Showing metabocard for LysoPE(0:0/16:1(9Z)) (BMDB0011474)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:04 UTC
Update Date2020-05-11 19:17:24 UTC
BMDB IDBMDB0011474
Secondary Accession Numbers
  • BMDB11474
Metabolite Identification
Common NameLysoPE(0:0/16:1(9Z))
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(0:0/16:1(9Z)), in particular, consists of one 9Z-hexadecenoyl 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-Hexadecenoyl)-lysophosphatidylethanolamineHMDB
1-Hydroxy-2-palmitoleoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/16:1)HMDB
LPE(0:0/16:1n7)HMDB
LPE(0:0/16:1W7)HMDB
LPE(16:1)HMDB
Lyso-pe(0:0/16:1)HMDB
Lyso-pe(0:0/16:1n7)HMDB
Lyso-pe(0:0/16:1W7)HMDB
Lyso-pe(16:1)HMDB
LysoPE(0:0/16:1)HMDB
LysoPE(0:0/16:1n7)HMDB
LysoPE(0:0/16:1W7)HMDB
LysoPE(16:1)HMDB
Lysophosphatidylethanolamine(0:0/16:1)HMDB
Lysophosphatidylethanolamine(0:0/16:1n7)HMDB
Lysophosphatidylethanolamine(0:0/16:1W7)HMDB
Lysophosphatidylethanolamine(16:1)HMDB
1-Hydroxy-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(0:0/16:1(9Z))Lipid Annotator
Chemical FormulaC21H42NO7P
Average Molecular Weight451.5344
Monoisotopic Molecular Weight451.269889215
IUPAC Name(2-aminoethoxy)[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C21H42NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)29-20(18-23)19-28-30(25,26)27-17-16-22/h7-8,20,23H,2-6,9-19,22H2,1H3,(H,25,26)/b8-7-/t20-/m1/s1
InChI KeyMAFRHGZTIOAXEL-WHXUGTBJSA-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 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
logP3.89ALOGPS
logP3.17ChemAxon
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
Refractivity118.53 m³·mol⁻¹ChemAxon
Polarizability50.79 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, Positivesplash10-0a5a-7931200000-4e157e94c0352237161eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9770300000-49dfb795abdac255f1c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9120200000-68006cd587483027d5d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-2db08b3ed401e49d9851View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-6a4e1197d6c85ed5de32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2671900000-1448323f87aa08c6efe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9530200000-a60b187bccbe0ab7ba78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-42eb9ce8adecb7e9e623View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1102900000-96d5b86f5445c6a2c949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-6951300000-3ae8cdc1bc9d718efc50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-9c3c401c147cd5b851b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-114i-2014900000-ab5d4e7ff6b246d05a3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-6329300000-e3e8d58a4dde3cc5ace1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-9a518a2b0df937328784View 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 IDHMDB0011474
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028190
KNApSAcK IDNot Available
Chemspider ID24769355
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480923
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available