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Human Metabolome Database Version 2.5

 

Showing metabocard for Delta-12-Prostaglandin J2 (HMDB04238)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 15:59:53
Update Date 2009-05-05 20:59:55
Accession Number HMDB04238
Secondary Accession Numbers Not Available
Common Name Delta-12-Prostaglandin J2
Description delta-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.
Synonyms
  1. delta-12-PGJ2
  2. prostaglandin J2
  3. delta-12-Prostaglandin J2
Chemical IUPAC Name (Z)-7-[(1S,5E)-5-[(3S)-3-hydroxyoctylidene]-4-oxo-1-cyclopent-2-enyl]hept-5-enoic acid
Chemical Formula C20H30O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Prostanoids
Sub Class
  • Prostaglandins
Family
  • Mammalian Metabolite
Species
  • ketone
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 334.450
Monoisotopic Molecular Weight 334.214417
Isomeric SMILES CCCCC[C@H](O)CC=C1/[C@@H](CC=C/CCCC(O)=O)C=CC1=O
Canonical SMILES CCCCCC(O)CC=C1C(CC=CCCCC(O)=O)C=CC1=O
KEGG Compound ID C05958 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04238 Link Image
Metagene Link HMDB04238 Link Image
METLIN ID 7034 Link Image
PubChem Compound 5280885 Link Image
PubChem Substance 700968 Link Image
ChEBI ID 28130 Link Image
CAS Registry Number 87893-54-7
InChI Identifier InChI=1/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
Synthesis Reference Kobayashi, Yuichi. Preparation of prostaglandin derivatives, especially D12-PGJ2 derivatives, and their intermediates, and pharmaceuticals containing them. Jpn. Kokai Tokkyo Koho (2005), 40 pp.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0217 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 4.28 [Predicted by ALOGPS]; 3.872 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Urine
Value 0.00003 +/- 0.000004 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.000013 +/- 0.000001 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References
  1. Fukushima M: Prostaglandin J2--anti-tumour and anti-viral activities and the mechanisms involved. Eicosanoids. 1990;3(4):189-99. [PubMed Link Image]
  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 Link Image]