Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-14 15:44:42 UTC |
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HMDB ID | HMDB0000012 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Deoxyuridine |
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Description | Deoxyuridine, also known as dU, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. It is similar in chemical structure to uridine, but without the 2'-hydroxyl group. Deoxyuridine exists in all living organisms, ranging from bacteria to humans. Within humans, deoxyuridine participates in a number of enzymatic reactions. In particular, deoxyuridine can be biosynthesized from deoxycytidine through its interaction with the enzyme cytidine deaminase. In addition, deoxyuridine can be converted into uracil and deoxyribose 1-phosphate through its interaction with the enzyme thymidine phosphorylase. Deoxyuridine is considered to be an antimetabolite that is converted into deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies. In humans, deoxyuridine is involved in the metabolic disorder called UMP synthase deficiency (orotic aciduria). Outside of the human body, deoxyuridine has been detected, but not quantified in, several different foods, such as lichee, highbush blueberries, agaves, macadamia nut (M. tetraphylla), and red bell peppers. This could make deoxyuridine a potential biomarker for the consumption of these foods. |
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Structure | OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 |
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Synonyms | Value | Source |
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2-Deoxyuridine | ChEBI | dU | ChEBI | 2'-Deoxyuridine | Kegg | 1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione | HMDB | 1-(2-Deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione | HMDB | 1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione | HMDB | 1-(2-Deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione | HMDB | 1-(2-Deoxy-D-erythro-pentofuranosyl)uracil | HMDB | 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil | HMDB | 2'-Desoxyuridine | HMDB | Deoxyribose uracil | HMDB | Desoxyuridine | HMDB | Uracil deoxyriboside | HMDB | Uracil desoxyuridine | HMDB | (beta 1-(2-Deoxyribopyranosyl))thymidine | HMDB | Deoxyuridine | ChEBI |
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Chemical Formula | C9H12N2O5 |
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Average Molecular Weight | 228.202 |
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Monoisotopic Molecular Weight | 228.074621504 |
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IUPAC Name | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | 2'-deoxyuridine |
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CAS Registry Number | 951-78-0 |
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SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O |
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InChI Identifier | InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 |
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InChI Key | MXHRCPNRJAMMIM-SHYZEUOFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Pyrimidine 2'-deoxyribonucleosides |
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Direct Parent | Pyrimidine 2'-deoxyribonucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine 2'-deoxyribonucleoside
- Pyrimidone
- Hydropyrimidine
- Pyrimidine
- Heteroaromatic compound
- Tetrahydrofuran
- Vinylogous amide
- Lactam
- Secondary alcohol
- Urea
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen 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 | |
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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 | 167 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -1.51 | BALZARINI,JM ET AL. (1989) |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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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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Deoxyuridine,1TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)[NH]C2=O)C[C@@H]1O | 2254.6 | Semi standard non polar | 33892256 | Deoxyuridine,1TMS,isomer #2 | C[Si](C)(C)O[C@H]1C[C@H](N2C=CC(=O)[NH]C2=O)O[C@@H]1CO | 2287.1 | Semi standard non polar | 33892256 | Deoxyuridine,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)C=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O | 2319.1 | Semi standard non polar | 33892256 | Deoxyuridine,2TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C | 2260.2 | Semi standard non polar | 33892256 | Deoxyuridine,2TMS,isomer #2 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O | 2329.4 | Semi standard non polar | 33892256 | Deoxyuridine,2TMS,isomer #3 | C[Si](C)(C)O[C@H]1C[C@H](N2C=CC(=O)N([Si](C)(C)C)C2=O)O[C@@H]1CO | 2334.8 | Semi standard non polar | 33892256 | Deoxyuridine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C | 2350.5 | Semi standard non polar | 33892256 | Deoxyuridine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C | 2455.2 | Standard non polar | 33892256 | Deoxyuridine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C | 2627.7 | Standard polar | 33892256 | Deoxyuridine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)[NH]C2=O)C[C@@H]1O | 2512.4 | Semi standard non polar | 33892256 | Deoxyuridine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=CC(=O)[NH]C2=O)O[C@@H]1CO | 2524.5 | Semi standard non polar | 33892256 | Deoxyuridine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)C=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O | 2545.3 | Semi standard non polar | 33892256 | Deoxyuridine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 2714.5 | Semi standard non polar | 33892256 | Deoxyuridine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O | 2784.0 | Semi standard non polar | 33892256 | Deoxyuridine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)O[C@@H]1CO | 2796.4 | Semi standard non polar | 33892256 | Deoxyuridine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3014.6 | Semi standard non polar | 33892256 | Deoxyuridine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3067.8 | Standard non polar | 33892256 | Deoxyuridine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 2903.6 | Standard polar | 33892256 |
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Spectra |
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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 - Deoxyuridine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udi-0900000000-c680f47a48626bc1de41 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udi-0900000000-13135426d5efdf47090c | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-MS (3 TMS) | splash10-0v4i-2910000000-b0c82cef369c86d585bc | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-MS (3 TMS) | splash10-0udi-2900000000-c2cdba9e46defe05a225 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-EI-TOF (Non-derivatized) | splash10-0udi-0900000000-c680f47a48626bc1de41 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-EI-TOF (Non-derivatized) | splash10-0udi-0900000000-13135426d5efdf47090c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-MS (Non-derivatized) | splash10-0v4i-2910000000-b0c82cef369c86d585bc | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyuridine GC-MS (Non-derivatized) | splash10-0udi-2900000000-c2cdba9e46defe05a225 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (Non-derivatized) - 70eV, Positive | splash10-01r7-9610000000-dfaab249ec8e9361b4bf | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (2 TMS) - 70eV, Positive | splash10-0g06-9621000000-32e72b8293f4e226223b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyuridine GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | 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 - Deoxyuridine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-03di-1900000000-6610506190427bbb3b6c | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-03di-9800000000-af237f79161aa13a5893 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-022d-9100000000-a06cdd7ea870d049c8a9 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-001r-0900000000-87d0da98372c9c5a167a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-001r-0900000000-795c89de7cd09998501c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-03di-0910000000-0f40c1aaec53591fe03d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-03di-0900000000-35312c7170aff90afa68 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-004i-0090000000-dd791cff5aab8928952f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , negative-QTOF | splash10-004i-0090000000-e5c282f6027560386d07 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine , negative-QTOF | splash10-001l-5900000000-4660ec5181499087824f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , positive-QTOF | splash10-001i-0910000000-8cef8299b80deeefe1ae | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine Linear Ion Trap , positive-QTOF | splash10-001i-0900000000-043d88b7ac473889f319 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 20V, Negative-QTOF | splash10-0006-9100000000-5731c423bed1902e4aa1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 10V, Negative-QTOF | splash10-000x-9820000000-29ea64a90c8736117d03 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 40V, Positive-QTOF | splash10-006t-9400000000-edbb071fcbfdfc740d5c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 10V, Positive-QTOF | splash10-03di-2910000000-76f9f11531932d11318e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 20V, Positive-QTOF | splash10-03di-4900000000-996ec7312bb565deb6f8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 35V, Negative-QTOF | splash10-001i-0900000000-45855a2f2673a9e095e8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyuridine 40V, Positive-QTOF | splash10-006w-9100000000-75bb83f5ee43bb79add3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 10V, Positive-QTOF | splash10-03di-1900000000-4e3e387ebbab12abe1fd | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 20V, Positive-QTOF | splash10-03di-5900000000-e483c01cc3a2bd6439c1 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 40V, Positive-QTOF | splash10-03di-9800000000-e0e5bb84af10a0c46b95 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 10V, Negative-QTOF | splash10-0036-8960000000-f6a195e38452cd824d19 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 20V, Negative-QTOF | splash10-000f-7910000000-8de672c701d38c2dd5d3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyuridine 40V, Negative-QTOF | splash10-00kf-9100000000-6e86ecc024dbcde80d90 | 2017-07-26 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | 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 | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Mitochondria
- Nucleus
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | - Bladder
- Bone Marrow
- Fibroblasts
- Intestine
- Leukocyte
- Neuron
- Pancreas
- Placenta
- Prostate
- Skeletal Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.1 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.052 (0.049-0.056) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.200 (0.100-0.300) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.6 +/- 0.6 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0 - 0.1 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0-2 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <0.3 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 1.00 (0.00-2.00) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <1 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 20 uM | Adult (>18 years old) | Male | Thymidine phosphorylase deficiency | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Urine | Detected and Quantified | 1.195 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 51 umol/mmol creatinine | Adult (>18 years old) | Male | Thymidine phosphorylase deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | Thymidine phosphorylase deficiency |
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- Bakker JA, Schlesser P, Smeets HJ, Francois B, Bierau J: Biochemical abnormalities in a patient with thymidine phosphorylase deficiency with fatal outcome. J Inherit Metab Dis. 2010 Dec;33 Suppl 3:S139-43. doi: 10.1007/s10545-010-9049-y. Epub 2010 Feb 12. [PubMed:20151198 ]
| Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Crohn's disease |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Eosinophilic esophagitis |
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- Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
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Associated OMIM IDs | - 603041 (Thymidine phosphorylase deficiency)
- 114500 (Colorectal cancer)
- 266600 (Crohn's disease)
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB02256 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021870 |
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KNApSAcK ID | C00019697 |
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Chemspider ID | 13118 |
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KEGG Compound ID | C00526 |
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BioCyc ID | DEOXYURIDINE |
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BiGG ID | 35251 |
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Wikipedia Link | Deoxyuridine |
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METLIN ID | 5086 |
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PubChem Compound | 13712 |
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PDB ID | Not Available |
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ChEBI ID | 16450 |
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Food Biomarker Ontology | Not Available |
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VMH ID | DURI |
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MarkerDB ID | MDB00000006 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Huang, Haoqiang; Chu, Chung K. A practical synthesis of 2'-deoxyuridine from uridine. Synthetic Communications (1990), 20(7), 1039-46. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Li KM, Rivory LP, Clarke SJ: Rapid quantitation of plasma 2'-deoxyuridine by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry and its application to pharmacodynamic studies in cancer patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):121-30. Epub 2005 Apr 19. [PubMed:15866500 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Di Stefano G, Busi C, Derenzini M, Trere D, Fiume L: Conjugation of 5-fluoro-2'-deoxyuridine with lactosaminated poly-l-lysine to reduce extrahepatic toxicity in the treatment of hepatocarcinomas. Ital J Gastroenterol Hepatol. 1998 Apr;30(2):173-7. [PubMed:9675653 ]
- Reidy JA: Deoxyuridine increases folate-sensitive fragile site expression in human lymphocytes. Am J Med Genet. 1987 Jan;26(1):1-5. [PubMed:3812550 ]
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
- Huong PL, Kolk AH, Eggelte TA, Verstijnen CP, Gilis H, Hendriks JT: Measurement of antigen specific lymphocyte proliferation using 5-bromo-deoxyuridine incorporation. An easy and low cost alternative to radioactive thymidine incorporation. J Immunol Methods. 1991 Jul 5;140(2):243-8. [PubMed:1906076 ]
- Kanazawa S, Herbert V: Detection of folate deficiency in alcoholism using the peripheral blood lymphocyte deoxyuridine suppression test. J Nutr Sci Vitaminol (Tokyo). 1986 Jun;32(3):251-7. [PubMed:3761048 ]
- Zittoun J, Zittoun R: Modern clinical testing strategies in cobalamin and folate deficiency. Semin Hematol. 1999 Jan;36(1):35-46. [PubMed:9930567 ]
- Fairbanks LD, Marinaki AM, Carrey EA, Hammans SR, Duley JA: Deoxyuridine accumulation in urine in thymidine phosphorylase deficiency (MNGIE). J Inherit Metab Dis. 2002 Nov;25(7):603-4. [PubMed:12638947 ]
- Remacha A, Barcelo MJ, Pastor M, Ubeda J, Espadaler M, Gimferrer E: The deoxyuridine suppression test in peripheral lymphocytes. Eur J Haematol. 1990 Mar;44(3):196-200. [PubMed:2328792 ]
- Galanis E, Goldberg R, Reid J, Atherton P, Sloan J, Pitot H, Rubin J, Adjei AA, Burch P, Safgren SL, Witzig TE, Ames MM, Erlichman C: Phase I trial of sequential administration of raltitrexed (Tomudex) and 5-iodo-2'-deoxyuridine (IdUrd). Ann Oncol. 2001 May;12(5):701-7. [PubMed:11432631 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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