Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:42 UTC |
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HMDB ID | HMDB0014672 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cyclophosphamide |
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Description | Cyclophosphamide, also known as cytoxan or cytophosphan, 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. In humans, cyclophosphamide is involved in the cyclophosphamide action pathway. Cyclophosphamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Cyclophosphamide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Cyclophosphamide. |
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Structure | InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12) |
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Synonyms | Value | Source |
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(+-)-Cyclophosphamide | ChEBI | (RS)-Cyclophosphamide | ChEBI | 2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide | ChEBI | Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester | ChEBI | Cyclophosphamide anhydrous | ChEBI | N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide | ChEBI | Cytoxan | Kegg | Cyclophosphamide monohydrate | HMDB | Cytophosphan | HMDB | Sendoxan | HMDB | Anhydrous, cyclophosphamide | HMDB | Cyclophosphamide, (S)-isomer | HMDB | Cyclophosphane | HMDB | Cytophosphane | HMDB | Endoxan | HMDB | Neosar | HMDB | Cyclophosphamide, (R)-isomer | HMDB | Monohydrate, cyclophosphamide | HMDB | Procytox | HMDB | (+,-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate | HMDB |
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Chemical Formula | C7H15Cl2N2O2P |
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Average Molecular Weight | 261.086 |
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Monoisotopic Molecular Weight | 260.02481966 |
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IUPAC Name | 2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one |
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Traditional Name | 2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one |
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CAS Registry Number | 6055-19-2 |
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SMILES | ClCCN(CCCl)P1(=O)NCCCO1 |
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InChI Identifier | InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12) |
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InChI Key | CMSMOCZEIVJLDB-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
- Oxazaphosphinane
- Organic phosphoric acid amide
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organochloride
- Organopnictogen compound
- Organohalogen compound
- Organic oxygen compound
- Alkyl chloride
- 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 | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 41 - 45 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 15.1 g/L | Not Available | LogP | 0.8 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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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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Cyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 2041.3 | Semi standard non polar | 33892256 | Cyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 1917.6 | Standard non polar | 33892256 | Cyclophosphamide,1TMS,isomer #1 | C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 2667.1 | Standard polar | 33892256 | Cyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 2272.9 | Semi standard non polar | 33892256 | Cyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 2163.3 | Standard non polar | 33892256 | Cyclophosphamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl | 2799.3 | 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 - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dj-2930000000-a5e2529d99bd261703f0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-08fr-9470000000-53f4a8ff83c415492e03 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF | splash10-0059-1490000000-36d8ebdb421248c38c7b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF | splash10-03di-1390000000-b8dc1a824ec33e388213 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF | splash10-03di-0390000000-66983035d1db7ac36bd6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-001l-0970000000-939110a705ed71803ab8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-03di-0090000000-2bdfe4296c2bdf8d4a99 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-03di-0190000000-1e8e017f8e39fa5d73cf | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0930000000-d7459c8d20a8fc59f6f0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0900000000-33cb20e845200f9d2618 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-2900000000-09d33a8387b9d152f24a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-01ox-6900000000-cdebe09ff6df7c25b477 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-03di-0090000000-d749f27c3144da2c431c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-03di-0190000000-a6fa921df18384671a7c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0930000000-abdb40162fc8a44200f7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0900000000-8c0705ee62a5f9c7d44e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-2900000000-a299026342c77e92c48c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-01ox-6900000000-fc2845c75bbccc83ad99 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-001l-0970000000-83e0f5b88b6fbe0a1ea7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0900000000-5490a2b493bfde967fa3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF | splash10-0006-0900000000-456626f46e480e0ac670 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Positive-QTOF | splash10-0006-9150000000-28408c9f0486cc7568f2 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Positive-QTOF | splash10-052f-9600000000-fd85ba5646421fb4dd68 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Positive-QTOF | splash10-0006-9100000000-dc67f093f2419f82cb18 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Negative-QTOF | splash10-0002-1920000000-ef90686fe8c9da71ccd6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Negative-QTOF | splash10-0a4i-9000000000-c974342f3a086d037df6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Negative-QTOF | splash10-002u-9600000000-142aeef910da3ef2f6b3 | 2016-08-03 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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