WordNet
- the 2nd letter of the Roman alphabet (同)b
- the blood group whose red cells carry the B antigen (同)type_B, group B
- any of a group of organic substances essential in small quantities to normal metabolism
PrepTutorEJDIC
- 『ビタミン』,栄養素(身体の喜常な機能を維持するために少量ながら必要な有機化合物)
- black(鉛筆の軟度を示す;硬度は『H』(=hard)で表す) / boronの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/11 22:08:22」(JST)
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Orotic acid
|
| Systematic (IUPAC) name |
|
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
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| Clinical data |
| Drugs.com |
International Drug Names |
| Identifiers |
| CAS Number |
65-86-1 Y |
| ATC code |
none |
| PubChem |
CID 967 |
| IUPHAR/BPS |
4690 |
| DrugBank |
DB02262 N |
| ChemSpider |
942 N |
| UNII |
61H4T033E5 N |
| KEGG |
C00295 N |
| Chemical data |
| Formula |
C5H4N2O4 |
| Molar mass |
156.10 g/mol |
SMILES
-
O=C(O)\C1=C\C(=O)NC(=O)N1
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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) N
-
Key:PXQPEWDEAKTCGB-UHFFFAOYSA-N N
|
| NY (what is this?) (verify) |
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.
Contents
- 1 Synthesis
- 2 Safety
- 3 Pathology
- 4 See also
- 5 References
- 6 External links
Synthesis
Dihydroorotate is synthesized to orotic acid by the enzyme dihydroorotate 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.
Orotic aciduria is a cause of megaloblastic anaemia.
See also
- Magnesium orotate
- Pyrimidine biosynthesis
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
|
Wikimedia Commons has media related to Orotic acid. |
- 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): 6052–6054. doi:10.1021/ja01652a056.
|
Nucleotide metabolic intermediates
|
|
| Purine metabolism |
| Anabolism |
| R5P→IMP: |
- R5P
- PRPP
- PRA
- GAR
- FGAR
- FGAM
- AIR
- CAIR
- SAICAR
- AICAR
- FAICAR
|
|
| IMP→AMP: |
|
|
| IMP→GMP: |
|
|
|
| Catabolism |
- Hypoxanthine
- Xanthine
- Uric acid
- 5-Hydroxyisourate
|
|
|
| Pyrimidine metabolism |
| Anabolism |
- Carbamoyl phosphate
- Carbamoyl aspartic acid
- 4,5-Dihydroorotic acid
- Orotic acid
- Orotidine 5'-monophosphate
- Uridine monophosphate
|
|
| Catabolism |
| uracil: |
- Dihydrouracil
- 3-Ureidopropionic acid
- β-Alanine
|
|
| thymine: |
- Dihydrothymine
- β-Ureidoisobutyric acid
- 3-Aminoisobutyric acid
|
|
|
|
UpToDate Contents
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English Journal
- Efficient differentiation of AR42J cells towards insulin-producing cells using pancreatic transcription factors in combination with growth factors.
- Lima MJ1, Docherty HM, Chen Y, Docherty K.
- Molecular and cellular endocrinology.Mol Cell Endocrinol.2012 Jul 6;358(1):69-80. doi: 10.1016/j.mce.2012.02.024. Epub 2012 Mar 10.
- The AR42J-B13 rat pancreatic acinar cell line was used to identify pancreatic transcription factors and exogenous growth factors (GFs) that might facilitate the reprogramming of exocrine cells into islets. Adenoviruses were used to induce exogenous expression of the pancreatic transcription factors
- PMID 22429991
- Food allergy: only a pediatric disease?
- Diesner SC1, Untersmayr E, Pietschmann P, Jensen-Jarolim E.
- Gerontology.Gerontology.2011;57(1):28-32. doi: 10.1159/000279756. Epub 2010 Jan 29.
- Epidemiologic studies report an increase in food allergies in industrialized countries, but mainly focus on children and young adults. This leads to the impression that food allergies do not occur in the older population. However, age-related changes dramatically affect both the innate as well as th
- PMID 20110662
Japanese Journal
- Determination of orotic acid (vitamin B13) in human serum and urine by differential-pulse polarography
Related Links
- ビタミンB13 - 栄養成分と食品の効用 食は生命を維持していく上の基本です。現代社会は生活の多様性からか食生活が乱れ気味と言われますが正しい食生活を送るためには栄養成分の正しい知識が必要です。当サイトは食品の効果と必要 ...
- ビタミンB13は、牛乳から発見された栄養素で、体内で合成されることがわかり、現在は、ビタミン様作用物質として扱われています。 ビタミンB12や葉酸の代謝（体内での化学反応）を助ける働きがあり、肝臓病の予防やアンチエイ ...
★リンクテーブル★
[★]
- 英
- orotate, orotic acid
- 同
- オロチン酸、ビタミンB13 vitamin B13、6-カルボキシウラシル 6-carboxyuracil
- 関
- オロット酸
[★]
- Mg2+存在下でC3, B, Dが反応してC3bBbとなり、これがC3転換酵素(C3bBb)あるいはC5転換酵素(C3bBb3b)を形成する。これらはP(properdin)と結合して活性化し、それぞれC3、C5を活性化する