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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:20 UTC |
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Update Date | 2020-05-21 16:28:29 UTC |
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BMDB ID | BMDB0000076 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dihydrouracil |
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Description | Dihydrouracil 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. Dihydrouracil exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Dihydrouracil exists in all living organisms, ranging from bacteria to humans. Dihydrouracil is a potentially toxic compound. Dihydrouracil has been found to be associated with several diseases known as liver disease, colorectal cancer, hypertension, and cerebral infarction; also dihydrouracil has been linked to the inborn metabolic disorders including dihydropyrimidine dehydrogenase deficiency. |
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Structure | |
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Synonyms | Value | Source |
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2,4-Dioxotetrahydropyrimidine | ChEBI | 5,6-Dihydro-2,4-dihydroxypyrimidine | ChEBI | Dihydro-2,4(1H,3H)-pyrimidinedione | ChEBI | DIHYDROPYRIMIDINE-2,4(1H,3H)-dione | ChEBI | Dihydrouracile | ChEBI | Hydrouracil | ChEBI | 5,6-Dihydro-2,4(1H,3H)-pyrimidinedione | HMDB | 5,6-Dihydrouracil | HMDB | Dihydro-pyrimidine-2,4-dione | HMDB |
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Chemical Formula | C4H6N2O2 |
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Average Molecular Weight | 114.1026 |
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Monoisotopic Molecular Weight | 114.042927446 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 504-07-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8) |
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InChI Key | OIVLITBTBDPEFK-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 | - N-acyl urea
- Pyrimidone
- Ureide
- 1,3-diazinane
- Dicarboximide
- Urea
- Carbonic acid derivative
- Azacycle
- Carboxylic acid derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- 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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Status | Detected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | 279 - 281 °C | 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 | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Fibroblasts
- Kidney
- Liver
- Mammary Gland
- Milk
- Prostate Tissue
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Pathways | |
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Normal Concentrations |
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Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000076 |
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DrugBank ID | DB01849 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030556 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 629 |
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KEGG Compound ID | C00429 |
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BioCyc ID | DI-H-URACIL |
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BiGG ID | 34956 |
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Wikipedia Link | Dihydrouracil |
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METLIN ID | 285 |
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PubChem Compound | 649 |
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PDB ID | Not Available |
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ChEBI ID | 15901 |
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References |
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Synthesis Reference | Bhat, K. S.; Rao, A. S. Synthesis of uracil, 6-methyluracil and some dihydrouracils. Organic Preparations and Procedures International (1983), 15(5), 303-13. |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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