Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-02-22 10:05:38 UTC |
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Update Date | 2023-02-21 17:15:50 UTC |
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HMDB ID | HMDB0001857 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1,3-Dimethyluric acid |
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Description | 1,3-Dimethyluric acid is a product of theophylline metabolism in man. 1,3-Dimethyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID:11712316 , 15833286 , 3506820 , 15013152 , 4039734 ). |
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Structure | CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13) |
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Synonyms | Value | Source |
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Oxytheophylline | ChEBI | 1,3-Dimethylate | Generator | 1,3-Dimethylic acid | Generator | 1,3-Dimethylurate | HMDB |
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Chemical Formula | C7H8N4O3 |
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Average Molecular Weight | 196.1634 |
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Monoisotopic Molecular Weight | 196.059640142 |
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IUPAC Name | 1,3-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione |
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Traditional Name | 1,3-dimethyluric acid |
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CAS Registry Number | 944-73-0 |
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SMILES | CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O |
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InChI Identifier | InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13) |
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InChI Key | OTSBKHHWSQYEHK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | Xanthines |
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Alternative Parents | |
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Substituents | - Xanthine
- 6-oxopurine
- Purinone
- Alkaloid or derivatives
- Pyrimidone
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Lactam
- Urea
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 408 - 410 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.52 mg/mL at 18 °C | Not Available | LogP | -0.52 | GASPARI,F & BONATI,M (1987) |
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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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1,3-Dimethyluric acid,1TMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O | 2030.6 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,1TMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O | 2201.2 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,1TMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O | 2870.7 | Standard polar | 33892256 | 1,3-Dimethyluric acid,1TMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2 | 1968.3 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,1TMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2 | 2217.6 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,1TMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2 | 2955.0 | Standard polar | 33892256 | 1,3-Dimethyluric acid,2TMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C | 1999.7 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,2TMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C | 2253.1 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,2TMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C | 2487.7 | Standard polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O | 2210.4 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O | 2398.3 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #1 | CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O | 2830.6 | Standard polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2 | 2182.7 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2 | 2421.5 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,1TBDMS,isomer #2 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2 | 2889.9 | Standard polar | 33892256 | 1,3-Dimethyluric acid,2TBDMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C | 2403.8 | Semi standard non polar | 33892256 | 1,3-Dimethyluric acid,2TBDMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C | 2670.7 | Standard non polar | 33892256 | 1,3-Dimethyluric acid,2TBDMS,isomer #1 | CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C | 2593.5 | 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 - 1,3-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kr-1900000000-572b5e917ae798f7285d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1,3-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1,3-Dimethyluric acid 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Negative-QTOF | splash10-0002-0900000000-7e858efa4500086bcd70 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Negative-QTOF | splash10-0012-1900000000-1524d46953fcc6d20c7c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Negative-QTOF | splash10-0006-9200000000-b367b1622a53667ca97a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Negative-QTOF | splash10-01px-5900000000-ab0ac771da751bdacb1e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Negative-QTOF | splash10-01q0-1900000000-e48fc1c8a03d0a4a26c4 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Negative-QTOF | splash10-0012-0900000000-598f50fb01c7b3d61958 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Negative-QTOF | splash10-0002-0900000000-41ed7be7644a8ea7bb0d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Negative-QTOF | splash10-0006-9100000000-1d833087dad5d5e4729a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-01ot-1900000000-bbb1123e337bff47c690 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-02mr-7900000000-fad7e7de9dee95b2d94b | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-047i-6900000000-b985a0b78d94b88e5577 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Positive-QTOF | splash10-066s-4900000000-2bebf7701e7270029983 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Positive-QTOF | splash10-0a4i-9000000000-63cd602ba4ec338dced4 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF | splash10-0002-0900000000-85bd64c90cc931b94c6d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Positive-QTOF | splash10-0a4i-9000000000-0cdabbf6e8f8f82a9c92 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF | splash10-0a4i-9300000000-bb25898e6cd1e8fd7df6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 0V, Positive-QTOF | splash10-0002-0900000000-8abc1aacd1e330f9d566 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF | splash10-0a4i-9000000000-de880ba189f670404158 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 0V, Positive-QTOF | splash10-0002-0900000000-c398e5bc602974ed2c8e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF | splash10-0a4i-9300000000-370654114c452519f68c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF | splash10-014l-8900000000-fcc11a5a39d775601b50 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF | splash10-0002-0900000000-5e9ba94ec6b6d85ef52c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF | splash10-0002-0900000000-621c9fb937a1a620e4e7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Positive-QTOF | splash10-066s-3900000000-4f97c73f84de6fce24f9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Negative-QTOF | splash10-0002-0900000000-f5b0e3ac88c5546199d9 | 2017-09-01 | 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 | 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 | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | 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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Disease References | Inflammatory bowel disease |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| Colorectal cancer |
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- 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 ]
| Asthma |
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- Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
| 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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