1.02011-09-21 00:19:20 UTC2015-10-09 22:32:55 UTCFDB0227729-Methyluric acid9-Methyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 9-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]7,9-Dihydro-9-methyl-1H-purine-2,6,8(3H)-trione9-Methyl-2,6,8-trihydroxypurineMUAC6H6N4O3182.1368182.0439900789-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione9-methyl uric acid55441-71-9CN1C(=O)NC2=C1NC(=O)NC2=OInChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)XJEJWDFDVPDMAS-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.XanthinesOrganic compoundsOrganoheterocyclic compoundsImidazopyrimidinesPurines and purine derivativesAromatic heteropolycyclic compounds6-oxopurinesAlkaloids and derivativesAzacyclic compoundsHeteroaromatic compoundsHydrocarbon derivativesLactamsN-substituted imidazolesOrganic oxidesOrganonitrogen compoundsOrganooxygen compoundsOrganopnictogen compoundsPyrimidonesUreasVinylogous amides6-oxopurineAlkaloid or derivativesAromatic heteropolycyclic compoundAzacycleAzoleHeteroaromatic compoundHydrocarbon derivativeImidazoleLactamN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPurinonePyrimidinePyrimidoneUreaVinylogous amideXanthineSolidlogp-1.05logs-1.70solubility3.60e+00 g/llogp-1.3pka_strongest_acidic7.25pka_strongest_basic-6.2iupac9-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneaverage_mass182.1368mono_mass182.043990078smilesCN1C(=O)NC2=C1NC(=O)NC2=OformulaC6H6N4O3inchiInChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)inchikeyXJEJWDFDVPDMAS-UHFFFAOYSA-Npolar_surface_area90.54refractivity50.53polarizability15.67rotatable_bond_count0acceptor_count3donor_count3physiological_charge0formal_charge0Specdb::CMs8638Specdb::CMs131881Specdb::CMs139615Specdb::NmrTwoD1766Specdb::MsIr1499Specdb::MsIr1500Specdb::MsIr1501Specdb::NmrOneD1826Specdb::NmrOneD102838Specdb::NmrOneD102839Specdb::NmrOneD102840Specdb::NmrOneD102841Specdb::NmrOneD102842Specdb::NmrOneD102843Specdb::NmrOneD102844Specdb::NmrOneD102845Specdb::NmrOneD102846Specdb::NmrOneD102847Specdb::NmrOneD102848Specdb::NmrOneD102849Specdb::NmrOneD102850Specdb::NmrOneD102851Specdb::NmrOneD102852Specdb::NmrOneD102853Specdb::NmrOneD102854Specdb::NmrOneD102855Specdb::NmrOneD102856Specdb::NmrOneD102857Specdb::MsMs1917Specdb::MsMs1918Specdb::MsMs1919Specdb::MsMs260838Specdb::MsMs260839Specdb::MsMs260840Specdb::MsMs280773Specdb::MsMs280774Specdb::MsMs280775Specdb::MsMs3039206Specdb::MsMs3039207Specdb::MsMs3039208Specdb::MsMs3101783Specdb::MsMs3101784Specdb::MsMs3101785HMDB01973MUA#<Reference:0x00005556745e88d0>#<Reference:0x00005556745e86a0>#<Reference:0x00005556745e84e8>#<Reference:0x00005556745e82e0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823