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Identification
YMDB IDYMDB00172
NameS-(Hydroxymethyl)glutathione
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-(Hydroxymethyl)glutathione, also known as sergsh, 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. S-(Hydroxymethyl)glutathione is a very strong basic compound (based on its pKa). S-(Hydroxymethyl)glutathione exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • S-Hydroxymethyl-glutathione
  • S-Hydroxymethylglutathione
  • 2-Amino-4-[1-carboxymethyl-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACID
  • 2-Amino-4-[1-carboxymethyl-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrate
  • 2-Amino-4-[1-carboxymethyl-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrate
  • 2-Amino-4-[1-carboxymethyl-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acid
  • SerGSH
CAS number32260-87-0
WeightAverage: 337.349
Monoisotopic: 337.094370667
InChI KeyPIUSLWSYOYFRFR-BQBZGAKWSA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
Traditional IUPAC NameS-hydroxymethylglutathione
Chemical FormulaC11H19N3O7S
SMILES[H]OC(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H])C([H])([H])SC([H])([H])O[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Methane metabolismec00680 Map00680
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID48926
HMDB IDHMDB04662
Pubchem Compound ID447123
Kegg IDC14180
ChemSpider ID394301
FOODB IDFDB023393
Wikipedia IDNot Available
BioCyc IDS-HYDROXYMETHYLGLUTATHIONE

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Oxidizes long-chain alcohols and, in the presence of glutathione, is able to oxidize formaldehyde. Is responsible for yeast resistance to formaldehyde
Gene Name:
SFA1
Uniprot ID:
P32771
Molecular weight:
41041.69922
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) → S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) → an aldehyde or ketone + NADH.