2.0 2012-05-31 14:50:47 -0600 2015-06-03 17:20:18 -0600 ECMDB20562 M2MDB001366 GMP-Lysine GMP-lysine is a member of the chemical class known as Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. GMP-lysine is a nucleotidyl-modified amino acid. The hinT gene product is capable of cleaving lysine from GMP and AMP. Though specific protein targets remain to be identified, it is has been hypothesized that Hint hydrolases may reverse nucleotidylylated protein modifications of lysine. In E. coli, the Hint-homologous hinT gene is required for resistance to elevated levels of certain salts. GMP-lysine C16H27N7O9P 492.4008 492.160787009 9-[(2R,3R,4S,5R)-5-{[({[(2R)-2,6-diazaniumylhexanoyl]oxy}(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-2-imino-3,9-dihydro-2H-7λ⁵-purin-7-ylium-3-id-7-yl 9-[(2R,3R,4S,5R)-5-[({[(2R)-2,6-diammoniohexanoyl]oxy(hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-2-imino-3H-7λ⁵-purin-7-ylium-3-id-7-yl [H][C@@]([NH3+])(CCCC[NH3+])C(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=[N+]C3=C2[N-]C(=N)N=C3O)[C@]([H])(O)[C@]1([H])O InChI=1S/C16H25N7O9P/c17-4-2-1-3-7(18)15(27)32-33(28,29)30-5-8-10(24)11(25)14(31-8)23-6-20-9-12(23)21-16(19)22-13(9)26/h6-8,10-11,14,24-25H,1-5,17-18H2,(H3-,19,21,22,26,28,29)/p+2/t7-,8-,10-,11-,14-/m1/s1 XRYPUFFHVWYVTB-BAYCTPFLSA-P Cytoplasm Periplasm logp -1.47 ALOGPS logs -2.72 ALOGPS solubility 1.17e+00 g/l ALOGPS logp -9.1 ChemAxon pka_strongest_acidic -0.94 ChemAxon pka_strongest_basic 10.22 ChemAxon iupac 9-[(2R,3R,4S,5R)-5-{[({[(2R)-2,6-diazaniumylhexanoyl]oxy}(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-2-imino-3,9-dihydro-2H-7λ⁵-purin-7-ylium-3-id-7-yl ChemAxon average_mass 492.4008 ChemAxon mono_mass 492.160787009 ChemAxon smiles [H][C@@]([NH3+])(CCCC[NH3+])C(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=[N+]C3=C2[N-]C(=N)N=C3O)[C@]([H])(O)[C@]1([H])O ChemAxon formula C16H27N7O9P ChemAxon inchi InChI=1S/C16H25N7O9P/c17-4-2-1-3-7(18)15(27)32-33(28,29)30-5-8-10(24)11(25)14(31-8)23-6-20-9-12(23)21-16(19)22-13(9)26/h6-8,10-11,14,24-25H,1-5,17-18H2,(H3-,19,21,22,26,28,29)/p+2/t7-,8-,10-,11-,14-/m1/s1 ChemAxon inchikey XRYPUFFHVWYVTB-BAYCTPFLSA-P ChemAxon polar_surface_area 261.29 ChemAxon refractivity 160.2 ChemAxon polarizability 45.35 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge 1 ChemAxon formal_charge 2 ChemAxon Specdb::NmrOneD 248108 Specdb::NmrOneD 248109 Specdb::NmrOneD 248110 Specdb::NmrOneD 248111 Specdb::NmrOneD 248112 Specdb::NmrOneD 248113 Specdb::NmrOneD 248114 Specdb::NmrOneD 248115 Specdb::NmrOneD 248116 Specdb::NmrOneD 248117 Specdb::NmrOneD 248118 Specdb::NmrOneD 248119 Specdb::NmrOneD 248120 Specdb::NmrOneD 248121 Specdb::NmrOneD 248122 Specdb::NmrOneD 248123 Specdb::NmrOneD 248124 Specdb::NmrOneD 248125 Specdb::NmrOneD 248126 Specdb::NmrOneD 248127 Specdb::MsMs 28832 Specdb::MsMs 28833 Specdb::MsMs 28834 Specdb::MsMs 35390 Specdb::MsMs 35391 Specdb::MsMs 35392 25202936 GMP-LYSINE-PHOSPHORAMIDATE 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 GMP-Lysine + Water > Guanosine monophosphate + N-alpha-acetyl lysine methyl ester RXN0-4121