Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:15:15 UTC |
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Update Date | 2019-07-23 07:15:40 UTC |
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HMDB ID | HMDB0061051 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-desmethyltoremifene |
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Description | N-desmethyltoremifene belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. N-desmethyltoremifene is a metabolite of toremifene. N-desmethyltoremifene is a very strong basic compound (based on its pKa). Toremifene citrate is an oral selective estrogen receptor modulator (SERM) which helps oppose the actions of estrogen in the body. Licensed in the United States under the brand name Fareston, toremifene citrate is FDA-approved for use in advanced breast cancer. It is also being evaluated for prevention of prostate cancer under the brand name Acapodene. |
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Structure | CNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1 InChI=1S/C25H26ClNO/c1-27-18-19-28-23-14-12-22(13-15-23)25(21-10-6-3-7-11-21)24(16-17-26)20-8-4-2-5-9-20/h2-15,27H,16-19H2,1H3/b25-24- |
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Synonyms | Value | Source |
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N-Demethyltoremifene | HMDB | N-Desmethyltoremifene, (e)-isomer | HMDB |
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Chemical Formula | C25H26ClNO |
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Average Molecular Weight | 391.933 |
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Monoisotopic Molecular Weight | 391.170292166 |
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IUPAC Name | (2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amine |
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Traditional Name | (2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amine |
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CAS Registry Number | Not Available |
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SMILES | CNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C25H26ClNO/c1-27-18-19-28-23-14-12-22(13-15-23)25(21-10-6-3-7-11-21)24(16-17-26)20-8-4-2-5-9-20/h2-15,27H,16-19H2,1H3/b25-24- |
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InChI Key | WKJKBQYEFAFHCY-IZHYLOQSSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Stilbenes |
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Sub Class | Not Available |
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Direct Parent | Stilbenes |
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Alternative Parents | |
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Substituents | - Stilbene
- Diphenylmethane
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Secondary amine
- Ether
- Secondary aliphatic amine
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Alkyl halide
- Hydrocarbon derivative
- Alkyl chloride
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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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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N-desmethyltoremifene,1TMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C | 3412.7 | Semi standard non polar | 33892256 | N-desmethyltoremifene,1TMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C | 3216.4 | Standard non polar | 33892256 | N-desmethyltoremifene,1TMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C | 4015.2 | Standard polar | 33892256 | N-desmethyltoremifene,1TBDMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C | 3624.3 | Semi standard non polar | 33892256 | N-desmethyltoremifene,1TBDMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C | 3396.4 | Standard non polar | 33892256 | N-desmethyltoremifene,1TBDMS,isomer #1 | CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C | 4055.6 | 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 - N-desmethyltoremifene GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9033000000-3948160a9f73f997e92a | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-desmethyltoremifene 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 - N-desmethyltoremifene 10V, Positive-QTOF | splash10-0006-1119000000-7fe104edfdaaacaf8b96 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Positive-QTOF | splash10-0a4i-9237000000-c914a2d48019610106d4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Positive-QTOF | splash10-0a4l-7091000000-c50fa529f1f94d67648e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Negative-QTOF | splash10-0006-1009000000-68ba93a0d04446c5d4c1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Negative-QTOF | splash10-001l-1029000000-f0d5f189dbdcb8eb7525 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Negative-QTOF | splash10-001i-6189000000-b4470fdb0dda4e06d65b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Negative-QTOF | splash10-0006-1009000000-c63f847dc3e5831b77e3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Negative-QTOF | splash10-001l-9038000000-013adbca58f359999630 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Negative-QTOF | splash10-0002-0094000000-6e0338f47c66abc25cef | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Positive-QTOF | splash10-0006-0009000000-f75a20bf7b62259d06fc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Positive-QTOF | splash10-0006-0049000000-210bbd22f64b6df7e4e8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Positive-QTOF | splash10-015c-1951000000-14f8d51171c4453b945d | 2021-09-24 | Wishart Lab | View Spectrum |
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