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 15:44:40 UTC |
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HMDB ID | HMDB0000283 |
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Secondary Accession Numbers | - HMDB0012194
- HMDB00283
- HMDB12194
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Metabolite Identification |
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Common Name | D-Ribose |
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Description | D-Ribose, commonly referred to as simply ribose, is a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP. In nature, small amounts of ribose can be found in ripe fruits and vegetables. Brewer's yeast, which has a high concentration of RNA, is another rich source of ribose. D-ribose is also a component of many so-called energy drinks and anti-ageing products available on the market today. Ribose is a structural component of ATP, which is the primary energy source for exercising muscle. The adenosine component is an adenine base attached to the five-carbon sugar ribose. ATP provides energy to working muscles by releasing a phosphate group, hence becoming ADP, which in turn may release a phosphate group, then becoming AMP. During intense muscular activity, the total amount of ATP available is quickly depleted. In an effort to correct this imbalance, AMP is broken down in the muscle and secreted from the cell. Once the breakdown products of AMP are released from the cell, the energy potential (TAN pool) of the muscle is reduced and ATP must then be reformed using ribose. Ribose helps restore the level of adenine nucleotides by bypassing the rate-limiting step in the de novo (oxidative pentose phosphate) pathway, which regenerates phosphoribosyl pyrophosphate (PRPP), the essential precursor for ATP. If ribose is not readily available to a cell, glucose may be converted to ribose. Ribose supplementation has been shown to increase the rate of ATP resynthesis following intense exercise. The use of ribose in men with severe coronary artery disease resulted in improved exercise tolerance. Hence, there is interest in the potential of ribose supplements to boost muscular performance in athletic activities (PMID: 17618002 , Curr Sports Med Rep. 2007 Jul;6(4):254-7.). |
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Structure | OC[C@H]1OC(O)[C@H](O)[C@@H]1O InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1 |
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Synonyms | Value | Source |
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(3R,4S,5R)-5-(Hydroxymethyl)tetrahydrofuran-2,3,4-triol | ChEBI | Ribose | ChEBI | D-Ribofuranoside | HMDB | D-Ribofuranose | HMDB | Ribofuranoside | HMDB | Ribofuranose | HMDB |
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Chemical Formula | C5H10O5 |
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Average Molecular Weight | 150.1299 |
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Monoisotopic Molecular Weight | 150.05282343 |
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IUPAC Name | (3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol |
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Traditional Name | D-ribofuranoside |
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CAS Registry Number | 613-83-2 |
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SMILES | OC[C@H]1OC(O)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1 |
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InChI Key | HMFHBZSHGGEWLO-SOOFDHNKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Pentoses |
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Alternative Parents | |
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Substituents | - Pentose monosaccharide
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 | 95 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -2.32 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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D-Ribose,1TMS,isomer #1 | C[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O | 1505.7 | Semi standard non polar | 33892256 | D-Ribose,1TMS,isomer #2 | C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O | 1544.9 | Semi standard non polar | 33892256 | D-Ribose,1TMS,isomer #3 | C[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O | 1526.5 | Semi standard non polar | 33892256 | D-Ribose,1TMS,isomer #4 | C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@@H]1O | 1518.1 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #1 | C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O)[C@@H]1O | 1596.6 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #2 | C[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C)[C@@H]1O | 1575.7 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #3 | C[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O[Si](C)(C)C | 1564.9 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #4 | C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O | 1574.0 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #5 | C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C | 1572.6 | Semi standard non polar | 33892256 | D-Ribose,2TMS,isomer #6 | C[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O[Si](C)(C)C | 1563.3 | Semi standard non polar | 33892256 | D-Ribose,3TMS,isomer #1 | C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O | 1646.3 | Semi standard non polar | 33892256 | D-Ribose,3TMS,isomer #2 | C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C | 1623.2 | Semi standard non polar | 33892256 | D-Ribose,3TMS,isomer #3 | C[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C | 1633.0 | Semi standard non polar | 33892256 | D-Ribose,3TMS,isomer #4 | C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C | 1606.1 | Semi standard non polar | 33892256 | D-Ribose,4TMS,isomer #1 | C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C | 1603.5 | Semi standard non polar | 33892256 | D-Ribose,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O | 1731.7 | Semi standard non polar | 33892256 | D-Ribose,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O | 1753.8 | Semi standard non polar | 33892256 | D-Ribose,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O | 1746.3 | Semi standard non polar | 33892256 | D-Ribose,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@@H]1O | 1746.3 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O | 2028.4 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O | 2021.9 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C | 2013.5 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O | 2022.7 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C | 2015.4 | Semi standard non polar | 33892256 | D-Ribose,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C | 2028.0 | Semi standard non polar | 33892256 | D-Ribose,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O | 2304.0 | Semi standard non polar | 33892256 | D-Ribose,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C | 2306.4 | Semi standard non polar | 33892256 | D-Ribose,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | 2310.8 | Semi standard non polar | 33892256 | D-Ribose,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C | 2290.3 | Semi standard non polar | 33892256 | D-Ribose,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | 2543.5 | Semi standard non 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 - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udi-0920000000-c414574c94624914be8c | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0fk9-9831000000-d0b33cef6c46219ea9a8 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udi-0920000000-e3647dbf79b8733c3bfd | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udi-0921000000-e8a202c64cf867b21cef | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udi-0920000000-272c588a02a550b79c74 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0ldi-0941000000-999cd264e51df6d784b4 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0udi-0910000000-54f42f17ff952d787b86 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0uxr-0920000000-d29b5079ba0fde220b0d | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS; 1 MEOX) | splash10-0fk9-8920000000-71080ebc024c820bf8fd | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0udi-0920000000-c414574c94624914be8c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0fk9-9831000000-d0b33cef6c46219ea9a8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0udi-0920000000-e3647dbf79b8733c3bfd | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0udi-0921000000-e8a202c64cf867b21cef | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0udi-0920000000-272c588a02a550b79c74 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0ldi-0941000000-999cd264e51df6d784b4 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0udi-0910000000-54f42f17ff952d787b86 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0uxr-0920000000-d29b5079ba0fde220b0d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized) | splash10-0fk9-8920000000-71080ebc024c820bf8fd | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (Non-derivatized) - 70eV, Positive | splash10-05cu-9300000000-e24e80da64b2475ddfd8 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (4 TMS) - 70eV, Positive | splash10-00g0-7349300000-49b1e72358e4fd020b5d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_4) - 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 - D-Ribose Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-014r-4900000000-76daa3235c9f82ef4f5a | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-000i-9100000000-b44f013dcb4efe64039d | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0a4i-9000000000-64a1b88f0cb22f5b729a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0a4i-9000000000-a05552744534bc6dc8c5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOF | splash10-0a4i-9000000000-23b475cbcd2c9fafde18 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOF | splash10-0a4i-9000000000-88ff2c607ed1b08ed6b9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0a4i-9000000000-7c7662a3e6e7923d84cb | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0a4i-9000000000-ce0d2af497d6da39f1f1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0a4i-9000000000-f0409fb19110a197badc | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOF | splash10-0udi-8900000000-41d386e0f57f435290c8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOF | splash10-0a4i-9300000000-2ea2e21fb5412f962d7f | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 10V, Positive-QTOF | splash10-0ue9-2900000000-6c1199d377747f0e5b49 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 20V, Positive-QTOF | splash10-0f89-2900000000-8a9f89ac0a25c323249e | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 40V, Positive-QTOF | splash10-052p-9100000000-eaebbbf2fa629ce04160 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOF | splash10-0002-1900000000-6c48df798a58fc7029d9 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOF | splash10-001j-2900000000-816419eb5dad5bd99819 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOF | splash10-0006-9200000000-91d11d896b253dfd9693 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 10V, Positive-QTOF | splash10-0gc0-1900000000-346af5e1437ac746833b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 20V, Positive-QTOF | splash10-0nc4-9400000000-74fd6af917cb088bef2b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 40V, Positive-QTOF | splash10-0a4i-9000000000-55c82f4fa793a5fd288b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOF | splash10-0pc1-5900000000-6953077be254812d8b25 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOF | splash10-0a4i-9100000000-fcc3022a655e16f83b2c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOF | splash10-0006-9000000000-750ecddfae4eefc71996 | 2021-09-23 | 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) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | - Adrenal Gland
- Epidermis
- Fibroblasts
- Kidney
- Lung
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate
- Skeletal Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 2.3 (0.0-5.0) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.5 (0.0 - 5.0) uM | Adolescent (13-18 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) | 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 | Feces | Detected and Quantified | 1131.0205 +/- 706.721 nmol/g wet feces | Not Specified | 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 | Not Specified | Not Specified | Normal | | details | Feces | Detected and Quantified | 1494 nmol/g wet feces | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected and Quantified | 2199 nmol/g wet feces | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected and Quantified | 1184 nmol/g wet feces | Adult (>18 years old) | Not Specified | 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 | 2.5 (0.0 - 5.0) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 39.757 +/- 18.872 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 3.0 (2.6-4.4) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 6.35 +/- 4.59 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 2.4 (0.0-5.0) uM | Adult (>18 years old) | Both | Ribose-5-phosphate isomerase deficiency | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 90.0 (47.0 - 146.0) uM | Adolescent (13-18 years old) | Both | Ribose-5-phosphate isomerase 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 | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 50.0 (5.0 - 102.0) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Ribose-5-Phosphate Isomerase Deficiency | | details | Urine | Detected and Quantified | 26.892 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | 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 ]
| Ribose-5-phosphate isomerase deficiency |
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- Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
| 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)
- 608611 (Ribose-5-phosphate isomerase deficiency)
- 610247 (Eosinophilic esophagitis)
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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 | FDB031292 |
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KNApSAcK ID | C00034198 |
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Chemspider ID | 5575 |
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KEGG Compound ID | C00121 |
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BioCyc ID | Not Available |
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BiGG ID | 33936 |
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Wikipedia Link | Ribose |
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METLIN ID | 313 |
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PubChem Compound | 5779 |
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PDB ID | Not Available |
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ChEBI ID | 47013 |
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Food Biomarker Ontology | Not Available |
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VMH ID | RIB_D |
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MarkerDB ID | MDB00000133 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Park, Yong-Cheol; Choi, Jin-Ho; Bennett, George N.; Seo, Jin-Ho. Characterization of D-ribose biosynthesis in Bacillus subtilis JY200 deficient in transketolase gene. Journal of Biotechnology (2006), 121(4), 508-516. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- Drel VR, Pacher P, Stevens MJ, Obrosova IG: Aldose reductase inhibition counteracts nitrosative stress and poly(ADP-ribose) polymerase activation in diabetic rat kidney and high-glucose-exposed human mesangial cells. Free Radic Biol Med. 2006 Apr 15;40(8):1454-65. Epub 2006 Jan 31. [PubMed:16631535 ]
- Dancis J, Lee J, Mendoza S, Liebes L: Nucleoside transport by perfused human placenta. Placenta. 1993 Sep-Oct;14(5):547-54. [PubMed:8290494 ]
- Quadrilatero J, Rush JW: Increased DNA fragmentation and altered apoptotic protein levels in skeletal muscle of spontaneously hypertensive rats. J Appl Physiol (1985). 2006 Oct;101(4):1149-61. Epub 2006 Jun 15. [PubMed:16778006 ]
- Carloto A, Costas MJ, Cameselle JC, McLennan AG, Ribeiro JM: The specific, submicromolar-Km ADP-ribose pyrophosphatase purified from human placenta is enzymically indistinguishable from recombinant NUDT9 protein, including a selectivity for Mn2+ as activating cation and increase in Km for ADP-ribose, both elicited by H2O2. Biochim Biophys Acta. 2006 Oct;1760(10):1545-51. Epub 2006 Jun 9. [PubMed:16860484 ]
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- Abe H, Tanuma S: Properties of poly(ADP-ribose) glycohydrolase purified from pig testis nuclei. Arch Biochem Biophys. 1996 Dec 1;336(1):139-46. [PubMed:8951044 ]
- Augustin A, Muller-Steffner H, Schuber F: Molecular cloning and functional expression of bovine spleen ecto-NAD+ glycohydrolase: structural identity with human CD38. Biochem J. 2000 Jan 1;345 Pt 1:43-52. [PubMed:10600637 ]
- Dodd SL, Johnson CA, Fernholz K, St Cyr JA: The role of ribose in human skeletal muscle metabolism. Med Hypotheses. 2004;62(5):819-24. [PubMed:15082114 ]
- Cheng C, Zochodne DW: Sensory neurons with activated caspase-3 survive long-term experimental diabetes. Diabetes. 2003 Sep;52(9):2363-71. [PubMed:12941777 ]
- Szabo E, Virag L, Bakondi E, Gyure L, Hasko G, Bai P, Hunyadi J, Gergely P, Szabo C: Peroxynitrite production, DNA breakage, and poly(ADP-ribose) polymerase activation in a mouse model of oxazolone-induced contact hypersensitivity. J Invest Dermatol. 2001 Jul;117(1):74-80. [PubMed:11442752 ]
- Jacobson EL, Giacomoni PU, Roberts MJ, Wondrak GT, Jacobson MK: Optimizing the energy status of skin cells during solar radiation. J Photochem Photobiol B. 2001 Oct;63(1-3):141-7. [PubMed:11684461 ]
- Wurzer G, Herceg Z, Wesierska-Gadek J: Increased resistance to anticancer therapy of mouse cells lacking the poly(ADP-ribose) polymerase attributable to up-regulation of the multidrug resistance gene product P-glycoprotein. Cancer Res. 2000 Aug 1;60(15):4238-44. [PubMed:10945636 ]
- Okamoto H: The Reg gene family and Reg proteins: with special attention to the regeneration of pancreatic beta-cells. J Hepatobiliary Pancreat Surg. 1999;6(3):254-62. [PubMed:10526060 ]
- McNealy T, Frey M, Trojan L, Knoll T, Alken P, Michel MS: Intrinsic presence of poly (ADP-ribose) is significantly increased in malignant prostate compared to benign prostate cell lines. Anticancer Res. 2003 Mar-Apr;23(2B):1473-8. [PubMed:12820412 ]
- Alexy T, Toth A, Marton Z, Horvath B, Koltai K, Feher G, Kesmarky G, Kalai T, Hideg K, Sumegi B, Toth K: Inhibition of ADP-evoked platelet aggregation by selected poly(ADP-ribose) polymerase inhibitors. J Cardiovasc Pharmacol. 2004 Mar;43(3):423-31. [PubMed:15076227 ]
- Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN: gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci U S A. 2004 Dec 21;101(51):17825-30. Epub 2004 Dec 13. [PubMed:15596715 ]
- Toth O, Szabo C, Kecskes M, Poto L, Nagy A, Losonczy H: In vitro effect of the potent poly(ADP-ribose) polymerase (PARP) inhibitor INO-1001 alone and in combination with aspirin, eptifibatide, tirofiban, enoxaparin or alteplase on haemostatic parameters. Life Sci. 2006 Jun 20;79(4):317-23. Epub 2006 Feb 9. [PubMed:16480745 ]
- Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. Biochem J. 1998 Nov 1;335 ( Pt 3):631-6. [PubMed:9794804 ]
- Tamagno E, Parola M, Bardini P, Piccini A, Borghi R, Guglielmotto M, Santoro G, Davit A, Danni O, Smith MA, Perry G, Tabaton M: Beta-site APP cleaving enzyme up-regulation induced by 4-hydroxynonenal is mediated by stress-activated protein kinases pathways. J Neurochem. 2005 Feb;92(3):628-36. [PubMed:15659232 ]
- Boros LG, Steinkamp MP, Fleming JC, Lee WN, Cascante M, Neufeld EJ: Defective RNA ribose synthesis in fibroblasts from patients with thiamine-responsive megaloblastic anemia (TRMA). Blood. 2003 Nov 15;102(10):3556-61. Epub 2003 Jul 31. [PubMed:12893755 ]
- Takeda Y, Usukura M, Yoneda T, Oda N, Ito Y, Mabuchi H: The expression of messenger RNA for ADP-ribosyl cyclase in aldosterone-producing adenomas. Clin Endocrinol (Oxf). 2005 Apr;62(4):504-8. [PubMed:15807884 ]
- Thomas D, Yang H, Boffa DJ, Ding R, Sharma VK, Lagman M, Li B, Hering B, Mohanakumar T, Lakey J, Kapur S, Hancock WW, Suthanthiran M: Proapoptotic Bax is hyperexpressed in isolated human islets compared with antiapoptotic Bcl-2. Transplantation. 2002 Dec 15;74(11):1489-96. [PubMed:12490780 ]
- Dhanoa TS, Housner JA: Ribose: more than a simple sugar? Curr Sports Med Rep. 2007 Jul;6(4):254-7. [PubMed:17618002 ]
- 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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