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Topic summary

Uric acid

Uric acid
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
3D model (JSmol)
156158 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.655EC Number
  • 200-720-7
KEGG
MeSHUric+Acid
UNII
  • 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)
    Key: DZGSAURIFGGOJK-UHFFFAOYSA-N
  • 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 C5H4N4O3Molar mass168.112 g·mol Appearance White crystals Melting point300 °C (572 °F; 573 K) 6 mg/100 mL (at 20 °C) log P−1.107 Acidity (pKa) 5.6 Basicity (pKb) 8.4 −6.62×10 cm molThermochemistry 166.15 J K mol (at 24.0 °C) 173.2 J K mol −619.69 to −617.93 kJ mol −1921.2 to −1919.56 kJ mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 purinenucleotides, 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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