2.0 2012-05-31 13:55:22 -0600 2015-06-03 15:54:14 -0600 ECMDB02069 M2MDB000435 Pyrazinic acid Pyrazinic acid is a member of the chemical class known as Pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazinamide (PZA), an analog of nicotinamide, is a prodrug that requires conversion to the bactericidal compound pyrazinoic acid (POA) by the bacterial pyrazinamidase (PZase) activity of nicotinamidase to show activity against Mycobacterium tuberculosis. (PMID 10049264) 2-Pyrazine carboxylate 2-Pyrazine carboxylic acid 2-Pyrazinecarboxylate 2-Pyrazinecarboxylic 2-Pyrazinecarboxylic acid 2-Pyrazinoate 2-Pyrazinoic acid Paradiazinecarboxylate Paradiazinecarboxylic acid Piazinecarboxylate Piazinecarboxylic acid Pyrazinate Pyrazine-2-carboxylate Pyrazine-2-carboxylic acid Pyrazinecarboxylate Pyrazinecarboxylic acid Pyrazinemonocarboxylate Pyrazinemonocarboxylic acid Pyrazinoate Pyrazinoic acid Pyrazoate Pyrazoic acid C5H4N2O2 124.0975 124.027277382 pyrazine-2-carboxylic acid pyrazinoic acid 98-97-5 OC(=O)C1=CN=CC=N1 InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9) NIPZZXUFJPQHNH-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.52 ALOGPS logs -0.61 ALOGPS solubility 3.05e+01 g/l ALOGPS melting_point 225 oC logp -0.42 ChemAxon pka_strongest_acidic 3.44 ChemAxon pka_strongest_basic -0.96 ChemAxon iupac pyrazine-2-carboxylic acid ChemAxon average_mass 124.0975 ChemAxon mono_mass 124.027277382 ChemAxon smiles OC(=O)C1=CN=CC=N1 ChemAxon formula C5H4N2O2 ChemAxon inchi InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9) ChemAxon inchikey NIPZZXUFJPQHNH-UHFFFAOYSA-N ChemAxon polar_surface_area 63.08 ChemAxon refractivity 28.63 ChemAxon polarizability 10.72 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 27716 Specdb::CMs 36478 Specdb::CMs 47874 Specdb::CMs 102336 Specdb::CMs 163572 Specdb::NmrOneD 52322 Specdb::NmrOneD 52323 Specdb::NmrOneD 52324 Specdb::NmrOneD 52325 Specdb::NmrOneD 52326 Specdb::NmrOneD 52327 Specdb::NmrOneD 52328 Specdb::NmrOneD 52329 Specdb::NmrOneD 52330 Specdb::NmrOneD 52331 Specdb::NmrOneD 52332 Specdb::NmrOneD 52333 Specdb::NmrOneD 52334 Specdb::NmrOneD 52335 Specdb::NmrOneD 52336 Specdb::NmrOneD 52337 Specdb::NmrOneD 52338 Specdb::NmrOneD 52339 Specdb::NmrOneD 52340 Specdb::NmrOneD 52341 Specdb::MsMs 23639 Specdb::MsMs 23640 Specdb::MsMs 23641 Specdb::MsMs 30437 Specdb::MsMs 30438 Specdb::MsMs 30439 Specdb::MsMs 2274405 Specdb::MsMs 2274406 Specdb::MsMs 2274407 Specdb::MsMs 3091834 Specdb::MsMs 3091835 Specdb::MsMs 3091836 1047 1018 C19915 PYRAZINOIC-ACID VGL 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Sun, Z., Zhang, Y. (1999). "Reduced pyrazinamidase activity and the natural resistance of Mycobacterium kansasii to the antituberculosis drug pyrazinamide." Antimicrob Agents Chemother 43:537-542. 10049264 Pyrazinamidase/nicotinamidase P21369 PNCA_ECOLI pncA http://ecmdb.ca/proteins/P21369.xml + Water Hydrogen ion + Pyrazinic acid + Ammonia PYRAZIN-RXN