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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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