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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-08 17:22:55 UTC
Update Date2017-10-23 19:05:50 UTC
HMDB IDHMDB0011470
Secondary Accession Numbers
  • HMDB11470
Metabolite Identification
Common NameLysoPE(0:0/14:0)
DescriptionLysoPE(0:0/14:0) 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.
Structure
Thumb
Synonyms
ValueSource
1-Hydroxy-2-myristoyl-sn-glycero-3-phosphoethanolamineHMDB
LPE(0:0/14:0)HMDB
LPE(14:0)HMDB
lyso-PE(0:0/14:0)HMDB
lyso-PE(14:0)HMDB
LysoPE(14:0)HMDB
Lysophosphatidylethanolamine(0:0/14:0)HMDB
Lysophosphatidylethanolamine(14:0)HMDB
Tetradecanoyl-lysophosphatidylethanolamineHMDB
1-hydroxy-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine; LPE(0:0/14:0)Lipid Annotator
LysoPE(0:0/14:0)Lipid Annotator
1-hydroxy-2-tetradecanoyl-sn-glycero-3-phosphoethanolamineLipid Annotator
Chemical FormulaC19H40NO7P
Average Molecular Weight425.4972
Monoisotopic Molecular Weight425.254239151
IUPAC Name(2-aminoethoxy)[(2R)-3-hydroxy-2-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional Name2-aminoethoxy(2R)-3-hydroxy-2-(tetradecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)27-18(16-21)17-26-28(23,24)25-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/t18-/m1/s1
InChI KeyDDUZNLUWXLYPCP-GOSISDBHSA-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:

  Tissue and substructures:

  Biofluid and excreta:

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 Solubility0.0094 g/LALOGPS
logP3.21ALOGPS
logP2.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.31 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity108.21 m³·mol⁻¹ChemAxon
Polarizability47.95 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, Positivesplash10-001j-6900000000-d93f79ef10954d2724bfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03n9-6590300000-1d5d4e5a130e6fd7c0d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9230200000-1d286caad36e3fe7a245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220000000-978040a71454c7599aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-aa2d283fa9214ebca0a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-3894700000-faa0fec16ab99068b6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9621100000-a50b46ebf5aefea76d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9110000000-cd9501e0109659ce2df8View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028186
KNApSAcK IDNot Available
Chemspider ID24769351
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480919
PDB IDNot Available
ChEBI IDNot Available
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