Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-10-25 09:59:41 UTC |
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Update Date | 2022-03-07 02:49:25 UTC |
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HMDB ID | HMDB0005079 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 15-Deoxy-d-12,14-PGJ2 |
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Description | 15-deoxy-PGJ2 (15d-PGJ2) is a metabolite of the PGJ2 prostanoid family that influences multiple signaling pathways by covalently binding with key signaling molecules. Among them, 15d-PGJ2 has displayed highest potency as an inducer of gene expression. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 , 16857669 ). 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. | Read more...
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Structure | CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1 |
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Synonyms | Value | Source |
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15-Deoxy-delta-12,14-PGJ2 | ChEBI | 15-Deoxy-delta-12,14-prostaglandin J2 | ChEBI | 15-Deoxy-PGJ2 | ChEBI | delta-12,14-15-Deoxy-PGJ2 | ChEBI | 15-Deoxy-Delta12,14-prostaglandin J2 | Kegg | 15-Deoxy-δ-12,14-PGJ2 | Generator | 15-Deoxy-δ-12,14-prostaglandin J2 | Generator | Δ-12,14-15-deoxy-PGJ2 | Generator | 15-Deoxy-δ12,14-prostaglandin J2 | Generator | (5Z,12E,14E) 11-oxo Prosta-5,9,12,14-tetraen-1-Oate | HMDB | (5Z,12E,14E) 11-oxo Prosta-5,9,12,14-tetraen-1-Oic acid | HMDB | (5Z,12E,14E)-11-oxo-Prosta-5,9,12,14-tetraen-1-Oate | HMDB | (5Z,12E,14E)-11-oxo-Prosta-5,9,12,14-tetraen-1-Oic acid | HMDB | 11-oxo-5Z,9,12,14-Prostatetraenoate | HMDB | 11-oxo-5Z,9,12,14-Prostatetraenoic acid | HMDB | 15-Deoxy-delta 12, 14-prostaglandin J2 | HMDB | 15-Deoxy-delta-12, 14 PGJ-2 | HMDB | 15-Deoxy-delta12,14-PGJ2 | HMDB | 15-Deoxy-delta12,14-prostaglandin | HMDB | 15-Deoxy-prostaglandin J2 | HMDB | 15D-PGJ2 | HMDB | Delta12,14-PGJ2 | HMDB | 15-Deoxyprostaglandin J2 | HMDB | 15-Deoxy-delta(12,14)-prostaglandin J2 | HMDB | 15-Deoxy-12,14-prostaglandin J2 | HMDB | 15-Deoxy-delta(12,14)PGJ2 | HMDB |
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Chemical Formula | C20H28O3 |
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Average Molecular Weight | 316.4345 |
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Monoisotopic Molecular Weight | 316.203844762 |
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IUPAC Name | (5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid |
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Traditional Name | delta12,14-PGJ2 |
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CAS Registry Number | 87893-55-8 |
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SMILES | CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O |
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InChI Identifier | InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1 |
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InChI Key | VHRUMKCAEVRUBK-GODQJPCRSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Prostaglandins and related compounds |
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Alternative Parents | |
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Substituents | - Prostaglandin skeleton
- Long-chain fatty acid
- Fatty acid
- Unsaturated fatty acid
- Cyclic ketone
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 3.983 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 15-Deoxy-d-12,14-PGJ2 GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-6290000000-3dc60f4b59ef5f20d684 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 15-Deoxy-d-12,14-PGJ2 GC-MS (1 TMS) - 70eV, Positive | splash10-007c-9352000000-0ced364db9c5f3e628e4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 15-Deoxy-d-12,14-PGJ2 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 10V, Positive-QTOF | splash10-014j-0294000000-a09703fda20ef890154e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 20V, Positive-QTOF | splash10-0a4j-2590000000-7a0889bba7bd7ec5abd5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 40V, Positive-QTOF | splash10-0gbc-9410000000-6716fa5d4535af90b53b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 10V, Negative-QTOF | splash10-014i-0029000000-1568a862c2a207983dd6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 20V, Negative-QTOF | splash10-01b9-1297000000-85bb29f3a42e11f9c53a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 40V, Negative-QTOF | splash10-0a4i-9520000000-05e5fcf470c134176904 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 10V, Positive-QTOF | splash10-000t-1292000000-b96f27a7a0fb5f4a4574 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 20V, Positive-QTOF | splash10-001i-9730000000-e86765cb72eecd2feb8c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 40V, Positive-QTOF | splash10-05rr-9500000000-43060ace2e2f26804b0f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 10V, Negative-QTOF | splash10-014i-0029000000-c1967ca10292a13ad947 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 20V, Negative-QTOF | splash10-066r-0294000000-ecdf0c0084d7f716f9a5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deoxy-d-12,14-PGJ2 40V, Negative-QTOF | splash10-053r-1930000000-dd5d68b51f67954b6ba6 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.000083 +/- 0.000003 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000206 +/- 0.000011 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <0.0003 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0000023 +/- 0.000001 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.00005 +/- 0.000018 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.000018 +/- 0.000004 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB112223 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4470730 |
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KEGG Compound ID | C14717 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5311211 |
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PDB ID | Not Available |
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ChEBI ID | 34159 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Bickley, Jamie F.; Jadhav, Vasudev; Roberts, Stanley M.; Santoro, M. Gabriella; Steiner, Alexander; Sutton, Peter W. Synthesis of optically active prostaglandin-J2 and 15-deoxy-D12,14-prostaglandin-J2. Synlett (2003), (8), 1170-1174. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Yu X, Egner PA, Wakabayashi J, Wakabayashi N, Yamamoto M, Kensler TW: Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase. J Biol Chem. 2006 Sep 8;281(36):26245-52. Epub 2006 Jul 20. [PubMed:16857669 ]
- Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- Lipid Maps (LMFA03010021) [Link]
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