2.0 2012-05-31 14:02:50 -0600 2015-09-13 12:56:13 -0600 ECMDB04034 M2MDB000570 Cyclic GMP Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. 3',5'-Cyclic GMP 3',5'-Guanosine 3',5'-Guanosine monophosphate 3',5'-Guanosine monophosphoric acid CGMP Cyclic 3',5'-guanosine monophosphate Cyclic 3',5'-guanosine monophosphoric acid Cyclic GMP Cyclic guanosine 3',5'-monophosphate Cyclic guanosine 3',5'-monophosphoric acid Cyclic-GMP Guanosine 3',5'-cyclic phosphate Guanosine 3',5'-cyclic phosphoric acid Guanosine 3',5'-cyclic-monophosphate Guanosine 3',5'-cyclic-monophosphoric acid Guanosine 3',5'-monophosphate Guanosine 3',5'-monophosphoric acid Guanosine cyclic-monophosphate Guanosine cyclic-monophosphoric acid Guanosine-cyclic-phosphoric-acid C10H12N5O7P 345.2053 345.047434275 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one cyclic-GMP 7665-99-8 NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N Solid Cytosol logp -1.98 ALOGPS logs -1.96 ALOGPS solubility 3.79e+00 g/l ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 2.05 ChemAxon pka_strongest_basic 1.41 ChemAxon iupac 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one ChemAxon average_mass 345.2053 ChemAxon mono_mass 345.047434275 ChemAxon smiles NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 ChemAxon formula C10H12N5O7P ChemAxon inchi InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey ZOOGRGPOEVQQDX-UUOKFMHZSA-N ChemAxon polar_surface_area 170.52 ChemAxon refractivity 71.72 ChemAxon polarizability 29.19 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Specdb::CMs 2262 Specdb::CMs 23461 Specdb::CMs 31308 Specdb::CMs 38019 Specdb::CMs 137880 Specdb::CMs 145614 Specdb::NmrOneD 248448 Specdb::NmrOneD 248449 Specdb::NmrOneD 248450 Specdb::NmrOneD 248451 Specdb::NmrOneD 248452 Specdb::NmrOneD 248453 Specdb::NmrOneD 248454 Specdb::NmrOneD 248455 Specdb::NmrOneD 248456 Specdb::NmrOneD 248457 Specdb::NmrOneD 248458 Specdb::NmrOneD 248459 Specdb::NmrOneD 248460 Specdb::NmrOneD 248461 Specdb::NmrOneD 248462 Specdb::NmrOneD 248463 Specdb::NmrOneD 248464 Specdb::NmrOneD 248465 Specdb::NmrOneD 248466 Specdb::NmrOneD 248467 Specdb::MsMs 25964 Specdb::MsMs 25965 Specdb::MsMs 25966 Specdb::MsMs 32522 Specdb::MsMs 32523 Specdb::MsMs 32524 Specdb::MsMs 439074 Specdb::MsMs 439590 Specdb::MsMs 439591 Specdb::MsMs 439592 Specdb::MsMs 439593 Specdb::MsMs 439594 Specdb::MsMs 440098 Specdb::MsMs 448015 Specdb::MsMs 449660 Specdb::MsMs 449661 Specdb::MsMs 449662 Specdb::MsMs 449663 Specdb::MsMs 449664 Specdb::MsMs 449665 Specdb::MsMs 449666 Specdb::MsMs 449667 Specdb::MsMs 449668 Specdb::MsMs 449669 Specdb::MsMs 449670 HMDB01314 24316 22734 C00942 16356 CGMP PCG Cyclic GMP Keseler, I. 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Gastroenterology. 1998 Apr;114(4):782-90. 9516399 Sekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146. http://hmdb.ca/system/metabolites/msds/000/001/176/original/HMDB01314.pdf?1358461388 Adenylate cyclase P00936 CYAA_ECOLI cyaA http://ecmdb.ca/proteins/P00936.xml Oxygen sensor protein DosP P76129 DOSP_ECOLI dosP http://ecmdb.ca/proteins/P76129.xml Cyclic GMP + Water > Guanosine monophosphate + Hydrogen ion Guanosine triphosphate <> Cyclic GMP + Pyrophosphate R00434 GUANYLCYC-RXN Guanosine triphosphate <> Cyclic GMP + Pyrophosphate