Showing Metabocard for S-formylglutathione (BASm0002886)

Common NameS-formylglutathione
DescriptionS-Formylglutathione, also known as L-gamma-glutamyl-S-formyl-L-cysteinylglycine, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of three to ten alpha-amino acids joined by peptide bonds. S-Formylglutathione is a very strong basic compound (based on its pKa). S-Formylglutathione exists in all living species, ranging from bacteria to humans. Outside of the human body, S-formylglutathione has been detected, but not quantified in, several different foods, such as sweet marjorams, muscadine grapes, amaranths, lemon verbena, and garden tomato. This could make S-formylglutathione a potential biomarker for the consumption of these foods. S-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 (PMID: 2806555 ).
Structure
Molecular FormulaC11H17N3O7S
Average Mass335.33400
Monoisotopic Mass335.07872
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid
Traditional Name(2s)-2-amino-4-{[(1r)-1-(carboxymethylcarbamoyl)-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid
CAS Registry Number50409-81-9
SMILES[NH3+][C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(=O)[O-])C(=O)[O-]
InChI IdentifierInChI=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
CHEBI IDCHEBI:57688
HMDB IDHMDB0001550
StateSolid
Water Solubility3.62e+00 g/l
logP-2.87
logS-1.97
pKa (Strongest Acidic)1.76
pKa (Strongest Basic)9.31
Hydrogen Acceptor Count8
Hydrogen Donor Count5
Polar Surface Area175.89 Ų
Rotatable Bond Count11
Physiological Charge-1
Formal Charge0
Refractivity74.09 m³·mol⁻¹
Polarizability31.17

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT