Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-05-17 01:20:31 UTC |
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Update Date | 2019-07-23 07:14:19 UTC |
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HMDB ID | HMDB0060433 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Aldophosphamide |
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Description | Detoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. Detoxification of aldophosphamide may also be effected by enzymes, viz. Thus, NAD-linked oxidation and NADPH-linked reduction of aldophosphamide catalyzed by relevant erythrocyte enzymes were quantified. (PMID: 9394035 ) Class 1 aldehyde dehydrogenases (ALDH-1) function as drug resistance gene products by catalyzing the irreversible conversion of aldophosphamide, an active metabolite of cyclophosphamide, to an inert compound. (PMID: 9322086 ) |
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Structure | NP(=O)(OCCC=O)N(CCCl)CCCl InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h6H,1-5,7H2,(H2,10,13) |
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Synonyms | Value | Source |
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Cyclophosphamide-mustard | HMDB | Cyp-mustard | HMDB |
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Chemical Formula | C7H15Cl2N2O3P |
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Average Molecular Weight | 277.085 |
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Monoisotopic Molecular Weight | 276.019734282 |
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IUPAC Name | 3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanal |
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Traditional Name | aldophosphamide |
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CAS Registry Number | Not Available |
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SMILES | NP(=O)(OCCC=O)N(CCCl)CCCl |
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InChI Identifier | InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h6H,1-5,7H2,(H2,10,13) |
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InChI Key | QMGUSPDJTPDFSF-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
- Phosphoric monoester diamide
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Organic phosphoric acid amide
- Alpha-hydrogen aldehyde
- Organic oxide
- Organooxygen compound
- Organochloride
- Organopnictogen compound
- Organohalogen compound
- Organic oxygen compound
- Carbonyl group
- Aldehyde
- Alkyl halide
- Alkyl chloride
- Hydrocarbon derivative
- 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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Aldophosphamide,1TMS,isomer #1 | C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 2199.4 | Semi standard non polar | 33892256 | Aldophosphamide,1TMS,isomer #1 | C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 2021.2 | Standard non polar | 33892256 | Aldophosphamide,1TMS,isomer #1 | C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 3924.0 | Standard polar | 33892256 | Aldophosphamide,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 2130.8 | Semi standard non polar | 33892256 | Aldophosphamide,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 1997.8 | Standard non polar | 33892256 | Aldophosphamide,1TMS,isomer #2 | C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 2886.3 | Standard polar | 33892256 | Aldophosphamide,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl | 2204.1 | Semi standard non polar | 33892256 | Aldophosphamide,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl | 2162.5 | Standard non polar | 33892256 | Aldophosphamide,2TMS,isomer #1 | C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl | 2708.3 | Standard polar | 33892256 | Aldophosphamide,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2239.6 | Semi standard non polar | 33892256 | Aldophosphamide,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2189.2 | Standard non polar | 33892256 | Aldophosphamide,2TMS,isomer #2 | C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2630.1 | Standard polar | 33892256 | Aldophosphamide,3TMS,isomer #1 | C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 2309.4 | Semi standard non polar | 33892256 | Aldophosphamide,3TMS,isomer #1 | C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 2316.9 | Standard non polar | 33892256 | Aldophosphamide,3TMS,isomer #1 | C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C | 2581.1 | Standard polar | 33892256 | Aldophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 2421.1 | Semi standard non polar | 33892256 | Aldophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 2264.2 | Standard non polar | 33892256 | Aldophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl | 4043.7 | Standard polar | 33892256 | Aldophosphamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 2398.8 | Semi standard non polar | 33892256 | Aldophosphamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 2244.8 | Standard non polar | 33892256 | Aldophosphamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl | 2930.9 | Standard polar | 33892256 | Aldophosphamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2640.7 | Semi standard non polar | 33892256 | Aldophosphamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2571.4 | Standard non polar | 33892256 | Aldophosphamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl | 2842.4 | Standard polar | 33892256 | Aldophosphamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2695.1 | Semi standard non polar | 33892256 | Aldophosphamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2541.9 | Standard non polar | 33892256 | Aldophosphamide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl | 2713.4 | Standard polar | 33892256 | Aldophosphamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2940.2 | Semi standard non polar | 33892256 | Aldophosphamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2806.2 | Standard non polar | 33892256 | Aldophosphamide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2740.8 | 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 - Aldophosphamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-01r6-3930000000-ff6f36c8b42295802040 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aldophosphamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aldophosphamide 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 - Aldophosphamide 10V, Positive-QTOF | splash10-0a6r-3190000000-ab09c0d99d6be0494721 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 20V, Positive-QTOF | splash10-0a4i-9100000000-4f52a98720e48a89bf67 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 40V, Positive-QTOF | splash10-0bvl-9300000000-b456c4d19d6e29b11aa4 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 10V, Negative-QTOF | splash10-03di-1390000000-f2cfbeebb17c18444fc4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 20V, Negative-QTOF | splash10-03xr-9330000000-e296d1c2deb7425c67d6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 40V, Negative-QTOF | splash10-0udu-2910000000-ab68ba84f4c31e2560ee | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 10V, Positive-QTOF | splash10-004i-0390000000-85648cd89df23d147468 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 20V, Positive-QTOF | splash10-00dl-0790000000-9db4ba9eb9886927554f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 40V, Positive-QTOF | splash10-0btc-9100000000-d3145b5a45da48514901 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 10V, Negative-QTOF | splash10-004i-0090000000-6cd6113372d1d0808e1d | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 20V, Negative-QTOF | splash10-0059-2390000000-09ec42c4941802f6cb3d | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aldophosphamide 40V, Negative-QTOF | splash10-0pyi-4910000000-eb2eb8022150d34149a4 | 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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