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 18:55:11 UTC |
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Update Date | 2019-07-23 07:14:51 UTC |
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HMDB ID | HMDB0060686 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Ketocyclophosphamide |
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Description | 4-Ketocyclophosphamide 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 | ClCCN(CCCl)P1(=O)NC(=O)CCO1 InChI=1S/C7H13Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h1-6H2,(H,10,12,13) |
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Synonyms | Value | Source |
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4-Ketocyclophosphamide, (S)-isomer | HMDB | 4-Ketocyclophosphamide, (R)-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 | 2-[bis(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione |
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Traditional Name | 2-[bis(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione |
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CAS Registry Number | Not Available |
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SMILES | ClCCN(CCCl)P1(=O)NC(=O)CCO1 |
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InChI Identifier | InChI=1S/C7H13Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h1-6H2,(H,10,12,13) |
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InChI Key | VBMZHOCORXMDJU-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 derivative
- Organic phosphoric acid amide
- Organoheterocyclic compound
- Oxacycle
- Azacycle
- Alkyl chloride
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organochloride
- Organopnictogen compound
- Organohalogen compound
- Organic oxygen compound
- Alkyl halide
- 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-Ketocyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2090.8 | Semi standard non polar | 33892256 | 4-Ketocyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2124.4 | Standard non polar | 33892256 | 4-Ketocyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2864.8 | Standard polar | 33892256 | 4-Ketocyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2354.4 | Semi standard non polar | 33892256 | 4-Ketocyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2388.6 | Standard non polar | 33892256 | 4-Ketocyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl | 2982.3 | 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 - 4-Ketocyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-01q0-3960000000-d4ee69c4b1af29ee0b79 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Ketocyclophosphamide 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-Ketocyclophosphamide 10V, Positive-QTOF | splash10-0a6r-9150000000-a5fe23eb32924f1c101d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Positive-QTOF | splash10-006x-9800000000-6de17123e0f5162e9a8b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Positive-QTOF | splash10-0bvi-9000000000-99792497718e2c066f20 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Negative-QTOF | splash10-03di-1690000000-0ae369eead37fb2bb6ea | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Negative-QTOF | splash10-00dl-9000000000-ffa9969f204bd6d68bb8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Negative-QTOF | splash10-0007-9000000000-7c9a945230dd65d33ef4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Positive-QTOF | splash10-004i-1490000000-06cf3f86b8a2918caea1 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Positive-QTOF | splash10-057i-2940000000-bd20f30390805f5f11c7 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Positive-QTOF | splash10-03di-9200000000-46a634ff820fbda1e6db | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Negative-QTOF | splash10-00di-0090000000-25eb03240c1ec5a1c446 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Negative-QTOF | splash10-00e9-2390000000-be3c5228dbf1f7a8f8bb | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Negative-QTOF | splash10-01si-9210000000-7758cd4ad83b31237ca4 | 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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