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 19:13:46 UTC |
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Update Date | 2019-07-23 07:14:52 UTC |
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HMDB ID | HMDB0060689 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Phosphoramide mustard |
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Description | Phosphoramide mustard is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia) |
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Structure | InChI=1S/C4H11Cl2N2O2P/c5-1-3-8(4-2-6)11(7,9)10/h1-4H2,(H3,7,9,10) |
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Synonyms | Value | Source |
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Friedman acid | ChEBI | Phosphamide mustard | ChEBI | Phosphorodiamidic mustard | ChEBI |
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Chemical Formula | C4H11Cl2N2O2P |
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Average Molecular Weight | 221.022 |
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Monoisotopic Molecular Weight | 219.993519532 |
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IUPAC Name | amino[bis(2-chloroethyl)amino]phosphinic acid |
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Traditional Name | phosphoramide mustard |
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CAS Registry Number | Not Available |
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SMILES | NP(O)(=O)N(CCCl)CCCl |
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InChI Identifier | InChI=1S/C4H11Cl2N2O2P/c5-1-3-8(4-2-6)11(7,9)10/h1-4H2,(H3,7,9,10) |
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InChI Key | RJXQSIKBGKVNRT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Nitrogen mustard compounds |
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Direct Parent | Nitrogen mustard compounds |
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Alternative Parents | |
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Substituents | - Nitrogen mustard
- Organic phosphoric acid amide
- Organic phosphoric acid diamide
- Organic phosphoric acid derivative
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organochloride
- Organohalogen compound
- Alkyl halide
- Alkyl chloride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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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Phosphoramide mustard,1TMS,isomer #1 | C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 1802.4 | Semi standard non polar | 33892256 | Phosphoramide mustard,1TMS,isomer #1 | C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 1704.8 | Standard non polar | 33892256 | Phosphoramide mustard,1TMS,isomer #1 | C[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 3132.8 | Standard polar | 33892256 | Phosphoramide mustard,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 1852.2 | Semi standard non polar | 33892256 | Phosphoramide mustard,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 1718.6 | Standard non polar | 33892256 | Phosphoramide mustard,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 2603.4 | Standard polar | 33892256 | Phosphoramide mustard,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl | 1846.8 | Semi standard non polar | 33892256 | Phosphoramide mustard,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl | 1806.7 | Standard non polar | 33892256 | Phosphoramide mustard,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(O[Si](C)(C)C)N(CCCl)CCCl | 2106.6 | Standard polar | 33892256 | Phosphoramide mustard,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl | 1946.0 | Semi standard non polar | 33892256 | Phosphoramide mustard,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl | 1948.5 | Standard non polar | 33892256 | Phosphoramide mustard,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(O)N(CCCl)CCCl | 2365.1 | Standard polar | 33892256 | Phosphoramide mustard,3TMS,isomer #1 | C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 1983.9 | Semi standard non polar | 33892256 | Phosphoramide mustard,3TMS,isomer #1 | C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 1999.3 | Standard non polar | 33892256 | Phosphoramide mustard,3TMS,isomer #1 | C[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 2041.9 | Standard polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 2058.3 | Semi standard non polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 1927.3 | Standard non polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(N)(=O)N(CCCl)CCCl | 3265.9 | Standard polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 2125.4 | Semi standard non polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 1999.8 | Standard non polar | 33892256 | Phosphoramide mustard,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(O)N(CCCl)CCCl | 2660.4 | Standard polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2333.7 | Semi standard non polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2244.7 | Standard non polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2319.5 | Standard polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl | 2385.4 | Semi standard non polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl | 2365.5 | Standard non polar | 33892256 | Phosphoramide mustard,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(O)N(CCCl)CCCl | 2478.3 | Standard polar | 33892256 | Phosphoramide mustard,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2618.9 | Semi standard non polar | 33892256 | Phosphoramide mustard,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2551.4 | Standard non polar | 33892256 | Phosphoramide mustard,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2319.6 | 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 - Phosphoramide mustard GC-MS (Non-derivatized) - 70eV, Positive | splash10-004l-9800000000-9972fd7a6e0c1422d231 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phosphoramide mustard 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 - Phosphoramide mustard 10V, Positive-QTOF | splash10-00di-0290000000-25ff81c3728c97ca3c79 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Positive-QTOF | splash10-0gvo-6890000000-829ce130e33191766175 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Positive-QTOF | splash10-03fr-9200000000-9bb5c816df0fb9b6d5c8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Negative-QTOF | splash10-0a4i-2920000000-c8f586cd1a182aa03251 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Negative-QTOF | splash10-01t9-9110000000-3c16b08c4682a336aba3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Negative-QTOF | splash10-056s-9200000000-320fe847d1c97b4d2d64 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Positive-QTOF | splash10-00dr-0590000000-6100597620b7eda157e9 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Positive-QTOF | splash10-00dl-4970000000-76b0fe2ec1924e262a1a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Positive-QTOF | splash10-03di-9500000000-d00884a1a3f1a0ae5875 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 10V, Negative-QTOF | splash10-014i-1090000000-3898894eceeeafe3be0c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 20V, Negative-QTOF | splash10-00pi-9450000000-dbf00c87965fd13c5766 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phosphoramide mustard 40V, Negative-QTOF | splash10-03fr-9000000000-e4d1785ffbced7da2a23 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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