Record Information |
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Version | 4.0 |
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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 | 2020-02-26 21:23:25 UTC |
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HMDB ID | HMDB0001489 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ribose 1-phosphate |
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Description | Ribose 1-phosphate, also known as D-ribose-1P, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Ribose 1-phosphate is a drug. Ribose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ribose 1-phosphate is an intermediate in the metabolism of Pyrimidine and the metabolism of Nicotinate and nicotinamide. Ribose 1-phosphate exists in all living species, ranging from bacteria to humans. Within humans, ribose 1-phosphate participates in a number of enzymatic reactions. In particular, guanine and ribose 1-phosphate can be biosynthesized from guanosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, xanthine and ribose 1-phosphate can be biosynthesized from xanthosine; which is catalyzed by the enzyme purine nucleoside phosphorylase. As a result of this purine pathway, guanosine is converted into xanthosine, thus overcoming the lack of guanosine deaminase in mammals. In humans, ribose 1-phosphate is involved in the metabolic disorder called the mitochondrial dna depletion syndrome pathway. Outside of the human body, ribose 1-phosphate has been detected, but not quantified in, several different foods, such as apricots, sesbania flowers, italian sweet red peppers, lupines, and olives. This could make ribose 1-phosphate a potential biomarker for the consumption of these foods. It is a substrate for Uridine phosphorylase 2, Phosphoglucomutase, Purine nucleoside phosphorylase and Uridine phosphorylase 1. The activated ribose moiety in Ribose 1-phosphate which stems from the catabolism of purine nucleosides can be transferred to uracil and, in the presence of ATP, used for the synthesis of pyrimidine nucleotides; therefore, purine nucleosides can act as ribose donors for the salvage of pyrimidine bases. The presence of guanase, which irreversibly converts guanine to xanthine, affects the overall process of guanosine transformation. Ribose 1-phosphate can be formed from guanosine through the action of purine nucleoside phosphorylase. Ribose 1-phosphate can also act as a ribose donor in the synthesis of xanthosine as catalyzed by the same enzyme (purine nucleoside phosphorylase). |
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Structure | |
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Synonyms | Value | Source |
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1-O-Phosphono-alpha-D-ribofuranose | ChEBI | 1-Phospho-alpha-D-ribofuranose | ChEBI | D-Ribose 1-phosphate | ChEBI | 1-O-Phosphono-a-D-ribofuranose | Generator | 1-O-Phosphono-α-D-ribofuranose | Generator | 1-Phospho-a-D-ribofuranose | Generator | 1-Phospho-α-D-ribofuranose | Generator | D-Ribose 1-phosphoric acid | Generator | Ribose 1-phosphoric acid | Generator | 1-O-Phosphono-D-ribofuranose | HMDB | a-D-Ribofuranose 1-(dihydrogen phosphate) | HMDB | a-D-Ribose 1-phosphate | HMDB | alpha-D-Ribofuranose 1-(dihydrogen phosphate) | HMDB | alpha-D-Ribofuranose 1-phosphate | HMDB | alpha-D-Ribose 1-phosphate | HMDB | D-Ribofuranose 1-(dihydrogen phosphate) | HMDB | D-Ribofuranose 1-phosphate | HMDB | D-Ribose-1-phosphate | HMDB | D-Ribose-1P | HMDB | Ribofuranose 1-phosphate | HMDB | Ribose 1-phosphate, (beta-D)-isomer | HMDB | Ribose 1-phosphate, (alpha-D)-isomer | HMDB |
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Chemical Formula | C5H11O8P |
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Average Molecular Weight | 230.1098 |
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Monoisotopic Molecular Weight | 230.01915384 |
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IUPAC Name | {[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid |
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Traditional Name | ribose 1-phosphate |
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CAS Registry Number | 14075-00-4 |
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SMILES | OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1 |
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InChI Key | YXJDFQJKERBOBM-TXICZTDVSA-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
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- 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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9110000000-add01bb15cc1fd9e2e29 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-014i-2931000000-fe633c386d1b3ab9db9a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0090000000-e2c9f6f60320b17dd479 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-01t9-9250000000-029c27941ed85100b53c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-311ca08c80d0a6c765da | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-36d97c26c72c69ab56c6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-08796c6cb24ecefd9abf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9230000000-bf825c0a48e8f3fb1db5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9330000000-af34500034734754adda | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-9000000000-ea509fab4675ba638745 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9180000000-4449ca89ca00716d8cef | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9110000000-c74e6f3e6a87ec4b57fb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-81a191a3e73e8031cb23 | Spectrum |
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General References | - Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
- Giorgelli F, Bottai C, Mascia L, Scolozzi C, Camici M, Ipata PL: Recycling of alpha-D-ribose 1-phosphate for nucleoside interconversion. Biochim Biophys Acta. 1997 Apr 17;1335(1-2):6-22. [PubMed:9133638 ]
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