2.0 2012-05-31 14:35:05 -0600 2015-06-03 17:19:37 -0600 ECMDB20246 M2MDB001089 8-Hydroxydeoxyguanosine 5'-triphosphate 8-hydroxydeoxyguanosine 5'-triphosphate (8-hydroxy-dGTP) is a member of the chemical class known as Purine 2'-deoxyribonucleoside Triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking an hydroxyl group at position 2. Hydroxylated nucleotides can appear in DNA that has been oxidatively damaged. Escherichia coli Orf135 protein is thought to be an enzyme that efficiently hydrolyzes oxidatively damaged nucleotides such as 2-hydroxy-dATP, 8-hydroxy-dGTP and 5-hydroxy-CTP, in addition to 5-methyl-dCTP, dCTP and CTP, thus preventing mutations in cells caused by unfavorable base pairing. [PMID:21553121] 8-Hydroxydeoxyguanosine 5'-triphosphoric acid 8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT C10H12N5O14P3 519.1487 518.959359653 9-[4-hydroxy-5-({[hydroxy({[hydroxy(phosphonatooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purine-6,8-bis(olate) 9-{4-hydroxy-5-[({hydroxy[hydroxy(phosphonatooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl}-2-imino-3H-purine-6,8-bis(olate) OC1CC(OC1COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)N1C([O-])=NC2=C1NC(=N)N=C2[O-] InChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/p-4 BUZOGVVQWCXXDP-UHFFFAOYSA-J Cytoplasm Periplasm logp -0.75 ALOGPS logs -1.74 ALOGPS solubility 1.07e+01 g/l ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 0.9 ChemAxon pka_strongest_basic 5.36 ChemAxon iupac 9-[4-hydroxy-5-({[hydroxy({[hydroxy(phosphonatooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purine-6,8-bis(olate) ChemAxon average_mass 519.1487 ChemAxon mono_mass 518.959359653 ChemAxon smiles OC1CC(OC1COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)N1C([O-])=NC2=C1NC(=N)N=C2[O-] ChemAxon formula C10H12N5O14P3 ChemAxon inchi InChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/p-4 ChemAxon inchikey BUZOGVVQWCXXDP-UHFFFAOYSA-J ChemAxon polar_surface_area 307.12 ChemAxon refractivity 126.62 ChemAxon polarizability 38.15 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge -4 ChemAxon Specdb::NmrOneD 333658 Specdb::NmrOneD 333659 Specdb::NmrOneD 333660 Specdb::NmrOneD 333661 Specdb::NmrOneD 333662 Specdb::NmrOneD 333663 Specdb::NmrOneD 333664 Specdb::NmrOneD 333665 Specdb::NmrOneD 333666 Specdb::NmrOneD 333667 Specdb::NmrOneD 333668 Specdb::NmrOneD 333669 Specdb::NmrOneD 333670 Specdb::NmrOneD 333671 Specdb::NmrOneD 333672 Specdb::NmrOneD 333673 Specdb::NmrOneD 333674 Specdb::NmrOneD 333675 Specdb::NmrOneD 333676 Specdb::NmrOneD 333677 Specdb::MsMs 25679 Specdb::MsMs 25680 Specdb::MsMs 25681 Specdb::MsMs 32237 Specdb::MsMs 32238 Specdb::MsMs 32239 25201462 24784983 8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Kawasaki, K., Yoneyama, M., Murata-Kamiya, N., Harashima, H., Kojima, C., Ito, Y., Kamiya, H., Mishima, M. (2012). "(1)H, (1)(3)C and (1)(5)N NMR assignments of the Escherichia coli Orf135 protein." Biomol NMR Assign 6:1-4. 21553121 CTP pyrophosphohydrolase P77788 NUDG_ECOLI nudG http://ecmdb.ca/proteins/P77788.xml