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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-29 08:43:47 UTC
Update Date2017-12-07 02:29:07 UTC
HMDB IDHMDB0011129
Secondary Accession Numbers
  • HMDB11129
Metabolite Identification
Common NameLysoPE(0:0/18:0)
DescriptionLysoPE(0:0/18:0) or LPE(0:0/18:0) is 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.
Structure
Thumb
Synonyms
ValueSource
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-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphoethanolamineHMDB
1-Hydroxyl-2-stearoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/18:0)HMDB
LPE(18:0)HMDB
LysoPE(18:0)HMDB
Lysophosphatidylethanolamine(0:0/18:0)HMDB
Octadecanoyl-lysophosphatidylethanolamineHMDB
Stearoyl phosphatidylethanolamineHMDB
1-hydroxy-2-octadecanoyl-sn-glycero-3-phosphoethanolamine; LysoPE(18:0)Lipid Annotator
1-hydroxy-2-stearoyl-sn-glycero-3-phosphoethanolamineLipid Annotator
Lysophosphatidylethanolamine(18:0)Lipid Annotator
Lyso-PE(0:0/18:0)Lipid Annotator
Lyso-PE(18:0)Lipid Annotator
LysoPE(0:0/18:0)Lipid Annotator
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 chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

  Food and nutrition:

Biological role:

Physiological effect

Organoleptic effect:

  Touch:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
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
Bioavailability1ChemAxon
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 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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027908
KNApSAcK IDNot Available
Chemspider ID24769218
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480667
PDB IDNot Available
ChEBI ID133144
References
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.

Enzymes

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.
Gene Name:
ENPP2
Uniprot ID:
Q13822
Molecular weight:
98992.78