Uric acid

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
3D model (JSmol)
3DMet
156158
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.655 Edit this at Wikidata
EC Number
  • 200-720-7
KEGG
MeSH Uric+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) ☒N
    Key: DZGSAURIFGGOJK-UHFFFAOYSA-N ☒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
C5H4N4O3
Molar mass 168.112 g·mol−1
Appearance White crystals
Melting point 300 °C (572 °F; 573 K)
6 mg/100 mL (at 20 °C)
log P −1.107
Acidity (pKa) 5.6
Basicity (pKb) 8.4
−6.62×10−5 cm3 mol−1
Thermochemistry
166.15 J K−1 mol−1 (at 24.0 °C)
173.2 J K−1 mol−1
−619.69 to −617.93 kJ mol−1
−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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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.[1] 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.