2.02012-05-31 14:23:35 -06002015-06-03 17:19:09 -0600ECMDB20026M2MDB0008751-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene1-nitro-7-glutathionyl-8-hydroxy-7,8-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-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate(2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acidL-g-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycineL-gamma-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycineL-γ-Glutamyl-S-(1-hydroxy-8-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycineC20H24N4O9S496.491496.126399076(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-[(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C(C(=CC=C2)N(=O)=O)C1([H])O)C(O)=NCC(O)=O)C(O)=OInChI=1S/C20H24N4O9S/c21-11(20(30)31)5-7-15(25)23-12(19(29)22-8-16(26)27)9-34-14-6-4-10-2-1-3-13(24(32)33)17(10)18(14)28/h1-4,6,11-12,14,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t11-,12-,14?,18?/m0/s1FCTXJUPCCZHZHU-WXFCVCCESA-NCytoplasmPeriplasmlogp-1.47logs-4.09solubility4.03e-02 g/llogp-1.7pka_strongest_acidic1.83pka_strongest_basic9.54iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-8-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acidaverage_mass496.491mono_mass496.126399076smiles[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C(C(=CC=C2)N(=O)=O)C1([H])O)C(O)=NCC(O)=O)C(O)=OformulaC20H24N4O9SinchiInChI=1S/C20H24N4O9S/c21-11(20(30)31)5-7-15(25)23-12(19(29)22-8-16(26)27)9-34-14-6-4-10-2-1-3-13(24(32)33)17(10)18(14)28/h1-4,6,11-12,14,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t11-,12-,14?,18?/m0/s1inchikeyFCTXJUPCCZHZHU-WXFCVCCESA-Npolar_surface_area231.85refractivity121.43polarizability47.08rotatable_bond_count12acceptor_count12donor_count6physiological_charge-3formal_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::CMs34183Specdb::CMs48137Specdb::CMs134955Specdb::CMs142689Specdb::CMs167476Specdb::CMs167478Specdb::CMs167480Specdb::CMs167482Specdb::CMs167484Specdb::CMs280609Specdb::NmrOneD57252Specdb::NmrOneD57253Specdb::NmrOneD57254Specdb::NmrOneD57255Specdb::NmrOneD57256Specdb::NmrOneD57257Specdb::NmrOneD57258Specdb::NmrOneD57259Specdb::NmrOneD57260Specdb::NmrOneD57261Specdb::NmrOneD57262Specdb::NmrOneD57263Specdb::NmrOneD57264Specdb::NmrOneD57265Specdb::NmrOneD57266Specdb::NmrOneD57267Specdb::NmrOneD57268Specdb::NmrOneD57269Specdb::NmrOneD57270Specdb::NmrOneD57271Specdb::MsMs26084Specdb::MsMs26085Specdb::MsMs26086Specdb::MsMs32642Specdb::MsMs32643Specdb::MsMs326441195405510128350C14804Kanehisa, 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-7,8-oxide + Glutathione <> 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthaleneR07024Glutathione + 1-Nitronaphthalene-7,8-oxide > 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalenePW_R005412