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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002710
Secondary Accession Numbers
  • HMDB0005078
  • 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 signalling pathways.
Structure
Data?1582752254
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
Description 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
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.86630932474
DeepCCS[M-H]-186.47130932474
DeepCCS[M-2H]-220.18330932474
DeepCCS[M+Na]+195.3730932474
AllCCS[M+H]+187.932859911
AllCCS[M+H-H2O]+185.132859911
AllCCS[M+NH4]+190.632859911
AllCCS[M+Na]+191.332859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-189.232859911
AllCCS[M+HCOO]-190.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin J2CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O4408.3Standard polar33892256
Prostaglandin J2CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O2586.1Standard non polar33892256
Prostaglandin J2CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O2776.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin J2,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2796.6Semi standard non polar33892256
Prostaglandin J2,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2737.8Semi standard non polar33892256
Prostaglandin J2,1TMS,isomer #3CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O2885.5Semi standard non polar33892256
Prostaglandin J2,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2754.9Semi standard non polar33892256
Prostaglandin J2,2TMS,isomer #2CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2911.3Semi standard non polar33892256
Prostaglandin J2,2TMS,isomer #3CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2858.9Semi standard non polar33892256
Prostaglandin J2,3TMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2887.8Semi standard non polar33892256
Prostaglandin J2,3TMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2741.4Standard non polar33892256
Prostaglandin J2,3TMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3087.8Standard polar33892256
Prostaglandin J2,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3039.4Semi standard non polar33892256
Prostaglandin J2,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2983.3Semi standard non polar33892256
Prostaglandin J2,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O3112.0Semi standard non polar33892256
Prostaglandin J2,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3241.2Semi standard non polar33892256
Prostaglandin J2,2TBDMS,isomer #2CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3344.9Semi standard non polar33892256
Prostaglandin J2,2TBDMS,isomer #3CCCCC[C@H](O)/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3326.9Semi standard non polar33892256
Prostaglandin J2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3570.7Semi standard non polar33892256
Prostaglandin J2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3289.9Standard non polar33892256
Prostaglandin J2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/C1=C(O[Si](C)(C)C(C)(C)C)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3274.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-067u-5392000000-9b45d3f37955c67682bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin J2 GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9212200000-d9dcb4c0bb23a56c81d02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-01b9-0089000000-78fdf4aa71747b22d9f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-00xr-0097000000-d507bda3b27e80eb99662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-00di-0094000000-f6f67078fe3ecda593412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-00di-0091000000-240dba66bc1f4401b0c12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-00di-0090000000-1cb619054c8aa83a868d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-0fk9-0190000000-505725a881b9d2e93ec92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-0uk9-0290000000-de982b17f44086e4d4ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-0udi-0590000000-8f4c01a7293ad0cf72352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Prostaglandin J2 LC-ESI-QIT , negative-QTOFsplash10-0uka-0950000000-219ff8b09fa3a4091f0e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Positive-QTOFsplash10-014j-0069000000-a381e76c384ef4a00dd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Positive-QTOFsplash10-01bj-2592000000-31c78f2cc310297d596e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Positive-QTOFsplash10-05to-9320000000-0ffe9cf3d89d027670502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Negative-QTOFsplash10-001i-0019000000-09381487459f4a98eaef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Negative-QTOFsplash10-0159-2159000000-e8aa48903843629c85752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Negative-QTOFsplash10-0a4i-9330000000-ccd52bfaf256d7ac20242017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Negative-QTOFsplash10-00lr-0009000000-3a01c9a41ab9915ff4112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Negative-QTOFsplash10-00si-0297000000-26f532b6f59ff7845c982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Negative-QTOFsplash10-0911-7930000000-05c866b3a6adf47ee4712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 10V, Positive-QTOFsplash10-00kk-0596000000-3753a6f26d8178114c132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 20V, Positive-QTOFsplash10-05mt-5971000000-9fb5b5e59d1fca621a862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin J2 40V, Positive-QTOFsplash10-0a4i-9810000000-3362a9f0c438d0c276a72021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Neuron
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000027 +/- 0.000003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000072 +/- 0.000065 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
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDC05957
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]