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 | HMDB0000071 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Deoxyinosine |
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Description | Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Moreover, deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism. |
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Structure | OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1 |
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Synonyms | Value | Source |
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9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol | ChEBI | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-ol | Generator | 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-ol | Generator | 2'-Deoxyinosine | HMDB | 2-Deoxy-inosine | HMDB | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one | HMDB | 9-(2-Deoxy-b-D-erythro-pentofuranosyl)-hypoxanthine | HMDB | 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-hypoxanthine | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one | HMDB | 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthine | HMDB | D-Ino | HMDB | delta-Ino | HMDB | DInosine | HMDB | Deoxyribose-inosine | HMDB | Deoxyinosine | ChEBI |
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Chemical Formula | C10H12N4O4 |
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Average Molecular Weight | 252.23 |
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Monoisotopic Molecular Weight | 252.085854882 |
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IUPAC Name | 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol |
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Traditional Name | 2'-deoxy-inosine |
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CAS Registry Number | 890-38-0 |
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SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O |
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InChI Identifier | InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1 |
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InChI Key | VGONTNSXDCQUGY-RRKCRQDMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine 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 | Purine nucleosides |
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Sub Class | Purine 2'-deoxyribonucleosides |
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Direct Parent | Purine 2'-deoxyribonucleosides |
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Alternative Parents | |
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Substituents | - Purine 2'-deoxyribonucleoside
- Hypoxanthine
- Imidazopyrimidine
- Purine
- Hydroxypyrimidine
- N-substituted imidazole
- Pyrimidine
- Tetrahydrofuran
- Heteroaromatic compound
- Azole
- Imidazole
- Secondary alcohol
- Azacycle
- Organoheterocyclic compound
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Organic nitrogen compound
- Organopnictogen 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 | |
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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 | 250 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -1.71 | FORD,H ET AL. (1991) |
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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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Deoxyinosine,1TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O | 2444.3 | Semi standard non polar | 33892256 | Deoxyinosine,1TMS,isomer #2 | C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO | 2465.2 | Semi standard non polar | 33892256 | Deoxyinosine,1TMS,isomer #3 | C[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O | 2550.0 | Semi standard non polar | 33892256 | Deoxyinosine,2TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C | 2397.8 | Semi standard non polar | 33892256 | Deoxyinosine,2TMS,isomer #2 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O | 2509.6 | Semi standard non polar | 33892256 | Deoxyinosine,2TMS,isomer #3 | C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)O[C@@H]1CO | 2521.1 | Semi standard non polar | 33892256 | Deoxyinosine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C | 2507.8 | Semi standard non polar | 33892256 | Deoxyinosine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C | 2766.2 | Standard non polar | 33892256 | Deoxyinosine,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C | 3283.4 | Standard polar | 33892256 | Deoxyinosine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O | 2677.5 | Semi standard non polar | 33892256 | Deoxyinosine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO | 2691.1 | Semi standard non polar | 33892256 | Deoxyinosine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O | 2786.2 | Semi standard non polar | 33892256 | Deoxyinosine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 2846.0 | Semi standard non polar | 33892256 | Deoxyinosine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O | 2958.6 | Semi standard non polar | 33892256 | Deoxyinosine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO | 2970.6 | Semi standard non polar | 33892256 | Deoxyinosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3163.6 | Semi standard non polar | 33892256 | Deoxyinosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3408.6 | Standard non polar | 33892256 | Deoxyinosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3426.5 | 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 - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0udi-0933100000-09d719c947c60bf0f309 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0zfr-0940000000-e72ee71b7bb48b638ddc | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyinosine GC-MS (3 TMS) | splash10-0zfr-2930000000-4781d246f6996b2513f8 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized) | splash10-0udi-0933100000-09d719c947c60bf0f309 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized) | splash10-0zfr-0940000000-e72ee71b7bb48b638ddc | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) | splash10-0zfr-2930000000-4781d246f6996b2513f8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, Positive | splash10-059x-9460000000-45b38a8f7526df1e95a5 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (2 TMS) - 70eV, Positive | splash10-0v6u-8976000000-3868aac5f35f48870953 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f79-9300000000-1d2cd609ae1f49c1960f | 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 - Deoxyinosine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-000i-0900000000-699f2e0add16852a454c | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-000i-1900000000-ab78094925c0c212f113 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-000i-5900000000-f14b9bd6e2a698307815 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOF | splash10-000i-0920000000-a304c7b397cc865f33d1 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOF | splash10-000i-0900000000-984f375947cefdcfb884 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOF | splash10-01p9-0900000000-9bc9620b62695f652342 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOF | splash10-0udi-0290000000-5c34e254b55e1aa880cc | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOF | splash10-000i-0910000000-877252e0b2d402f920ab | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOF | splash10-052u-3900000000-d17c7ebc047d144462a1 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOF | splash10-0f79-0970000000-3ec5c5a89b8c9af39d7e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOF | splash10-052r-0900000000-40c1b23e6815e6181307 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOF | splash10-0a5l-3900000000-9d7c6bf0280c77658451 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOF | splash10-000i-0900000000-b2e36fb98660834d7d24 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOF | splash10-000i-0900000000-f660b2a54215a2689fa2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOF | splash10-000i-1900000000-4cf4a407cd370c6b4927 | 2021-09-24 | 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) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | 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 | - Cytoplasm
- Extracellular
- Nucleus
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | 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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | 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 | < 0.1 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0-6 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <0.1 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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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 | Adult (>18 years old) | Both | Colorectal cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | Urine | Detected and Quantified | 1.573 +/- 1.68 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 3.2 umol/mmol creatinine | Adult (>18 years old) | Both | Purine nucleoside phosphorylase (PNP) deficiency | | details |
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Associated Disorders and Diseases |
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Disease References | 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 ]
- 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 ]
- 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 ]
| Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Purine nucleoside phosphorylase deficiency |
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- Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
| 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 | - 114500 (Colorectal cancer)
- 164050 (Purine nucleoside phosphorylase deficiency )
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB02380 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012323 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 58569 |
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KEGG Compound ID | C05512 |
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BioCyc ID | DEOXYINOSINE |
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BiGG ID | 45942 |
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Wikipedia Link | Not Available |
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METLIN ID | 3383 |
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PubChem Compound | 65058 |
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PDB ID | Not Available |
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ChEBI ID | 28997 |
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Food Biomarker Ontology | Not Available |
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VMH ID | DIN |
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MarkerDB ID | MDB00000037 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Robins, Morris J.; Basom, Gerald L. Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase. Canadian Journal of Chemistry, 1973, 51(19): 3161-3169, https://doi.org/10.1139/v73-471 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Cohen A, Doyle D, Martin DW Jr, Ammann AJ: Abnormal purine metabolism and purine overproduction in a patient deficient in purine nucleoside phosphorylase. N Engl J Med. 1976 Dec 23;295(26):1449-54. [PubMed:825775 ]
- Kewn S, Hoggard PG, Henry-Mowatt JS, Veal GJ, Sales SD, Barry MG, Back DJ: Intracellular activation of 2',3'-dideoxyinosine and drug interactions in vitro. AIDS Res Hum Retroviruses. 1999 Jun 10;15(9):793-802. [PubMed:10381167 ]
- Bemi V, Tazzni N, Banditelli S, Giorgelli F, Pesi R, Turchi G, Mattana A, Sgarrella F, Tozzi MG, Camici M: Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin. Int J Cancer. 1998 Mar 2;75(5):713-20. [PubMed:9495239 ]
- Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
- Ablett E, Pedley J, Dannoy PA, Sturm RA, Parsons PG: UVB-specific regulation of gene expression in human melanocytic cells: cell cycle effects and implication in the generation of melanoma. Mutat Res. 1998 Nov 9;422(1):31-41. [PubMed:9920426 ]
- Bazar LS, Collier GB, Vanek PG, Siles BA, Kow YW, Doetsch PW, Cunningham RP, Chirikjian JG: Mutation identification DNA analysis system (MIDAS) for detection of known mutations. Electrophoresis. 1999 Jun;20(6):1141-8. [PubMed:10380753 ]
- Sjoberg AH, Wang L, Eriksson S: Substrate specificity of human recombinant mitochondrial deoxyguanosine kinase with cytostatic and antiviral purine and pyrimidine analogs. Mol Pharmacol. 1998 Feb;53(2):270-3. [PubMed:9463485 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- 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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