Allantoic acid

Last updated
Allantoic acid
Allantoic acid.svg
Names
Preferred IUPAC name
Bis(carbamoylamino)acetic acid [1]
Other names
Identifiers
3D model (JSmol)
3DMet
1790227
ChEBI
ChemSpider
ECHA InfoCard 100.002.487 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-735-4
240954
KEGG
MeSH allantoic+acid
PubChem CID
UNII
  • InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12) Yes check.svgY
    Key: NUCLJNSWZCHRKL-UHFFFAOYSA-N Yes check.svgY
  • NC(=O)NC(NC(N)=O)C(O)=O
Properties
C4H8N4O4
Molar mass 176.132 g·mol−1
Density 1.618 g mL−1
Hazards
Flash point 219.4 °C (426.9 °F; 492.5 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Allantoic acid is an organic compound with the chemical formula C4H8N4O4. It is a crystalline acid obtained by hydrolysis of allantoin.

In nature, allantoic acid is produced from allantoin by the enzyme allantoinase (encoded by the gene AllB (Uniprot: P77671) in Escherichia coli and other bacteria).

Related Research Articles

Nitric acid is the inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.

<span class="mw-page-title-main">Organic compound</span> Chemical compound with carbon-hydrogen bonds

In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate, millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds, along with a few other exceptions, are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive.

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

<span class="mw-page-title-main">Uric acid</span> End product of nucleic acid degradation

Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown of purine nucleotides, and it is a normal component of urine. High blood concentrations of uric acid can lead to gout and are associated with other medical conditions, including diabetes and the formation of ammonium acid urate kidney stones.

<span class="mw-page-title-main">Allantoin</span> Chemical compound

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which itself is a degradation product of nucleic acids, by action of urate oxidase (uricase). The occurs as a natural mineral compound (IMA symbol Aan).

Keratolytic therapy is a type of medical treatment to remove warts, calluses and other lesions in which the epidermis produces excess skin. In this therapy, acidic topical medicines, such as Whitfield's ointment or Jessner's solution, are applied to the lesion in order to thin the skin on and around it. This therapy causes the outer layer of the skin to loosen and shed.

<span class="mw-page-title-main">Urate oxidase</span> Pseudogene in the species Homo sapiens

The enzyme urate oxidase (UO), uricase or factor-independent urate hydroxylase, absent in humans, catalyzes the oxidation of uric acid to 5-hydroxyisourate:

<span class="mw-page-title-main">Rasburicase</span>

Rasburicase is a medication that helps to clear uric acid from the blood. It is a recombinant version of urate oxidase, an enzyme that metabolizes uric acid to allantoin. Urate oxidase is known to be present in many mammals but does not naturally occur in humans. Rasburicase is produced by a genetically modified Saccharomyces cerevisiae strain. The complementary DNA (cDNA) coding for rasburicase was cloned from a strain of Aspergillus flavus.

Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to a groups and a class of compounds with the same ring structure as the parent. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.

<span class="mw-page-title-main">Alloxan</span> Chemical compound

Alloxan, sometimes referred to as alloxan hydrate, is the name of the organic compound with the formula OC(N(H)CO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative OC(N(H)CO)2CO is also known, as well as a dimeric derivative. These are some of the earliest known organic compounds. They exhibit a variety of biological activities.

<span class="mw-page-title-main">Panthenol</span> Pair / mixture of stereoisomers

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.

<span class="mw-page-title-main">Glycolaldehyde</span> Organic compound (HOCH2−CHO)

Glycolaldehyde is the organic compound with the formula HOCH2−CHO. It is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is a highly reactive molecule that occurs both in the biosphere and in the interstellar medium. It is normally supplied as a white solid. Although it conforms to the general formula for carbohydrates, Cn(H2O)n, it is not generally considered to be a saccharide.

<span class="mw-page-title-main">Dihydroxymalonic acid</span> Chemical compound

Dihydroxymalonic acid is an organic compound with formula C3H4O6 or HO-(C=O)-C(OH)2-(C=O)-OH, found in some plants such as alfalfa and in beet molasses.

In enzymology, an allantoin racemase is an enzyme that catalyzes the chemical reaction

Pegloticase is a medication for the treatment of severe, treatment-refractory, chronic gout. It is a third line treatment in those in whom other treatments are not tolerated. The drug is administered by infusion intravenously.

In molecular biology 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase EC 4.1.1.n1 is an enzyme involved in purine catabolism. It catalyses the decarboxylation of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (OHCU) into S(+)-allantoin. It is the third step of the conversion of uric acid to allantoin. Step one is catalysed by urate oxidase and step two is catalysed by hydroxyisourate hydrolase.

Bacillus fastidiosus is an aerobic, motile, rod-shaped bacterium that has been isolated from soil and poultry litter. The species was first isolated and described by the scientist Den Dooren de Jong in 1929. This organism is a mesophile that contains ellipsoidal spores that do not cause swelling of the sporangia. Bacillus fastidiosus is only able to grow in the presence of uric acid, allantoin, or allantoic acid.

<span class="mw-page-title-main">Acylurea</span> Class of chemical compounds formally derived from the acylation of urea

Acylureas are a class of chemical compounds formally derived from the acylation of urea.

Cordia salicifolia, also called Cordia ecalyculata and chá de bugre, is a species of evergreen flowering tree in the borage family, Boraginaceae, that occurs mainly in Brazil and is used as a medicinal plant. Its red fruit, which resembles a coffee bean and contains caffeine, is roasted and brewed as a coffee substitute.

References

  1. "allantoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 27 June 2012.