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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-03-02 21:26:40 UTC
HMDB IDHMDB01550
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-Formylglutathione
DescriptionS-Formylglutathione is formed from the oxidation of S-hydroxymethylglutathione by the enzyme formaldehyde dehydrogenase (FDH; EC 1.2.1.1) in the presence of NAD (PubMed ID 2806555).
Structure
Thumb
Synonyms
ValueSource
N-(S-(Formyl-N-L-gamma-glutamyl)-L-cysteinyl)glycineChEBI
N-(S-(Formyl-N-L-g-glutamyl)-L-cysteinyl)glycineGenerator
N-(S-(Formyl-N-L-γ-glutamyl)-L-cysteinyl)glycineGenerator
Chemical FormulaC11H17N3O7S
Average Molecular Weight335.334
Monoisotopic Molecular Weight335.078720603
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid
Traditional NameS-formylglutathione
CAS Registry Number50409-81-9
SMILES
N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1
InChI KeyFHXAGOICBFGEBF-BQBZGAKWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • S-acylglutathione
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Amino acid
  • Carboxamide group
  • Carbothioic s-ester
  • Sulfenyl compound
  • Carboxylic acid
  • Thiocarboxylic acid or derivatives
  • Organosulfur compound
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Methane metabolism
  • Component of Pyruvate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility3.62 mg/mLALOGPS
logP-2.9ALOGPS
logP-5.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.76ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area175.89 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity74.09 m3·mol-1ChemAxon
Polarizability31.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mx-1195000000-93ac994a9ac61ae6c14cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fcc-4890000000-fbee4581354032da3ef0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zos-3920000000-743fa6d73cbb62d84f60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1159000000-214301d7e8c99ddf96fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-060r-3393000000-78df0617238659fc6300View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9300000000-0f76d8993b5fd4cd5b6bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022685
KNApSAcK IDNot Available
Chemspider ID164320
KEGG Compound IDC01031
BioCyc IDCPD-548
BiGG ID1485290
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01550
Metagene LinkHMDB01550
METLIN ID3469
PubChem Compound189122
PDB IDNot Available
ChEBI ID16225
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
Reactions
S-Formylglutathione + Water → Glutathione + Formic aciddetails
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