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| Identification |
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| YMDB ID | YMDB00405 |
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| Name | Orotic acid |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Orotic acid, also known as orotate or orotsaeure, belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring. Orotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Orotic acid exists in all living species, ranging from bacteria to humans. Within yeast, orotic acid participates in a number of enzymatic reactions. In particular, orotic acid and phosphoribosyl pyrophosphate can be converted into orotidylic acid through the action of the enzyme orotate phosphoribosyltransferase. In addition, ubiquinol-1 and orotic acid can be biosynthesized from 4,5-dihydroorotic acid and ubiquinone-1 through the action of the enzyme dihydroorotate dehydrogenase, type 2. In yeast, orotic acid is involved in the metabolic pathway called the pyrimidine metabolism pathway. Orotic acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | - 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid
- 2,6-dihydroxy-4-pyrimidinecarboxylic acid
- 2,6-Dihydroxypyrimidine-4-carboxylic acid
- 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid
- 6-Carboxy-2,4-dihydroxypyrimidine
- 6-Carboxyuracil
- 6-Uracilcarboxylic acid
- Animal galactose factor
- Lactinium
- ORO
- Orodin
- Oropur
- Orotate
- Orotic acid
- Orotonin
- Orotonsan
- Oroturic
- Orotyl
- uracil-6-carboxylate
- Uracil-6-carboxylic acid
- Vitamin B13
- Whey factor
- Orotsaeure
- 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
- 1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure
- 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
- Acide orotique
- Acido orotico
- Acidum oroticum
- Molkensaeure
- Orotsaure
- Uracil-6-carbosaeure
- Zinc orotate
- Orotate, zinc
- Acid, orotic
- Orotate, potassium
- Potassium orotate
- Orotate, sodium
- Sodium orotate
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| CAS number | 65-86-1 |
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| Weight | Average: 156.0963
Monoisotopic: 156.017106626 |
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| InChI Key | PXQPEWDEAKTCGB-UHFFFAOYSA-N |
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| InChI | InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) |
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| IUPAC Name | 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid |
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| Traditional IUPAC Name | orotic acid |
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| Chemical Formula | C5H4N2O4 |
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| SMILES | [H]OC(=O)C1=C([H])C(=O)N([H])C(=O)N1[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring. |
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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 | Pyrimidinecarboxylic acids |
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| Alternative Parents | |
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| Substituents | - Pyrimidine-6-carboxylic acid
- Hydropyrimidine carboxylic acid derivative
- Pyrimidone
- Hydropyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Urea
- Lactam
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- 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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| Charge | 0 |
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| Melting point | 345.5 °C |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | 1.82 mg/mL at 18 oC [YALKOWSKY,SH & HE,Y (2003)] | PhysProp | | LogP | -0.83 [SANGSTER (1994)] | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | |
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | |
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| SMPDB Reactions | |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra |
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| References |
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| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
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| Synthesis Reference: | Mitchell, Herschel K.; Nyc, Joseph F. Intermediates in the synthesis of orotic acid from oxalacetic ester and urea. Journal of the American Chemical Society (1947), 69 674-7. |
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| External Links: | |
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