Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-04-12 20:10:44 UTC |
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Update Date | 2021-09-14 15:40:25 UTC |
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HMDB ID | HMDB0006002 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethyltestosterone |
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Description | Ethyltestosterone is a steroid metabolite; it can be the result of the administration of synthetic steroids used in the past in different anabolic therapies, such as in tuberculosis (i.e.: Dianabon in 1946), or in gynecology (1960's). These abandoned or never commercialized anabolic steroids have been taken up by producers of 'designer steroids' and re-introduced as aids in sports, sometimes with modifications to their structure to avoid being detected in regular screening for doping. These anabolic steroids constitute a threat to the spirit of integrity and fairness in sport and to the health of athletes, since their side effects are unknown. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Ethyltestosterone is a common standard used in the screening for human steroids in human urine in sport doping control. (PMID: 15934041 , 15712346 ). |
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Structure | [H][C@@]12CC[C@@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h13,16-18,23H,4-12H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 |
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Synonyms | Value | Source |
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(17a)-17-Hydroxy-pregn-4-en-3-one | HMDB | 17-Ethyl-testosterone | HMDB | 17-Hydroxy-17a-pregn-4-en-3-one | HMDB | 17a-Ethyltestosterone | HMDB |
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Chemical Formula | C21H32O2 |
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Average Molecular Weight | 316.4776 |
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Monoisotopic Molecular Weight | 316.240230268 |
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IUPAC Name | (1S,2R,10R,11S,14S,15S)-14-ethyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one |
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Traditional Name | ethyltestosterone |
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CAS Registry Number | 1235-97-8 |
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SMILES | [H][C@@]12CC[C@@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h13,16-18,23H,4-12H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 |
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InChI Key | FGPGANCDNDLUST-CEGNMAFCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. |
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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 | Pregnane steroids |
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Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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Alternative Parents | |
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Substituents | - Progestogin-skeleton
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Tertiary alcohol
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organooxygen compound
- Organic oxide
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | - C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030201 )
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Ontology |
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Not Available | 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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Ethyltestosterone,1TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 2914.9 | Semi standard non polar | 33892256 | Ethyltestosterone,1TMS,isomer #2 | CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 2752.4 | Semi standard non polar | 33892256 | Ethyltestosterone,2TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 2827.8 | Semi standard non polar | 33892256 | Ethyltestosterone,2TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 2839.5 | Standard non polar | 33892256 | Ethyltestosterone,2TMS,isomer #1 | CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3067.4 | Standard polar | 33892256 | Ethyltestosterone,1TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3162.0 | Semi standard non polar | 33892256 | Ethyltestosterone,1TBDMS,isomer #2 | CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3031.7 | Semi standard non polar | 33892256 | Ethyltestosterone,2TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3347.8 | Semi standard non polar | 33892256 | Ethyltestosterone,2TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3306.7 | Standard non polar | 33892256 | Ethyltestosterone,2TBDMS,isomer #1 | CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C | 3288.3 | 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 - Ethyltestosterone GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-0391000000-618e0793d83ff1637b47 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyltestosterone GC-MS (1 TMS) - 70eV, Positive | splash10-074i-1119000000-b0ce3502e9b25d58384c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethyltestosterone 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 - Ethyltestosterone 10V, Positive-QTOF | splash10-00kb-0196000000-8d1460d87776ffdbdeff | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 20V, Positive-QTOF | splash10-00kb-0291000000-5231471c8c160ef1cdea | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 40V, Positive-QTOF | splash10-00b9-1890000000-2d014b813ce5344f9686 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 10V, Negative-QTOF | splash10-014i-0029000000-8719e0bdbdfd8c016ebf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 20V, Negative-QTOF | splash10-014i-0059000000-44e8d55983e75dc8a170 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 40V, Negative-QTOF | splash10-052k-0090000000-98ed1a6b511bf1cdea5f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 10V, Positive-QTOF | splash10-014i-0039000000-0029392ce9fd7cfba055 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 20V, Positive-QTOF | splash10-0wos-0950000000-20b1192ed5108970ab0b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 40V, Positive-QTOF | splash10-066r-4900000000-23d23bc98f7da2f6ba21 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 10V, Negative-QTOF | splash10-014i-0009000000-be6e06313d0abca8e664 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 20V, Negative-QTOF | splash10-014i-0029000000-9712a87b24c18d9ef7c5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethyltestosterone 40V, Negative-QTOF | splash10-014i-0092000000-909ab322dc3c13a6ac3b | 2021-09-22 | Wishart Lab | View Spectrum |
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