Orotic acid

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Orotic acid
Clinical data
Other namesuracil-6-carboxylic acid
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
  • 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
JSmol)
  • O=C(O)\C1=C\C(=O)NC(=O)N1
  • InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) ☒N
  • Key:PXQPEWDEAKTCGB-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Orotic acid (

vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin
.

The compound is synthesized in the body via a

dietary supplements (to increase their bioavailability), most commonly for lithium orotate
.

Synthesis

ribose sugar, whereas purine synthesis happens by building the base directly on the sugar.[3]

Chemistry

Orotic acid is a

anion, is able to bind to metals. Lithium orotate, for example, has been investigated for use in treating alcoholism,[4][5] and complexes of cobalt, manganese, nickel, and zinc are known.[6] The pentahydrate nickel orotate coordination complex converts into a polymeric trihydrate upon heating in water at 100 °C.[6][7][8] Crystals of the trihydrate can be obtained by hydrothermal treatment of nickel(II) acetate and orotic acid. When the reactions are run with bidentate nitrogen ligands such as 2,2'-bipyridine
present, other solids can be obtained.

Pathology

A buildup of orotic acid can lead to

urea cycle disorder
.

In

tricarboxylic acid cycle (TCA) decreasing adenosine triphosphate
(ATP) production.

Orotic aciduria is a cause of megaloblastic anaemia.

Biochemistry

Orotic acid is a precursor to a RNA base, uracil. [10] The breast milk of smokers has a higher concentration of orotic acid than that of a non smoking woman. It is reasoned that the smoking causes the pyrimidine biosynthesis process in the mother to be altered thus causing the orotic acid concentration to increase.[11]

A modified orotic acid (5-fluoroorotic acid) is toxic to yeast. The mutant yeasts which are resistant to 5-fluoroorotic acid require a supply of uracil.[12]

See also

References

  1. ^ "Orotic acid". Merriam-Webster.com Dictionary. Retrieved 2023-02-07.
  2. PMID 10727948
    .
  3. ^ Harvey D, Ferrier D, eds. (2008). Biochemistry (PDF) (5th ed.). Lippincott, Williams & Wilkins. p. 302.
  4. doi:10.1002/cber.19901231207
    .
  5. PMID 3718672
    .
  6. ^
    doi:10.1016/S0020-1693(02)00728-4
    .
  7. doi:10.5517/cc6cgmm
    .
  8. doi:10.1107/S0108270186090856
    .
  9. S2CID 25297304
    .
  10. doi:10.1034/j.1399-3054.2000.108001025.x
    .
  11. S2CID 29181790
    .
  12. S2CID 84498320
    .

Further reading

External links

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