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Record Information
StatusDetected but not Quantified
Creation Date2009-01-08 17:22:58 UTC
Update Date2018-03-01 03:33:58 UTC
Secondary Accession Numbers
  • HMDB11473
Metabolite Identification
Common NameLysoPE(0:0/16:0)
DescriptionLysoPE(0:0/16:0) is a lysophosphatidylethanolamine or 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. 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. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.
1-hydroxy-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine; Lysophosphatidylethanolamine(0:0/16:0)Lipid Annotator
LysoPE(0:0/16:0)Lipid Annotator
1-hydroxy-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineLipid Annotator
Chemical FormulaC21H44NO7P
Average Molecular Weight453.5503
Monoisotopic Molecular Weight453.285539279
IUPAC Name(2-aminoethoxy)[(2R)-2-(hexadecanoyloxy)-3-hydroxypropoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-2-(hexadecanoyloxy)-3-hydroxypropoxyphosphinic acid
CAS Registry NumberNot Available
InChI Identifier
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
Sub ClassGlycerophosphoethanolamines
Direct Parent2-acyl-sn-glycero-3-phosphoethanolamines
Alternative Parents
  • 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

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0026 g/LALOGPS
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
Polarizability52.23 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-7920000000-0f7021db46d5608b57faView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-9680300000-35c171d3b82fe2b5f28cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9120200000-a9cd2925a0ffc301065eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120000000-98072e597f0a7dc24230View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-83089b5450c4c7d34416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-2681900000-c10a7994dc8aff7b1a4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9530100000-f5432377675aebf08bfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-a2aac060ccbe1b901045View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028189
KNApSAcK IDNot Available
Chemspider ID24769354
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480922
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.


General function:
Involved in catalytic activity
Specific function:
Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
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