2.02012-05-31 14:20:30 -06002015-06-03 17:19:02 -0600ECMDB11629M2MDB000818Guanosine 2',3'-cyclic phosphate2',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' cGMP2',3'-cGMP2',3'-Cyclic GMPCyclic 2',3'-(hydrogen phosphate)-GuanosineCyclic 2',3'-(hydrogen phosphoric acid)-guanosineGuanosine 2',3'-cyclic monophosphateGuanosine 2',3'-cyclic phosphoric acidC10H12N5O7P345.2053345.0474342759-[(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-one9-[(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-one15718-49-7NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12InChI=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/s1UASRYODFRYWBRC-UUOKFMHZSA-NSolidExtra-organismPeriplasmlogp-1.61logs-1.99solubility3.53e+00 g/llogp-2.4pka_strongest_acidic1.7pka_strongest_basic2.64iupac9-[(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-oneaverage_mass345.2053mono_mass345.047434275smilesNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12formulaC10H12N5O7PinchiInChI=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/s1inchikeyUASRYODFRYWBRC-UUOKFMHZSA-Npolar_surface_area170.52refractivity71.28polarizability29.11rotatable_bond_count2acceptor_count9donor_count4physiological_charge-1formal_charge0Purine metabolismec00230Specdb::CMs2267Specdb::CMs18890Specdb::CMs31554Specdb::CMs39730Specdb::CMs147996Specdb::NmrOneD93592Specdb::NmrOneD93593Specdb::NmrOneD93594Specdb::NmrOneD93595Specdb::NmrOneD93596Specdb::NmrOneD93597Specdb::NmrOneD93598Specdb::NmrOneD93599Specdb::NmrOneD93600Specdb::NmrOneD93601Specdb::NmrOneD93602Specdb::NmrOneD93603Specdb::NmrOneD93604Specdb::NmrOneD93605Specdb::NmrOneD93606Specdb::NmrOneD93607Specdb::NmrOneD93608Specdb::NmrOneD93609Specdb::NmrOneD93610Specdb::NmrOneD93611Specdb::MsMs26312Specdb::MsMs26313Specdb::MsMs26314Specdb::MsMs32870Specdb::MsMs32871Specdb::MsMs32872Specdb::MsMs2260684Specdb::MsMs2260685Specdb::MsMs2260686Specdb::MsMs3077994Specdb::MsMs3077995Specdb::MsMs3077996HMDB116299282383792C06194CPD-3709Genschik, 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 16:2955-2967.9184239Keseler, 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-D114.22080510Hamada, 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 326:71-82.7528887Filipowicz, 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 45:895-906.10397337Diamantstein, T., Ulmer, A. (1975). "Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells." Immunol Commun 4:51-62.1637862',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidaseP08331CPDB_ECOLIcpdBhttp://ecmdb.ca/proteins/P08331.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.xmlGuanosine 2',3'-cyclic phosphate + Water > Guanosine 3'-phosphate + Hydrogen ionR05135Guanosine 2',3'-cyclic phosphate + Water <> Guanosine 3'-phosphateR05135