Showing metabocard for LysoPE(0:0/18:0) (BMDB0011129)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:17 UTC
Update Date2020-05-11 20:42:12 UTC
BMDB IDBMDB0011129
Secondary Accession Numbers
  • BMDB11129
Metabolite Identification
Common NameLysoPE(0:0/18:0)
DescriptionPE(0:0/18:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(0:0/18:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
octadecanoyl-lysophosphatidylethanolamineLipid Annotator, HMDB
1-hydroxy-2-stearoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
LPE(0:0/18:0)Lipid Annotator, HMDB
Lysophosphatidylethanolamine(0:0/18:0)Lipid Annotator, HMDB
Lysophosphatidylethanolamine(18:0)Lipid Annotator, HMDB
Lyso-PE(0:0/18:0)Lipid Annotator, HMDB
Lyso-PE(18:0)Lipid Annotator, HMDB
LPE(18:0)Lipid Annotator, HMDB
LysoPE(0:0/18:0)Lipid Annotator
1-hydroxy-2-octadecanoyl-sn-glycero-3-phosphoethanolamineLipid Annotator, HMDB
LysoPE(18:0)Lipid Annotator, HMDB
2-Stearoyl-gpeChEBI
2-Stearoyl-gpe (18:0)ChEBI
2-Stearoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
GPE(0:0/18:0)ChEBI
GPE(18:0)ChEBI
Lysophosphatidylethanolamine zwitterion (0:0/18:0)ChEBI
Lysophosphatidylethanolamine zwitterion (18:0)ChEBI
PE(0:0/18:0)ChEBI
PE(18:0)ChEBI
Phosphatidylethanolamine zwitterion (0:0/18:0)ChEBI
Phosphatidylethanolamine zwitterion (18:0)ChEBI
1-Hydroxyl-2-stearoyl-sn-glycero-3-phosphoethanolamineHMDB
Stearoyl phosphatidylethanolamineHMDB
2-Stearoyl-3-glycerylphosphorylethanolamineHMDB
2-Stearoyl-lysophosphatidylethanolamineHMDB
2-Stearoyl-sn-glycero-3-phosphoethanolamineHMDB
Chemical FormulaC23H48NO7P
Average Molecular Weight481.6035
Monoisotopic Molecular Weight481.316839407
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-(octadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C23H48NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)31-22(20-25)21-30-32(27,28)29-19-18-24/h22,25H,2-21,24H2,1H3,(H,27,28)/t22-/m1/s1
InChI KeyKIHAGWUUUHJRMS-JOCHJYFZSA-N
Chemical Taxonomy
DescriptionThis compound 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
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
logP4.74ALOGPS
logP4.42ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity126.61 m³·mol⁻¹ChemAxon
Polarizability56.55 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, Positivesplash10-001d-9850200000-9b9f225929fb8e136b36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9580120000-5a4035d56eb935326c3aView 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, Positivesplash10-0006-9130200000-4e9fcf520a02df956d4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-ebc5c409f172dc421d5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-0bdf8499750e6dda288dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2570900000-31f74f210efc7e13ed67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9530200000-e28d9aa3600567215b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-74478f12c2118e94bb91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0016-2015900000-40d2fd876ff57a908546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3219300000-5daa0fce87d456c97f31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-81df7f2f8b12479ce3e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100900000-0741d2952848d7dcefa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2390100000-c6402cf49dc5678ece72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9310000000-85beb15cc8fab41135cdView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Blood
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress		 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available