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Uric acid information


Uric acid

Crystals of urate in polarized light
Names
Preferred IUPAC name
7,9-Dihydro-1H-purine-2,6,8(3H)-trione
Other names
2,6,8-Trioxypurine; 2,6,8-Trihydroxypurine; 2,6,8-Trioxopurine; 1H-Purine-2,6,8-trione
Identifiers
CAS Number
  • 69-93-2 checkY
3D model (JSmol)
  • lactam form: Interactive image
  • intermediate form: Interactive image
  • lactim form: Interactive image
  • urate monoanion: Interactive image
3DMet
  • B00094
Beilstein Reference
156158
ChEBI
  • CHEBI:27226 ☒N
ChEMBL
  • ChEMBL792 checkY
ChemSpider
  • 1142 checkY
DrugBank
  • DB01696 checkY
ECHA InfoCard 100.000.655 Edit this at Wikidata
EC Number
  • 200-720-7
IUPHAR/BPS
  • 4731
KEGG
  • C00366 ☒N
MeSH Uric+Acid
PubChem CID
  • 1175
UNII
  • 268B43MJ25 checkY
CompTox Dashboard (EPA)
  • DTXSID3042508 Edit this at Wikidata
InChI
  • InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h5,12H,(H,9,10)(H,7,8,11) ☒N
    Key: DZGSAURIFGGOJK-UHFFFAOYSA-N ☒N
SMILES
  • lactam form: O=C1Nc2nc(=O)nc2C(=O)N1
  • intermediate form: Oc0nc(O)nc1c0NC(=O)N1
  • lactim form: Oc0nc(O)nc1c0N=C(O)N1
  • urate monoanion: Oc0nc(O)nc1c0N=C([O-])N1
Properties
Chemical formula
C5H4N4O3
Molar mass 168.112 g·mol−1
Appearance White crystals
Melting point 300 °C (572 °F; 573 K)
Solubility in water
6 mg/100 mL (at 20 °C)
log P −1.107
Acidity (pKa) 5.6
Basicity (pKb) 8.4
Magnetic susceptibility (χ)
−6.62×10−5 cm3 mol−1
Thermochemistry
Heat capacity (C)
166.15 J K−1 mol−1 (at 24.0 °C)
Std molar
entropy (S298)
173.2 J K−1 mol−1
Std enthalpy of
formation fH298)
−619.69 to −617.93 kJ mol−1
Std enthalpy of
combustion cH298)
−1921.2 to −1919.56 kJ mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

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Uric acid

Last Update:

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...

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Gout

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and swollen joint, caused by the deposition of needle-like crystals of uric acid known as monosodium urate crystals. Pain typically comes on rapidly, reaching...

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Kidney stone disease

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uric acid. Serum uric acid level at or below 6 mg/100 mL is often a therapeutic goal. Hyperuricemia is not necessary for the formation of uric acid stones;...

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Hyperuricemia

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high level of uric acid in the blood. In the pH conditions of body fluid, uric acid exists largely as urate, the ion form. Serum uric acid concentrations...

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Acute uric acid nephropathy

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Acute uric acid nephropathy (AUAN, also acute urate nephropathy) is a rapidly worsening (decreasing) kidney function (acute kidney injury) that is caused...

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Nucleic acid metabolism

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which is then converted to uric acid. Oxygen is the final electron acceptor in the degradation of both purines. Uric acid is then excreted from the body...

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Dalmatian dog

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livers have trouble breaking down uric acid, which can build up in the blood serum (hyperuricemia) causing gout. Uric acid can also be excreted in high concentration...

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Barbituric acid

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a key), because Baeyer had regarded barbituric acid as central (or "key") to understanding uric acid and its derivatives. However, Fieser subsequently...

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Bempedoic acid

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hyperuricemia (high blood levels of uric acid), pain in arms or legs, and anemia (low red blood cell counts). Bempedoic acid blocks an enzyme in the liver called...

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Allantoin

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glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which...

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Antioxidant

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Uric acid has the highest concentration of any blood antioxidant and provides over half of the total antioxidant capacity of human serum. Uric acid's...

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Alloxan

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from allantoin, a product of uric acid excreted by the fetus into the allantois, and oxaluric acid derived from oxalic acid and urea, found in urine. Alloxan...

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Allopurinol

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high blood uric acid levels. It is specifically used to prevent gout, prevent specific types of kidney stones and for the high uric acid levels that...

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Urate oxidase

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hydroxylase, absent in humans, catalyzes the oxidation of uric acid to 5-hydroxyisourate: Uric acid + O2 + H2O → 5-hydroxyisourate + H2O2 5-hydroxyisourate...

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Organic acid

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organic acids. A few common examples include: Lactic acid Acetic acid Formic acid Citric acid Oxalic acid Uric acid Malic acid Tartaric acid Butyric acid Folic...

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Rasburicase

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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...

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Tumor lysis syndrome

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phosphate (hyperphosphatemia), low blood calcium (hypocalcemia), high blood uric acid (hyperuricemia), and higher than normal levels of blood urea nitrogen...

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Excretion

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produce waste products such as carbon dioxide, water, salts, urea and uric acid. Accumulation of these wastes beyond a level inside the body is harmful...

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Hyperuricosuria

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Hyperuricosuria is a medical term referring to the presence of excessive amounts of uric acid in the urine. For men this is at a rate greater than 800 mg/day, and for...

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Purine

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the reaction sequence was uric acid (8), which had been isolated from kidney stones by Carl Wilhelm Scheele in 1776. Uric acid (8) was reacted with PCl5...

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Uricosuric

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substances that increase the excretion of uric acid in the urine, thus reducing the concentration of uric acid in blood plasma. In general, this effect...

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Nucleotide

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xanthine and finally to uric acid. Instead of uric acid secretion, guanine and IMP can be used for recycling purposes and nucleic acid synthesis in the presence...

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Sucrose

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of uric acid in the body increases, so does the concentration of uric acid in the joint liquid and beyond a critical concentration, the uric acid begins...

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Rheumatism

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determine whether the body is producing too much uric acid or the body isn't excreting enough uric acid. Rheumatoid factor may be present, especially in...

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Protein toxicity

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effect of the buildup of protein metabolic waste compounds, like urea, uric acid, ammonia, and creatinine. Protein toxicity has many causes, including...

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Nephron

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acids, lactate, magnesium, calcium phosphate, uric acid, and bicarbonate. Substances secreted include urea, creatinine, potassium, hydrogen, and uric...

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Tophus

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monosodium urate crystals, in people with longstanding high levels of uric acid (urate) in the blood, a condition known as hyperuricemia. Tophi are pathognomonic...

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Bacillus fastidiosus

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Bacillus fastidiosus is only able to grow in the presence of uric acid, allantoin, or allantoic acid. This species has been recently transferred into the genus...

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