Showing metabocard for LysoPE(16:1(9Z)/0:0) (BMDB0011504)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:39 UTC
Update Date2020-05-11 19:17:49 UTC
BMDB IDBMDB0011504
Secondary Accession Numbers
  • BMDB11504
Metabolite Identification
Common NameLysoPE(16:1(9Z)/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(16:1(9Z)/0:0), 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-Palmitoleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(16:1)HMDB
LPE(16:1/0:0)HMDB
LPE(16:1n7/0:0)HMDB
LPE(16:1W7/0:0)HMDB
Lyso-pe(16:1)HMDB
Lyso-pe(16:1/0:0)HMDB
Lyso-pe(16:1n7/0:0)HMDB
Lyso-pe(16:1W7/0:0)HMDB
LysoPE(16:1)HMDB
LysoPE(16:1/0:0)HMDB
LysoPE(16:1n7/0:0)HMDB
LysoPE(16:1W7/0:0)HMDB
Lysophosphatidylethanolamine(16:1)HMDB
Lysophosphatidylethanolamine(16:1/0:0)HMDB
Lysophosphatidylethanolamine(16:1n7/0:0)HMDB
Lysophosphatidylethanolamine(16:1W7/0:0)HMDB
1-(9Z-Hexadecenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LysoPE(16:1(9Z)/0:0)Lipid Annotator
Chemical FormulaC21H42NO7P
Average Molecular Weight451.5344
Monoisotopic Molecular Weight451.269889215
IUPAC Name(2-aminoethoxy)[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/CCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C21H42NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h7-8,20,23H,2-6,9-19,22H2,1H3,(H,25,26)/b8-7-/t20-/m1/s1
InChI KeyDSOWUEHXZJUNID-WHXUGTBJSA-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
logP3.99ALOGPS
logP3.17ChemAxon
logS-5.2ALOGPS
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
Polarizability50.65 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, Positivesplash10-0k9x-2920100000-8c2c0054d14411307ccbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02ji-5390200000-4a4d2b8705acec22be32View 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, Positivesplash10-0006-9121200000-e5e030ac2247473d4bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-4afde7e41dde7e379bf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9220000000-688c27b38b2b5b649882View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-1290400000-c3d61005a3168aff7a5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug3-6490000000-ca7585f4e8dc6cb7f945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-50e7828921698bf2d0d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-5004900000-326e1e4670d78edb6e7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9103100000-bd046a3553de8be50ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-5f5b068a7f080cf81bdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-527770f0a202591b0703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4980800000-a8d6a1e3a6f4f756fda9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1490000000-4c772eece08c289ea51dView 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 IDHMDB0011504
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028220
KNApSAcK IDNot Available
Chemspider ID24769383
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925129
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available