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Record Information
Version4.0
Creation Date2006-05-22 15:12:05 UTC
Update Date2017-09-27 08:24:17 UTC
HMDB IDHMDB0002710
Secondary Accession Numbers
  • HMDB02710
  • HMDB05078
Metabolite Identification
Common NameProstaglandin J2
DescriptionProstaglandin J2 (PGJ2) is an endogenous product of inflammation in humans. It induces neuronal death and the accumulation of ubiquitinated proteins into distinct aggregates. It may play a role in neurodegenerative disorders inducing a chain of events that culminates in neuronal cell death. An altered expression of enzymes in PGJ2 synthesis may represent a novel pathogenic mechanism in human obesity. The peroxisome proliferator-activated receptor gamma (PPARγ) has a fundamental role in glucose homeostasis and adipocyte differentiation. Besides linoleate, linolenate and arachidonate, the most notable PPAR ligand is 15-deoxy-delta12-14-prostaglandin J2, a natural derivative of prostaglandin D2 and PGJ2. It is therefore plausible that the production of 15d-PGJ2 within adipose tissue may act as an endogenous mediator of adipocyte differentiation. PGJ2 disrupts the cytoskeleton in neuronal cells. This cyclopentenone prostaglandin triggered endoplasmic reticulum (ER) collapse and the redistribution of ER proteins, such as calnexin and catechol-O-methyltransferase, into a large centrosomal aggregate containing ubiquitinated proteins and alpha-synuclein. The PGJ2-dependent cytoskeletal rearrangement paralleled the development of the large centrosomal aggregate. Supporting a mechanism by which, upon PGJ2 treatment, cytoskeleton/ER collapse coincides with the relocation of ER proteins, other potentially neighboring proteins, and ubiquitinated proteins into centrosomal aggregates. Development of these large perinuclear aggregates is associated with disruption of the microtubule/ER network. This aberrant protein deposition, triggered by a product of inflammation, may be common to other compounds that disrupt microtubules and induce protein aggregation, such as MPP+ and rotenone, found to be associated with neurodegeneration. Many neurodegenerative disorders, such as Parkinson disease, exhibit inclusion bodies containing ubiquitinated proteins. Concentrations of PGJ2 in biofluids have not been established, since this prostaglandin is further metabolized into delta12-PGJ2, and 15-deoxy-delta12,14-PGJ2. (PMID: 16737963 , 16842938 , 16774923 )Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
Structure
Thumb
Synonyms
ValueSource
9-Deoxy-delta-9-PGD2ChEBI
9-Deoxy-delta-9-prostaglandin D2ChEBI
PGJ2ChEBI
9-Deoxy-δ-9-PGD2Generator
9-Deoxy-δ-9-prostaglandin D2Generator
11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoateHMDB
11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoic acidHMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
Traditional Nameprostaglandin J2
CAS Registry Number60203-57-8
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1
InChI KeyUQOQENZZLBSFKO-POPPZSFYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

    Element:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular 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 Solubility0.02 g/LALOGPS
logP4.1ALOGPS
logP4.38ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.09 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01b9-0089000000-78fdf4aa71747b22d9f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00xr-0097000000-d507bda3b27e80eb9966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0094000000-f6f67078fe3ecda59341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0091000000-240dba66bc1f4401b0c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0090000000-1cb619054c8aa83a868dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0fk9-0190000000-505725a881b9d2e93ec9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0uk9-0290000000-de982b17f44086e4d4aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0590000000-8f4c01a7293ad0cf7235View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0uka-0950000000-219ff8b09fa3a4091f0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0069000000-a381e76c384ef4a00dd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bj-2592000000-31c78f2cc310297d596eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05to-9320000000-0ffe9cf3d89d02767050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-09381487459f4a98eaefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2159000000-e8aa48903843629c8575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9330000000-ccd52bfaf256d7ac2024View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Neuron
  • Platelet
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.7E-5 +/- 3E-6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.2-E5 +/- 6.5-E5 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0003 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0003 uMAdult (>18 years old)Both
Normal
details
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 IDFDB023049
KNApSAcK IDNot Available
Chemspider ID4444407
KEGG Compound IDC05957
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3464
PubChem Compound5280884
PDB IDNot Available
ChEBI ID27485
References
Synthesis ReferenceZanoni, Giuseppe; Porta, Alessio; De Toma, Quintino; Castronovo, Francesca; Vidari, Giovanni. First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2. Journal of Organic Chemistry (2003), 68(16), 6437-6439.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ogburn KD, Bottiglieri T, Wang Z, Figueiredo-Pereira ME: Prostaglandin J2 reduces catechol-O-methyltransferase activity and enhances dopamine toxicity in neuronal cells. Neurobiol Dis. 2006 May;22(2):294-301. Epub 2006 Jan 5. [PubMed:16406650 ]
  2. Fukushima S, Takeuchi Y, Kishimoto S, Yamashita S, Uetsuki K, Shirakawa S, Suzuki M, Furuta K, Noyori R, Sasaki H, Kikuchi Y, Kita T, Yamori T, Sawada J, Kojima M, Hazato A, Kurozumi S, Fukushima M: Antitumor activity, optimum administration method and pharmacokinetics of 13,14-dihydro-15-deoxy-deoxy-Delta7 -prostaglandin A1 methyl ester (TEI-9826) integrated in lipid microspheres (Lipo TEI-9826). Anticancer Drugs. 2001 Mar;12(3):221-34. [PubMed:11290870 ]
  3. Coyle AT, O'Keeffe MB, Kinsella BT: 15-deoxy Delta12,14-prostaglandin J2 suppresses transcription by promoter 3 of the human thromboxane A2 receptor gene through peroxisome proliferator-activated receptor gamma in human erythroleukemia cells. FEBS J. 2005 Sep;272(18):4754-73. [PubMed:16156795 ]
  4. Wang Z, Aris VM, Ogburn KD, Soteropoulos P, Figueiredo-Pereira ME: Prostaglandin J2 alters pro-survival and pro-death gene expression patterns and 26 S proteasome assembly in human neuroblastoma cells. J Biol Chem. 2006 Jul 28;281(30):21377-86. Epub 2006 May 30. [PubMed:16737963 ]
  5. Quinkler M, Bujalska IJ, Tomlinson JW, Smith DM, Stewart PM: Depot-specific prostaglandin synthesis in human adipose tissue: a novel possible mechanism of adipogenesis. Gene. 2006 Oct 1;380(2):137-43. Epub 2006 Jun 10. [PubMed:16842938 ]
  6. Ogburn KD, Figueiredo-Pereira ME: Cytoskeleton/endoplasmic reticulum collapse induced by prostaglandin J2 parallels centrosomal deposition of ubiquitinated protein aggregates. J Biol Chem. 2006 Aug 11;281(32):23274-84. Epub 2006 Jun 14. [PubMed:16774923 ]