1.0 2010-04-08 22:07:38 UTC 2025-11-18 23:04:54 UTC FDB007481 5-Hydroxyuracil 5-hydroxyuracil, also known as dihydropyrimidine-2,4,5(3h)-trione or isobarbituric acid, is a member of the class of compounds known as hydroxypyrimidines. Hydroxypyrimidines are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5-hydroxyuracil is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxyuracil can be found in broad bean, which makes 5-hydroxyuracil a potential biomarker for the consumption of this food product. 5-hydroxyuracil is an oxidized form of cytosine that is produced by the oxidative deamination of cytosines by reactive oxygen species. It does not distort the DNA molecule and is bypassed by replicative DNA polymerases. It can miscode for adenine and is potentially mutagenic . 2,4,5-Trihydroxypyrimidine 2,4,5(3H)-Pyrimidinetrione, dihydro- 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy- 5-Hydroxyazouracil 5-hydroxypyrimidine-2,4(1H,3H)-dione Dihydropyrimidine-2,4,5(3H)-trione Isobarbituric acid Isobarbituric acid (van) Pyrimidine-2,4,5-triol C4H4N2O3 128.0862 128.022192004 5-hydroxy-1,2,3,4-tetrahydropyrimidine-2,4-dione 5-hydroxyuracil 496-76-4 OC1=CNC(=O)NC1=O InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9) OFJNVANOCZHTMW-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Hydroxypyrimidines Organic compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Polyols Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Polyol hydroxypyrimidine logp -1.41 ALOGPS logs -1.17 ALOGPS solubility 8.73e+00 g/l ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 8.8 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 5-hydroxy-1,2,3,4-tetrahydropyrimidine-2,4-dione ChemAxon average_mass 128.0862 ChemAxon mono_mass 128.022192004 ChemAxon smiles OC1=CNC(=O)NC1=O ChemAxon formula C4H4N2O3 ChemAxon inchi InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9) ChemAxon inchikey OFJNVANOCZHTMW-UHFFFAOYSA-N ChemAxon polar_surface_area 78.43 ChemAxon refractivity 27.94 ChemAxon polarizability 10.27 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 44466 Specdb::MsMs 44467 Specdb::MsMs 44468 Specdb::MsMs 170427 Specdb::MsMs 170428 Specdb::MsMs 170429 Specdb::MsMs 3604058 Specdb::MsMs 3604059 Specdb::MsMs 3604060 Specdb::MsMs 3604061 Specdb::MsMs 3604062 Specdb::MsMs 3604063 29115 Broad bean Type 1 specific Vicia faba 3906