2.0 2012-05-31 14:22:19 -0600 2015-06-03 17:19:06 -0600 ECMDB20003 M2MDB000852 (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene (1r)-glutathionyl-(2r)-hydroxy-1,2-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) (1R, 2S)-1,2-dihydronaphthalene-1,2-diol (1R,2S)-1,2-dihydro-1,2-dihyroxynaphthalene (1R,2S)-1,2-dihydronaphthalene-1,2-diol (1R,2S)-naphthalene-1,2-dihydrodiol (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1R,2R)-2-Hydroxy-1,2-dihydronaphthalen-1-ylsulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid 3,4-dihydronaphthalene-3,4-diol <i>cis</i>-1,2-dihydronaphthalene-1,2-diol cis-1,2-Dihydronaphthalene-1,2-diol Cis-1,2-dihydroxy-1,2-dihydronaphthalene L-g-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine L-gamma-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine L-γ-Glutamyl-S-(1R,2R)-2-hydroxy-1,2-dihydro-1-naphthalenyl-L-cysteinylglycine C20H25N3O7S 451.493 451.141320859 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid [H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=O InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1 UWBZAZWPTVBBEL-OIPACUDHSA-N Cytoplasm Periplasm logp -1.59 ALOGPS logs -3.89 ALOGPS solubility 5.81e-02 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 1.96 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 451.493 ChemAxon mono_mass 451.141320859 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=O ChemAxon formula C20H25N3O7S ChemAxon inchi InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1 ChemAxon inchikey UWBZAZWPTVBBEL-OIPACUDHSA-N ChemAxon polar_surface_area 186.03 ChemAxon refractivity 114.1 ChemAxon polarizability 45 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism 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. PW000833 ec00480 Metabolic Specdb::CMs 34134 Specdb::CMs 48123 Specdb::CMs 156456 Specdb::CMs 156458 Specdb::CMs 156460 Specdb::CMs 156462 Specdb::CMs 170938 Specdb::CMs 280113 Specdb::NmrOneD 56952 Specdb::NmrOneD 56953 Specdb::NmrOneD 56954 Specdb::NmrOneD 56955 Specdb::NmrOneD 56956 Specdb::NmrOneD 56957 Specdb::NmrOneD 56958 Specdb::NmrOneD 56959 Specdb::NmrOneD 56960 Specdb::NmrOneD 56961 Specdb::NmrOneD 56962 Specdb::NmrOneD 56963 Specdb::NmrOneD 56964 Specdb::NmrOneD 56965 Specdb::NmrOneD 56966 Specdb::NmrOneD 56967 Specdb::NmrOneD 56968 Specdb::NmrOneD 56969 Specdb::NmrOneD 56970 Specdb::NmrOneD 56971 Specdb::MsMs 29474 Specdb::MsMs 29475 Specdb::MsMs 29476 Specdb::MsMs 36032 Specdb::MsMs 36033 Specdb::MsMs 36034 11954046 10128341 C14793 CIS-12-DIHYDRONAPHTHALENE-12-DIOL 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 (1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene R07003 Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene PW_R005206