2.0 2012-05-31 14:24:02 -0600 2015-06-03 17:19:10 -0600 ECMDB20035 M2MDB000884 2-(S-Glutathionyl)acetyl glutathione 2-(s-glutathionyl)acetyl 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)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulfanyl-2-oxoethylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-oxopropylsulfanyl-2-oxoethylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulphanyl-2-oxoethylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-3-2-(2R)-2-(4S)-4-amino-4-carboxybutanoylamino-3-(carboxymethylamino)-3-Oxopropylsulphanyl-2-oxoethylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid (2S,7R,14R,19S)-2,19-diamino-7,14-Bis(carboxymethyl)carbamoyl-5,10,16-trioxo-9,12-dithia-6,15-diazaicosane-1,20-dioate (non-preferred name) (2S,7R,14R,19S)-2,19-Diamino-7,14-bis(carboxymethyl)carbamoyl-5,10,16-trioxo-9,12-dithia-6,15-diazaicosane-1,20-dioic acid (non-preferred name) C22H34N6O13S2 654.668 654.162526584 (2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}acetyl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid (2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}acetyl)sulfanyl]-1-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid [H][C@](N)(CCC(O)=N[C@@]([H])(CSCC(=O)SC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=O)C(O)=NCC(O)=O)C(O)=O InChI=1S/C22H34N6O13S2/c23-10(21(38)39)1-3-14(29)27-12(19(36)25-5-16(31)32)7-42-9-18(35)43-8-13(20(37)26-6-17(33)34)28-15(30)4-2-11(24)22(40)41/h10-13H,1-9,23-24H2,(H,25,36)(H,26,37)(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,38,39)(H,40,41)/t10-,11-,12-,13-/m0/s1 QEJUVDVAWJBQIG-CYDGBPFRSA-N Cytoplasm Periplasm logp -3.21 ALOGPS logs -3.84 ALOGPS solubility 9.54e-02 g/l ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 2.99 ChemAxon iupac (2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}acetyl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 654.668 ChemAxon mono_mass 654.162526584 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CSCC(=O)SC[C@]([H])(N=C(O)CC[C@]([H])(N)C(O)=O)C(O)=NCC(O)=O)C(O)=NCC(O)=O)C(O)=O ChemAxon formula C22H34N6O13S2 ChemAxon inchi InChI=1S/C22H34N6O13S2/c23-10(21(38)39)1-3-14(29)27-12(19(36)25-5-16(31)32)7-42-9-18(35)43-8-13(20(37)26-6-17(33)34)28-15(30)4-2-11(24)22(40)41/h10-13H,1-9,23-24H2,(H,25,36)(H,26,37)(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,38,39)(H,40,41)/t10-,11-,12-,13-/m0/s1 ChemAxon inchikey QEJUVDVAWJBQIG-CYDGBPFRSA-N ChemAxon polar_surface_area 348.67 ChemAxon refractivity 148.02 ChemAxon polarizability 63.02 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 19 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon glutathione metabolism III 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. PW002018 Metabolic Specdb::CMs 35953 Specdb::CMs 650772 Specdb::CMs 650773 Specdb::CMs 650774 Specdb::CMs 650775 Specdb::CMs 650776 Specdb::CMs 650777 Specdb::CMs 650778 Specdb::CMs 650779 Specdb::CMs 650780 Specdb::CMs 650781 Specdb::CMs 650782 Specdb::CMs 650783 Specdb::CMs 650784 Specdb::CMs 650785 Specdb::CMs 650786 Specdb::CMs 650787 Specdb::CMs 650788 Specdb::CMs 650789 Specdb::CMs 650790 Specdb::CMs 650791 Specdb::CMs 650792 Specdb::CMs 650793 Specdb::CMs 650794 Specdb::CMs 650795 Specdb::NmrOneD 57392 Specdb::NmrOneD 57393 Specdb::NmrOneD 57394 Specdb::NmrOneD 57395 Specdb::NmrOneD 57396 Specdb::NmrOneD 57397 Specdb::NmrOneD 57398 Specdb::NmrOneD 57399 Specdb::NmrOneD 57400 Specdb::NmrOneD 57401 Specdb::NmrOneD 57402 Specdb::NmrOneD 57403 Specdb::NmrOneD 57404 Specdb::NmrOneD 57405 Specdb::NmrOneD 57406 Specdb::NmrOneD 57407 Specdb::NmrOneD 57408 Specdb::NmrOneD 57409 Specdb::NmrOneD 57410 Specdb::NmrOneD 57411 Specdb::MsMs 28766 Specdb::MsMs 28767 Specdb::MsMs 28768 Specdb::MsMs 35324 Specdb::MsMs 35325 Specdb::MsMs 35326 Specdb::MsMs 3225061 Specdb::MsMs 3225062 Specdb::MsMs 3225063 Specdb::MsMs 3225946 Specdb::MsMs 3225947 Specdb::MsMs 3225948 0 10128367 C14863 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-(S-Glutathionyl)acetyl chloride + Glutathione <> 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid R07094 Glutathione + 2-(S-Glutathionyl)acetyl chloride > 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid PW_R005816