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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-08 17:23:48 UTC
Update Date2020-02-26 21:35:16 UTC
HMDB IDHMDB0011517
Secondary Accession Numbers
  • HMDB11517
Metabolite Identification
Common NameLysoPE(20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionLysoPE(20:4(5Z,8Z,11Z,14Z)/0:0) 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
Data?1582752916
Synonyms
ValueSource
(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-lysophosphatidylethanolamineChEBI
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineChEBI
1-Arachidonyl-sn-glycero-3-phosphoethanolamineChEBI
1-O-Arachidonoyl-sn-glycero-3-phosphoethanolamineChEBI
1-O-Arachidonyl-sn-glycero-3-phosphoethanolamineChEBI
LPE(20:4)ChEBI
LPE(20:4/0:0)ChEBI
LPE(20:4omega6/0:0)ChEBI
LysoPE(20:4)ChEBI
LysoPE(20:4/0:0)ChEBI
LysoPE(20:4omega6/0:0)ChEBI
Lysophosphatidylethanolamine(20:4)ChEBI
Lysophosphatidylethanolamine(20:4/0:0)ChEBI
PE(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
PE(20:4/0:0)ChEBI
1-Arachidonoyl-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
LPE(20:4n6/0:0)HMDB
LPE(20:4W6/0:0)HMDB
Lyso-pe(20:4)HMDB
Lyso-pe(20:4/0:0)HMDB
Lyso-pe(20:4n6/0:0)HMDB
Lyso-pe(20:4W6/0:0)HMDB
LysoPE(20:4n6/0:0)HMDB
LysoPE(20:4W6/0:0)HMDB
Lysophosphatidylethanolamine(20:4n6/0:0)HMDB
Lysophosphatidylethanolamine(20:4W6/0:0)HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-hydroxy-sn-glycero-3-phosphoethanolamineHMDB
1-ArachidonylglycerophosphoethanolamineHMDB
1-Arachidonoyl-gpeHMDB
1-Arachidonoyl-lysophosphatidylethanolamineHMDB
1-Arachidonoyl-sn-glycero-3-phosphoethanolamineHMDB
GPE(20:4(5Z,8Z,11Z,14Z))HMDB
GPE(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
GPE(20:4)HMDB
GPE(20:4n6)HMDB
GPE(20:4n6/0:0)HMDB
GPE(20:4W6)HMDB
GPE(20:4W6/0:0)HMDB
LPE(20:4(5Z,8Z,11Z,14Z))HMDB
LPE(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
LPE(20:4n6)HMDB
LPE(20:4W6)HMDB
LysoPE(20:4(5Z,8Z,11Z,14Z))HMDB
LysoPE(20:4n6)HMDB
LysoPE(20:4W6)HMDB
Lysophosphatidylethanolamine(20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylethanolamine(20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
Lysophosphatidylethanolamine(20:4n6)HMDB
Lysophosphatidylethanolamine(20:4W6)HMDB
1-Arachidonoyl-2-hydroxy-sn-glycerol-3-phosphatidyl ethanolamineHMDB
LysoPE(20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC25H44NO7P
Average Molecular Weight501.5931
Monoisotopic Molecular Weight501.285539279
IUPAC Name(2-aminoethoxy)[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy)phosphinic acid
CAS Registry Number652149-09-2
SMILES
[H][C@@](O)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OCCN
InChI Identifier
InChI=1S/C25H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26/h6-7,9-10,12-13,15-16,24,27H,2-5,8,11,14,17-23,26H2,1H3,(H,29,30)/b7-6-,10-9-,13-12-,16-15-/t24-/m1/s1
InChI KeyROPRRXYVXLDXQO-XSQXPFHXSA-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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.0032 g/LALOGPS
logP4.65ALOGPS
logP3.86ChemAxon
logS-5.2ALOGPS
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
Refractivity140.28 m³·mol⁻¹ChemAxon
Polarizability55.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgl-1930300000-2236e87d5bc1f07e55ecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-076r-3190200000-6b2b65ae182b013dd767Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9121110000-e69332874b8a3b68bd71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9121100000-13f14d49046b78c51f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9031000000-3045cfbacfc8a3c6f5f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-2479550000-df3affc60626c6eb7095Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-9868100000-86e9978369a5724d8747Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-6197c3cb09d1f6d23c7fSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
  • Placenta
Pathways
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
FooDB IDFDB028233
KNApSAcK IDNot Available
Chemspider ID21403171
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42607465
PDB IDNot Available
ChEBI ID64395
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. 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