2.0 2012-10-10 12:23:16 -0600 2015-06-03 17:26:14 -0600 ECMDB23235 M2MDB003625 GMP Guanosine monophosphate, also known as 5'-guanidylic acid or guanylic acid and abbreviated GMP, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleoside monophosphate. 5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphate 5-(2-amino-6-oxo-3H-Purin-9-yl)-3,4-dihydroxyoxolan-2-ylmethyl dihydrogen phosphoric acid C10H14N5O8P 363.2206 363.057998961 {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid guanylate OC1C(COP(O)(O)=O)OC(C1O)N1C=NC2=C1NC(=N)N=C2O InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18) RQFCJASXJCIDSX-UHFFFAOYSA-N logp -1.99 ALOGPS logs -2.01 ALOGPS solubility 3.56e+00 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.29 ChemAxon pka_strongest_basic 0.38 ChemAxon iupac {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 363.2206 ChemAxon mono_mass 363.057998961 ChemAxon smiles OC1C(COP(O)(O)=O)OC(C1O)N1C=NC2=C1NC(=N)N=C2O ChemAxon formula C10H14N5O8P ChemAxon inchi InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18) ChemAxon inchikey RQFCJASXJCIDSX-UHFFFAOYSA-N ChemAxon polar_surface_area 201.75 ChemAxon refractivity 75.49 ChemAxon polarizability 30.7 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon adenosylcobalamin salvage from cobinamide Cobinamide is incorporated from the extracellular space through a transport system into the cytosol. Once inside the cytosol, cobinamide interacts with ATP through a cobinamide adenosyl transferase resulting in the release of a triphosphate and an adenosylcobinamide. The latter compound is then phosphorylated through an ATP-dependent cobinamide kinase resulting in the release of ADP, a hydrogen ion and adenosyl-cobinamide phosphate. This last compound then interacts with GTP and a hydrogen ion through a cobinamide-P guanylyltransferase resulting in the release of a pyrophosphate and an adenosylcobinamide-GDP. A dimethylbenzimidazole interacts with a nicotinate D-ribonucleotide through a nicotinate-nucleotide dimethylbenzumidazole phosphoribosyltransferase resulting in the release of a nicotinate, a hydrogen ion and an alpha-ribazole 5' phosphate. The adenosylcobinamide-GDP and the alpha-ribazole 5' phosphate interact together through a cobalamin 5' phosphate synthase resulting in the release of a hydrogen ion, a GMP and Adenosylcobalamin 5'-phosphate. The latter compound then interacts with a water molecule through an adenosylcbalamin 5' phosphate phosphatase resulting in the release of a phosphate and a coenzyme B12. Likewise a cobalamin molecule can interact with ATP through a cobalamin adenosyltransferase resulting in the release of a triphosphate and a coenzyme B12 PW001884 Metabolic Specdb::CMs 2237 Specdb::CMs 14103 Specdb::CMs 31322 Specdb::CMs 32072 Specdb::CMs 38054 Specdb::CMs 173909 Specdb::NmrOneD 1696 Specdb::NmrOneD 9242 Specdb::NmrOneD 9243 Specdb::NmrOneD 9244 Specdb::NmrOneD 9245 Specdb::NmrOneD 9246 Specdb::NmrOneD 9247 Specdb::NmrOneD 9248 Specdb::NmrOneD 9249 Specdb::NmrOneD 9250 Specdb::NmrOneD 9251 Specdb::NmrOneD 9252 Specdb::NmrOneD 9253 Specdb::NmrOneD 9254 Specdb::NmrOneD 9255 Specdb::NmrOneD 9256 Specdb::NmrOneD 9257 Specdb::NmrOneD 9258 Specdb::NmrOneD 9259 Specdb::NmrOneD 9260 Specdb::NmrOneD 9261 Specdb::MsMs 1553 Specdb::MsMs 1554 Specdb::MsMs 1555 Specdb::MsMs 5249 Specdb::MsMs 5250 Specdb::MsMs 5251 Specdb::MsMs 5252 Specdb::MsMs 5253 Specdb::MsMs 179082 Specdb::MsMs 179083 Specdb::MsMs 179084 Specdb::MsMs 181407 Specdb::MsMs 181408 Specdb::MsMs 181409 Specdb::MsMs 439075 Specdb::MsMs 439194 Specdb::MsMs 448016 Specdb::MsMs 448017 Specdb::MsMs 448138 Specdb::MsMs 2253179 Specdb::MsMs 2255276 Specdb::MsMs 2255309 Specdb::MsMs 2257209 Specdb::MsMs 2257354 Specdb::MsMs 2259191 Specdb::NmrTwoD 1637 Cobalamin synthase P36561 COBS_ECOLI cobS http://ecmdb.ca/proteins/P36561.xml N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole + Adenosylcobinamide-GDP + Adenosylcobinamide-GDP > Hydrogen ion + GMP + Adenosylcobalamin 5'-phosphate PW_R005143