2.0 2012-05-31 14:20:30 -0600 2015-06-03 17:19:02 -0600 ECMDB11629 M2MDB000818 Guanosine 2',3'-cyclic phosphate 2',3'-Cyclic GMP is a cyclic guanosine derivative that is a precursor to 3'-GMP. The enzyme 2'3'-cyclic-nucleotide 2'-phosphodiesterase (E.C. 3.1.4.16) catalyses the hydrolysis of both 2',3'-cyclic AMP and 2',3'-cyclic GMP into 3'-AMP and 3'-GMP, respectively, at the 3'-terminal of RNA. 2',3'-cyclic phosphate termini are produced, as either intermediates or final products, during RNA cleavage by many different endoribonucleases. The enzyme RNA 3'-phosphate cyclase also converts the 3'-terminal phosphate in RNA into the 2',3'-cyclic phosphodiester in the ATP-dependent reaction which involves formation of the covalent cyclase-AMP and the RNA-N3' pp5' A intermediates (PMID: 10397337). This enzyme could be involved in the maintenance of cyclic ends in tRNA splicing intermediates or in the cyclization of the 3' end of U6 snRNA (PMID: 9184239). Guanosine-2',3'-cyclic phosphate is capable of blocking DNA synthesis in vitro (PMID: 7528887). 2', 3'-cGMP seems to preferentially stimulate mature T-cells while 3', 5'-cGMP preferentially acts on B-cells (PMID: 163786) 2',3' cGMP 2',3'-cGMP 2',3'-Cyclic GMP Cyclic 2',3'-(hydrogen phosphate)-Guanosine Cyclic 2',3'-(hydrogen phosphoric acid)-guanosine Guanosine 2',3'-cyclic monophosphate Guanosine 2',3'-cyclic phosphoric acid C10H12N5O7P 345.2053 345.047434275 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one 15718-49-7 NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12 InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(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 UASRYODFRYWBRC-UUOKFMHZSA-N Solid Extra-organism Periplasm logp -1.61 ALOGPS logs -1.99 ALOGPS solubility 3.53e+00 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 1.7 ChemAxon pka_strongest_basic 2.64 ChemAxon iupac 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one ChemAxon average_mass 345.2053 ChemAxon mono_mass 345.047434275 ChemAxon smiles NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12 ChemAxon formula C10H12N5O7P ChemAxon inchi InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(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 UASRYODFRYWBRC-UUOKFMHZSA-N ChemAxon polar_surface_area 170.52 ChemAxon refractivity 71.28 ChemAxon polarizability 29.11 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 9 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Specdb::CMs 2267 Specdb::CMs 18890 Specdb::CMs 31554 Specdb::CMs 39730 Specdb::CMs 147996 Specdb::NmrOneD 93592 Specdb::NmrOneD 93593 Specdb::NmrOneD 93594 Specdb::NmrOneD 93595 Specdb::NmrOneD 93596 Specdb::NmrOneD 93597 Specdb::NmrOneD 93598 Specdb::NmrOneD 93599 Specdb::NmrOneD 93600 Specdb::NmrOneD 93601 Specdb::NmrOneD 93602 Specdb::NmrOneD 93603 Specdb::NmrOneD 93604 Specdb::NmrOneD 93605 Specdb::NmrOneD 93606 Specdb::NmrOneD 93607 Specdb::NmrOneD 93608 Specdb::NmrOneD 93609 Specdb::NmrOneD 93610 Specdb::NmrOneD 93611 Specdb::MsMs 26312 Specdb::MsMs 26313 Specdb::MsMs 26314 Specdb::MsMs 32870 Specdb::MsMs 32871 Specdb::MsMs 32872 Specdb::MsMs 2260684 Specdb::MsMs 2260685 Specdb::MsMs 2260686 Specdb::MsMs 3077994 Specdb::MsMs 3077995 Specdb::MsMs 3077996 HMDB11629 92823 83792 C06194 CPD-3709 Genschik, P., Billy, E., Swianiewicz, M., Filipowicz, W. (1997). "The human RNA 3'-terminal phosphate cyclase is a member of a new family of proteins conserved in Eucarya, Bacteria and Archaea." EMBO J 16:2955-2967. 9184239 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 Hamada, K., Yokoro, K. (1995). "Blocking of DNA synthesis in vitro by a guanosine 2',3'-cyclic phosphate: a possible mechanism of chromosome aberrations induced by U5 snRNA." Mutat Res 326:71-82. 7528887 Filipowicz, W., Billy, E., Drabikowski, K., Genschik, P. (1998). "Cyclases of the 3'-terminal phosphate in RNA: a new family of RNA processing enzymes conserved in eucarya, bacteria and archaea." Acta Biochim Pol 45:895-906. 10397337 Diamantstein, T., Ulmer, A. (1975). "Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells." Immunol Commun 4:51-62. 163786 2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidase P08331 CPDB_ECOLI cpdB http://ecmdb.ca/proteins/P08331.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 Guanosine 2',3'-cyclic phosphate + Water > Guanosine 3'-phosphate + Hydrogen ion R05135 Guanosine 2',3'-cyclic phosphate + Water <> Guanosine 3'-phosphate R05135