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 02:51:56 UTC |
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HMDB ID | HMDB0015327 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Estramustine |
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Description | Estramustine is only found in individuals that have used or taken this drug. It is a nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties. [PubChem]Estramustine is a derivative of estradiol with a nitrogen mustard moiety. This gives it alkylating properties. In vivo, the nitrogen mustard component is active and can alklyate DNA and other cellular components (such as tubulin components) of rapidly dividing cells. This causes DNA strandbreaks or misscoding events. This leads to apoptosis and cell death. Also, due to the drugs estrogen component, it can bind more selectively to active estrogen receptors. |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H] InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1 |
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Synonyms | Value | Source |
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17beta-Estradiol 3-(bis(2-chloroethyl)carbamate) | ChEBI | Estradiol 3-(N,N-bis(2-chloroethyl)carbamate) | ChEBI | Estramustina | ChEBI | Estramustinum | ChEBI | 17b-Estradiol 3-(bis(2-chloroethyl)carbamate) | Generator | 17b-Estradiol 3-(bis(2-chloroethyl)carbamic acid) | Generator | 17beta-Estradiol 3-(bis(2-chloroethyl)carbamic acid) | Generator | 17Β-estradiol 3-(bis(2-chloroethyl)carbamate) | Generator | 17Β-estradiol 3-(bis(2-chloroethyl)carbamic acid) | Generator | Estradiol 3-(N,N-bis(2-chloroethyl)carbamic acid) | Generator | Estramustin sodium phosphate | HMDB | Estramustine sodium phosphate | HMDB | Estracyt | HMDB | Estramustine phosphate sodium | HMDB | Phosphate, estramustin | HMDB | Leo 275 | HMDB | Emcyt | HMDB | Estramustinphosphate | HMDB | Estramustin phosphate | HMDB | Leo-275 | HMDB | Phosphate sodium, estramustine | HMDB |
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Chemical Formula | C23H31Cl2NO3 |
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Average Molecular Weight | 440.403 |
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Monoisotopic Molecular Weight | 439.168099277 |
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IUPAC Name | (1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl N,N-bis(2-chloroethyl)carbamate |
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Traditional Name | estramustine |
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CAS Registry Number | 2998-57-4 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H] |
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InChI Identifier | InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1 |
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InChI Key | FRPJXPJMRWBBIH-RBRWEJTLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane 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 | Estrane steroids |
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Direct Parent | Estrane steroids |
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Alternative Parents | |
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Substituents | - Estrane-skeleton
- Hydroxysteroid
- 17-hydroxysteroid
- Phenanthrene
- Tetralin
- Nitrogen mustard
- Benzenoid
- Cyclic alcohol
- Carbamic acid ester
- Secondary alcohol
- Carbonic acid derivative
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organic oxide
- Alkyl chloride
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Alkyl halide
- Organic oxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic 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 | 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 | 104.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00038 g/L | Not Available | LogP | 5.7 | 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 IndicesUnderivatizedDerivatized |
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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 - Estramustine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-7427900000-b87366cc1573c4f6c93a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Estramustine GC-MS (1 TMS) - 70eV, Positive | splash10-0006-8704900000-9a612e46f22fe81c874c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Estramustine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Estramustine 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 - Estramustine 10V, Positive-QTOF | splash10-006x-0720900000-7d95b1bd74a3e1ae6ae2 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 20V, Positive-QTOF | splash10-0a4l-2971100000-a6f224fc389435653942 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 40V, Positive-QTOF | splash10-03fu-9510000000-032d08f0be5c8b065fa7 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 10V, Negative-QTOF | splash10-000i-0522900000-a880e700fad8ec3373b9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 20V, Negative-QTOF | splash10-0v4i-0962500000-ffc041fb7d64ff64e5e8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 40V, Negative-QTOF | splash10-0h4o-7980000000-eef6a5c5a61126ea9699 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 10V, Positive-QTOF | splash10-0006-0020900000-c6017d6c0b19d376975c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 20V, Positive-QTOF | splash10-01vo-0216900000-e073983c6de9895bcdc7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 40V, Positive-QTOF | splash10-0bt9-5910000000-1c6900d7579dfbd1cc68 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 10V, Negative-QTOF | splash10-0019-4002900000-5c59bbd62d2862fbf52d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 20V, Negative-QTOF | splash10-001i-9050000000-f5313068b0db56036aa5 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estramustine 40V, Negative-QTOF | splash10-001i-9000000000-c2fa753da65a4bac80a1 | 2021-10-11 | Wishart Lab | View Spectrum |
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