2.02012-05-31 14:32:13 -06002015-06-03 17:19:29 -0600ECMDB20189M2MDB001035S-(Formylmethyl)glutathioneS-(formylmethyl)glutathione belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulfanyl)propan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-oxoethylsulfanyl)propan-2-ylamino-5-oxopentanoic acid(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulphanyl)propan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-1-oxo-3-(2-Oxoethylsulphanyl)propan-2-ylamino-5-oxopentanoic acidL-g-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycineL-gamma-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycineL-γ-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycineC12H19N3O7S349.36349.094370667(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-oxoethyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acidS-(formylmethyl)glutathione[H][C@](N)(CCC(O)=N[C@@]([H])(CSCC=O)C(O)=NCC(O)=O)C(O)=OInChI=1S/C12H19N3O7S/c13-7(12(21)22)1-2-9(17)15-8(6-23-4-3-16)11(20)14-5-10(18)19/h3,7-8H,1-2,4-6,13H2,(H,14,20)(H,15,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1VKLQBAQSSOPXGF-YUMQZZPRSA-NCytoplasmPeriplasmlogp-2.59logs-3.08solubility2.88e-01 g/llogp-3.9pka_strongest_acidic1.91pka_strongest_basic9.54iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-oxoethyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acidaverage_mass349.36mono_mass349.094370667smiles[H][C@](N)(CCC(O)=N[C@@]([H])(CSCC=O)C(O)=NCC(O)=O)C(O)=OformulaC12H19N3O7SinchiInChI=1S/C12H19N3O7S/c13-7(12(21)22)1-2-9(17)15-8(6-23-4-3-16)11(20)14-5-10(18)19/h3,7-8H,1-2,4-6,13H2,(H,14,20)(H,15,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1inchikeyVKLQBAQSSOPXGF-YUMQZZPRSA-Npolar_surface_area182.87refractivity80.12polarizability33.85rotatable_bond_count12acceptor_count10donor_count5physiological_charge-2formal_charge0glutathione metabolism IIThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene through a glutathione S-transferase
PW001927MetabolicSpecdb::CMs35557Specdb::CMs48261Specdb::CMs152378Specdb::NmrOneD59492Specdb::NmrOneD59493Specdb::NmrOneD59494Specdb::NmrOneD59495Specdb::NmrOneD59496Specdb::NmrOneD59497Specdb::NmrOneD59498Specdb::NmrOneD59499Specdb::NmrOneD59500Specdb::NmrOneD59501Specdb::NmrOneD59502Specdb::NmrOneD59503Specdb::NmrOneD59504Specdb::NmrOneD59505Specdb::NmrOneD59506Specdb::NmrOneD59507Specdb::NmrOneD59508Specdb::NmrOneD59509Specdb::NmrOneD59510Specdb::NmrOneD59511Specdb::MsMs27824Specdb::MsMs27825Specdb::MsMs27826Specdb::MsMs34382Specdb::MsMs34383Specdb::MsMs34384Specdb::MsMs3225724Specdb::MsMs3225725Specdb::MsMs3225726Specdb::MsMs3225727Specdb::MsMs3225728Specdb::MsMs32257291195407410128369C14871Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Glutathione S-transferaseP0A9D2GST_ECOLIgsthttp://ecmdb.ca/proteins/P0A9D2.xmlGSH-dependent disulfide bond oxidoreductaseP77526yfcGhttp://ecmdb.ca/proteins/P77526.xml2-Bromoacetaldehyde + Glutathione <> S-(Formylmethyl)glutathione + Hydrobromic acidR07116Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathionePW_R005505