2.0 2012-05-31 14:30:32 -0600 2015-06-03 17:19:25 -0600 ECMDB20158 M2MDB001005 Guanosine 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'-bispyrophosphate Guanosine 3',5'-bispyrophosphoric acid Guanosine 3'-diphosphate 5'-diphosphate Guanosine 3'-diphosphoric acid 5'-diphosphoric acid Guanosine 5'-diphosphate,3'-diphosphate Guanosine 5'-diphosphoric acid,3'-diphosphoric acid Guanosine tetraphosphate Guanosine tetraphosphoric acid GUANOSINE-5',3'-TETRAPHOSPHATE GUANOSINE-5',3'-tetraphosphoric acid Magic spot Magic spot I Ppgpp C10H17N5O17P4 603.1603 602.956990191 {[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 acid 33503-72-9 [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)=O InChI=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/s1 BUFLLCUFNHESEH-UUOKFMHZSA-N Cytosol logp -0.50 ALOGPS logs -1.77 ALOGPS solubility 1.03e+01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.46 ChemAxon pka_strongest_basic 7.15 ChemAxon iupac {[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 ChemAxon average_mass 603.1603 ChemAxon mono_mass 602.956990191 ChemAxon smiles [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)=O ChemAxon formula C10H17N5O17P4 ChemAxon inchi InChI=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/s1 ChemAxon inchikey BUFLLCUFNHESEH-UUOKFMHZSA-N ChemAxon polar_surface_area 342.33 ChemAxon refractivity 118.69 ChemAxon polarizability 44.68 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 17 ChemAxon donor_count 10 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 ppGpp biosynthesis PPGPPMET-PWY Specdb::CMs 36411 Specdb::CMs 47830 Specdb::CMs 474614 Specdb::CMs 474615 Specdb::CMs 474616 Specdb::CMs 474617 Specdb::CMs 474618 Specdb::CMs 474619 Specdb::CMs 474620 Specdb::CMs 474621 Specdb::CMs 474622 Specdb::CMs 474623 Specdb::CMs 474624 Specdb::CMs 474625 Specdb::CMs 474626 Specdb::CMs 474627 Specdb::CMs 474628 Specdb::CMs 474629 Specdb::CMs 474630 Specdb::CMs 474631 Specdb::CMs 474632 Specdb::CMs 474633 Specdb::CMs 474634 Specdb::CMs 474635 Specdb::CMs 474636 Specdb::NmrOneD 51722 Specdb::NmrOneD 51723 Specdb::NmrOneD 51724 Specdb::NmrOneD 51725 Specdb::NmrOneD 51726 Specdb::NmrOneD 51727 Specdb::NmrOneD 51728 Specdb::NmrOneD 51729 Specdb::NmrOneD 51730 Specdb::NmrOneD 51731 Specdb::NmrOneD 51732 Specdb::NmrOneD 51733 Specdb::NmrOneD 51734 Specdb::NmrOneD 51735 Specdb::NmrOneD 51736 Specdb::NmrOneD 51737 Specdb::NmrOneD 51738 Specdb::NmrOneD 51739 Specdb::NmrOneD 51740 Specdb::NmrOneD 51741 Specdb::MsMs 26111 Specdb::MsMs 26112 Specdb::MsMs 26113 Specdb::MsMs 32669 Specdb::MsMs 32670 Specdb::MsMs 32671 Specdb::MsMs 2730328 Specdb::MsMs 2730329 Specdb::MsMs 2730330 Specdb::MsMs 2975975 Specdb::MsMs 2975976 Specdb::MsMs 2975977 439450 388557 C01228 17633 GUANOSINE-5DP-3DP G4P 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 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 diphosphate > Adenosine monophosphate + Hydrogen ion + Guanosine 3',5'-bis(diphosphate) GDPPYPHOSKIN-RXN Water + Guanosine 3',5'-bis(diphosphate) <> Guanosine diphosphate + Pyrophosphate R00336 PPGPPSYN-RXN Guanosine 3'-diphosphate 5'-triphosphate + Water <> Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) R03409 PPPGPPHYDRO-RXN Guanosine 3'-diphosphate 5'-triphosphate + Water <> Guanosine 3',5'-bis(diphosphate) + Phosphate R03409 Adenosine triphosphate + Guanosine diphosphate > Adenosine monophosphate + Guanosine 3',5'-bis(diphosphate) GDPPYPHOSKIN-RXN Guanosine 3',5'-bis(diphosphate) + Water > Hydrogen ion + Pyrophosphate + Guanosine diphosphate PPGPPSYN-RXN Water + Guanosine 3'-diphosphate 5'-triphosphate > Hydrogen ion + Phosphate + Guanosine 3',5'-bis(diphosphate) PPPGPPHYDRO-RXN Guanosine 3'-diphosphate 5'-triphosphate + Water > Guanosine 3',5'-bis(diphosphate) + Inorganic phosphate Guanosine 3',5'-bis(diphosphate) + Water > Guanosine diphosphate + Pyrophosphate Guanosine 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)