| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:28:03 UTC |
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| Update Date | 2020-06-04 20:52:17 UTC |
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| MCDB ID | BMDB0000300 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Uracil |
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| Description | Uracil, also known as U or hybar X, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uracil exists in all living species, ranging from bacteria to humans. Uracil is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,4(1H,3H)-Pyrimidinedione | ChEBI | | 2,4-Dioxopyrimidine | ChEBI | | 2,4-Pyrimidinedione | ChEBI | | U | ChEBI | | Ura | ChEBI | | Urazil | ChEBI | | 2,4-Dihydroxypyrimidine | HMDB | | 2,4-Pyrimidinediol | HMDB | | Hybar X | HMDB | | Pirod | HMDB | | Pyrod | HMDB |
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| Chemical Formula | C4H4N2O2 |
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| Average Molecular Weight | 112.0868 |
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| Monoisotopic Molecular Weight | 112.027277382 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 66-22-8 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) |
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| InChI Key | ISAKRJDGNUQOIC-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Diazines |
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| Sub Class | Pyrimidines and pyrimidine derivatives |
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| Direct Parent | Pyrimidones |
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| Alternative Parents | |
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| Substituents | - Pyrimidone
- Hydropyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Urea
- Lactam
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen 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 | 330 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 3.6 mg/mL | Not Available | | LogP | -1.07 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | Not Available |
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| Spectra |
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| Concentrations |
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| Detected but not Quantified | Not Applicable | | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected but not Quantified | Not Applicable | | | details |
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| External Links |
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| HMDB ID | HMDB0000300 |
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| DrugBank ID | DB03419 |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB006426 |
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| KNApSAcK ID | C00001513 |
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| Chemspider ID | 1141 |
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| KEGG Compound ID | C00106 |
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| BioCyc ID | URACIL |
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| BiGG ID | 33879 |
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| Wikipedia Link | Uracil |
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| METLIN ID | 258 |
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| PubChem Compound | 1174 |
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| PDB ID | Not Available |
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| ChEBI ID | 17568 |
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| References |
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| Synthesis Reference | Burckhalter, J. H.; Scarborough, Homer C. The synthesis of uracils as anticonvulsants. Journal of the American Pharmaceutical Association (1912-1977) (1955), 44 545-50. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- 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 ]
- 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.
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