2.0 2012-05-31 14:30:25 -0600 2015-06-03 17:19:25 -0600 ECMDB20156 M2MDB001003 Guanosine 3'-diphosphate 5'-triphosphate Guanosine 3'-diphosphate 5'-triphosphate is a member of the chemical class known as Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. The hallmark of the stringent response is the accumulation of guanosine tetra- (ppGpp) and pentaphosphates (pppGpp), which probably bind RNA polymerase to regulate gene expression at certain promoters. (PMID 11282471) Guanosine 5'-triphosphate 3'-diphosphate (pppGpp) and guanosine 5'-diphosphate 3'-diphosphate (ppGpp) are specifically degraded by a manganese-dependent pyrophosphorylase present in spoT+ but not in spoT- strains of Escherichia coli, indicating that the enzyme is the spoT gene product. (PMID 365225) The kinetics of the GTP level during starvation suggests that GTP is a precursor of pppGpp. (PMID 793688) Guanosine 3'-diphosphate 5'-triphosphate Guanosine 3'-diphosphoric acid 5'-triphosphoric acid Guanosine 5'-triphosphate,3'-diphosphate Guanosine 5'-triphosphoric acid,3'-diphosphoric acid Guanosine pentaphosphate Guanosine pentaphosphoric acid Magic spot Pppgpp C10H18N5O20P5 683.1402 682.923320601 {[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid {hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid 38918-96-6 [H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 KCPMACXZAITQAX-UUOKFMHZSA-N Cytosol logp 0.16 ALOGPS logs -1.61 ALOGPS solubility 1.68e+01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 0.84 ChemAxon iupac {[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid ChemAxon average_mass 683.1402 ChemAxon mono_mass 682.923320601 ChemAxon smiles [H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O ChemAxon formula C10H18N5O20P5 ChemAxon inchi InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey KCPMACXZAITQAX-UUOKFMHZSA-N ChemAxon polar_surface_area 388.86 ChemAxon refractivity 129.57 ChemAxon polarizability 49.15 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 19 ChemAxon donor_count 11 ChemAxon physiological_charge -6 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 ppGpp biosynthesis PPGPPMET-PWY Specdb::CMs 33917 Specdb::CMs 731240 Specdb::CMs 731241 Specdb::CMs 731242 Specdb::CMs 731243 Specdb::CMs 731244 Specdb::CMs 731245 Specdb::CMs 731246 Specdb::CMs 731247 Specdb::CMs 731248 Specdb::CMs 731249 Specdb::CMs 731250 Specdb::CMs 731251 Specdb::CMs 731252 Specdb::CMs 731253 Specdb::CMs 731254 Specdb::CMs 731255 Specdb::CMs 731256 Specdb::CMs 731257 Specdb::CMs 731258 Specdb::CMs 731259 Specdb::CMs 731260 Specdb::CMs 731261 Specdb::CMs 731262 Specdb::CMs 731263 Specdb::NmrOneD 59112 Specdb::NmrOneD 59113 Specdb::NmrOneD 59114 Specdb::NmrOneD 59115 Specdb::NmrOneD 59116 Specdb::NmrOneD 59117 Specdb::NmrOneD 59118 Specdb::NmrOneD 59119 Specdb::NmrOneD 59120 Specdb::NmrOneD 59121 Specdb::NmrOneD 59122 Specdb::NmrOneD 59123 Specdb::NmrOneD 59124 Specdb::NmrOneD 59125 Specdb::NmrOneD 59126 Specdb::NmrOneD 59127 Specdb::NmrOneD 59128 Specdb::NmrOneD 59129 Specdb::NmrOneD 59130 Specdb::NmrOneD 59131 Specdb::MsMs 28661 Specdb::MsMs 28662 Specdb::MsMs 28663 Specdb::MsMs 35219 Specdb::MsMs 35220 Specdb::MsMs 35221 Specdb::MsMs 3225601 Specdb::MsMs 3225602 Specdb::MsMs 3225603 Specdb::MsMs 3225604 Specdb::MsMs 3225605 Specdb::MsMs 3225606 38166 34987 C04494 GDP-TP 0O2 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Chaloner-Larsson, G., Yamazaki, H. (1976). "Synthesis of guanosine 5'-triphosphate,3'-diphosphate in a spo T strain of Escherichia coli." Can J Biochem 54:935-940. 793688 Heinemeyer, E. A., Richter, D. (1978). "Characterization of the guanosine 5'-triphosphate 3'-diphosphate and guanosine 5'-diphosphate 3'-diphosphate degradation reaction catalyzed by a specific pyrophosphorylase from Escherichia coli." Biochemistry 17:5368-5372. 365225 Chatterji, D., Ojha, A. K. (2001). "Revisiting the stringent response, ppGpp and starvation signaling." Curr Opin Microbiol 4:160-165. 11282471 Exopolyphosphatase P0AFL6 PPX_ECOLI ppx http://ecmdb.ca/proteins/P0AFL6.xml GTP pyrophosphokinase P0AG20 RELA_ECOLI relA http://ecmdb.ca/proteins/P0AG20.xml Bifunctional (p)ppGpp synthase/hydrolase SpoT P0AG24 SPOT_ECOLI spoT http://ecmdb.ca/proteins/P0AG24.xml Guanosine-5'-triphosphate,3'-diphosphate pyrophosphatase P25552 GPPA_ECOLI gppA http://ecmdb.ca/proteins/P25552.xml Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion R00429 GTPPYPHOSKIN-RXN Guanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine triphosphate + Pyrophosphate RXN0-6427 Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) R03409 PPPGPPHYDRO-RXN Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate R00429 Guanosine 3'-diphosphate 5'-triphosphate + Water <> Guanosine 3',5'-bis(diphosphate) + Phosphate R03409 Guanosine triphosphate + Adenosine triphosphate > Guanosine 3'-diphosphate 5'-triphosphate + Adenosine monophosphate GTPPYPHOSKIN-RXN Water + Guanosine 3'-diphosphate 5'-triphosphate > Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) PPPGPPHYDRO-RXN Guanosine 3'-diphosphate 5'-triphosphate + Water > Hydrogen ion + Guanosine triphosphate + Pyrophosphate RXN0-6427 Guanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine 3',5'-bis(diphosphate) + Inorganic phosphate Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) Adenosine triphosphate + Guanosine triphosphate <> Adenosine monophosphate + Guanosine 3'-diphosphate 5'-triphosphate + Hydrogen ion Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate)