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Identification
YMDB IDYMDB00320
NameS-Formylglutathione
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-Formylglutathione belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. S-Formylglutathione is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
  • S-Formylglutathione
  • N-(S-(Formyl-N-L-gamma-glutamyl)-L-cysteinyl)glycine
  • N-(S-(Formyl-N-L-g-glutamyl)-L-cysteinyl)glycine
  • N-(S-(Formyl-N-L-γ-glutamyl)-L-cysteinyl)glycine
CAS number50409-81-9
WeightAverage: 335.334
Monoisotopic: 335.078720603
InChI KeyFHXAGOICBFGEBF-BQBZGAKWSA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid
Traditional IUPAC NameS-formylglutathione
Chemical FormulaC11H17N3O7S
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])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.62 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity74.09 m³·mol⁻¹ChemAxon
Polarizability31.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Methane metabolismec00680 Map00680
SMPDB ReactionsNot Available
KEGG Reactions
Formaldehyde + NAD + GlutathioneS-Formylglutathione + NADH + hydron
S-Formylglutathione + waterGlutathione + Formic acid + hydron
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
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16225
HMDB IDHMDB01550
Pubchem Compound ID488
Kegg IDC01031
ChemSpider ID164320
FOODB IDFDB022685
Wikipedia IDNot Available
BioCyc IDCPD-548

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.
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde
Gene Name:
Not Available
Uniprot ID:
P40363
Molecular weight:
33934.0
Reactions
S-formylglutathione + H(2)O → glutathione + formate.
4-methylumbelliferyl acetate + H2O → 4-methylumbelliferone + acetate