2.0 2012-05-31 13:03:45 -0600 2015-09-13 12:56:09 -0600 ECMDB01044 M2MDB000231 2'-Deoxyguanosine 5'-monophosphate 2'-Deoxyguanosine 5'-monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis (Wikipedia). 2'-Deoxy-5'-GMP 2'-Deoxy-5'-guanylate 2'-Deoxy-5'-guanylic acid 2'-Deoxy-GMP 2'-Deoxy-Guanosine 5'-(dihydrogen phosphate) 2'-Deoxy-guanosine 5'-(dihydrogen phosphoric acid) 2'-Deoxy-Guanosine 5'-phosphate 2'-Deoxy-guanosine 5'-phosphoric acid 2'-Deoxy-Guanosine phosphate 2'-Deoxy-guanosine phosphoric acid 2'-Deoxyguanosine 5'-monophosphate 2'-Deoxyguanosine 5'-monophosphoric acid 2'-Deoxyguanosine 5'-phosphate 2'-Deoxyguanosine 5'-phosphoric acid 2'-Deoxyguanosine-5'-phosphate 2'-Deoxyguanosine-5'-phosphoric acid 2'-Deoxyguanylate 2'-Deoxyguanylic acid 2'-DG-5'-MP 2'-dGMP Deoxy-GMP Deoxyguanosine 5'-monophosphate Deoxyguanosine 5'-monophosphoric acid Deoxyguanosine 5'-phosphate Deoxyguanosine 5'-phosphoric acid Deoxyguanosine-phosphate Deoxyguanosine-phosphoric acid DGMP G Guanine riboside Vernine C10H14N5O7P 347.2212 347.063084339 {[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid deoxyguanylate 902-04-5 NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1 LTFMZDNNPPEQNG-KVQBGUIXSA-N Solid Cytosol Extra-organism Periplasm logp -1.87 ALOGPS logs -2.11 ALOGPS solubility 2.70e+00 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic 2.62 ChemAxon iupac {[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 347.2212 ChemAxon mono_mass 347.063084339 ChemAxon smiles NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 ChemAxon formula C10H14N5O7P ChemAxon inchi InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1 ChemAxon inchikey LTFMZDNNPPEQNG-KVQBGUIXSA-N ChemAxon polar_surface_area 181.52 ChemAxon refractivity 73.55 ChemAxon polarizability 29.72 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Specdb::CMs 25044 Specdb::CMs 37901 Specdb::CMs 173450 Specdb::NmrOneD 1634 Specdb::NmrOneD 4903 Specdb::NmrOneD 146170 Specdb::NmrOneD 146171 Specdb::NmrOneD 146172 Specdb::NmrOneD 146173 Specdb::NmrOneD 146174 Specdb::NmrOneD 146175 Specdb::NmrOneD 146176 Specdb::NmrOneD 146177 Specdb::NmrOneD 146178 Specdb::NmrOneD 146179 Specdb::NmrOneD 146180 Specdb::NmrOneD 146181 Specdb::NmrOneD 146182 Specdb::NmrOneD 146183 Specdb::NmrOneD 146184 Specdb::NmrOneD 146185 Specdb::NmrOneD 146186 Specdb::NmrOneD 146187 Specdb::NmrOneD 146188 Specdb::NmrOneD 146189 Specdb::MsMs 1396 Specdb::MsMs 5033 Specdb::MsMs 5034 Specdb::MsMs 179415 Specdb::MsMs 179416 Specdb::MsMs 179417 Specdb::MsMs 181743 Specdb::MsMs 181744 Specdb::MsMs 181745 Specdb::MsMs 439164 Specdb::MsMs 448113 Specdb::MsMs 2227305 Specdb::MsMs 2227396 Specdb::MsMs 2229735 Specdb::MsMs 2229769 Specdb::MsMs 2234379 Specdb::MsMs 2234586 Specdb::MsMs 2236509 Specdb::MsMs 2236850 Specdb::MsMs 2238677 Specdb::MsMs 2238914 Specdb::MsMs 2240637 Specdb::MsMs 2241043 Specdb::MsMs 2242702 Specdb::MsMs 2243150 Specdb::NmrTwoD 1575 HMDB01044 65059 58570 C00362 DGMP PG7 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 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 Warnecke A, Fichtner I, Garmann D, Jaehde U, Kratz F: Synthesis and biological activity of water-soluble maleimide derivatives of the anticancer drug carboplatin designed as albumin-binding prodrugs. Bioconjug Chem. 2004 Nov-Dec;15(6):1349-59. 15546202 Reichard, Peter. Formation of deoxyguanosine 5'-phosphate from guanosine 5'-phosphate with enzymes from chick embryos. Biochimica et Biophysica Acta (1960), 41 368-9. http://hmdb.ca/system/metabolites/msds/000/000/938/original/HMDB01044.pdf?1358461587 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 Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Protein mazG P0AEY3 MAZG_ECOLI mazG http://ecmdb.ca/proteins/P0AEY3.xml Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml Guanylate kinase P60546 KGUA_ECOLI gmk http://ecmdb.ca/proteins/P60546.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Mutator mutT protein P08337 MUTT_ECOLI mutT http://ecmdb.ca/proteins/P08337.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 dGTP + Water > 2'-Deoxyguanosine 5'-monophosphate + Hydrogen ion + Pyrophosphate R01855 RXN0-385 2'-Deoxyguanosine 5'-monophosphate + Water > Deoxyguanosine + Phosphate Adenosine triphosphate + 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDP R02090 GMKALT-RXN dGTP + Water <> 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate R01855 2'-Deoxyguanosine 5'-monophosphate + Water <> Deoxyguanosine + Phosphate R01968 Adenosine triphosphate + 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDP R02090 dGTP + Water > Hydrogen ion + 2'-Deoxyguanosine 5'-monophosphate + Pyrophosphate RXN0-385 Adenosine triphosphate + 2 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDP 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 50.7 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 202800 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