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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 14:59:53 UTC
Update Date2021-09-14 15:47:05 UTC
HMDB IDHMDB0004238
Secondary Accession Numbers
  • HMDB04238
Metabolite Identification
Common NameDelta-12-Prostaglandin J2
DescriptionDelta-12-Prostaglandin J2 (d12-PGJ2) is the ultimate metabolite of Prostaglandin D2 (PGD2). PGD2 is an unstable molecule and undergoes dehydration to form PGJ2 in aqueous solution, and is then converted to d12-PGJ2, in the presence of serum albumin or plasma. d12-PGJ2 forms a conjugate with the thiol of glutathione (GSH) and GSH suppresses the d12-PGJ2-induced HSP synthesis and subsequent inhibition of cell growth (HSPs are a set of proteins synthesized in response to heat shock or to other environmental stresses). d12-PGJ2 has been shown to stimulate alkaline phosphatase activity and calcification of human osteoblastic cells, the potency of the PGs being comparable to that of 1-a,25-dihydroxy vitamin D. d12-PGJ2 enhances the type-1 collagen synthesis in human osteoblasts during calcification. Thus, d12-PGJ2 modulates osteogenesis through induction of the syntheses of multiple proteins related to mineralization. Considering that PGD2 is a major arachidonate metabolite in bone marrow, d12-PGJ2, may be physiologically involved in the modulation of osteogenesis. d12-PGJ2 induces heme oxygenase, HO-l. Heme oxygenase is a key enzyme in heme catabolism, oxidatively clearing heme to yield biliverdin, iron and carbon monoxide. The biological function of this enzyme is the conversion of potentially toxic heme to bile and the recovery of the iron. Furthermore, carbon monoxide produced on the enzymatic degradation of heme has been suggested to function as a neural messenger. Two isozymes of heme oxygenase, HO-l and HO-2, have been identified. HO-2 is constitutively expressed, while HO-l is drastically induced in response to a variety of stresses, including heavy metals, heat shock and UV irradiation. (PMID: 8777585 )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?1582752303
Synonyms
ValueSource
9-Deoxy-9,10-didehydro-12,13-didehydro-13,14-dihydroprostaglandin D2ChEBI
9-Deoxy-delta(9), delta(12)-13,14-dihydroprostaglandin D2ChEBI
9-Deoxy-delta(9,12)-13,14-dihydro PGD2ChEBI
D12-PGJ2ChEBI
DDDD-PGD2ChEBI
delta(12)-PGJ2ChEBI
delta-12-PGJ2ChEBI
9-Deoxy-δ(9), δ(12)-13,14-dihydroprostaglandin D2Generator
9-Deoxy-δ(9,12)-13,14-dihydro PGD2Generator
Δ(12)-PGJ2Generator
Δ-12-PGJ2Generator
Δ-12-prostaglandin J2Generator
Prostaglandin J2HMDB
(5Z,12E,15S)-15-Hydroxy-11-oxo-prosta-5,9,12-trien-1-Oic acidMeSH
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5Z)-7-[(1S,5E)-5-[(3S)-3-hydroxyoctylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
Traditional Namedelta-12-prostaglandin J2
CAS Registry Number87893-54-7
SMILES
CCCCC[C@H](O)C\C=C1/[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/h4,7,12,14-17,21H,2-3,5-6,8-11,13H2,1H3,(H,23,24)/b7-4-,18-14+/t16-,17-/m0/s1
InChI KeyTUXFWOHFPFBNEJ-GJGHEGAFSA-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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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 Solubility0.022 g/LALOGPS
logP10(4.28) g/LALOGPS
logP10(4.43) g/LChemAxon
logS10(-4.2) g/LALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Delta-12-Prostaglandin J2CCCCC[C@H](O)C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O4407.5Standard polar33892256
Delta-12-Prostaglandin J2CCCCC[C@H](O)C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O2594.8Standard non polar33892256
Delta-12-Prostaglandin J2CCCCC[C@H](O)C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O2809.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Delta-12-Prostaglandin J2,1TMS,isomer #1CCCCC[C@@H](C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2897.8Semi standard non polar33892256
Delta-12-Prostaglandin J2,1TMS,isomer #2CCCCC[C@H](O)C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2852.1Semi standard non polar33892256
Delta-12-Prostaglandin J2,2TMS,isomer #1CCCCC[C@@H](C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2872.9Semi standard non polar33892256
Delta-12-Prostaglandin J2,1TBDMS,isomer #1CCCCC[C@@H](C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3135.0Semi standard non polar33892256
Delta-12-Prostaglandin J2,1TBDMS,isomer #2CCCCC[C@H](O)C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3100.6Semi standard non polar33892256
Delta-12-Prostaglandin J2,2TBDMS,isomer #1CCCCC[C@@H](C/C=C1/C(=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)C3351.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Delta-12-Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-07d3-7492000000-84e4a524519c7194d3f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Delta-12-Prostaglandin J2 GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9213200000-08bfe6bfadbf91ad015c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Delta-12-Prostaglandin J2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 10V, Positive-QTOFsplash10-014r-0159000000-53464c9859e74445f91d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 20V, Positive-QTOFsplash10-060a-2392000000-33943794bd1acfe51f7a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 40V, Positive-QTOFsplash10-0l0f-9510000000-1a7d8c281e9a8cb4ffbd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 10V, Negative-QTOFsplash10-001i-0029000000-c451d3694f1a7a9b2e262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 20V, Negative-QTOFsplash10-00lr-2279000000-d22b689b69a5a517f6192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 40V, Negative-QTOFsplash10-0a4i-9320000000-ff9d06a5ad9737c570552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 10V, Positive-QTOFsplash10-00kb-0197000000-f182b500732a4e3e956d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 20V, Positive-QTOFsplash10-00kk-6982000000-88a3e1b2014e2ec052342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 40V, Positive-QTOFsplash10-0aor-9700000000-354f185276245dda1f972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 10V, Negative-QTOFsplash10-00lr-0009000000-d47e7da9e96521e615162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 20V, Negative-QTOFsplash10-00o0-0497000000-11a36dd325ff00d18ecf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Delta-12-Prostaglandin J2 40V, Negative-QTOFsplash10-0a4l-9630000000-4a75d9847f3fc40011ed2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0003 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0003 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.000013 +/- 0.000001 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.00003 +/- 0.000004 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023343
KNApSAcK IDNot Available
Chemspider ID4444408
KEGG Compound IDC05958
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7034
PubChem Compound5280885
PDB IDNot Available
ChEBI ID28130
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKobayashi, Yuichi. Preparation of prostaglandin derivatives, especially D12-PGJ2 derivatives, and their intermediates, and pharmaceuticals containing them. Jpn. Kokai Tokkyo Koho (2005), 40 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fukushima M: Prostaglandin J2--anti-tumour and anti-viral activities and the mechanisms involved. Eicosanoids. 1990;3(4):189-99. [PubMed:2073399 ]
  2. Hirata Y, Hayashi H, Ito S, Kikawa Y, Ishibashi M, Sudo M, Miyazaki H, Fukushima M, Narumiya S, Hayaishi O: Occurrence of 9-deoxy-delta 9,delta 12-13,14-dihydroprostaglandin D2 in human urine. J Biol Chem. 1988 Nov 15;263(32):16619-25. [PubMed:3053696 ]
  3. Negishi M, Koizumi T, Ichikawa A: Biological actions of delta 12-prostaglandin J2. J Lipid Mediat Cell Signal. 1995 Oct;12(2-3):443-8. [PubMed:8777585 ]