Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-10-07 20:39:30 UTC |
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NP-MRD ID | NP0000638 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Uridine |
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Description | Uridine, also known as beta-uridine or 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, is a member of the class of compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. More specifically, uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Uridine can be synthesized from uracil. It is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C and G respectively. Uridine is also a parent compound for other transformation products, including but not limited to, nikkomycin Z, 3'-(enolpyruvyl)uridine 5'-monophosphate, and 5-aminomethyl-2-thiouridine. Uridine can be found in most biofluids, including urine, breast milk, cerebrospinal fluid (CSF), and blood. Within the cell, uridine is primarily located in the mitochondria, in the nucleus and the lysosome. It can also be found in the extracellular space. As an essential nucleoside, uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in several metabolic disorders, some of which include dhydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and beta-ureidopropionase deficiency. Moreover, uridine is found to be associated with Lesch-Nyhan syndrome, which is an inborn error of metabolism. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine plays a role in the glycolysis pathway of galactose. In humans there is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized via the normal glucose metabolism pathways. More specifically, consumed galactose is converted into galactose 1-phosphate (Gal-1-P). This molecule is a substrate for the enzyme galactose-1-phosphate uridyl transferase which transfers a UDP molecule to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose. Uridine is found in many foods (anything containing RNA) but is destroyed in the liver and gastrointestinal tract, and so no food, when consumed, has ever been reliably shown to elevate blood uridine levels. On the other hand, consumption of RNA-rich foods may lead to high levels of purines (adenine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout. |
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Structure | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 |
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Synonyms | Value | Source |
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1-beta-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione | ChEBI | 1-beta-D-Ribofuranosyluracil | ChEBI | beta-Uridine | ChEBI | u | ChEBI | Urd | ChEBI | Uridin | ChEBI | 1-b-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione | Generator | 1-Β-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione | Generator | 1-b-D-Ribofuranosyluracil | Generator | 1-Β-D-ribofuranosyluracil | Generator | b-Uridine | Generator | Β-uridine | Generator | 1-b-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione | HMDB | 1-beta-delta-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione | HMDB | 1-beta-delta-Ribofuranosyluracil | HMDB | b-D-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1 | HMDB | beta-delta-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1 | HMDB | Allo uridine | HMDB | Allo-uridine | HMDB | Allouridine | HMDB |
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Chemical Formula | C9H12N2O6 |
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Average Mass | 244.2014 Da |
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Monoisotopic Mass | 244.06954 Da |
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IUPAC Name | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | uridine |
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CAS Registry Number | 58-96-8 |
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SMILES | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O |
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InChI Identifier | InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 |
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InChI Key | DRTQHJPVMGBUCF-XVFCMESISA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, simulated) | Varshavi.d26 | | | 2021-08-23 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-15 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-07 | View Spectrum |
| Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Not Available |
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Direct Parent | Pyrimidine nucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine nucleoside
- Glycosyl compound
- N-glycosyl compound
- Pentose monosaccharide
- Pyrimidone
- Hydropyrimidine
- Monosaccharide
- Pyrimidine
- Vinylogous amide
- Tetrahydrofuran
- Heteroaromatic compound
- Urea
- Secondary alcohol
- Lactam
- Organoheterocyclic compound
- Oxacycle
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Primary alcohol
- Alcohol
- Organic oxygen compound
- Organic oxide
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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 | 163 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 61220 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | -1.98 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
- Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
- Pizzorno G, Cao D, Leffert JJ, Russell RL, Zhang D, Handschumacher RE: Homeostatic control of uridine and the role of uridine phosphorylase: a biological and clinical update. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):133-44. doi: 10.1016/s0925-4439(02)00076-5. [PubMed:12084455 ]
- Aird SD: Taxonomic distribution and quantitative analysis of free purine and pyrimidine nucleosides in snake venoms. Comp Biochem Physiol B Biochem Mol Biol. 2005 Jan;140(1):109-26. doi: 10.1016/j.cbpc.2004.09.020. [PubMed:15621516 ]
- Choi JW, Yoo BK, Shin CY, Ryu MK, Ryu JH, el Kouni MH, Lee JC, Kim WK, Ko KH: Uridine prevents the glucose deprivation-induced death of immunostimulated astrocytes via the action of uridine phosphorylase. Neurosci Res. 2006 Sep;56(1):111-8. doi: 10.1016/j.neures.2006.06.004. Epub 2006 Jul 12. [PubMed:16839635 ]
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