- Orotic acid
Orotic acid Systematic (IUPAC) name 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid Clinical data AHFS/Drugs.com International Drug Names Pregnancy cat. ? Legal status ? Identifiers CAS number 65-86-1 ATC code None PubChem CID 967 DrugBank EXPT02447 UNII 61H4T033E5 KEGG C00295 Chemical data Formula C5H4N2O4 Mol. mass 156.10 g/mol (what is this?) (verify)
Orotic acid is a heterocyclic compound and an acid; it is also known as pyrimidinecarboxylic acid. It was once believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin but is instead manufactured in the body by intestinal flora.
Its salts, known as orotates, are sometimes used as mineral carriers in some dietary supplements, to increase their bioavailability. Lithium orotate is the most frequently used in this manner.
Synthesis of orotate
Dihydroorotate is synthesized to orotic acid by the enzyme dihydroorate dehydrogenase, where it later combines with phosphoribosyl pyrophosphate (PRPP) to form orotidylate (OMP). A distinguishing characteristic of pyrimidine synthesis is that the pyrimidine ring is fully synthesized before being attached to the ribose sugar, whereas purine synthesis happens by building the base directly on the sugar.
Orotic acid diseases
A buildup of orotic acid can lead to orotic aciduria. It may be a symptom of an increased ammonia load due to a metabolic disorder, such as a urea cycle disorder.
In ornithine transcarbamoylase deficiency, a disorder of the urea cycle, excess carbamoyl phosphate is converted into orotic acid. This typically leads to increased urinary orotic acid excretion, because the orotic acid is not being properly utilized and must be eliminated.
Orotic acid can be mutagenic (causes mutations) in mammalian somatic cells. It is also mutagenic for bacteria and or yeast.
- Pyrimidine biosynthesis
- Lithium orotate
- ^ "Vitamin B13 (Orotic Acid)". http://www.dietandfitnesstoday.com/vitaminB13.php.
- ^ Husebye E, Skar V, Høverstad T, Melby K (1992). "Fasting hypochlorhydria with gram positive gastric flora is highly prevalent in healthy old people". Gut 33 (10): 1331–1337. doi:10.1136/gut.33.10.1331. PMC 1379599. PMID 1446855. http://gut.bmj.com/content/33/10/1331.abstract.
- ^ Greenbaum SB (1954). "Orotic acid antagonist: "6-Uracilsulfonic Acid, a Sulronic Acid Analog of Orotic Acid". J. Am. Chem. Soc. 76 (23): 6052–6054. doi:10.1021/ja01652a056.
- ^ Lippincott. Biochemistry 4th Edition. 2008
- MeSH Orotic+Acid
- Overview at ggc.org
- Overview at greatvistachemicals.com
- Overview of Potential Metabolic Antagonists
Nucleotide metabolic intermediates Purine metabolismAnabolismCatabolism Pyrimidine metabolismAnabolismCatabolismbiochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/iCategories:
- Carboxylic acids
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