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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/02 16:32:21」(JST)

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Orotic acid is a heterocyclic compound and an acid; it is also known as pyrimidinecarboxylic acid. Historically it was 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.

The compound is manufactured in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase.^[1] or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate.

Synthesis

Dihydroorotate is synthesized to orotic acid by the enzyme dihydroorate dehydrogenase, where it later combines with phosphoribosyl pyrophosphate (PRPP) to form orotidine-5'-monophosphate (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.^[2]

Safety

Orotic acid can be mutagenic in mammalian somatic cells. It is also mutagenic for bacteria and yeast.^[3]

Pathology

A buildup of orotic acid can lead to orotic aciduria and acidemia. 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, an X-linked inherited and the most common urea cycle disorder, excess carbamoyl phosphate is converted into orotic acid. This leads to an increased serum ammonia level, increased serum and urinary orotic acid levels and a decreased serum blood urea nitrogen level. This also leads to an increased urinary orotic acid excretion, because the orotic acid is not being properly utilized and must be eliminated. The hyperammonemia depletes alpha-ketoglutarate leading to the inhibition of the tricarboxylic acid cycle (TCA) decreasing adenosine triphosphate (ATP) production.

References

^ Rawls, J; Knecht, W; Diekert, K; Lill, R; Löffler, M (2000). "Requirements for the mitochondrial import and localization of dihydroorotate dehydrogenase". European journal of biochemistry / FEBS 267 (7): 2079–87. doi:10.1046/j.1432-1327.2000.01213.x. PMID 10727948.
^ Lippincott (2008). Biochemistry (4th ed.).
^ Orotic acid MSDS

External links

Orotic Acid at the US National Library of Medicine Medical Subject Headings (MeSH)
Greenbaum, Sheldon B. (1954). "Potential Metabolic Antagonists of Orotic Acid: 6-Uracilsulfonamide and 6-Uracil Methyl Sulfone1". Journal of the American Chemical Society 76 (23): 6052. doi:10.1021/ja01652a056.

UpToDate Contents

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1. 先天性代謝異常：疫学、病因、および臨床的特徴 inborn errors of metabolism epidemiology pathogenesis and clinical features
2. 小児における腎結石症の疫学および危険因子 epidemiology of and risk factors for nephrolithiasis in children
3. 再発性の痛風の予防：薬理学的尿酸低下療法および痛風結節の治療 prevention of recurrent gout pharmacologic urate lowering therapy and treatment of tophi
4. 有機酸血症 organic acidemias
5. 先天性代謝異常：代謝性救急疾患 inborn errors of metabolism metabolic emergencies

English Journal

Hereditary Orotic Aciduria and the Excretion of Orotidine.

Nyhan WL1, Gangoiti JA1.
Neuropediatrics.Neuropediatrics.2016 Aug 30. [Epub ahead of print]
Objective Orotic aciduria and deficiency of uridine monophosphate synthetase have been observed in a patient, studied over 10 years, who had no megaloblastic anemia. Excretion of orotic acid and orotidine were 8.24 and 0.52 mmol/mol of creatinine. The ratio of 15.85 differed appreciably from that
PMID 27574833

Metabolite amyloids: a new paradigm for inborn error of metabolism disorders.

Gazit E1.
Journal of inherited metabolic disease.J Inherit Metab Dis.2016 Jul;39(4):483-8. doi: 10.1007/s10545-016-9946-9. Epub 2016 Jun 6.
The formation of ordered amyloid assemblies is associated with major human degenerative disorders, including Alzheimer's disease, Parkinson's disease, and type 2 diabetes. Amyloid fibrils are elongated nanoscale structures that bind to specific dyes (including thioflavin T and Congo red). Amyloid fi
PMID 27271695

Japanese Journal

Fluorescence assay of dihydroorotate dehydrogenase that may become a cancer biomarker

Scientific Reports 7, 40670, 2017-01-13
NAID 120006221107

Production of orotic acid by a Klura3Δ mutant of Kluyveromyces lactis

Journal of bioscience and bioengineering 121(6), 625-630, 2016-06
NAID 40020873358

Ability of Food/Drink to Reduce the Bitterness Intensity of Topiramate as Determined by Taste Sensor Analysis

Chemical and Pharmaceutical Bulletin 64(1), 14-20, 2016
NAID 130005115802

「オロト酸」

Orotic acid
Systematic (IUPAC) name
	1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Registry Number	65-86-1
ATC code	None
PubChem	CID: 967
IUPHAR/BPS	4690
DrugBank	DB02262
ChemSpider	942
UNII	61H4T033E5
KEGG	C00295
Chemical data
Formula	C5H4N2O4
Molecular mass	156.10 g/mol
	SMILES O=C(O)\C1=C\C(=O)NC(=O)N1 ;
	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) ; Key:PXQPEWDEAKTCGB-UHFFFAOYSA-N ;
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