2.02012-05-31 13:03:45 -06002015-09-13 12:56:09 -0600ECMDB01044M2MDB0002312'-Deoxyguanosine 5'-monophosphate2'-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'-GMP2'-Deoxy-5'-guanylate2'-Deoxy-5'-guanylic acid2'-Deoxy-GMP2'-Deoxy-Guanosine 5'-(dihydrogen phosphate)2'-Deoxy-guanosine 5'-(dihydrogen phosphoric acid)2'-Deoxy-Guanosine 5'-phosphate2'-Deoxy-guanosine 5'-phosphoric acid2'-Deoxy-Guanosine phosphate2'-Deoxy-guanosine phosphoric acid2'-Deoxyguanosine 5'-monophosphate2'-Deoxyguanosine 5'-monophosphoric acid2'-Deoxyguanosine 5'-phosphate2'-Deoxyguanosine 5'-phosphoric acid2'-Deoxyguanosine-5'-phosphate2'-Deoxyguanosine-5'-phosphoric acid2'-Deoxyguanylate2'-Deoxyguanylic acid2'-DG-5'-MP2'-dGMPDeoxy-GMPDeoxyguanosine 5'-monophosphateDeoxyguanosine 5'-monophosphoric acidDeoxyguanosine 5'-phosphateDeoxyguanosine 5'-phosphoric acidDeoxyguanosine-phosphateDeoxyguanosine-phosphoric acidDGMPGGuanine ribosideVernineC10H14N5O7P347.2212347.063084339{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic aciddeoxyguanylate902-04-5NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1InChI=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/s1LTFMZDNNPPEQNG-KVQBGUIXSA-NSolidCytosolExtra-organismPeriplasmlogp-1.87logs-2.11solubility2.70e+00 g/llogp-2.8pka_strongest_acidic1.21pka_strongest_basic2.62iupac{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acidaverage_mass347.2212mono_mass347.063084339smilesNC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1formulaC10H14N5O7PinchiInChI=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/s1inchikeyLTFMZDNNPPEQNG-KVQBGUIXSA-Npolar_surface_area181.52refractivity73.55polarizability29.72rotatable_bond_count4acceptor_count10donor_count5physiological_charge-1formal_charge0Purine metabolismec00230Specdb::CMs25044Specdb::CMs37901Specdb::CMs173450Specdb::NmrOneD1634Specdb::NmrOneD4903Specdb::NmrOneD146170Specdb::NmrOneD146171Specdb::NmrOneD146172Specdb::NmrOneD146173Specdb::NmrOneD146174Specdb::NmrOneD146175Specdb::NmrOneD146176Specdb::NmrOneD146177Specdb::NmrOneD146178Specdb::NmrOneD146179Specdb::NmrOneD146180Specdb::NmrOneD146181Specdb::NmrOneD146182Specdb::NmrOneD146183Specdb::NmrOneD146184Specdb::NmrOneD146185Specdb::NmrOneD146186Specdb::NmrOneD146187Specdb::NmrOneD146188Specdb::NmrOneD146189Specdb::MsMs1396Specdb::MsMs5033Specdb::MsMs5034Specdb::MsMs179415Specdb::MsMs179416Specdb::MsMs179417Specdb::MsMs181743Specdb::MsMs181744Specdb::MsMs181745Specdb::MsMs439164Specdb::MsMs448113Specdb::MsMs2227305Specdb::MsMs2227396Specdb::MsMs2229735Specdb::MsMs2229769Specdb::MsMs2234379Specdb::MsMs2234586Specdb::MsMs2236509Specdb::MsMs2236850Specdb::MsMs2238677Specdb::MsMs2238914Specdb::MsMs2240637Specdb::MsMs2241043Specdb::MsMs2242702Specdb::MsMs2243150Specdb::NmrTwoD1575HMDB010446505958570C00362DGMPPG7Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Bennett, 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 5:593-599.19561621Warnecke 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):1349-59.15546202Reichard, 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?1358461587Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlProtein mazGP0AEY3MAZG_ECOLImazGhttp://ecmdb.ca/proteins/P0AEY3.xmlNucleoside-triphosphatase rdgBP52061RDGB_ECOLIrdgBhttp://ecmdb.ca/proteins/P52061.xmlGuanylate kinaseP60546KGUA_ECOLIgmkhttp://ecmdb.ca/proteins/P60546.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlMutator mutT proteinP08337MUTT_ECOLImutThttp://ecmdb.ca/proteins/P08337.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.xmldGTP + Water > 2'-Deoxyguanosine 5'-monophosphate + Hydrogen ion + PyrophosphateR01855RXN0-3852'-Deoxyguanosine 5'-monophosphate + Water > Deoxyguanosine + PhosphateAdenosine triphosphate + 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDPR02090GMKALT-RXNdGTP + Water <> 2'-Deoxyguanosine 5'-monophosphate + PyrophosphateR018552'-Deoxyguanosine 5'-monophosphate + Water <> Deoxyguanosine + PhosphateR01968Adenosine triphosphate + 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDPR02090dGTP + Water > Hydrogen ion + 2'-Deoxyguanosine 5'-monophosphate + PyrophosphateRXN0-385Adenosine triphosphate + 2 2'-Deoxyguanosine 5'-monophosphate <> ADP + dGDPGutnick 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 culture50.7uM0.037 oCK12 NCM3722Mid-Log Phase2028000Bennett, 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