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 15:16:51 UTC |
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Update Date | 2023-02-21 17:18:22 UTC |
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HMDB ID | HMDB0015052 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Metronidazole |
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Description | Metronidazole, also known as metrogel-vaginal or flagyl, belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. Metronidazole is a moderately basic compound (based on its pKa). Metronidazole is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. |
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Structure | CC1=NC=C(N1CCO)[N+]([O-])=O InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 |
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Synonyms | Value | Source |
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1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazole | ChEBI | 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole | ChEBI | 1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrrole | ChEBI | 1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole | ChEBI | 1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole | ChEBI | 2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazole | ChEBI | 2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazole | ChEBI | 2-Methyl-5-nitroimidazole-1-ethanol | ChEBI | Metronidazol | ChEBI | Metronidazolum | ChEBI | Flagyl | Kegg | Metrogel-vaginal | Kegg | Noritate | Kegg | 1-(b-Ethylol)-2-methyl-5-nitro-3-azapyrrole | Generator | 1-(Β-ethylol)-2-methyl-5-nitro-3-azapyrrole | Generator | 1-(b-Hydroxyethyl)-2-methyl-5-nitroimidazole | Generator | 1-(Β-hydroxyethyl)-2-methyl-5-nitroimidazole | Generator | 1-(b-Oxyethyl)-2-methyl-5-nitroimidazole | Generator | 1-(Β-oxyethyl)-2-methyl-5-nitroimidazole | Generator | Noritic acid | Generator | Methronidazole | HMDB | Metronidazole benzoate | HMDB | Metronidazole in plastic container | HMDB | Metronidazolo | HMDB | Danizol | HMDB | Gineflavir | HMDB | Metric | HMDB | Metrodzhil | HMDB | Metrogyl | HMDB | Metronidazole phosphoester | HMDB | Metronidazole hydrochloride | HMDB | Phosphoester, metronidazole | HMDB | 2 Methyl 5 nitroimidazole 1 ethanol | HMDB | Clont | HMDB | Metronidazole phosphate | HMDB | Phosphate, metronidazole | HMDB | Trivazol | HMDB | Bayer 5360 | HMDB | Hydrochloride, metronidazole | HMDB | MetroGel | HMDB | Metronidazole monohydrochloride | HMDB | Monohydrochloride, metronidazole | HMDB | Satric | HMDB | Trichazol | HMDB | Trichopol | HMDB | Vagilen | HMDB |
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Chemical Formula | C6H9N3O3 |
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Average Molecular Weight | 171.154 |
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Monoisotopic Molecular Weight | 171.064391169 |
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IUPAC Name | 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol |
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Traditional Name | metronidazole |
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CAS Registry Number | 443-48-1 |
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SMILES | CC1=NC=C(N1CCO)[N+]([O-])=O |
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InChI Identifier | InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 |
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InChI Key | VAOCPAMSLUNLGC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Imidazoles |
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Direct Parent | Nitroimidazoles |
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Alternative Parents | |
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Substituents | - 1,2,5-trisubstituted-imidazole
- Nitroaromatic compound
- Nitroimidazole
- Trisubstituted imidazole
- N-substituted imidazole
- Heteroaromatic compound
- Organic nitro compound
- C-nitro compound
- Alkanolamine
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Allyl-type 1,3-dipolar organic compound
- Organic oxoazanium
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic zwitterion
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic 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 | 160 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5.92 g/L | Not Available | LogP | -0.1 | 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 IndicesUnderivatizedDerivatized |
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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 - Metronidazole GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udl-9700000000-f1b60dcdd221dbdf9eaa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Metronidazole GC-MS (1 TMS) - 70eV, Positive | splash10-0fmi-9410000000-3cec2097481329b98054 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Metronidazole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0ul0-9300000000-2268b08f47fed3f6d263 | 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 - Metronidazole LC-ESI-QTOF , positive-QTOF | splash10-004i-1900000000-659f2bbb83f8ef5a85d1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-50c7cfe79eb17c4440a8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-00di-0900000000-b06d808767cc01c0d494 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-00fr-0900000000-e9c07cc448b8fb519022 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-8ad03b44aa7557127e34 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-ed7ba5c872a6309a31d4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-2900000000-e0ead4b0eec72b9c44b6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-5900000000-2da8a7b45537f9063220 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-00di-0900000000-24d94f1704e577b05eb7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-00fr-0900000000-fbb1c4e8457cd3d799b9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-fd6166313a17f944f530 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-5ebb32a580e1f5d00170 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-2900000000-811a6e7e45b7ea1a6184 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-5900000000-082e6de6c0fa3f382d84 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOF | splash10-004i-0900000000-baf9e195c01d875e77b5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOF | splash10-00di-0900000000-ec181c008a10dac8040b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOF | splash10-004i-1900000000-2a218e19a8fadb9c66d6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOF | splash10-003r-9500000000-ed02acd36b190c189cc9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOF | splash10-001i-9000000000-71ea79659ccd75c64bef | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 10V, Positive-QTOF | splash10-00di-0900000000-b28839ace139ee8a385b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 20V, Positive-QTOF | splash10-01ox-0900000000-94e5ccc473c03e521e89 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 40V, Positive-QTOF | splash10-01po-9500000000-64f688b22d9371ed56c1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 10V, Negative-QTOF | splash10-00di-0900000000-5f65f2637682eccd62a2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 20V, Negative-QTOF | splash10-05fu-3900000000-dbc213039f9c3a43948e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Metronidazole 40V, Negative-QTOF | splash10-0007-9300000000-935f6b6b00b1b6b723b5 | 2016-08-03 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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 |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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