1.0 2011-09-21 01:38:21 UTC 2015-07-21 06:59:23 UTC FDB028348 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine 2,6-Diamino-4-hydroxy-5-N-methylformamidopyrimidine is a methylated derivative of 2,6-Diamino-4-hydroxy-5-N-formamidopyrimidine or FapyGua. It is produced by DNA-formamidopyrimidine glycosylase (EC 3.2.2.23). This enzyme catalyzes the hydrolysis of DNA containing ring-opened 7-methylguanine residues, releasing 2,6-diamino-4-hydroxy-5-(N-methyl)formamidopyrimidine. More specifically, this enzyme catalyzes the removal of oxidized purine bases by cleaving the N-C1' glycosidic bond between the oxidized purine and the deoxyribose sugar. The reaction involves the formation of a covalent enzyme substrate intermediate. Release of the enzyme and free base by a beta-elimination or a beta, gamma-elimination mechanism results in the cleavage of the DNA backbone 3' of the apurinic (AP) site. The presence of this compound in urine is indicative of oxidative damage to DNA (oxidized purine base lesions) [HMDB] 2,6-diamino-4-hydroxy- 5- formamidopyrimidine 2,6-Diamino-4-hydroxy-5-(N-methyl)formamidopyrimidine Me-FapyGua N-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)-N-methyl-Formamide N5-Methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine C6H9N5O2 183.168 183.075624557 N-(2,4-diamino-6-hydroxypyrimidin-5-yl)-N-methylformamide N-(2,4-diamino-6-hydroxypyrimidin-5-yl)-N-methylformamide 77440-13-2 CN(C=O)C1=C(N)N=C(N)N=C1O InChI=1S/C6H9N5O2/c1-11(2-12)3-4(7)9-6(8)10-5(3)13/h2H,1H3,(H5,7,8,9,10,13) CGWDNAFNQOBSCK-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Hydroxypyrimidines Organic compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Aromatic heteromonocyclic compounds Amino acids and derivatives Aminopyrimidines and derivatives Azacyclic compounds Carbonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Organic oxides Organopnictogen compounds Primary amines Tertiary carboxylic acid amides Amine Amino acid or derivatives Aminopyrimidine Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Hydroxypyrimidine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Tertiary carboxylic acid amide aminopyrimidine formamidopyrimidine hydroxypyrimidine Solid logp -0.76 ALOGPS logs -1.05 ALOGPS solubility 1.63e+01 g/l ALOGPS logp -0.99 ChemAxon pka_strongest_acidic 11.96 ChemAxon pka_strongest_basic 2.86 ChemAxon iupac N-(2,4-diamino-6-hydroxypyrimidin-5-yl)-N-methylformamide ChemAxon average_mass 183.168 ChemAxon mono_mass 183.075624557 ChemAxon smiles CN(C=O)C1=C(N)N=C(N)N=C1O ChemAxon formula C6H9N5O2 ChemAxon inchi InChI=1S/C6H9N5O2/c1-11(2-12)3-4(7)9-6(8)10-5(3)13/h2H,1H3,(H5,7,8,9,10,13) ChemAxon inchikey CGWDNAFNQOBSCK-UHFFFAOYSA-N ChemAxon polar_surface_area 118.36 ChemAxon refractivity 48.17 ChemAxon polarizability 16.81 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2559 Specdb::MsIr 2560 Specdb::MsIr 2561 Specdb::CMs 14974 Specdb::CMs 39747 Specdb::CMs 132876 Specdb::CMs 140610 Specdb::MsMs 299161 Specdb::MsMs 299162 Specdb::MsMs 299163 Specdb::MsMs 341089 Specdb::MsMs 341090 Specdb::MsMs 341091 Specdb::MsMs 2299839 Specdb::MsMs 2299840 Specdb::MsMs 2299841 Specdb::MsMs 2638726 Specdb::MsMs 2638727 Specdb::MsMs 2638728 Specdb::NmrOneD 93872 Specdb::NmrOneD 93873 Specdb::NmrOneD 93874 Specdb::NmrOneD 93875 Specdb::NmrOneD 93876 Specdb::NmrOneD 93877 Specdb::NmrOneD 93878 Specdb::NmrOneD 93879 Specdb::NmrOneD 93880 Specdb::NmrOneD 93881 Specdb::NmrOneD 93882 Specdb::NmrOneD 93883 Specdb::NmrOneD 93884 Specdb::NmrOneD 93885 Specdb::NmrOneD 93886 Specdb::NmrOneD 93887 Specdb::NmrOneD 93888 Specdb::NmrOneD 93889 Specdb::NmrOneD 93890 Specdb::NmrOneD 93891 HMDB11657 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