1.0 2016-09-30 22:27:52 UTC 2020-06-04 20:51:39 UTC BMDB0000289 BMDB00289 Uric acid Uric acid, also known as urate or acid, uric, 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. Uric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uric acid exists in all living species, ranging from bacteria to humans. Uric acid is a potentially toxic compound. Uric acid has been found to be associated with several diseases known as fanconi syndrome, impaired glucose tolerance, and d-lactic acidosis; also uric acid has been linked to several inborn metabolic disorders including atic deficiency and lesch-nyhan syndrome. 2,6,8-Trioxopurine 2,6,8-Trioxypurine Purine-2,6,8(1H,3H,9H)-trione Urate 1H-Purine-2,6,8-triol 2,6,8-Trihydroxypurine Lithate Lithic acid Acid urate, ammonium Ammonium acid urate Monohydrate, sodium urate Urate, ammonium acid Urate, monosodium Acid, uric Monosodium urate monohydrate Sodium acid urate Sodium urate Trioxopurine Urate, sodium acid Monohydrate, monosodium urate Monosodium urate Potassium urate Sodium acid urate monohydrate Urate monohydrate, sodium Acid urate, sodium Sodium urate monohydrate Urate monohydrate, monosodium Urate, potassium Urate, sodium C5H4N4O3 168.1103 168.028340014 2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione uric acid 69-93-2 O=C1NC2=C(N1)C(=O)NC(=O)N2 InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12) LEHOTFFKMJEONL-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. Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Xanthines 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 Aromatic heteropolycyclic compounds uric acid Solid melting_point > 300 °C water_solubility 0.06 mg/mL logp -2.17 NAHUM,A & HORVATH,C (1980) logp -1.12 ALOGPS logs -1.98 ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 7.25 ChemAxon pka_strongest_basic -6.5 ChemAxon iupac 2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione ChemAxon average_mass 168.1103 ChemAxon mono_mass 168.028340014 ChemAxon smiles O=C1NC2=C(N1)C(=O)NC(=O)N2 ChemAxon formula C5H4N4O3 ChemAxon inchi InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12) ChemAxon inchikey LEHOTFFKMJEONL-UHFFFAOYSA-N ChemAxon polar_surface_area 99.33 ChemAxon refractivity 45.63 ChemAxon polarizability 13.61 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Purine Metabolism SMP0087239 Specdb::MsIr 378 Specdb::MsIr 379 Specdb::MsIr 380 Specdb::NmrOneD 5049 Specdb::NmrOneD 326072 Specdb::NmrOneD 326073 Specdb::NmrOneD 326074 Specdb::NmrOneD 326075 Specdb::NmrOneD 326076 Specdb::NmrOneD 326077 Specdb::NmrOneD 326078 Specdb::NmrOneD 326079 Specdb::NmrOneD 326080 Specdb::NmrOneD 326081 Specdb::EiMs 1045 Specdb::CMs 521 Specdb::CMs 1798 Specdb::CMs 1827 Specdb::CMs 3199 Specdb::CMs 30708 Specdb::CMs 31115 Specdb::CMs 31116 Specdb::CMs 31919 Specdb::CMs 137909 Specdb::CMs 145643 Specdb::MsMs 489 Specdb::MsMs 490 Specdb::MsMs 491 Specdb::MsMs 21341 Specdb::MsMs 21342 Specdb::MsMs 21343 Specdb::MsMs 22892 Specdb::MsMs 22893 Specdb::MsMs 22894 Specdb::MsMs 440020 Specdb::MsMs 447345 Specdb::MsMs 2239914 Specdb::MsMs 2241783 Specdb::MsMs 2244113 Specdb::MsMs 2244370 Specdb::MsMs 2245751 Specdb::MsMs 2245995 Specdb::MsMs 2246210 Specdb::MsMs 2247814 Specdb::MsMs 2248059 Specdb::MsMs 2248203 Specdb::MsMs 2250186 Specdb::MsMs 2250226 Specdb::MsMs 2252163 Specdb::MsMs 2308149 Adipose Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Bladder Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Blood 91.0117-191.541 uM Detected by procedure of Folin and Wu (1919) Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348 doi: 10.3168/jds.S0022-0302(30)93530-8 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Erythrocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 53.536 - 142.764 uM Whole milk Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22. 15084094 Milk 199.3 uM Raw whole milk Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. 6539345 Milk 56.200 +/- 12.300 uM Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0. 7962859 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk 122.539 +/- 0.595 uM Carbohydrate Polymers 37 (1998) 225-229 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was identified by probable match parameters of the NIST Mass Spectral Search Program Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Spleen Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00366 DB08844 FDB015350 1142 1175 17775 C00007301 URATE Uric_acid 34768 88 Brenner-Holzach, O.; Leuthardt, F. Uric acid formation from glucose carbon in Drosophila melanogaster. Preliminary report. Helvetica Chimica Acta (1963), 46(4), 1426-8. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. 6539345 Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0. 7962859 Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22. 15084094 Carbohydrate Polymers 37 (1998) 225-229 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 BMDBP00603 Xanthine dehydrogenase/oxidase P80457 XDH Enzyme BMDBP01253 Uricase Q3MHG7 UOX Enzyme