Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-04-12 20:59:06 UTC |
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Update Date | 2023-02-21 17:17:13 UTC |
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HMDB ID | HMDB0006039 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 8-Chloroxanthine |
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Description | 8-Chloroxanthine is a derivative of xanthine, found occasionally in human urine. 8-Chloroxanthine originates from the metabolism of methylxanthines (caffeine, theophylline and theobromine. 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 ). |
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Structure | ClC1=NC2=C(N1)C(=O)NC(=O)N2 InChI=1S/C5H3ClN4O2/c6-4-7-1-2(8-4)9-5(12)10-3(1)11/h(H3,7,8,9,10,11,12) |
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Synonyms | Value | Source |
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6-Hydroxy-7,9-dihydro-8H-purin-8-one | HMDB | 8-chloro-3, 7-dihydro-1H-Purine-2,6-dione | HMDB | 8-chloro-9H-Purine-2,6-diol | HMDB | 8-chloro-Xanthine | HMDB |
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Chemical Formula | C5H3ClN4O2 |
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Average Molecular Weight | 186.556 |
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Monoisotopic Molecular Weight | 185.994453067 |
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IUPAC Name | 8-chloro-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
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Traditional Name | 8-chloroxanthine |
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CAS Registry Number | 13548-68-0 |
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SMILES | ClC1=NC2=C(N1)C(=O)NC(=O)N2 |
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InChI Identifier | InChI=1S/C5H3ClN4O2/c6-4-7-1-2(8-4)9-5(12)10-3(1)11/h(H3,7,8,9,10,11,12) |
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InChI Key | OZPCWWUKRLUQSS-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
- Aryl chloride
- Aryl halide
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Vinylogous amide
- Lactam
- Urea
- Azacycle
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.17 mg/mL at 20 °C | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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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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8-Chloroxanthine,1TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2047.0 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2017.2 | Standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2786.0 | Standard polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 1989.8 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 2112.5 | Standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 2815.3 | Standard polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 1994.7 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 2063.7 | Standard non polar | 33892256 | 8-Chloroxanthine,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 2837.7 | Standard polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C | 2047.9 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C | 2113.6 | Standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #1 | C[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C | 2380.1 | Standard polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(Cl)=N2 | 2096.8 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(Cl)=N2 | 2144.8 | Standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #2 | C[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(Cl)=N2 | 2366.7 | Standard polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C)C1=O | 2038.6 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C)C1=O | 2173.1 | Standard non polar | 33892256 | 8-Chloroxanthine,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C)C1=O | 2372.3 | Standard polar | 33892256 | 8-Chloroxanthine,3TMS,isomer #1 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2127.8 | Semi standard non polar | 33892256 | 8-Chloroxanthine,3TMS,isomer #1 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2139.6 | Standard non polar | 33892256 | 8-Chloroxanthine,3TMS,isomer #1 | C[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O | 2190.8 | Standard polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2238.5 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2269.5 | Standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)[NH]2 | 2794.0 | Standard polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 2175.9 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 2329.3 | Standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C([NH]C(Cl)=N2)C1=O | 2809.9 | Standard polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 2180.6 | Semi standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 2292.2 | Standard non polar | 33892256 | 8-Chloroxanthine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=C1N=C(Cl)[NH]2 | 2819.9 | Standard polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C | 2450.7 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C | 2538.5 | Standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(Cl)=NC2=C1C(=O)[NH]C(=O)N2[Si](C)(C)C(C)(C)C | 2490.9 | Standard polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(Cl)=N2 | 2486.3 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(Cl)=N2 | 2573.6 | Standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(Cl)=N2 | 2489.6 | Standard polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O | 2388.4 | Semi standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O | 2558.6 | Standard non polar | 33892256 | 8-Chloroxanthine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O | 2493.0 | Standard polar | 33892256 | 8-Chloroxanthine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2727.9 | Semi standard non polar | 33892256 | 8-Chloroxanthine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2787.1 | Standard non polar | 33892256 | 8-Chloroxanthine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C(=O)C2=C(N=C(Cl)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O | 2514.9 | 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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Predicted GC-MS | Predicted GC-MS Spectrum - 8-Chloroxanthine GC-MS (Non-derivatized) - 70eV, Positive | splash10-03y0-1900000000-17cacb12b2a02542993c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 8-Chloroxanthine 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 10V, Positive-QTOF | splash10-000i-0900000000-328b540ae0ce13d3cf97 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 20V, Positive-QTOF | splash10-000l-0900000000-cbd2837bf99daaa07037 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 40V, Positive-QTOF | splash10-05mo-8900000000-21cdab55b94df6db945e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 10V, Negative-QTOF | splash10-001i-0900000000-845a916f990368686252 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 20V, Negative-QTOF | splash10-0006-9400000000-70808ccea687d51625e7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 40V, Negative-QTOF | splash10-0006-9100000000-fe68b8167bc2a234b67c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 10V, Positive-QTOF | splash10-000i-0900000000-66d01670831f1da9ad0f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 20V, Positive-QTOF | splash10-000i-0900000000-356ab4444bf97b111168 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 40V, Positive-QTOF | splash10-00ko-7900000000-124b2f0d4c558b5147bc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 10V, Negative-QTOF | splash10-001i-0900000000-70ed9aed39a2fdeafe72 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 20V, Negative-QTOF | splash10-001i-4900000000-cf6e656896a3558da8a9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Chloroxanthine 40V, Negative-QTOF | splash10-0006-9100000000-15a9044318b70008180d | 2021-09-24 | 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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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023815 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 24315 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 26103 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Robins, Roland K. Potential purine antagonists. XV. Preparation of some 6,8-disubstituted purines. Journal of the American Chemical Society (1958), 80 6671-9. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
- Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
- Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
- Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]
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