2.0 2012-05-31 09:56:57 -0600 2015-09-13 12:56:06 -0600 ECMDB00085 M2MDB000031 Deoxyguanosine Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. It is like guanosine, but with one oxygen atom removed. It is a nucleoside component of DNA. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-OHdG is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. 2'-Deoxy-Guanosine 2'-Deoxyguanosine 2-Deoxyguanosine 9-(2-deoxy-b-D-erythro-pentofuranosyl)-Guanine 9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)-guanine 9-(2-Deoxy-b-delta-erythro-pentofuranosyl)guanine 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)-guanine 9-(2-Deoxy-b-δ-erythro-pentofuranosyl)guanine 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-Guanine 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)guanine 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-Guanine 9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine 9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)-guanine 9-(2-Deoxy-β-δ-erythro-pentofuranosyl)guanine Deoxyguanosine Desoxyguanosine DGuanosine Guanine deoxy nucleoside Guanine deoxyriboside C10H13N5O4 267.2413 267.096753929 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one 2-deoxyguanosine 961-07-9 NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1 InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1 YKBGVTZYEHREMT-KVQBGUIXSA-N Solid Cytosol Extra-organism Periplasm logp -1.75 ALOGPS logs -1.37 ALOGPS solubility 1.15e+01 g/l ALOGPS melting_point 300 oC logp -1.8 ChemAxon pka_strongest_acidic 10.16 ChemAxon pka_strongest_basic 0.46 ChemAxon iupac 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one ChemAxon average_mass 267.2413 ChemAxon mono_mass 267.096753929 ChemAxon smiles NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1 ChemAxon formula C10H13N5O4 ChemAxon inchi InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1 ChemAxon inchikey YKBGVTZYEHREMT-KVQBGUIXSA-N ChemAxon polar_surface_area 134.99 ChemAxon refractivity 63.11 ChemAxon polarizability 25.24 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 purine deoxyribonucleosides degradation PW002077 Metabolic purine deoxyribonucleosides degradation PWY0-1297 Specdb::CMs 316 Specdb::CMs 2119 Specdb::CMs 2122 Specdb::CMs 2656 Specdb::CMs 30422 Specdb::CMs 30989 Specdb::CMs 30990 Specdb::CMs 37286 Specdb::CMs 168402 Specdb::CMs 1049758 Specdb::CMs 1049760 Specdb::CMs 1049762 Specdb::CMs 1049764 Specdb::CMs 1049766 Specdb::CMs 1049768 Specdb::CMs 1049770 Specdb::CMs 1049772 Specdb::CMs 1049774 Specdb::CMs 1049775 Specdb::CMs 1049777 Specdb::CMs 1049779 Specdb::CMs 1049781 Specdb::CMs 1049783 Specdb::CMs 1049785 Specdb::CMs 1049787 Specdb::NmrOneD 1075 Specdb::NmrOneD 4902 Specdb::NmrOneD 5652 Specdb::NmrOneD 5653 Specdb::NmrOneD 5654 Specdb::NmrOneD 5655 Specdb::NmrOneD 5656 Specdb::NmrOneD 5657 Specdb::NmrOneD 5658 Specdb::NmrOneD 5659 Specdb::NmrOneD 5660 Specdb::NmrOneD 5661 Specdb::NmrOneD 5662 Specdb::NmrOneD 5663 Specdb::NmrOneD 5664 Specdb::NmrOneD 5665 Specdb::NmrOneD 5666 Specdb::NmrOneD 5667 Specdb::NmrOneD 5668 Specdb::NmrOneD 5669 Specdb::NmrOneD 5670 Specdb::NmrOneD 5671 Specdb::MsMs 135 Specdb::MsMs 136 Specdb::MsMs 137 Specdb::MsMs 2795 Specdb::MsMs 2796 Specdb::MsMs 2797 Specdb::MsMs 2798 Specdb::MsMs 2799 Specdb::MsMs 2800 Specdb::MsMs 2801 Specdb::MsMs 2802 Specdb::MsMs 2803 Specdb::MsMs 2804 Specdb::MsMs 2805 Specdb::MsMs 2806 Specdb::MsMs 178617 Specdb::MsMs 178618 Specdb::MsMs 178619 Specdb::MsMs 180936 Specdb::MsMs 180937 Specdb::MsMs 180938 Specdb::MsMs 437559 Specdb::MsMs 437560 Specdb::MsMs 437561 Specdb::MsMs 437562 Specdb::NmrTwoD 951 Specdb::NmrTwoD 1133 HMDB00085 187790 163230 C00330 17172 DEOXYGUANOSINE GNG Deoxyguanosine 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 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gao K, Henning SM, Niu Y, Youssefian AA, Seeram NP, Xu A, Heber D: The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells. J Nutr Biochem. 2006 Feb;17(2):89-95. Epub 2005 Jun 20. 16111881 Podmore K, Farmer PB, Herbert KE, Jones GD, Martin EA: 32P-postlabelling approaches for the detection of 8-oxo-2'-deoxyguanosine-3'-monophosphate in DNA. Mutat Res. 1997 Aug 1;378(1-2):139-49. 9288892 Shibata T, Iio K, Kawai Y, Shibata N, Kawaguchi M, Toi S, Kobayashi M, Kobayashi M, Yamamoto K, Uchida K: Identification of a lipid peroxidation product as a potential trigger of the p53 pathway. J Biol Chem. 2006 Jan 13;281(2):1196-204. Epub 2005 Oct 26. 16251187 Gackowski D, Ciecierski M, Jawien A, Olinski R: Background level of 8-oxo-2'-deoxyguanosine in lymphocyte DNA does not correlate with the concentration of antioxidant vitamins in blood plasma. Acta Biochim Pol. 2001;48(2):535-9. 11732622 Takamura-Enya T, Watanabe M, Totsuka Y, Kanazawa T, Matsushima-Hibiya Y, Koyama K, Sugimura T, Wakabayashi K: Mono(ADP-ribosyl)ation of 2'-deoxyguanosine residue in DNA by an apoptosis-inducing protein, pierisin-1, from cabbage butterfly. Proc Natl Acad Sci U S A. 2001 Oct 23;98(22):12414-9. Epub 2001 Oct 9. 11592983 Palozza P, Serini S, Di Nicuolo F, Boninsegna A, Torsello A, Maggiano N, Ranelletti FO, Wolf FI, Calviello G, Cittadini A: beta-Carotene exacerbates DNA oxidative damage and modifies p53-related pathways of cell proliferation and apoptosis in cultured cells exposed to tobacco smoke condensate. Carcinogenesis. 2004 Aug;25(8):1315-25. Epub 2004 Apr 8. 15073048 Zaidi SN, Laidlaw I, Howell A, Potten CS, Cooper DP, O'Connor PJ: Normal human breast xenografts activate N-nitrosodimethylamine: identification of potential target cells for an environmental nitrosamine. Br J Cancer. 1992 Jul;66(1):79-83. 1637681 Gackowski D, Banaszkiewicz Z, Rozalski R, Jawien A, Olinski R: Persistent oxidative stress in colorectal carcinoma patients. Int J Cancer. 2002 Oct 1;101(4):395-7. 12209966 Araki S, Hayashi M, Tamagawa K, Saito M, Kato S, Komori T, Sakakihara Y, Mizutani T, Oda M: Neuropathological analysis in spinal muscular atrophy type II. Acta Neuropathol (Berl). 2003 Nov;106(5):441-8. Epub 2003 Jul 25. 12898156 Kato I, Ren J, Heilbrun LK, Djuric Z: Intra- and inter-individual variability in measurements of biomarkers for oxidative damage in vivo: Nutrition and Breast Health Study. Biomarkers. 2006 Mar-Apr;11(2):143-52. 16766390 Izzedine H, Launay-Vacher V, Aymard G, Legrand M, Deray G: Pharmacokinetics of abacavir in HIV-1-infected patients with impaired renal function. Nephron. 2001 Sep;89(1):62-7. 11528234 Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. 10102915 Bowen P, Chen L, Stacewicz-Sapuntzakis M, Duncan C, Sharifi R, Ghosh L, Kim HS, Christov-Tzelkov K, van Breemen R: Tomato sauce supplementation and prostate cancer: lycopene accumulation and modulation of biomarkers of carcinogenesis. Exp Biol Med (Maywood). 2002 Nov;227(10):886-93. 12424330 Staal GE, Stoop JW, Zegers BJ, Siegenbeek van Heukelom LH, van der Vlist MJ, Wadman SK, Martin DW: Erythrocyte metabolism in purine nucleoside phosphorylase deficiency after enzyme replacement therapy by infusion of erythrocytes. J Clin Invest. 1980 Jan;65(1):103-8. 6765955 Blair IA: Lipid hydroperoxide-mediated DNA damage. Exp Gerontol. 2001 Sep;36(9):1473-81. 11525870 Schramm VL: Development of transition state analogues of purine nucleoside phosphorylase as anti-T-cell agents. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):107-17. 12084452 Schilderman PA, Rhijnsburger E, Zwingmann I, Kleinjans JC: Induction of oxidative DNA damages and enhancement of cell proliferation in human lymphocytes in vitro by butylated hydroxyanisole. Carcinogenesis. 1995 Mar;16(3):507-12. 7697806 Kaneko T, Tahara S: Formation of 8-oxo-2'-deoxyguanosine in the DNA of human diploid fibroblasts by treatment with linoleic acid hydroperoxide and ferric ion. Lipids. 2000 Sep;35(9):961-5. 11026616 Hou SM, Nori P, Fang JL, Vaca CE: Methylglyoxal induces hprt mutation and DNA adducts in human T-lymphocytes in vitro. Environ Mol Mutagen. 1995;26(4):286-91. 8575417 Bialkowski K, Kowara R, Windorbska W, Olinski R: 8-Oxo-2'-deoxyguanosine level in lymphocytes DNA of cancer patients undergoing radiotherapy. Cancer Lett. 1996 Jan 19;99(1):93-7. 8564935 Noguchi, Toshitada; Hamamoto, Tomoki; Okuyama, Kiyoshi; Shibuya, Susumu. Process for producing 2'-deoxyguanosine. PCT Int. Appl. (2003), 31 pp. http://hmdb.ca/system/metabolites/msds/000/000/060/original/HMDB00085.pdf?1358462938 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Deoxyguanosinetriphosphate triphosphohydrolase P15723 DGTP_ECOLI dgt http://ecmdb.ca/proteins/P15723.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Xanthosine phosphorylase P45563 XAPA_ECOLI xapA http://ecmdb.ca/proteins/P45563.xml Nucleoside permease nupG P0AFF4 NUPG_ECOLI nupG http://ecmdb.ca/proteins/P0AFF4.xml Nucleoside permease nupX P33021 NUPX_ECOLI nupX http://ecmdb.ca/proteins/P33021.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml 2'-Deoxyguanosine 5'-monophosphate + Water > Deoxyguanosine + Phosphate Deoxyguanosine + Phosphate <> Deoxyribose 1-phosphate + Guanine R01969 dGTP + Water <> Deoxyguanosine + Triphosphate R01856 DGTPTRIPHYDRO-RXN 2'-Deoxyguanosine 5'-monophosphate + Water <> Deoxyguanosine + Phosphate R01968 Deoxyguanosine + Phosphate <> deoxyribose-1-phosphate + Guanine DEOXYGUANPHOSPHOR-RXN Water + dGTP > Hydrogen ion + Triphosphate + Deoxyguanosine DGTPTRIPHYDRO-RXN dGTP + Water > Deoxyguanosine + Triphosphate dGTP + Water <> Deoxyguanosine + Triphosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 0.52 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 2080 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621