Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:18 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0002904 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2,3-Dinor-TXB2 |
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Description | Fatty Acyl-Eicosanoid - metabolite of thromboxane. Found to be excreted via urinary tract at a higher level in diabetic rats. A study demonstrates that thromboxane as well as prostacyclin biosynthesis is increased in 2 murine models of atherogenesis and is secondary to increased in vivo platelet activation. Assessment of their generation in these models may afford the basis for future studies on the functional role of these eicosanoids in the evolution and progression of atherosclerosisThromboxanes 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. |
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Structure | CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CC(O)=O InChI=1S/C18H30O6/c1-2-3-4-7-13(19)10-11-16-14(8-5-6-9-17(21)22)15(20)12-18(23)24-16/h5-6,10-11,13-16,18-20,23H,2-4,7-9,12H2,1H3,(H,21,22)/b6-5-,11-10+/t13-,14-,15-,16+,18?/m0/s1 |
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Synonyms | Value | Source |
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2,3-Dinor-thromboxane | HMDB | 2,3-Dinorthromboxane | HMDB | 2,3-Dinor TXB2 | HMDB | 2,3-Dinor-thromboxane b2 | HMDB |
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Chemical Formula | C18H30O6 |
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Average Molecular Weight | 342.4272 |
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Monoisotopic Molecular Weight | 342.204238692 |
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IUPAC Name | (3Z)-5-[(2R,3S,4S)-4,6-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxan-3-yl]pent-3-enoic acid |
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Traditional Name | 2,3-dinor-thromboxane |
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CAS Registry Number | 63250-09-9 |
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SMILES | CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CC(O)=O |
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InChI Identifier | InChI=1S/C18H30O6/c1-2-3-4-7-13(19)10-11-16-14(8-5-6-9-17(21)22)15(20)12-18(23)24-16/h5-6,10-11,13-16,18-20,23H,2-4,7-9,12H2,1H3,(H,21,22)/b6-5-,11-10+/t13-,14-,15-,16+,18?/m0/s1 |
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InChI Key | RJHNVFKNIJQTQF-LMIBIYGPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring. |
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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 | Thromboxanes |
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Alternative Parents | |
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Substituents | - Thromboxane
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Oxane
- Fatty acid
- Unsaturated fatty acid
- Hemiacetal
- Secondary alcohol
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Not Available |
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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 | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2,3-Dinor-TXB2,1TMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C | 2789.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TMS,isomer #2 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O | 2732.6 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TMS,isomer #3 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O | 2688.1 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C | 2733.8 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C | 2747.7 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #2 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C | 2688.6 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #3 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2749.3 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O | 2713.8 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #5 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C | 2713.3 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TMS,isomer #6 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C | 2679.0 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C | 2679.8 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TMS,isomer #2 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2699.0 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TMS,isomer #3 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2657.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C | 2665.2 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,4TMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2671.4 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TBDMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C(C)(C)C | 3024.1 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TBDMS,isomer #2 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O | 2943.6 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TBDMS,isomer #3 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O | 2905.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,1TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C | 2981.0 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C(C)(C)C | 3188.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #2 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C(C)(C)C | 3149.5 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #3 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3252.0 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O | 3130.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #5 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C | 3165.6 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,2TBDMS,isomer #6 | CCCCC[C@H](O)/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C | 3135.5 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O)O[Si](C)(C)C(C)(C)C | 3361.1 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TBDMS,isomer #2 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3395.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TBDMS,isomer #3 | CCCCC[C@@H](/C=C/[C@H]1OC(O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3365.9 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,3TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C | 3339.0 | Semi standard non polar | 33892256 | 2,3-Dinor-TXB2,4TBDMS,isomer #1 | CCCCC[C@@H](/C=C/[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3516.6 | Semi standard non polar | 33892256 |
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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 - 2,3-Dinor-TXB2 GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-8983000000-6670f464141af0be2e50 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2,3-Dinor-TXB2 GC-MS (4 TMS) - 70eV, Positive | splash10-014i-4400179000-20a281a734fc918affa0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2,3-Dinor-TXB2 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 - 2,3-Dinor-TXB2 10V, Positive-QTOF | splash10-056r-0359000000-5f9e6cceab7c3f7a9cbd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 20V, Positive-QTOF | splash10-056r-4196000000-fdbaed01f5494e2612fb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 40V, Positive-QTOF | splash10-0lkc-9200000000-e8fea20e7b1476c8517d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 10V, Negative-QTOF | splash10-00kf-0096000000-fe2510f0641448d03e95 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 20V, Negative-QTOF | splash10-010c-2895000000-da0962ceb32a19fafd35 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 40V, Negative-QTOF | splash10-0a4l-9550000000-a56f9116ee1c3deadd2f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 10V, Negative-QTOF | splash10-0006-0009000000-f06a87e4cd9775888635 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 20V, Negative-QTOF | splash10-0006-3069000000-a9c4ca81a902cb920d57 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 40V, Negative-QTOF | splash10-00ku-9680000000-072c422c4b7e434204e2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 10V, Positive-QTOF | splash10-004i-0029000000-86f656cdda4b71fa4cdd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 20V, Positive-QTOF | splash10-0a4i-9314000000-c05525088475e906eac5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2,3-Dinor-TXB2 40V, Positive-QTOF | splash10-0a4l-9500000000-360bebc4fdec8cafc418 | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Tsikas D, Gutzki FM, Bohme M, Fuchs I, Frolich JC: Solid- and liquid-phase extraction for the gas chromatographic-tandem mass spectrometric quantification of 2,3-dinor-thromboxane B2 and 2,3-dinor-6-oxo-prostaglandin F1 alpha in human urine. J Chromatogr A. 2000 Jul 14;885(1-2):351-9. [PubMed:10941682 ]
- Okumura M, Imanishi M, Okamura M, Hosoi M, Okada N, Konishi Y, Morikawa T, Miura K, Nakatani T, Fujii S: Role for thromboxane A2 from glomerular thrombi in nephropathy with type 2 diabetic rats. Life Sci. 2003 May 2;72(24):2695-705. [PubMed:12679187 ]
- Pratico D, Cyrus T, Li H, FitzGerald GA: Endogenous biosynthesis of thromboxane and prostacyclin in 2 distinct murine models of atherosclerosis. Blood. 2000 Dec 1;96(12):3823-6. [PubMed:11090066 ]
- Djurup R, Chiabrando C, Jorres A, Fanelli R, Foegh M, Soerensen HU, Joergensen PN: Rapid, direct enzyme immunoassay of 11-keto-thromboxane B2 in urine, validated by immunoaffinity/gas chromatography-mass spectrometry. Clin Chem. 1993 Dec;39(12):2470-7. [PubMed:8252718 ]
- Block HU, Sziegoleit W, Mest HJ: Estimation of thromboxane B2 in the clotting human whole blood by gas chromatography. Biomed Biochim Acta. 1984;43(8-9):S385-8. [PubMed:6517904 ]
- Aitokallio-Tallberg AM, Jung JK, Kim SJ, Viinikka LU, Ylikorkala RO: Urinary excretion of degradation products of prostacyclin and thromboxane is increased in patients with gestational choriocarcinoma. Cancer Res. 1991 Aug 15;51(16):4146-8. [PubMed:1868436 ]
- Foegh ML, Zhao Y, Madren L, Rolnick M, Stair TO, Huang KS, Ramwell PW: Urinary thromboxane A2 metabolites in patients presenting in the emergency room with acute chest pain. J Intern Med. 1994 Feb;235(2):153-61. [PubMed:8308478 ]
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