z)/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(20:3(11Z,14Z,17Z)/0:0), in particular, consists of one 11Z,14Z,17Z-eicosatrienoyl 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
(11Z,14Z,17Z-Eicosatetraenoyl)-lysophosphatidylethanolamineHMDB
LysoPE(20:3/0:0)HMDB
LPE(20:3)HMDB
LPE(20:3/0:0)HMDB
Lysophosphatidylethanolamine(20:3/0:0)HMDB
Lysophosphatidylethanolamine(20:3)HMDB
1-Eicosatrienoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
Lyso-pe(20:3/0:0)HMDB
LysoPE(20:3)HMDB
1-(11Z,14Z,17Z-Eicosatetraenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
Lyso-pe(20:3)HMDB
LysoPE(20:3(11Z,14Z,17Z)/0:0)Lipid Annotator
Chemical FormulaC25H46NO7P
Average Molecular Weight503.609
Monoisotopic Molecular Weight503.301189343
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-hydroxy-3-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCC\C=C/C\C=C/C\C=C/CC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26/h3-4,6-7,9-10,24,27H,2,5,8,11-23,26H2,1H3,(H,29,30)/b4-3-,7-6-,10-9-/t24-/m1/s1
InChI KeyUEONHLLDVDPRRN-WCABUCBOSA-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 DescriptorsNot Available
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
logP5.03ALOGPS
logP4.22ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity139.17 m³·mol⁻¹ChemAxon
Polarizability57.16 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, Positivesplash10-0udl-2920200000-a90c63c747de0af5522cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-4290200000-7a223a62784555aa2370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9111110000-693ba99d8a6d26852c3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121100000-77af6dd70ec0ef0d3583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-e02a594b9c0eff185408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-2489450000-2082d2eb181960e749b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-9657100000-3f77b284ae6fd75ffbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9100000000-2a5012ca171d327049b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6009380000-496048eba5b80cd14911View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9004100000-f13355f9d1c2eddf0611View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9411000000-b9ae955ee0ff4cd5ea2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000490000-786daf9c93de8a3f30f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-5934250000-ad29a7ae0f25189520aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2509000000-9516148c39c1fbc821e1View 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 IDHMDB0011514
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028230
KNApSAcK IDNot Available
Chemspider ID24769392
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480950
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available