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 | 2023-02-21 17:18:14 UTC |
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HMDB ID | HMDB0014684 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Fluorouracil |
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Description | Fluorouracil is only found in individuals that have used or taken this drug. It is a pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis. |
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Structure | InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
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Synonyms | Value | Source |
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5-Fluoracil | ChEBI | 5-Fluoropyrimidine-2,4-dione | ChEBI | 5-FU | ChEBI | Fluorouracilo | ChEBI | Fluorouracilum | ChEBI | 5-Fluorouracil | Kegg | Adrucil | Kegg | Carac | Kegg | Fluoroplex | Kegg | 5-FU medac | HMDB | 5-Fluorouracil-biosyn | HMDB | 5FU | HMDB | Dermatech brand OF fluorouracil | HMDB | Efudex | HMDB | Fluoro uracile icn | HMDB | Fluorouracil gry | HMDB | Fluorouracil monopotassium salt | HMDB | Neocorp brand OF fluorouracil | HMDB | Roche brand OF fluorouracil | HMDB | Teva brand OF fluorouracil | HMDB | 5 FU medac | HMDB | 5 HU hexal | HMDB | 5-HU hexal | HMDB | Dakota, fluorouracile | HMDB | Efudix | HMDB | Fluorouracil-gry | HMDB | Fluorouracile dakota | HMDB | Haemato brand OF fluorouracil | HMDB | Haemato fu | HMDB | ICN brand OF fluorouracil | HMDB | Neofluor | HMDB | 5 Fluorouracil biosyn | HMDB | 5-FU lederle | HMDB | CSP Brand OF fluorouracil | HMDB | Dakota brand OF fluorouracil | HMDB | Ferrer brand OF fluorouracil | HMDB | Fluoro-uracile icn | HMDB | Fluorouracil mononitrate | HMDB | Fluorouracil monosodium salt | HMDB | Fluorouracil teva brand | HMDB | Fluorouracilo ferrer far | HMDB | Fluracedyl | HMDB | Onkofluor | HMDB | Pharmachemie brand OF fluorouracil monosodium salt | HMDB | Biosyn brand OF fluorouracil | HMDB | 5 FU lederle | HMDB | 5 Fluorouracil | HMDB | Allergan brand OF fluorouracil | HMDB | Dermik brand OF fluorouracil | HMDB | Fluorouracil potassium salt | HMDB | Fluoruracil | HMDB | Flurodex | HMDB | Gry brand OF fluorouracil | HMDB | Haemato-fu | HMDB | Hexal brand OF fluorouracil | HMDB | Onkoworks brand OF fluorouracil | HMDB | Ribofluor | HMDB | Riemser brand OF fluorouracil | HMDB | Medac brand OF fluorouracil | HMDB | Ribosepharm brand OF fluorouracil | HMDB |
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Chemical Formula | C4H3FN2O2 |
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Average Molecular Weight | 130.0772 |
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Monoisotopic Molecular Weight | 130.017855555 |
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IUPAC Name | 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | fluorouracil |
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CAS Registry Number | 51-21-8 |
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SMILES | FC1=CNC(=O)NC1=O |
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InChI Identifier | InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
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InChI Key | GHASVSINZRGABV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Halopyrimidines |
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Alternative Parents | |
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Substituents | - Hydroxypyrimidine
- Halopyrimidine
- Aryl halide
- Aryl fluoride
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organofluoride
- Organohalogen compound
- 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 | |
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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 | 280 - 282 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5.86 g/L | Not Available | LogP | -0.8 | 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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Fluorouracil,1TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1448.7 | Semi standard non polar | 33892256 | Fluorouracil,1TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1261.8 | Standard non polar | 33892256 | Fluorouracil,1TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1777.3 | Standard polar | 33892256 | Fluorouracil,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1389.3 | Semi standard non polar | 33892256 | Fluorouracil,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1252.0 | Standard non polar | 33892256 | Fluorouracil,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1754.6 | Standard polar | 33892256 | Fluorouracil,2TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O | 1613.7 | Semi standard non polar | 33892256 | Fluorouracil,2TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O | 1416.4 | Standard non polar | 33892256 | Fluorouracil,2TMS,isomer #1 | C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O | 1652.0 | Standard polar | 33892256 | Fluorouracil,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1730.2 | Semi standard non polar | 33892256 | Fluorouracil,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1458.0 | Standard non polar | 33892256 | Fluorouracil,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O | 1896.8 | Standard polar | 33892256 | Fluorouracil,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1623.6 | Semi standard non polar | 33892256 | Fluorouracil,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1449.9 | Standard non polar | 33892256 | Fluorouracil,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O | 1849.9 | Standard polar | 33892256 | Fluorouracil,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 1943.5 | Semi standard non polar | 33892256 | Fluorouracil,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 1820.7 | Standard non polar | 33892256 | Fluorouracil,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 1881.9 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Fluorouracil EI-B (Non-derivatized) | splash10-001i-9800000000-a3301f9fea9145d07480 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-001i-0900000000-76691bd3cba2765d3687 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-001i-0900000000-d801d8209e9a5aa4830b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-0002-0900000000-7521695ae4a96b4a5a98 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil EI-B (Non-derivatized) | splash10-001i-9800000000-a3301f9fea9145d07480 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-001i-0900000000-76691bd3cba2765d3687 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-001i-0900000000-d801d8209e9a5aa4830b | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Fluorouracil CI-B (Non-derivatized) | splash10-0002-0900000000-7521695ae4a96b4a5a98 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fluorouracil GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-9600000000-8c2b278c2716f3e6b27c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fluorouracil GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9400000000-b8247c8f5c45b12efaa6 | 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 - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-c639ed1b5365f368b59c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-1a7a70df49a360e1458c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-d89f2d944fe1cac39f55 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-50b33770c08680863cf6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-cd5bef421a05073cb1f3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-3900000000-ec9c9e1dfc9a16f625a2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-df98a4532ca49a0a0436 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-50b33770c08680863cf6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-50b33770c08680863cf6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-df98a4532ca49a0a0436 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-004i-0900000000-b117f5fa58c8f98b5c15 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOF | splash10-0a4i-9000000000-f3e71a41b6d4417d33fd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-001i-9200000000-29362607b7c48b82973c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-693d492f316b0c7d5ed5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-001i-1900000000-0c0ee9469bf49688c5d2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-001i-1900000000-0cecca0d265e958e19d7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-03e9-1900000000-46f20f71dbc96630cee7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-03di-1900000000-4330f38956afe6c47636 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOF | splash10-03di-2900000000-f935071622b89177697b | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 10V, Positive-QTOF | splash10-001i-1900000000-3fa9b91447db7dc7ba77 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 20V, Positive-QTOF | splash10-01q9-9800000000-32bf878787078ce9d817 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 40V, Positive-QTOF | splash10-03di-9000000000-3ef559051a5b99c94b29 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 10V, Negative-QTOF | splash10-004i-4900000000-82764fbca3290816328d | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 20V, Negative-QTOF | splash10-000f-9100000000-2da5eb3c925c027b5022 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fluorouracil 40V, Negative-QTOF | splash10-0006-9000000000-1cf432837297c55833a5 | 2015-04-25 | 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) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | 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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