2.0 2012-05-31 14:32:13 -0600 2015-06-03 17:19:29 -0600 ECMDB20189 M2MDB001035 S-(Formylmethyl)glutathione S-(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 acid L-g-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine L-gamma-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine L-γ-Glutamyl-S-(2-oxoethyl)-L-cysteinylglycine C12H19N3O7S 349.36 349.094370667 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-oxoethyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid S-(formylmethyl)glutathione [H][C@](N)(CCC(O)=N[C@@]([H])(CSCC=O)C(O)=NCC(O)=O)C(O)=O InChI=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/s1 VKLQBAQSSOPXGF-YUMQZZPRSA-N Cytoplasm Periplasm logp -2.59 ALOGPS logs -3.08 ALOGPS solubility 2.88e-01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.91 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-oxoethyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 349.36 ChemAxon mono_mass 349.094370667 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CSCC=O)C(O)=NCC(O)=O)C(O)=O ChemAxon formula C12H19N3O7S ChemAxon inchi InChI=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/s1 ChemAxon inchikey VKLQBAQSSOPXGF-YUMQZZPRSA-N ChemAxon polar_surface_area 182.87 ChemAxon refractivity 80.12 ChemAxon polarizability 33.85 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 10 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon glutathione metabolism II The 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 PW001927 Metabolic Specdb::CMs 35557 Specdb::CMs 48261 Specdb::CMs 152378 Specdb::NmrOneD 59492 Specdb::NmrOneD 59493 Specdb::NmrOneD 59494 Specdb::NmrOneD 59495 Specdb::NmrOneD 59496 Specdb::NmrOneD 59497 Specdb::NmrOneD 59498 Specdb::NmrOneD 59499 Specdb::NmrOneD 59500 Specdb::NmrOneD 59501 Specdb::NmrOneD 59502 Specdb::NmrOneD 59503 Specdb::NmrOneD 59504 Specdb::NmrOneD 59505 Specdb::NmrOneD 59506 Specdb::NmrOneD 59507 Specdb::NmrOneD 59508 Specdb::NmrOneD 59509 Specdb::NmrOneD 59510 Specdb::NmrOneD 59511 Specdb::MsMs 27824 Specdb::MsMs 27825 Specdb::MsMs 27826 Specdb::MsMs 34382 Specdb::MsMs 34383 Specdb::MsMs 34384 Specdb::MsMs 3225724 Specdb::MsMs 3225725 Specdb::MsMs 3225726 Specdb::MsMs 3225727 Specdb::MsMs 3225728 Specdb::MsMs 3225729 11954074 10128369 C14871 Kanehisa, 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. 22080510 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml 2-Bromoacetaldehyde + Glutathione <> S-(Formylmethyl)glutathione + Hydrobromic acid R07116 Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathione PW_R005505