2.0 2012-05-31 13:51:01 -0600 2015-09-13 12:56:11 -0600 ECMDB01368 M2MDB000358 3-Mercaptopyruvic acid 3-Mercaptopyruvic acid is an intermediate in the metabolism of Cysteine and the production of hydrogen sulfide. It is a substrate for3-mercaptopyruvate sulfurtransferase which catalyzes the following reaction: H+ + 3-Mercaptopyruvic acid <=> Pyruvic acid + Hydrogen sulfide. β-mercaptopyruvate β-mercaptopyruvic acid β-thiopyruvate β-thiopyruvic acid 3-Mercapto-pyruvate 3-Mercapto-pyruvic acid 3-Mercaptopyruvate 3-Mercaptopyruvic acid b-3-mercapto-2-oxo-Propanoate b-3-mercapto-2-oxo-Propanoic acid b-Mercaptopyruvate b-Mercaptopyruvic acid b-Thiopyruvate b-Thiopyruvic acid Beta-3-Mercapto-2-oxo-propanoate Beta-3-Mercapto-2-oxo-propanoic acid Beta-Mercaptopyruvate Beta-Mercaptopyruvic acid Beta-Thiopyruvate Beta-Thiopyruvic acid Mercaptopyruvate Mercaptopyruvic acid MercPyr Thiopyruvate Thiopyruvic acid β-3-mercapto-2-oxo-Propanoate β-3-mercapto-2-oxo-Propanoic acid β-Mercaptopyruvate β-Mercaptopyruvic acid β-Thiopyruvate β-Thiopyruvic acid C3H4O3S 120.127 119.988114684 2-oxo-3-sulfanylpropanoic acid β-mercaptopyruvic acid 2464-23-5 OC(=O)C(=O)CS InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6) OJOLFAIGOXZBCI-UHFFFAOYSA-N Solid Cytosol logp 0.15 ALOGPS logs -1.12 ALOGPS solubility 9.09e+00 g/l ALOGPS logp 0.29 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -9.9 ChemAxon iupac 2-oxo-3-sulfanylpropanoic acid ChemAxon average_mass 120.127 ChemAxon mono_mass 119.988114684 ChemAxon smiles OC(=O)C(=O)CS ChemAxon formula C3H4O3S ChemAxon inchi InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6) ChemAxon inchikey OJOLFAIGOXZBCI-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 25.82 ChemAxon polarizability 10.15 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 Hydrogen Sulfide Biosynthesis I It has long been known that many bacteria are able to produce hydrogen sulfide [Barrett87]. However, the physiological role of H2S in nonsulfur bacteria was unknown. A recent report has now shown that production of H2S serves to defend cells from antibiotics by mitigating oxidative stress. This pathway is one of two pathways for hydrogen sulfide biosynthesis. Neither of the two activities have been shown biochemically for the E. coli enzymes. The function of AspC as a cysteine transaminase is hypothesized based on sequence similarity to mammalian enzymes. The function of SseA was determined based on the phenotype of an sseA null mutant, which does not produce hydrogen sulfide. PW002066 Metabolic hydrogen sulfide biosynthesis PWY0-1534 Specdb::CMs 12794 Specdb::CMs 38041 Specdb::CMs 134735 Specdb::CMs 142469 Specdb::NmrOneD 1689 Specdb::MsMs 1534 Specdb::MsMs 1535 Specdb::MsMs 1536 Specdb::MsMs 294094 Specdb::MsMs 294095 Specdb::MsMs 294096 Specdb::MsMs 334732 Specdb::MsMs 334733 Specdb::MsMs 334734 Specdb::MsMs 2256853 Specdb::MsMs 2258900 Specdb::MsMs 2259694 Specdb::MsMs 2677374 Specdb::MsMs 2677375 Specdb::MsMs 2677376 Specdb::MsMs 3028763 Specdb::MsMs 3028764 Specdb::MsMs 3028765 Specdb::NmrTwoD 1630 HMDB01368 98 96 C00957 16208 3-MERCAPTO-PYRUVATE 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 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 http://hmdb.ca/system/metabolites/msds/000/001/230/original/HMDB01368.pdf?1358462125 Aspartate aminotransferase P00509 AAT_ECOLI aspC http://ecmdb.ca/proteins/P00509.xml 3-mercaptopyruvate sulfurtransferase P31142 THTM_ECOLI sseA http://ecmdb.ca/proteins/P31142.xml Thiosulfate sulfurtransferase YnjE P78067 YNJE_ECOLI ynjE http://ecmdb.ca/proteins/P78067.xml Hydrogen cyanide + 3-Mercaptopyruvic acid + Cyanide <> Hydrogen ion + Pyruvic acid + Thiocyanate R03106 MERCAPYSTRANS-RXN L-Cysteine + alpha-Ketoglutarate <> 3-Mercaptopyruvic acid + DL-Glutamic acid R00896 3-Mercaptopyruvic acid + Sulfite <> Thiosulfate + Pyruvic acid R03105 Hydrogen cyanide + 3-Mercaptopyruvic acid <> Thiocyanate + Pyruvic acid R03106 MERCAPYSTRANS-RXN Hydrogen ion + 3-Mercaptopyruvic acid > Pyruvic acid + Hydrogen sulfide RXN0-6945 Oxoglutaric acid + L-Cysteine > L-Glutamate + 3-Mercaptopyruvic acid CYSTEINE-AMINOTRANSFERASE-RXN Hydrogen cyanide + 3-Mercaptopyruvic acid Hydrogen ion + Pyruvic acid + Thiocyanate MERCAPYSTRANS-RXN 3-Mercaptopyruvic acid + Hydrogen cyanide > Pyruvic acid + Thiocyanate 3-Mercaptopyruvic acid > Pyruvic acid + Hydrogen sulfide PW_R006040