2.0 2012-05-31 13:54:21 -0600 2015-06-03 15:54:11 -0600 ECMDB01550 M2MDB000417 S-Formylglutathione S-Formylglutathione is formed from the oxidation of S-hydroxymethylglutathione by the enzyme formaldehyde dehydrogenase (FDH; EC 1.2.1.1) in the presence of NAD (PubMed ID 2806555) S-Formylglutathione C11H17N3O7S 335.334 335.078720603 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid S-formylglutathione 50409-81-9 N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=O InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 FHXAGOICBFGEBF-BQBZGAKWSA-N Solid Cytosol logp -2.87 ALOGPS logs -1.97 ALOGPS solubility 3.62e+00 g/l ALOGPS logp -5.1 ChemAxon pka_strongest_acidic 1.76 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid ChemAxon average_mass 335.334 ChemAxon mono_mass 335.078720603 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C11H17N3O7S ChemAxon inchi InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 ChemAxon inchikey FHXAGOICBFGEBF-BQBZGAKWSA-N ChemAxon polar_surface_area 175.89 ChemAxon refractivity 74.09 ChemAxon polarizability 31.17 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycolysis / Gluconeogenesis ec00010 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 formaldehyde oxidation II (glutathione-dependent) PWY-1801 Specdb::CMs 3201 Specdb::CMs 38121 Specdb::CMs 156433 Specdb::NmrOneD 296015 Specdb::NmrOneD 296016 Specdb::NmrOneD 296017 Specdb::NmrOneD 296018 Specdb::NmrOneD 296019 Specdb::NmrOneD 296020 Specdb::NmrOneD 296021 Specdb::NmrOneD 296022 Specdb::NmrOneD 296023 Specdb::NmrOneD 296024 Specdb::NmrOneD 296025 Specdb::NmrOneD 296026 Specdb::NmrOneD 296027 Specdb::NmrOneD 296028 Specdb::NmrOneD 296029 Specdb::NmrOneD 296030 Specdb::NmrOneD 296031 Specdb::NmrOneD 296032 Specdb::NmrOneD 296033 Specdb::NmrOneD 296034 Specdb::MsMs 29564 Specdb::MsMs 29565 Specdb::MsMs 29566 Specdb::MsMs 36122 Specdb::MsMs 36123 Specdb::MsMs 36124 Specdb::MsMs 3042139 Specdb::MsMs 3042140 Specdb::MsMs 3042141 Specdb::MsMs 3098419 Specdb::MsMs 3098420 Specdb::MsMs 3098421 HMDB01550 488 164320 C01031 16225 CPD-548 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Koivusalo M, Baumann M, Uotila L: Evidence for the identity of glutathione-dependent formaldehyde dehydrogenase and class III alcohol dehydrogenase. FEBS Lett. 1989 Oct 23;257(1):105-9. 2806555 S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml S-formylglutathione hydrolase yeiG P33018 SFGH2_ECOLI yeiG http://ecmdb.ca/proteins/P33018.xml S-formylglutathione hydrolase frmB P51025 SFGH1_ECOLI frmB http://ecmdb.ca/proteins/P51025.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml S-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ion R00527 S-FORMYLGLUTATHIONE-HYDROLASE-RXN S-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADH R06983 S-Formylglutathione + Water <> Formic acid + Glutathione R00527 NAD(P)⁺ + S-(Hydroxymethyl)glutathione <> NAD(P)H + S-Formylglutathione + Hydrogen ion RXN-2962 S-Formylglutathione + Water > Hydrogen ion + Formic acid + Glutathione S-FORMYLGLUTATHIONE-HYDROLASE-RXN S-(Hydroxymethyl)glutathione + NAD(P)(+) > S-Formylglutathione + NAD(P)H S-Formylglutathione + Water > Glutathione + Formic acid S-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ion R06983 R07140 S-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ion