1.0 2011-09-21 00:35:05 UTC 2015-07-21 06:57:53 UTC FDB023813 8-Hydroxy-7-methylguanine 8-Hydroxy-7-methylguanine is a modified nucleoside. 8-Hydroxy-7-methylguanine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls. Human exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair; the N2 position of guanine is one of the major sites for DNA modification by various carcinogens. Measurements of RNA or DNA catabolites in urine can be used as a measure for the metabolism of each of the three major species of RNA. An accumulation of modified ribonucleosides appears in the serum of uremic patients. (PMID: 3506820, 5961889, 16527824, 16061253, 8043914, 2428556, 7159514, 9607216) [HMDB] 8-hydroxy-7-methylguanine C6H7N5O2 181.1521 181.059974493 2-amino-7-methyl-6,7,8,9-tetrahydro-3H-purine-6,8-dione 2-amino-7-methyl-3,9-dihydropurine-6,8-dione 1688-85-3 CN1C(=O)NC2=C1C(=O)N=C(N)N2 InChI=1S/C6H7N5O2/c1-11-2-3(9-6(11)13)8-5(7)10-4(2)12/h1H3,(H4,7,8,9,10,12,13) VHPXSVXJBWZORQ-UHFFFAOYSA-N belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Hypoxanthines Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Aromatic heteropolycyclic compounds 6-oxopurines Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives N-substituted imidazoles Organic oxides Organooxygen compounds Organopnictogen compounds Primary amines Pyrimidones Ureas Vinylogous amides 6-oxopurine Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Pyrimidine Pyrimidone Urea Vinylogous amide 2-aminopurines oxopurine Solid logp -1.15 ALOGPS logs -1.78 ALOGPS solubility 3.03e+00 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 8.17 ChemAxon pka_strongest_basic 0.51 ChemAxon iupac 2-amino-7-methyl-6,7,8,9-tetrahydro-3H-purine-6,8-dione ChemAxon average_mass 181.1521 ChemAxon mono_mass 181.059974493 ChemAxon smiles CN1C(=O)NC2=C1C(=O)N=C(N)N2 ChemAxon formula C6H7N5O2 ChemAxon inchi InChI=1S/C6H7N5O2/c1-11-2-3(9-6(11)13)8-5(7)10-4(2)12/h1H3,(H4,7,8,9,10,12,13) ChemAxon inchikey VHPXSVXJBWZORQ-UHFFFAOYSA-N ChemAxon polar_surface_area 99.82 ChemAxon refractivity 52.5 ChemAxon polarizability 16.29 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2347 Specdb::MsIr 2348 Specdb::MsIr 2349 Specdb::CMs 11431 Specdb::CMs 158548 Specdb::MsMs 107649 Specdb::MsMs 107650 Specdb::MsMs 107651 Specdb::MsMs 174669 Specdb::MsMs 174670 Specdb::MsMs 174671 Specdb::MsMs 2316647 Specdb::MsMs 2316648 Specdb::MsMs 2316649 Specdb::MsMs 2621888 Specdb::MsMs 2621889 Specdb::MsMs 2621890 Specdb::NmrOneD 61532 Specdb::NmrOneD 61533 Specdb::NmrOneD 61534 Specdb::NmrOneD 61535 Specdb::NmrOneD 61536 Specdb::NmrOneD 61537 Specdb::NmrOneD 61538 Specdb::NmrOneD 61539 Specdb::NmrOneD 61540 Specdb::NmrOneD 61541 Specdb::NmrOneD 61542 Specdb::NmrOneD 61543 Specdb::NmrOneD 61544 Specdb::NmrOneD 61545 Specdb::NmrOneD 61546 Specdb::NmrOneD 61547 Specdb::NmrOneD 61548 Specdb::NmrOneD 61549 Specdb::NmrOneD 61550 Specdb::NmrOneD 61551 HMDB06037 #<Reference:0x000055ce32c6baf0> #<Reference:0x000055ce32c6b910> #<Reference:0x000055ce32c6b708> #<Reference:0x000055ce32c6b488> #<Reference:0x000055ce32c6b258> #<Reference:0x000055ce32c6afb0> #<Reference:0x000055ce32c6ad30> #<Reference:0x000055ce32c6ab28> 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