Showing metabocard for LysoPE(16:0/0:0) (BMDB0011503)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:19:38 UTC
Update Date2020-05-21 16:28:41 UTC
BMDB IDBMDB0011503
Secondary Accession Numbers
  • BMDB11503
Metabolite Identification
Common NameLysoPE(16:0/0:0)
DescriptionLysolysope(16:0/0:0), also known as Lysolysope(16:0/0:0) or lysolysope(16:0/0:0), 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. Thus, lysolysope(16:0/0:0) is considered to be a glycerophosphoethanolamine lipid molecule. Lysolysope(16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lysolysope(16:0/0:0) exists in all living species, ranging from bacteria to humans. In cattle, lysolysope(16:0/0:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Palmitoyl-gpeChEBI
1-Palmitoyl-gpe (16:0)ChEBI
1-Palmitoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphateChEBI
GPE(16:0)ChEBI
GPE(16:0/0:0)ChEBI
PE(16:0/0:0)ChEBI
2-Ammonioethyl (2R)-2-hydroxy-3-(palmitoyloxy)propyl phosphoric acidGenerator
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
Hexadecanoyl-lysophosphatidylethanolamineHMDB
LPE(16:0)HMDB
LPE(16:0/0:0)HMDB
Lyso-pe(16:0)HMDB
Lyso-pe(16:0/0:0)HMDB
LysoPE(16:0)HMDB
Lysophosphatidylethanolamine(16:0)HMDB
Lysophosphatidylethanolamine(16:0/0:0)HMDB
1-Hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
1-HexadecanoylglycerophosphoethanolamineHMDB
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamineHMDB
1-Palmitoyl-3-glycerylphosphorylethanolamineHMDB
1-Palmitoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-L-α-phosphorylethanolamineHMDB
1-Palmitoyl-sn-glycerol-3-phosphylethanolamineHMDB
1-Palmitoyl-sn-glycerophosphatidylethanolamineHMDB
1-Palmitoylglycero-3-phosphorylethanolamineHMDB
1-PalmitoylglycerophosphoethanolamineHMDB
3-Palmitoyl-DL-glycerol-1-phosphorylethanolamineHMDB
Palmitoyl lysophosphatidylethanolamineHMDB
1-Palmitoyl-lysophosphatidylethanolamineHMDB
LysoPE(16:0/0:0)Lipid Annotator
Chemical FormulaC21H44NO7P
Average Molecular Weight453.5503
Monoisotopic Molecular Weight453.285539279
IUPAC Name(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C21H44NO7P/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/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
InChI KeyYVYMBNSKXOXSKW-HXUWFJFHSA-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
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
logP4.1ALOGPS
logP3.53ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity117.41 m³·mol⁻¹ChemAxon
Polarizability52.25 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, Positivesplash10-0gvo-3920100000-42e56a40b9f2f651e243View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-4290100000-9d4961833a31a61505d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-97d2ee81d43b3bd577a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009200000-f0bf5c950a6907bcfdb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-7029000000-95a7a790a5eea029d0c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9110200000-adac1ea4ba52b6c32a6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-9cc034fa9a4c6eeac716View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-1e7e20f5d5acdebdbeadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-1290500000-c144e6d1cc68b4901cb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-6490000000-d52a88743171a228301cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-93d9fa86c2fd00af0101View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-22a78e3986af43ab255eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1390400000-c75746e1322e5add0887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1390000000-ead0e380f07431d54e75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3003900000-aa1d7b02acdc1b34723eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9104100000-e9614e19f5cf4a3f6310View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-707e02754187fe4a66c7View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011503
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028219
KNApSAcK IDNot Available
Chemspider ID7826019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547069
PDB IDNot Available
ChEBI ID73004
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytosolic phospholipase A2
General function:
Involved in calcium ion binding
Specific function:
Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (By similarity). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway. In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids. Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific. Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides. Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (By similarity).
Gene Name:
PLA2G4A
Uniprot ID:
A4IFJ5
Molecular weight:
85350.0
Reactions
PE(16:0/16:0) → LysoPE(16:0/0:0)details