Orotic acid

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 YesY
ATC code None
PubChem CID 967
DrugBank EXPT02447
UNII 61H4T033E5 N
KEGG C00295 N
Chemical data
Formula C5H4N2O4 
Mol. mass 156.10 g/mol
 N(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.[1][2][3]

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.

Contents

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.[4]

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)". http://www.dietandfitnesstoday.com/vitaminB13.php. 
  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 (10): 1331–1337. doi:10.1136/gut.33.10.1331. PMC 1379599. PMID 1446855. http://gut.bmj.com/content/33/10/1331.abstract. 
  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. doi:10.1021/ja01652a056. 
  4. ^ Lippincott. Biochemistry 4th Edition. 2008

External links

v · d · eNucleotide metabolic intermediates
Purine metabolism
Anabolism

R5P→IMP: R5P · PRPP · PRA · GAR · FGAR · FGAM · AIR · CAIR · SAICAR · AICAR · FAICAR

IMP→AMP: Adenylosuccinate

IMP→GMP: Xanthosine monophosphate
Catabolism
Pyrimidine metabolism
Anabolism
Catabolism

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

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Look at other dictionaries:

  • orotic acid — orotic acid. См. оротовая кислота. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • orotic acid — oroto rūgštis statusas T sritis chemija formulė (HO)₂C₄HN₂COOH santrumpa( os) Oro atitikmenys: angl. orotic acid; vitamin B₁₃ rus. витамин B₁₃; оротовая кислота ryšiai: sinonimas – 2,6 dihidroksi 4 pirimidinkarboksirūgštis sinonimas – vitaminas… …   Chemijos terminų aiškinamasis žodynas

  • orotic acid — (ˈ)ȯ|räd.ik noun Etymology: orotic probably from orot (from Greek oros whey) + icmore at serum : a crystalline acid C4H4N2O4 that was first found in milk, is a growth factor for various microorganisms (as Lactobacillus bulgaricus), and is a… …   Useful english dictionary

  • orotic acid — 6 Carboxyuracil; uracil 6 carboxylic acid; an important intermediate in the formation of the pyrimidine nucleotides; elevated in certain inherited defects of pyrimidine biosynthesis. SYN: uracil 6 carboxylic acid. * * * orot·ic acid ȯr .ät ik n …   Medical dictionary

  • orotic acid — noun pyrimidine carboxylic acid …   Wiktionary

  • orotic acid — (= orotate) Intermediate in the de novo synthesis of pyrimidines. Linked glycosidically to ribose 5 phosphate, orotate forms the pyrimidine nucleotide orotidylate, that on decarboxylation at position 5 of the pyrimidine ring yields the major… …   Dictionary of molecular biology

  • Orotic aciduria — Classification and external resources orotic acid ICD 9 281 …   Wikipedia

  • orotic aciduria — A rare disorder of pyrimidine metabolism characterized by hypochromic anemia with megaloblastic changes in bone marrow, leukopenia, retarded growth, and urinary excretion of orotic acid; …   Medical dictionary

  • orotic — adjective Of or pertaining to orotic acid or its derivatives …   Wiktionary

  • 4,5-Dihydroorotic acid — IUPAC name 2,6 dioxo 1,3 diazinane 4 carboxylic acid …   Wikipedia

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