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 02:51:49 UTC |
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HMDB ID | HMDB0014996 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Drostanolone |
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Description | Drostanolone is only found in individuals that have used or taken this drug. It is a potent synthetic androgenic anabolic steroid similar to testosterone. Drostanolone is indicated in postmenopausal women with recurrent breast cancer, in a combined hormone therapy.Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production. |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)[C@H](C)C[C@]12C InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1 |
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Synonyms | Value | Source |
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17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-one | ChEBI | 2alpha-Methyldihydrotestosterone | ChEBI | Dihydro-2alpha-methyltestosterone | ChEBI | Dromostanolone | ChEBI | Drostanolona | ChEBI | Drostanolonum | ChEBI | Medrosteron | ChEBI | Medrotestron | ChEBI | 17b-Hydroxy-2a-methyl-5a-androstan-3-one | Generator | 17Β-hydroxy-2α-methyl-5α-androstan-3-one | Generator | 2a-Methyldihydrotestosterone | Generator | 2Α-methyldihydrotestosterone | Generator | Dihydro-2a-methyltestosterone | Generator | Dihydro-2α-methyltestosterone | Generator | Drolban | HMDB | Metholone | HMDB | Dromostanolone, (5alpha,17beta)-isomer | HMDB | Prometholone | HMDB | Drostanolon | HMDB | 17 beta-Hydroxy-2 alpha-methyl-5 alpha-androstan-3-one | HMDB | Methalone | HMDB | Drostanolone | ChEBI |
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Chemical Formula | C20H32O2 |
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Average Molecular Weight | 304.4669 |
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Monoisotopic Molecular Weight | 304.240230268 |
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IUPAC Name | (1S,2S,4R,7S,10R,11S,14S,15S)-14-hydroxy-2,4,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one |
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Traditional Name | drostanolone |
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CAS Registry Number | 58-19-5 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)[C@H](C)C[C@]12C |
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InChI Identifier | InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1 |
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InChI Key | IKXILDNPCZPPRV-RFMGOVQKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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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 | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- 3-oxosteroid
- 3-oxo-5-alpha-steroid
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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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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Drostanolone,1TMS,isomer #1 | C[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]32)CC1=O | 2668.0 | Semi standard non polar | 33892256 | Drostanolone,1TMS,isomer #2 | CC1=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)C1 | 2696.3 | Semi standard non polar | 33892256 | Drostanolone,1TMS,isomer #3 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12 | 2572.9 | Semi standard non polar | 33892256 | Drostanolone,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 2681.9 | Semi standard non polar | 33892256 | Drostanolone,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 2695.7 | Standard non polar | 33892256 | Drostanolone,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 2974.3 | Standard polar | 33892256 | Drostanolone,2TMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C)[C@@]3(C)CC[C@@H]12 | 2564.3 | Semi standard non polar | 33892256 | Drostanolone,2TMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C)[C@@]3(C)CC[C@@H]12 | 2673.2 | Standard non polar | 33892256 | Drostanolone,2TMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C)[C@@]3(C)CC[C@@H]12 | 2972.4 | Standard polar | 33892256 | Drostanolone,1TBDMS,isomer #1 | C[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]32)CC1=O | 2909.2 | Semi standard non polar | 33892256 | Drostanolone,1TBDMS,isomer #2 | CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)C1 | 2923.8 | Semi standard non polar | 33892256 | Drostanolone,1TBDMS,isomer #3 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12 | 2818.9 | Semi standard non polar | 33892256 | Drostanolone,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 3215.5 | Semi standard non polar | 33892256 | Drostanolone,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 3107.3 | Standard non polar | 33892256 | Drostanolone,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]34)[C@@]2(C)C1 | 3220.3 | Standard polar | 33892256 | Drostanolone,2TBDMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3088.9 | Semi standard non polar | 33892256 | Drostanolone,2TBDMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3031.2 | Standard non polar | 33892256 | Drostanolone,2TBDMS,isomer #2 | C[C@@H]1C[C@@]2(C)[C@H](C=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3220.3 | 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 - Drostanolone GC-MS (Non-derivatized) - 70eV, Positive | splash10-01u9-0290000000-692c470ca66bdb33f8cd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Drostanolone GC-MS (1 TMS) - 70eV, Positive | splash10-08fs-3249000000-faaa19221c2eb1b1a219 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Drostanolone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f6w-8931000000-0d33c997ec04e3071c8c | 2014-09-20 | Not Available | 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 - Drostanolone 10V, Negative-QTOF | splash10-0udi-0029000000-601877ac3c6aed55c1c2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 20V, Negative-QTOF | splash10-0udi-0059000000-70257557fd2f0d3d532c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 40V, Negative-QTOF | splash10-0079-3090000000-cca24aebaf0ba5f4c845 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 10V, Negative-QTOF | splash10-0udi-0009000000-f9d10b76ade80bd401ad | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 20V, Negative-QTOF | splash10-0udi-0009000000-f9d10b76ade80bd401ad | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 40V, Negative-QTOF | splash10-0udi-0098000000-eb87ce2a04744f9a7151 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 10V, Positive-QTOF | splash10-052r-0195000000-d6ce78753754982edcde | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 20V, Positive-QTOF | splash10-052r-0291000000-dce1079644608ccf2d76 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 40V, Positive-QTOF | splash10-0gbm-2790000000-bb7896733d6ff696a1fa | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 10V, Positive-QTOF | splash10-000i-0092000000-5f392111cd6198b67db7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 20V, Positive-QTOF | splash10-0a6r-1951000000-454d26a526f739add98a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Drostanolone 40V, Positive-QTOF | splash10-0a6r-1900000000-0194bfdeaee7cb6f33e8 | 2021-10-11 | Wishart Lab | View Spectrum |
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