1.0 2011-09-21 00:19:19 UTC 2015-07-21 06:57:21 UTC FDB022770 3-Methyluric acid 3-Methyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3-Methyluracil is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152) [HMDB] 3-Methyl-2,6,8-trioxopurine 3-Methyl-7,9-dihydro-3H-purine-2,6,8-trione 3-Methylate 3-Methylic acid 3-Methylurate 4,9-Dihydro-3-methyl-1H-purine-2,6,8(3H)-trione C6H6N4O3 182.1368 182.043990078 3-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione 3-methyluric acid 605-99-2 CN1C2=C(NC(=O)N2)C(=O)NC1=O InChI=1S/C6H6N4O3/c1-10-3-2(7-5(12)8-3)4(11)9-6(10)13/h1H3,(H2,7,8,12)(H,9,11,13) ODCYDGXXCHTFIR-UHFFFAOYSA-N belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Xanthines Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Aromatic heteropolycyclic compounds 6-oxopurines Alkaloids and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Imidazoles Lactams Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Pyrimidones Ureas Vinylogous amides 6-oxopurine Alkaloid or derivatives Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Imidazole Lactam Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Purinone Pyrimidine Pyrimidone Urea Vinylogous amide Xanthine a small molecule Solid logp -1.04 ALOGPS logs -1.68 ALOGPS solubility 3.79e+00 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 7.66 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 3-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione ChemAxon average_mass 182.1368 ChemAxon mono_mass 182.043990078 ChemAxon smiles CN1C2=C(NC(=O)N2)C(=O)NC1=O ChemAxon formula C6H6N4O3 ChemAxon inchi InChI=1S/C6H6N4O3/c1-10-3-2(7-5(12)8-3)4(11)9-6(10)13/h1H3,(H2,7,8,12)(H,9,11,13) ChemAxon inchikey ODCYDGXXCHTFIR-UHFFFAOYSA-N ChemAxon polar_surface_area 90.54 ChemAxon refractivity 50.53 ChemAxon polarizability 15.62 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 1493 Specdb::MsIr 1494 Specdb::MsIr 1495 Specdb::NmrOneD 102798 Specdb::NmrOneD 102799 Specdb::NmrOneD 102800 Specdb::NmrOneD 102801 Specdb::NmrOneD 102802 Specdb::NmrOneD 102803 Specdb::NmrOneD 102804 Specdb::NmrOneD 102805 Specdb::NmrOneD 102806 Specdb::NmrOneD 102807 Specdb::NmrOneD 102808 Specdb::NmrOneD 102809 Specdb::NmrOneD 102810 Specdb::NmrOneD 102811 Specdb::NmrOneD 102812 Specdb::NmrOneD 102813 Specdb::NmrOneD 102814 Specdb::NmrOneD 102815 Specdb::NmrOneD 102816 Specdb::NmrOneD 102817 Specdb::CMs 15950 Specdb::CMs 130656 Specdb::CMs 138390 Specdb::MsMs 62577 Specdb::MsMs 62578 Specdb::MsMs 62579 Specdb::MsMs 119328 Specdb::MsMs 119329 Specdb::MsMs 119330 Specdb::MsMs 2252729 Specdb::MsMs 2253739 Specdb::MsMs 2254839 Specdb::MsMs 2255749 Specdb::MsMs 2256893 Specdb::MsMs 2257687 Specdb::MsMs 2258867 Specdb::MsMs 2259719 Specdb::MsMs 2332823 Specdb::MsMs 2332824 Specdb::MsMs 2332825 Specdb::MsMs 2633297 Specdb::MsMs 2633298 Specdb::MsMs 2633299 HMDB01970 #<Reference:0x000055ce304c6d60> #<Reference:0x000055ce304c6b58> #<Reference:0x000055ce304c69a0> #<Reference:0x000055ce304c67e8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823