1.0 2016-09-30 22:49:40 UTC 2020-05-11 20:22:59 UTC BMDB0001991 BMDB01991 7-Methylxanthine 7-Methylxanthine, also known as 7-methylxanthine, 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. 7-Methylxanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 7-Methylxanthine exists in all living organisms, ranging from bacteria to humans. 7-Methylxanthine participates in a number of enzymatic reactions, within cattle. In particular, 7-Methylxanthine and formaldehyde can be biosynthesized from paraxanthine; which is catalyzed by the enzyme cytochrome P450 1A2. In addition, 7-Methylxanthine can be converted into 7-methyluric acid; which is mediated by the enzyme xanthine dehydrogenase/oxidase. In cattle, 7-methylxanthineee is involved in the metabolic pathway called the caffeine metabolism pathway. 3,7-Dihydro-7-methyl-1H-purine-2,6-dione 7-Methylxanthin Heteroxanthin Heteroxanthine 7-Methylxanthine, 7-(13)C-labeled 2,6-Dihydroxy-7-methylpurine 7-Methyl-3,7-dihydro-1H-purine-2,6-dione 7-Methyl-7H-purine-2,6-diol Methylxanthine C6H6N4O2 166.1374 166.049075456 7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione 7-methylxanthine 552-62-5 CN1C=NC2=C1C(=O)NC(=O)N2 InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12) PFWLFWPASULGAN-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 Alkaloids and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyrimidines N-substituted imidazoles Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Alkaloid or derivatives Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Imidazole N-substituted imidazole Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrimidine Xanthine Aromatic heteropolycyclic compounds Purine alkaloids a small molecule oxopurine purine alkaloid Solid melting_point > 300 °C logp -0.89 GASPARI,F & BONATI,M (1987) logp -0.59 ALOGPS logs -1.38 ALOGPS logp 0.017 ChemAxon pka_strongest_acidic 9.31 ChemAxon pka_strongest_basic -0.85 ChemAxon iupac 7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione ChemAxon average_mass 166.1374 ChemAxon mono_mass 166.049075456 ChemAxon smiles CN1C=NC2=C1C(=O)NC(=O)N2 ChemAxon formula C6H6N4O2 ChemAxon inchi InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12) ChemAxon inchikey PFWLFWPASULGAN-UHFFFAOYSA-N ChemAxon polar_surface_area 76.02 ChemAxon refractivity 41.82 ChemAxon polarizability 14.77 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 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 Caffeine Metabolism SMP0087186 Specdb::NmrTwoD 1770 Specdb::CMs 22836 Specdb::CMs 156970 Specdb::MsIr 1514 Specdb::MsIr 1515 Specdb::MsIr 1516 Specdb::NmrOneD 1830 Specdb::NmrOneD 102958 Specdb::NmrOneD 102959 Specdb::NmrOneD 102960 Specdb::NmrOneD 102961 Specdb::NmrOneD 102962 Specdb::NmrOneD 102963 Specdb::NmrOneD 102964 Specdb::NmrOneD 102965 Specdb::NmrOneD 102966 Specdb::NmrOneD 102967 Specdb::NmrOneD 102968 Specdb::NmrOneD 102969 Specdb::NmrOneD 102970 Specdb::NmrOneD 102971 Specdb::NmrOneD 102972 Specdb::NmrOneD 102973 Specdb::NmrOneD 102974 Specdb::NmrOneD 102975 Specdb::NmrOneD 102976 Specdb::NmrOneD 102977 Specdb::NmrOneD 166628 Specdb::MsMs 1932 Specdb::MsMs 1933 Specdb::MsMs 1934 Specdb::MsMs 316681 Specdb::MsMs 316682 Specdb::MsMs 316683 Specdb::MsMs 363001 Specdb::MsMs 363002 Specdb::MsMs 363003 Specdb::MsMs 1470919 Specdb::MsMs 1470920 Specdb::MsMs 1470921 Specdb::MsMs 1471427 Specdb::MsMs 1473842 Specdb::MsMs 1473843 Specdb::MsMs 1473844 Specdb::MsMs 1473845 Specdb::MsMs 1473846 Specdb::MsMs 1473847 Specdb::MsMs 1473848 Specdb::MsMs 1473849 Specdb::MsMs 1473850 Specdb::MsMs 1473851 Specdb::MsMs 1473852 Specdb::MsMs 1477318 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 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 FDB001978 61660 68374 C16353 48991 C00007326 7-METHYLXANTHINE Xanthine Hutzenlaub, Wolfgang; Pfleiderer, Wolfgang. Purines. XIII. Simplified syntheses of 7-methyl- and 1,7-dimethylxanthines and -uric acids. Liebigs Annalen der Chemie (1979), (11), 1847-54.