S-(Hydroxymethyl)glutathione (PAMDB000659)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000659
Identification
Name: S-(Hydroxymethyl)glutathione
Description:S-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Chemical Formula: C11H19N3O7S
Average Molecular Weight: 337.349
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl peptides. These are oligo- and polypeptides consisting of any C-terminal alpha peptide having a gamma-glutamyl residue attached at the N alpha-position.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Gamma-glutamyl peptides
Alternative Parents
Substituents
  • Gamma-glutamyl alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.27 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity75.2 m3·mol-1ChemAxon
Polarizability32.23 Å3ChemAxon
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
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
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
• 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
Locus Tag:
PA3629
Molecular weight:
39.2 kDa
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.

Transporters