2.0 2012-10-10 12:20:40 -0600 2015-06-03 17:26:05 -0600 ECMDB23177 M2MDB003567 Cyclic di-3',5'-guanylate Cyclic di-3',5'-guanylate or Cyclic-di-GMP is a second messenger which controls cell surface-associated traits in bacteria. It is a substrate for the enzyme Cyclic di-GMP phosphodiesterase which catalyzes the reaction Cyclic di-3',5'-guanylate + H2O = 5'-phosphoguanylyl(3'->5')guanosine. 3',5'-cyclic di-GMP 3',5'-Cyclic diGMP 3',5'-Cyclic diguanylate 3',5'-Cyclic diguanylic acid Bis(3',5')-cyclic diguanylate Bis(3',5')-cyclic diguanylic acid Bis-(3',5')-cyclic diGMP Bis-(3'-5')-cyclic dimeric guanosine monophosphate Bis-(3'-5')-cyclic dimeric guanosine monophosphoric acid C-(GpGp) CdiGMP CGpGp Cyclic di-3',5'-guanylic acid Cyclic di-GMP Cyclic diguanylate Cyclic diguanylic acid Cyclic dinucleotide di-GMP Cyclic-bis(3',5')diguanylate Cyclic-bis(3',5')diguanylic acid Cyclic-bis(3'->5') dimeric GMP Guanosine 3',5'-cyclic monophosphate Guanosine 3',5'-cyclic monophosphoric acid Guanylyl-(3'->5')-3'-guanylate, cyclic 3'->5'''-nucleotide Guanylyl-(3'->5')-3'-guanylic acid, cyclic 3'->5'''-nucleotide C20H24N10O14P2 690.4107 690.09486855 (1S,6R,8R,9R,10S,15R,17R,18R)-3,9,12,18-tetrahydroxy-8,17-bis(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione cyclic di-GMP [H][C@@]12COP(O)(=O)O[C@]3([H])[C@@]([H])(COP(O)(=O)O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(O2)N1C=NC2=C1NC(=N)N=C2O)O[C@@]([H])(N1C=NC2=C1NC(=N)N=C2O)[C@]3([H])O InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 PKFDLKSEZWEFGL-MHARETSRSA-N logp -1.04 ALOGPS logs -2.26 ALOGPS solubility 3.77e+00 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.53 ChemAxon pka_strongest_basic 5.18 ChemAxon iupac (1S,6R,8R,9R,10S,15R,17R,18R)-3,9,12,18-tetrahydroxy-8,17-bis(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione ChemAxon average_mass 690.4107 ChemAxon mono_mass 690.09486855 ChemAxon smiles [H][C@@]12COP(O)(=O)O[C@]3([H])[C@@]([H])(COP(O)(=O)O[C@@]1([H])[C@@]([H])(O)[C@@]([H])(O2)N1C=NC2=C1NC(=N)N=C2O)O[C@@]([H])(N1C=NC2=C1NC(=N)N=C2O)[C@]3([H])O ChemAxon formula C20H24N10O14P2 ChemAxon inchi InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 ChemAxon inchikey PKFDLKSEZWEFGL-MHARETSRSA-N ChemAxon polar_surface_area 343.02 ChemAxon refractivity 164.59 ChemAxon polarizability 60.01 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 18 ChemAxon donor_count 10 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1085480 Specdb::NmrOneD 269838 Specdb::NmrOneD 269839 Specdb::NmrOneD 269840 Specdb::NmrOneD 269841 Specdb::NmrOneD 269842 Specdb::NmrOneD 269843 Specdb::NmrOneD 269844 Specdb::NmrOneD 269845 Specdb::NmrOneD 269846 Specdb::NmrOneD 269847 Specdb::NmrOneD 269848 Specdb::NmrOneD 269849 Specdb::NmrOneD 269850 Specdb::NmrOneD 269851 Specdb::NmrOneD 269852 Specdb::NmrOneD 269853 Specdb::NmrOneD 269854 Specdb::NmrOneD 269855 Specdb::NmrOneD 269856 Specdb::NmrOneD 269857 Specdb::MsMs 25934 Specdb::MsMs 25935 Specdb::MsMs 25936 Specdb::MsMs 32492 Specdb::MsMs 32493 Specdb::MsMs 32494 C16463 C2E Cyclic di-GMP phosphodiesterase yahA P21514 YAHA_ECOLI yahA http://ecmdb.ca/proteins/P21514.xml Oxygen sensor protein DosP P76129 DOSP_ECOLI dosP http://ecmdb.ca/proteins/P76129.xml diguanylate cyclase; cold- and stationary phase-induced oxygen-dependent biofilm regulator; positively regulates csgBAC and pgaABCD P0AA89 dosC http://ecmdb.ca/proteins/P0AA89.xml diguanylate cyclase P76245 yeaP http://ecmdb.ca/proteins/P76245.xml Probable diguanylate cyclase AdrA P0AAP1 ADRA_ECOLI adrA http://ecmdb.ca/proteins/P0AAP1.xml Cyclic di-GMP phosphodiesterase Gmr P77334 GMR_ECOLI gmr http://ecmdb.ca/proteins/P77334.xml 2 Guanosine triphosphate >2 Pyrophosphate + Cyclic di-3',5'-guanylate Cyclic di-3',5'-guanylate + Water > 5'-phosphoguanylyl(3'->5')guanosine 3',5'-Cyclic diGMP + Water + Cyclic di-3',5'-guanylate <> Linear dimeric GMP R08991 2 Guanosine triphosphate <> 3',5'-Cyclic diGMP +2 Pyrophosphate + Cyclic di-3',5'-guanylate R08057