2.02012-05-31 09:56:57 -06002015-09-13 12:56:06 -0600ECMDB00085M2MDB000031DeoxyguanosineDeoxyguanosine 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-Guanosine2'-Deoxyguanosine2-Deoxyguanosine9-(2-deoxy-b-D-erythro-pentofuranosyl)-Guanine9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine9-(2-Deoxy-b-delta-erythro-pentofuranosyl)-guanine9-(2-Deoxy-b-delta-erythro-pentofuranosyl)guanine9-(2-Deoxy-b-δ-erythro-pentofuranosyl)-guanine9-(2-Deoxy-b-δ-erythro-pentofuranosyl)guanine9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-Guanine9-(2-Deoxy-beta-D-erythro-pentofuranosyl)guanine9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-Guanine9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine9-(2-Deoxy-β-δ-erythro-pentofuranosyl)-guanine9-(2-Deoxy-β-δ-erythro-pentofuranosyl)guanineDeoxyguanosineDesoxyguanosineDGuanosineGuanine deoxy nucleosideGuanine deoxyribosideC10H13N5O4267.2413267.0967539292-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one2-deoxyguanosine961-07-9NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1InChI=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/s1YKBGVTZYEHREMT-KVQBGUIXSA-NSolidCytosolExtra-organismPeriplasmlogp-1.75logs-1.37solubility1.15e+01 g/lmelting_point300 oClogp-1.8pka_strongest_acidic10.16pka_strongest_basic0.46iupac2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-oneaverage_mass267.2413mono_mass267.096753929smilesNC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1formulaC10H13N5O4inchiInChI=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/s1inchikeyYKBGVTZYEHREMT-KVQBGUIXSA-Npolar_surface_area134.99refractivity63.11polarizability25.24rotatable_bond_count2acceptor_count7donor_count4physiological_charge0formal_charge0Purine metabolismec00230purine deoxyribonucleosides degradationPW002077Metabolicpurine deoxyribonucleosides degradationPWY0-1297Specdb::CMs316Specdb::CMs2119Specdb::CMs2122Specdb::CMs2656Specdb::CMs30422Specdb::CMs30989Specdb::CMs30990Specdb::CMs37286Specdb::CMs168402Specdb::CMs1049758Specdb::CMs1049760Specdb::CMs1049762Specdb::CMs1049764Specdb::CMs1049766Specdb::CMs1049768Specdb::CMs1049770Specdb::CMs1049772Specdb::CMs1049774Specdb::CMs1049775Specdb::CMs1049777Specdb::CMs1049779Specdb::CMs1049781Specdb::CMs1049783Specdb::CMs1049785Specdb::CMs1049787Specdb::NmrOneD1075Specdb::NmrOneD4902Specdb::NmrOneD5652Specdb::NmrOneD5653Specdb::NmrOneD5654Specdb::NmrOneD5655Specdb::NmrOneD5656Specdb::NmrOneD5657Specdb::NmrOneD5658Specdb::NmrOneD5659Specdb::NmrOneD5660Specdb::NmrOneD5661Specdb::NmrOneD5662Specdb::NmrOneD5663Specdb::NmrOneD5664Specdb::NmrOneD5665Specdb::NmrOneD5666Specdb::NmrOneD5667Specdb::NmrOneD5668Specdb::NmrOneD5669Specdb::NmrOneD5670Specdb::NmrOneD5671Specdb::MsMs135Specdb::MsMs136Specdb::MsMs137Specdb::MsMs2795Specdb::MsMs2796Specdb::MsMs2797Specdb::MsMs2798Specdb::MsMs2799Specdb::MsMs2800Specdb::MsMs2801Specdb::MsMs2802Specdb::MsMs2803Specdb::MsMs2804Specdb::MsMs2805Specdb::MsMs2806Specdb::MsMs178617Specdb::MsMs178618Specdb::MsMs178619Specdb::MsMs180936Specdb::MsMs180937Specdb::MsMs180938Specdb::MsMs437559Specdb::MsMs437560Specdb::MsMs437561Specdb::MsMs437562Specdb::NmrTwoD951Specdb::NmrTwoD1133HMDB00085187790163230C0033017172DEOXYGUANOSINEGNGDeoxyguanosineKeseler, I. 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(2003), 31 pp.http://hmdb.ca/system/metabolites/msds/000/000/060/original/HMDB00085.pdf?1358462938Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlDeoxyguanosinetriphosphate triphosphohydrolaseP15723DGTP_ECOLIdgthttp://ecmdb.ca/proteins/P15723.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmlNucleoside permease nupGP0AFF4NUPG_ECOLInupGhttp://ecmdb.ca/proteins/P0AFF4.xmlNucleoside permease nupXP33021NUPX_ECOLInupXhttp://ecmdb.ca/proteins/P33021.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xml2'-Deoxyguanosine 5'-monophosphate + Water > Deoxyguanosine + PhosphateDeoxyguanosine + Phosphate <> Deoxyribose 1-phosphate + GuanineR01969dGTP + Water <> Deoxyguanosine + TriphosphateR01856DGTPTRIPHYDRO-RXN2'-Deoxyguanosine 5'-monophosphate + Water <> Deoxyguanosine + PhosphateR01968Deoxyguanosine + Phosphate <> deoxyribose-1-phosphate + GuanineDEOXYGUANPHOSPHOR-RXNWater + dGTP > Hydrogen ion + Triphosphate + DeoxyguanosineDGTPTRIPHYDRO-RXNdGTP + Water > Deoxyguanosine + TriphosphatedGTP + Water <> Deoxyguanosine + TriphosphateGutnick 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 glucoseShake flask and filter culture0.52uM0.037 oCK12 NCM3722Mid-Log Phase20800Bennett, 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