Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-18 19:13:49 UTC |
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Update Date | 2019-07-23 07:14:52 UTC |
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HMDB ID | HMDB0060690 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Ketoifosfamide |
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Description | 4-Ketoifosfamide belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains. 4-Ketoifosfamide is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. 4-Ketoifosfamide is a very weakly acidic compound (based on its pKa). In humans, 4-ketoifosfamide is involved in ifosfamide metabolism pathway. It is sometimes abbreviated 'IFO'. |
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Structure | ClCCNP1(=O)OCCC(=O)N1CCCl InChI=1S/C7H13Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h1-6H2,(H,10,13) |
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Synonyms | Value | Source |
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4-Ketoifosfamide, (S)-isomer | HMDB |
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Chemical Formula | C7H13Cl2N2O3P |
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Average Molecular Weight | 275.069 |
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Monoisotopic Molecular Weight | 274.004084218 |
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IUPAC Name | 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione |
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Traditional Name | 4-ketoifosfamide |
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CAS Registry Number | Not Available |
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SMILES | ClCCNP1(=O)OCCC(=O)N1CCCl |
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InChI Identifier | InChI=1S/C7H13Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h1-6H2,(H,10,13) |
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InChI Key | PEZLCTIXHCOEOG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Oxazaphosphinanes |
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Sub Class | Isofamides |
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Direct Parent | Isofamides |
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Alternative Parents | |
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Substituents | - Isofamide
- Organic phosphoric acid derivative
- Organic phosphoric acid amide
- Carboxylic acid derivative
- Azacycle
- Oxacycle
- Alkyl chloride
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organic oxygen compound
- Organohalogen compound
- Organic nitrogen compound
- Carbonyl group
- Alkyl halide
- Hydrocarbon derivative
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | |
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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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4-Ketoifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 2156.9 | Semi standard non polar | 33892256 | 4-Ketoifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 2126.1 | Standard non polar | 33892256 | 4-Ketoifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 3066.6 | Standard polar | 33892256 | 4-Ketoifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 2424.7 | Semi standard non polar | 33892256 | 4-Ketoifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 2372.7 | Standard non polar | 33892256 | 4-Ketoifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl | 3196.8 | 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 - 4-Ketoifosfamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-03g1-4890000000-70b09f3838e2ec71629d | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Ketoifosfamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Ketoifosfamide 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 - 4-Ketoifosfamide 10V, Positive-QTOF | splash10-0a4i-9020000000-61b100347818e415b7a8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Positive-QTOF | splash10-001i-9000000000-1913777d6533a9470ec5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Positive-QTOF | splash10-0a4i-9000000000-55575a2a20e4b5270778 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Negative-QTOF | splash10-03di-3790000000-65c483ba55dc262acdb7 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Negative-QTOF | splash10-001i-8900000000-d416672ac210c11662ec | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Negative-QTOF | splash10-004l-9000000000-bebe75fba33a4f3c3605 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Positive-QTOF | splash10-004i-0190000000-857350524f92bcf3baa7 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Positive-QTOF | splash10-004i-1390000000-125e4d12e3fd0e230a4f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Positive-QTOF | splash10-03di-9400000000-b8e82bcd1f6f05491553 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Negative-QTOF | splash10-00di-0090000000-f86efbbe1892f50c3efc | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Negative-QTOF | splash10-00dl-0960000000-ad8a206b47214fd39275 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Negative-QTOF | splash10-03dr-2900000000-865ce1fbfb062cd90eb4 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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