| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:28:00 UTC |
|---|
| Update Date | 2020-06-04 20:49:44 UTC |
|---|
| BMDB ID | BMDB0000296 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Uridine |
|---|
| Description | Uridine, also known as beta-uridine or allo uridine, 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. Uridine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uridine exists in all living species, ranging from bacteria to humans. In cattle, uridine is involved in the metabolic pathway called lactose synthesis pathway. Uridine has been found to be associated with several diseases known as degenerative disc disease, canavan disease, and ulcerative colitis; also uridine has been linked to several inborn metabolic disorders including argininemia and lesch-nyhan syndrome. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| 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 |
|
|---|
| Chemical Formula | C9H12N2O6 |
|---|
| Average Molecular Weight | 244.2014 |
|---|
| Monoisotopic Molecular Weight | 244.069536126 |
|---|
| IUPAC Name | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
|---|
| Traditional Name | uridine |
|---|
| CAS Registry Number | 58-96-8 |
|---|
| SMILES | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O |
|---|
| 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 |
|---|
| InChI Key | DRTQHJPVMGBUCF-XVFCMESISA-N |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Nucleosides, nucleotides, and analogues |
|---|
| Class | Pyrimidine nucleosides |
|---|
| Sub Class | Not Available |
|---|
| Direct Parent | Pyrimidine nucleosides |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aromatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | - Lysosome
- Mitochondria
- Nucleus
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 163 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | -1.98 | HANSCH,C ET AL. (1995) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | - Lysosome
- Mitochondria
- Nucleus
|
|---|
| Biospecimen Locations | - Blood
- Colostrum
- Liver
- Mammary Gland
- Milk
- Muscle
- Placenta
- Ruminal Fluid
- Testis
- Urine
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| Blood | Detected and Quantified | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 344 +/- 86 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 16.07 +/- 4.91 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14.690 +/- 4.730 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 31 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 27 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 28 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 30 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 73.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14.7 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.76 +/- 1.81 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.78 +/- 2.37 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 18 +/- 10 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 2-17 uM | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 156 +/- 36 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| HMDB ID | HMDB0000296 |
|---|
| DrugBank ID | DB02745 |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB007411 |
|---|
| KNApSAcK ID | C00019674 |
|---|
| Chemspider ID | 5807 |
|---|
| KEGG Compound ID | C00299 |
|---|
| BioCyc ID | URIDINE |
|---|
| BiGG ID | 34541 |
|---|
| Wikipedia Link | Uridine |
|---|
| METLIN ID | 90 |
|---|
| PubChem Compound | 6029 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 16704 |
|---|
| References |
|---|
| Synthesis Reference | Doi, Muneharu; Asahi, Satoru; Izawa, Motoo. Fermentative production of uridine and cytidine. Baiosaiensu to Indasutori (1993), 51(12), 972-6. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
- Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
- Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. [PubMed:11242448 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
|
|---|