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Orotic acid

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Pharmaceutical compound
Orotic acid
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
CAS Number
PubChem CID
DrugBank
CompTox Dashboard (EPA)
ECHA InfoCard100.000.563 Edit this at Wikidata
Chemical and physical data
FormulaC5H4N2O4
Molar mass156.10 g/mol g·mol
  (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 Dihydroorate Dehydrogenase, where it later combines with PRPP (Phosphoribosyl Pyrophosphate) 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.

See also

References

  1. "Vitamin B13 (Orotic Acid)".
  2. 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: 1331–1337. doi:10.1136/gut.33.10.1331.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Greenbaum SB (1954). "Orotic acid antagonist: "6-Uracilsulfonic Acid, a Sulronic Acid Analog of Orotic Acid". J. Am. Chem. Soc. 76 (23): 6052–6054.
  4. Lippincott. Biochemistry 4th Edition. 2008

External links

Nucleotide metabolic intermediates
purine
metabolism
anabolism
R5PIMP:
IMPAMP:Adenylosuccinate
IMPGMP:Xanthosine monophosphate
catabolism
pyrimidine
metabolism
anabolism
catabolism
uracil:
thymine:


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