2.0 2012-05-31 14:39:19 -0600 2015-06-03 17:19:47 -0600 ECMDB20324 M2MDB001158 ppGp Ppgp belongs to the class of Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. (inferred from compound structure)<br/><br/>Unusual guanosine nucleotides guanosine 5'-diphosphate 3'-diphosphate (ppGpp, also known as MSI) and guanosine 5'-diphosphate 3'-monophosphate (ppGp, also known as MSIII) accumulate to high concentrations in wild-type cells of Escherichia coli during amino acid starvation. (PMID 6117328) Guanosine 5'-diphosphate-3'-monophosphate Guanosine 5'-diphosphoric acid-3'-monophosphoric acid GUANOSINE-3'-MONOPHOSPHATE-5'-DIPHOSPHATE GUANOSINE-3'-monophosphoric acid-5'-diphosphoric acid MsIII C10H16N5O14P3 523.1804 522.990659781 {[(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}phosphonic acid [(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-3-yl]oxyphosphonic acid 58902-76-4 [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)=O InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(28-30(18,19)20)3(27-9)1-26-32(24,25)29-31(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 HEYSFDAMRDTCJM-UUOKFMHZSA-N Cytoplasm Periplasm logp -1.13 ALOGPS logs -1.86 ALOGPS solubility 7.23e+00 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic 4.89 ChemAxon iupac {[(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}phosphonic acid ChemAxon average_mass 523.1804 ChemAxon mono_mass 522.990659781 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)=O ChemAxon formula C10H16N5O14P3 ChemAxon inchi InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(28-30(18,19)20)3(27-9)1-26-32(24,25)29-31(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey HEYSFDAMRDTCJM-UUOKFMHZSA-N ChemAxon polar_surface_area 295.8 ChemAxon refractivity 107.82 ChemAxon polarizability 40.1 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1083433 Specdb::NmrOneD 268268 Specdb::NmrOneD 268269 Specdb::NmrOneD 268270 Specdb::NmrOneD 268271 Specdb::NmrOneD 268272 Specdb::NmrOneD 268273 Specdb::NmrOneD 268274 Specdb::NmrOneD 268275 Specdb::NmrOneD 268276 Specdb::NmrOneD 268277 Specdb::NmrOneD 268278 Specdb::NmrOneD 268279 Specdb::NmrOneD 268280 Specdb::NmrOneD 268281 Specdb::NmrOneD 268282 Specdb::NmrOneD 268283 Specdb::NmrOneD 268284 Specdb::NmrOneD 268285 Specdb::NmrOneD 268286 Specdb::NmrOneD 268287 Specdb::MsMs 24896 Specdb::MsMs 24897 Specdb::MsMs 24898 Specdb::MsMs 31454 Specdb::MsMs 31455 Specdb::MsMs 31456 188347 CPD0-1055 G3D 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