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S-(Hydroxymethyl)glutathione (M2MDB000659)

Record Information
Version2.0
Creation Date2012-05-31 14:07:45 -0600
Update Date2015-06-03 15:54:50 -0600
Secondary Accession Numbers
  • ECMDB04662
Identification
Name:S-(Hydroxymethyl)glutathione
DescriptionS-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Glycine, N-(N-L-γ-S-(hydroxymethyl)-L-cysteinyl)-
  • GS-CH2-OH
  • GS-CH2-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
Chemical Formula:C11H19N3O7S
Weight:Average: 337.349
Monoisotopic: 337.094370667
InChI Key:PIUSLWSYOYFRFR-BQBZGAKWSA-N
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
CAS number:32260-87-0
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
Traditional IUPAC Name:S-hydroxymethylglutathione
SMILES:N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Sulfenyl compound
  • Carboxylic acid
  • Organopnictogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.27 g/LALOGPS
logP-3.2ALOGPS
logP-5.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area179.05 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity75.2 m³·mol⁻¹ChemAxon
Polarizability32.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
S-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADH
Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione
S-(Hydroxymethyl)glutathione <> Formaldehyde + Glutathione
NAD(P)<sup>+</sup> + S-(Hydroxymethyl)glutathione <> NAD(P)H + S-Formylglutathione + Hydrogen ion
S-(Hydroxymethyl)glutathione + NAD(P)(+) > S-Formylglutathione + NAD(P)H
S-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ion
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
  • formaldehyde oxidation II (glutathione-dependent) PWY-1801
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01po-6291000000-700a78b68cd3c72dace0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ukl-9410370000-758e7d3d20ef5e803fa9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-0195000000-0fb852c5aa71ebfacbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0570-4690000000-74c4fbcadf9e75cea5e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4920000000-a75d217a2989134725abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-5089000000-0963b985ed393a77403bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-5393000000-80626db3d68b3e84d33fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-9200000000-c770bc62700bd5b4872cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0029000000-9285be543171793a7f61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-1941000000-3b0ed9e0505deb83df54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9400000000-cdcded7632edf6274abfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-0193000000-b9ae6fff6991f7a74ac1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-9440000000-4e976999daadff083f1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9400000000-49e525bdebda32941d94View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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. Pubmed: 8931553
  • 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. Pubmed: 1731906
  • 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. Pubmed: 8494891
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • 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. Pubmed: 2806555
  • 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. Pubmed: 12782305
  • 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. Pubmed: 12484756
  • 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. Pubmed: 10978156
  • 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. Pubmed: 9018047
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID48926
HMDB IDHMDB04662
Pubchem Compound ID447123
Kegg IDC14180
ChemSpider ID394301
Wikipedia IDNot Available
BioCyc IDS-HYDROXYMETHYLGLUTATHIONE
EcoCyc IDS-HYDROXYMETHYLGLUTATHIONE
Ligand ExpoAHE

Enzymes

Protein Details
1. S-(hydroxymethyl)glutathione dehydrogenase
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Protein Details
2. Oligopeptide transport system permease protein oppB
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
Protein Details
3. Oligopeptide transport system permease protein oppC
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022

Transporters

Protein Details
1. Oligopeptide transport system permease protein oppB
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
Protein Details
2. Oligopeptide transport system permease protein oppC
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022