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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 23:23:11 UTC
Update Date2017-12-07 01:53:52 UTC
HMDB IDHMDB0004662
Secondary Accession Numbers
  • HMDB04662
Metabolite Identification
Common NameS-(Hydroxymethyl)glutathione
DescriptionS-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710 ). formaldehyde dehydrogenase (FDH; EC 1.2.1.1), a widely occurring enzyme catalyzes the oxidation of S-hydroxymethylglutathione into S-formylglutathione in the presence of NAD (PubMed ID 2806555).
Structure
Thumb
Synonyms
ValueSource
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACIDChEBI
S-HydroxymethylglutathioneChEBI
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrateGenerator
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrateGenerator
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acidGenerator
S-Hydroxymethyl-glutathioneHMDB
SerGSHMeSH
Chemical FormulaC11H19N3O7S
Average Molecular Weight337.349
Monoisotopic Molecular Weight337.094370667
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
Traditional NameS-hydroxymethylglutathione
CAS Registry Number32260-87-0
SMILES
N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
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
InChI KeyPIUSLWSYOYFRFR-BQBZGAKWSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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 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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023393
KNApSAcK IDNot Available
Chemspider ID394301
KEGG Compound IDC14180
BioCyc IDS-HYDROXYMETHYLGLUTATHIONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7068
PubChem Compound447123
PDB IDAHE
ChEBI ID48926
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gutheil WG, Holmquist B, Vallee BL: Purification, characterization, and partial sequence of the glutathione-dependent formaldehyde dehydrogenase from Escherichia coli: a class III alcohol dehydrogenase. Biochemistry. 1992 Jan 21;31(2):475-81. [PubMed:1731906 ]
  7. 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 ]
  8. 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 ]

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
S-(Hydroxymethyl)glutathione + NAD(P)(+) → S-Formylglutathione + NAD(P)Hdetails
S-(Hydroxymethyl)glutathione + NAD → S-Formylglutathione + NADH + Hydrogen Iondetails