2.0 2012-05-31 14:07:45 -0600 2015-06-03 15:54:50 -0600 ECMDB04662 M2MDB000659 S-(Hydroxymethyl)glutathione S-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710) Glycine, N-(N-L-γ-S-(hydroxymethyl)-L-cysteinyl)- GS-CH2-OH GS-CH<SUB>2</SUB>-OH HM-GSH HMGSH Hydroxymethylglutathione N-(N-L-g-S-(Hydroxymethyl)-L-cysteinyl)-glycine N-(N-L-gamma-S-(Hydroxymethyl)-L-cysteinyl)-Glycine N-(N-L-γ-S-(Hydroxymethyl)-L-cysteinyl)-glycine S-Hydroxymethyl-glutathione S-Hydroxymethylglutathione C11H19N3O7S 337.349 337.094370667 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid S-hydroxymethylglutathione 32260-87-0 N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 PIUSLWSYOYFRFR-BQBZGAKWSA-N Solid Cytosol logp -3.16 ALOGPS logs -1.81 ALOGPS solubility 5.27e+00 g/l ALOGPS logp -5.5 ChemAxon pka_strongest_acidic 1.79 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid ChemAxon average_mass 337.349 ChemAxon mono_mass 337.094370667 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C11H19N3O7S ChemAxon inchi InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 ChemAxon inchikey PIUSLWSYOYFRFR-BQBZGAKWSA-N ChemAxon polar_surface_area 179.05 ChemAxon refractivity 75.2 ChemAxon polarizability 32.23 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 8 ChemAxon donor_count 6 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 3245 Specdb::CMs 38778 Specdb::CMs 156971 Specdb::NmrOneD 149920 Specdb::NmrOneD 149921 Specdb::NmrOneD 149922 Specdb::NmrOneD 149923 Specdb::NmrOneD 149924 Specdb::NmrOneD 149925 Specdb::NmrOneD 149926 Specdb::NmrOneD 149927 Specdb::NmrOneD 149928 Specdb::NmrOneD 149929 Specdb::NmrOneD 149930 Specdb::NmrOneD 149931 Specdb::NmrOneD 149932 Specdb::NmrOneD 149933 Specdb::NmrOneD 149934 Specdb::NmrOneD 149935 Specdb::NmrOneD 149936 Specdb::NmrOneD 149937 Specdb::NmrOneD 149938 Specdb::NmrOneD 149939 Specdb::MsMs 26051 Specdb::MsMs 26052 Specdb::MsMs 26053 Specdb::MsMs 32609 Specdb::MsMs 32610 Specdb::MsMs 32611 Specdb::MsMs 2730931 Specdb::MsMs 2730932 Specdb::MsMs 2730933 Specdb::MsMs 2975018 Specdb::MsMs 2975019 Specdb::MsMs 2975020 HMDB04662 447123 394301 C14180 S-HYDROXYMETHYLGLUTATHIONE AHE Gutheil, W. G., Holmquist, B., Vallee, B. L. (1992). "Purification, characterization, and partial sequence of the glutathione-dependent formaldehyde dehydrogenase from Escherichia coli: a class III alcohol dehydrogenase." Biochemistry 31:475-481. 1731906 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 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 Holmquist B, Moulis JM, Engeland K, Vallee BL: Role of arginine 115 in fatty acid activation and formaldehyde dehydrogenase activity of human class III alcohol dehydrogenase. Biochemistry. 1993 May 18;32(19):5139-44. 8494891 Yang ZN, Bosron WF, Hurley TD: Structure of human chi chi alcohol dehydrogenase: a glutathione-dependent formaldehyde dehydrogenase. J Mol Biol. 1997 Jan 24;265(3):330-43. 9018047 Sanghani PC, Stone CL, Ray BD, Pindel EV, Hurley TD, Bosron WF: Kinetic mechanism of human glutathione-dependent formaldehyde dehydrogenase. Biochemistry. 2000 Sep 5;39(35):10720-9. 10978156 Lee SL, Wang MF, Lee AI, Yin SJ: The metabolic role of human ADH3 functioning as ethanol dehydrogenase. FEBS Lett. 2003 Jun 5;544(1-3):143-7. 12782305 Danielsson O, Shafqat J, Estonius M, el-Ahmad M, Jornvall H: Isozyme multiplicity with anomalous dimer patterns in a class III alcohol dehydrogenase. Effects on the activity and quaternary structure of residue exchanges at "nonfunctional" sites in a native protein. Biochemistry. 1996 Nov 19;35(46):14561-8. 8931553 Sanghani PC, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structural changes associated with ternary complex formation. Biochemistry. 2002 Dec 24;41(51):15189-94. 12484756 S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.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-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADH R06983 Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione RXN-2961 S-(Hydroxymethyl)glutathione <> Formaldehyde + Glutathione RXN-2961 NAD(P)<sup>+</sup> + S-(Hydroxymethyl)glutathione <> NAD(P)H + S-Formylglutathione + Hydrogen ion RXN-2962 S-(Hydroxymethyl)glutathione + NAD(P)(+) > S-Formylglutathione + NAD(P)H S-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ion R06983 R07140