2.02012-05-31 14:30:32 -06002015-06-03 17:19:25 -0600ECMDB20158M2MDB001005Guanosine 3',5'-bis(diphosphate)(p)ppGpp, guanosine pentaphosphate or tetraphosphate is an alarmone which is involved in the stringent response in bacteria, causing the inhibition of RNA synthesis when there is a shortage of amino acids present. This causes translation to decrease and the amino acids present are therefore conserved. (p)ppGpp is an effector molecule which is produced as a result of amino acid starvation within a bacterial cell.Guanosine 3',5'-bis(diphosphate)Guanosine 3',5'-bis(diphosphoric acid)Guanosine 3',5'-bis(trihydrogen diphosphate)Guanosine 3',5'-bis(trihydrogen diphosphoric acid)Guanosine 3',5'-bispyrophosphateGuanosine 3',5'-bispyrophosphoric acidGuanosine 3'-diphosphate 5'-diphosphateGuanosine 3'-diphosphoric acid 5'-diphosphoric acidGuanosine 5'-diphosphate,3'-diphosphateGuanosine 5'-diphosphoric acid,3'-diphosphoric acidGuanosine tetraphosphateGuanosine tetraphosphoric acidGUANOSINE-5',3'-TETRAPHOSPHATEGUANOSINE-5',3'-tetraphosphoric acidMagic spotMagic spot IPpgppC10H17N5O17P4603.1603602.956990191{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)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-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid33503-72-9[H][C@]1(COP(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)=OInChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1BUFLLCUFNHESEH-UUOKFMHZSA-NCytosollogp-0.50logs-1.77solubility1.03e+01 g/llogp-3.9pka_strongest_acidic1.46pka_strongest_basic7.15iupac{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acidaverage_mass603.1603mono_mass602.956990191smiles[H][C@]1(COP(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)=OformulaC10H17N5O17P4inchiInChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1inchikeyBUFLLCUFNHESEH-UUOKFMHZSA-Npolar_surface_area342.33refractivity118.69polarizability44.68rotatable_bond_count10acceptor_count17donor_count10physiological_charge-5formal_charge0Purine metabolismec00230ppGpp biosynthesisPPGPPMET-PWYSpecdb::CMs36411Specdb::CMs47830Specdb::CMs474614Specdb::CMs474615Specdb::CMs474616Specdb::CMs474617Specdb::CMs474618Specdb::CMs474619Specdb::CMs474620Specdb::CMs474621Specdb::CMs474622Specdb::CMs474623Specdb::CMs474624Specdb::CMs474625Specdb::CMs474626Specdb::CMs474627Specdb::CMs474628Specdb::CMs474629Specdb::CMs474630Specdb::CMs474631Specdb::CMs474632Specdb::CMs474633Specdb::CMs474634Specdb::CMs474635Specdb::CMs474636Specdb::NmrOneD51722Specdb::NmrOneD51723Specdb::NmrOneD51724Specdb::NmrOneD51725Specdb::NmrOneD51726Specdb::NmrOneD51727Specdb::NmrOneD51728Specdb::NmrOneD51729Specdb::NmrOneD51730Specdb::NmrOneD51731Specdb::NmrOneD51732Specdb::NmrOneD51733Specdb::NmrOneD51734Specdb::NmrOneD51735Specdb::NmrOneD51736Specdb::NmrOneD51737Specdb::NmrOneD51738Specdb::NmrOneD51739Specdb::NmrOneD51740Specdb::NmrOneD51741Specdb::MsMs26111Specdb::MsMs26112Specdb::MsMs26113Specdb::MsMs32669Specdb::MsMs32670Specdb::MsMs32671Specdb::MsMs2730328Specdb::MsMs2730329Specdb::MsMs2730330Specdb::MsMs2975975Specdb::MsMs2975976Specdb::MsMs2975977439450388557C0122817633GUANOSINE-5DP-3DPG4PKeseler, 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-D114.22080510ExopolyphosphataseP0AFL6PPX_ECOLIppxhttp://ecmdb.ca/proteins/P0AFL6.xmlGTP pyrophosphokinaseP0AG20RELA_ECOLIrelAhttp://ecmdb.ca/proteins/P0AG20.xmlBifunctional (p)ppGpp synthase/hydrolase SpoTP0AG24SPOT_ECOLIspoThttp://ecmdb.ca/proteins/P0AG24.xmlGuanosine-5'-triphosphate,3'-diphosphate pyrophosphataseP25552GPPA_ECOLIgppAhttp://ecmdb.ca/proteins/P25552.xmlAdenosine triphosphate + Guanosine diphosphate > Adenosine monophosphate + Hydrogen ion + Guanosine 3',5'-bis(diphosphate)GDPPYPHOSKIN-RXNWater + Guanosine 3',5'-bis(diphosphate) <> Guanosine diphosphate + PyrophosphateR00336PPGPPSYN-RXNGuanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate)R03409PPPGPPHYDRO-RXNGuanosine 3'-diphosphate 5'-triphosphate + Water <> Guanosine 3',5'-bis(diphosphate) + PhosphateR03409Adenosine triphosphate + Guanosine diphosphate > Adenosine monophosphate + Guanosine 3',5'-bis(diphosphate)GDPPYPHOSKIN-RXNGuanosine 3',5'-bis(diphosphate) + Water > Hydrogen ion + Pyrophosphate + Guanosine diphosphatePPGPPSYN-RXNWater + Guanosine 3'-diphosphate 5'-triphosphate > Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate)PPPGPPHYDRO-RXNGuanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine 3',5'-bis(diphosphate) + Inorganic phosphateGuanosine 3',5'-bis(diphosphate) + Water > Guanosine diphosphate + PyrophosphateGuanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate)Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate)