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Record Information
Version4.0
Creation Date2006-08-13 14:59:53 UTC
Update Date2017-09-27 08:24:27 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 signaling pathways.
Structure
Thumb
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
DDDD-PGD2ChEBI
delta(12)-PGJ2ChEBI
delta-12-PGJ2ChEBI
δ-12-prostaglandin J2Generator
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
Prostaglandin J2HMDB
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical 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 Solubility0.022 g/LALOGPS
logP4.28ALOGPS
logP4.43ChemAxon
logS-4.2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
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 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]