2.02012-05-31 14:23:28 -06002015-06-03 17:19:09 -0600ECMDB20024M2MDB0008731-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene1-nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene 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)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(2-Hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acidL-g-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycineL-gamma-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycineL-γ-Glutamyl-S-(2-hydroxy-5-nitro-1,2-dihydro-1-naphthalenyl)-L-cysteinylglycineC20H24N4O9S496.491496.126399076(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-[(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=C(C=CC1([H])O)C(=CC=C2)N(=O)=O)C(O)=NCC(O)=O)C(O)=OInChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(26)23-13(19(29)22-8-17(27)28)9-34-18-11-2-1-3-14(24(32)33)10(11)4-6-15(18)25/h1-4,6,12-13,15,18,25H,5,7-9,21H2,(H,22,29)(H,23,26)(H,27,28)(H,30,31)/t12-,13-,15?,18?/m0/s1ASZHPHJDCUIIBF-RJXQQRCHSA-NCytoplasmPeriplasmlogp-1.46logs-4.01solubility4.85e-02 g/llogp-1.8pka_strongest_acidic1.83pka_strongest_basic9.54iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-hydroxy-5-nitro-1,2-dihydronaphthalen-1-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acidaverage_mass496.491mono_mass496.126399076smiles[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=C(C=CC1([H])O)C(=CC=C2)N(=O)=O)C(O)=NCC(O)=O)C(O)=OformulaC20H24N4O9SinchiInChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(26)23-13(19(29)22-8-17(27)28)9-34-18-11-2-1-3-14(24(32)33)10(11)4-6-15(18)25/h1-4,6,12-13,15,18,25H,5,7-9,21H2,(H,22,29)(H,23,26)(H,27,28)(H,30,31)/t12-,13-,15?,18?/m0/s1inchikeyASZHPHJDCUIIBF-RJXQQRCHSA-Npolar_surface_area231.85refractivity121.43polarizability47.25rotatable_bond_count12acceptor_count12donor_count6physiological_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::CMs34260Specdb::CMs48134Specdb::CMs159211Specdb::CMs167456Specdb::CMs167458Specdb::CMs167460Specdb::CMs167463Specdb::CMs280607Specdb::NmrOneD57192Specdb::NmrOneD57193Specdb::NmrOneD57194Specdb::NmrOneD57195Specdb::NmrOneD57196Specdb::NmrOneD57197Specdb::NmrOneD57198Specdb::NmrOneD57199Specdb::NmrOneD57200Specdb::NmrOneD57201Specdb::NmrOneD57202Specdb::NmrOneD57203Specdb::NmrOneD57204Specdb::NmrOneD57205Specdb::NmrOneD57206Specdb::NmrOneD57207Specdb::NmrOneD57208Specdb::NmrOneD57209Specdb::NmrOneD57210Specdb::NmrOneD57211Specdb::MsMs25568Specdb::MsMs25569Specdb::MsMs25570Specdb::MsMs32126Specdb::MsMs32127Specdb::MsMs321281195405710128352C14806Kanehisa, 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.xml1-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthaleneR07026Glutathione + 1-Nitronaphthalene-5,6-oxide > 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalenePW_R005406