Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:50 UTC |
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HMDB ID | HMDB0015033 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Rimexolone |
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Description | Rimexolone is only found in individuals that have used or taken this drug. It is a glucocorticoid steroid used to treat inflammation in the eye. It is marketed as a 1% eye drop solution under the trade name VexolRimexolone is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. By binding to the glucocorticoid receptor, this drug ultimately leads to changes in genetic transcription involving the lipocortins and prostaglandins. |
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Structure | CCC(=O)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@]12C InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17?,18?,19+,21?,22+,23+,24-/m1/s1 |
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Synonyms | Value | Source |
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11 beta-Hydroxy-16 alpha,17 alpha,21-trimethylpregna-1,4-diene-3,20-dione | HMDB | Vexol | HMDB | Rimexel | HMDB |
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Chemical Formula | C24H34O3 |
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Average Molecular Weight | 370.525 |
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Monoisotopic Molecular Weight | 370.250794954 |
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IUPAC Name | (2R,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-14-propanoyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one |
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Traditional Name | rimexolone |
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CAS Registry Number | 49697-38-3 |
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SMILES | CCC(=O)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@]12C |
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InChI Identifier | InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17?,18?,19+,21?,22+,23+,24-/m1/s1 |
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InChI Key | QTTRZHGPGKRAFB-PAIWTFDUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Oxosteroids |
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Direct Parent | 20-oxosteroids |
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Alternative Parents | |
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Substituents | - 20-oxosteroid
- Androgen-skeleton
- Androstane-skeleton
- 3-oxo-delta-1,4-steroid
- 3-oxosteroid
- Hydroxysteroid
- 11-beta-hydroxysteroid
- 11-hydroxysteroid
- Delta-1,4-steroid
- Cyclic alcohol
- Ketone
- Secondary alcohol
- Cyclic ketone
- Organooxygen compound
- Alcohol
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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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 | 0.012 g/L | Not Available | LogP | 4.2 | 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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Rimexolone,1TMS,isomer #1 | CCC(=O)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C)C[C@@]21C | 3219.0 | Semi standard non polar | 33892256 | Rimexolone,1TMS,isomer #2 | CC=C(O[Si](C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@@]21C | 3135.5 | Semi standard non polar | 33892256 | Rimexolone,2TMS,isomer #1 | CC=C(O[Si](C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C)C[C@@]21C | 3065.7 | Semi standard non polar | 33892256 | Rimexolone,2TMS,isomer #1 | CC=C(O[Si](C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C)C[C@@]21C | 3080.6 | Standard non polar | 33892256 | Rimexolone,2TMS,isomer #1 | CC=C(O[Si](C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C)C[C@@]21C | 3376.2 | Standard polar | 33892256 | Rimexolone,1TBDMS,isomer #1 | CCC(=O)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3450.0 | Semi standard non polar | 33892256 | Rimexolone,1TBDMS,isomer #2 | CC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@@]21C | 3380.0 | Semi standard non polar | 33892256 | Rimexolone,2TBDMS,isomer #1 | CC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3547.2 | Semi standard non polar | 33892256 | Rimexolone,2TBDMS,isomer #1 | CC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3580.1 | Standard non polar | 33892256 | Rimexolone,2TBDMS,isomer #1 | CC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3592.9 | Standard 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 - Rimexolone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-2937000000-8656a48079e4d5543cd6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rimexolone GC-MS (1 TMS) - 70eV, Positive | splash10-01t9-6515900000-4129aaf91d10293087b6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Rimexolone 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 - Rimexolone 10V, Positive-QTOF | splash10-0uk9-0009000000-18a4a8fa1a276c8b2c74 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 20V, Positive-QTOF | splash10-0w99-1419000000-30896aac68efc889f206 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 40V, Positive-QTOF | splash10-0a4j-5669000000-c5f50da2702f2b75fd65 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 10V, Negative-QTOF | splash10-014i-0009000000-8d8659184e0c76f74e5f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 20V, Negative-QTOF | splash10-0gb9-0009000000-ebab4c2e16bf68ae4eae | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 40V, Negative-QTOF | splash10-0uds-1029000000-c0dee0feb1de6b2a65ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 10V, Positive-QTOF | splash10-00di-2019000000-0f7f14d013a50b3f45e8 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 20V, Positive-QTOF | splash10-08fr-0914000000-8e000acb0b84552ed282 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 40V, Positive-QTOF | splash10-0a4i-0900000000-4fd0585b1d8b52ae8e26 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 10V, Negative-QTOF | splash10-014i-0009000000-8d061930341382f43893 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 20V, Negative-QTOF | splash10-02t9-0009000000-8625352f375107351f34 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rimexolone 40V, Negative-QTOF | splash10-014i-1039000000-5d5c04496eff7ee9820f | 2021-10-11 | Wishart Lab | View Spectrum |
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