2.02012-05-31 13:54:21 -06002015-06-03 15:54:11 -0600ECMDB01550M2MDB000417S-FormylglutathioneS-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-FormylglutathioneC11H17N3O7S335.334335.078720603(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acidS-formylglutathione50409-81-9N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=OInChI=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/s1FHXAGOICBFGEBF-BQBZGAKWSA-NSolidCytosollogp-2.87logs-1.97solubility3.62e+00 g/llogp-5.1pka_strongest_acidic1.76pka_strongest_basic9.31iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acidaverage_mass335.334mono_mass335.078720603smilesN[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=OformulaC11H17N3O7SinchiInChI=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/s1inchikeyFHXAGOICBFGEBF-BQBZGAKWSA-Npolar_surface_area175.89refractivity74.09polarizability31.17rotatable_bond_count11acceptor_count8donor_count5physiological_charge-1formal_charge0Glycolysis / Gluconeogenesisec00010Methane metabolismec00680Microbial metabolism in diverse environmentsec01120formaldehyde oxidation II (glutathione-dependent)PWY-1801Specdb::CMs3201Specdb::CMs38121Specdb::CMs156433Specdb::NmrOneD296015Specdb::NmrOneD296016Specdb::NmrOneD296017Specdb::NmrOneD296018Specdb::NmrOneD296019Specdb::NmrOneD296020Specdb::NmrOneD296021Specdb::NmrOneD296022Specdb::NmrOneD296023Specdb::NmrOneD296024Specdb::NmrOneD296025Specdb::NmrOneD296026Specdb::NmrOneD296027Specdb::NmrOneD296028Specdb::NmrOneD296029Specdb::NmrOneD296030Specdb::NmrOneD296031Specdb::NmrOneD296032Specdb::NmrOneD296033Specdb::NmrOneD296034Specdb::MsMs29564Specdb::MsMs29565Specdb::MsMs29566Specdb::MsMs36122Specdb::MsMs36123Specdb::MsMs36124Specdb::MsMs3042139Specdb::MsMs3042140Specdb::MsMs3042141Specdb::MsMs3098419Specdb::MsMs3098420Specdb::MsMs3098421HMDB01550488164320C0103116225CPD-548Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Koivusalo 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):105-9.2806555S-(hydroxymethyl)glutathione dehydrogenaseP25437FRMA_ECOLIfrmAhttp://ecmdb.ca/proteins/P25437.xmlS-formylglutathione hydrolase yeiGP33018SFGH2_ECOLIyeiGhttp://ecmdb.ca/proteins/P33018.xmlS-formylglutathione hydrolase frmBP51025SFGH1_ECOLIfrmBhttp://ecmdb.ca/proteins/P51025.xmlOligopeptide transport system permease protein oppBP0AFH2OPPB_ECOLIoppBhttp://ecmdb.ca/proteins/P0AFH2.xmlOligopeptide transport system permease protein oppCP0AFH6OPPC_ECOLIoppChttp://ecmdb.ca/proteins/P0AFH6.xmlOligopeptide transport system permease protein oppBP0AFH2OPPB_ECOLIoppBhttp://ecmdb.ca/proteins/P0AFH2.xmlOligopeptide transport system permease protein oppCP0AFH6OPPC_ECOLIoppChttp://ecmdb.ca/proteins/P0AFH6.xmlS-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ionR00527S-FORMYLGLUTATHIONE-HYDROLASE-RXNS-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADHR06983S-Formylglutathione + Water <> Formic acid + GlutathioneR00527NAD(P)<sup>+</sup> + S-(Hydroxymethyl)glutathione <> NAD(P)H + S-Formylglutathione + Hydrogen ionRXN-2962S-Formylglutathione + Water > Hydrogen ion + Formic acid + GlutathioneS-FORMYLGLUTATHIONE-HYDROLASE-RXNS-(Hydroxymethyl)glutathione + NAD(P)(+) > S-Formylglutathione + NAD(P)HS-Formylglutathione + Water > Glutathione + Formic acidS-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ionR06983 R07140 S-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ion