2.0 2012-05-31 14:22:29 -0600 2015-06-03 17:19:06 -0600 ECMDB20006 M2MDB000855 (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene (1s)-hydroxy-(2s)-glutathionyl-1,2-dihydronaphthalene is a member of the chemical class known as 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. (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene (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 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 C20H25N3O7S 451.493 451.141320859 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid [H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@@]1([H])C=CC2=CC=CC=C2[C@]1([H])O)C(O)=NCC(O)=O)C(O)=O InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(H,29,30)/t13-,14-,15-,18-/m0/s1 HBBDHJOSZGOTBV-XSWJXKHESA-N Cytoplasm Periplasm logp -1.59 ALOGPS logs -3.89 ALOGPS solubility 5.76e-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-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-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])C=CC2=CC=CC=C2[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(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(H,29,30)/t13-,14-,15-,18-/m0/s1 ChemAxon inchikey HBBDHJOSZGOTBV-XSWJXKHESA-N ChemAxon polar_surface_area 186.03 ChemAxon refractivity 114.1 ChemAxon polarizability 45.87 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 36471 Specdb::CMs 48125 Specdb::CMs 156355 Specdb::CMs 156476 Specdb::CMs 156478 Specdb::CMs 156480 Specdb::CMs 156482 Specdb::CMs 156484 Specdb::CMs 280115 Specdb::NmrOneD 56992 Specdb::NmrOneD 56993 Specdb::NmrOneD 56994 Specdb::NmrOneD 56995 Specdb::NmrOneD 56996 Specdb::NmrOneD 56997 Specdb::NmrOneD 56998 Specdb::NmrOneD 56999 Specdb::NmrOneD 57000 Specdb::NmrOneD 57001 Specdb::NmrOneD 57002 Specdb::NmrOneD 57003 Specdb::NmrOneD 57004 Specdb::NmrOneD 57005 Specdb::NmrOneD 57006 Specdb::NmrOneD 57007 Specdb::NmrOneD 57008 Specdb::NmrOneD 57009 Specdb::NmrOneD 57010 Specdb::NmrOneD 57011 Specdb::MsMs 28001 Specdb::MsMs 28002 Specdb::MsMs 28003 Specdb::MsMs 34559 Specdb::MsMs 34560 Specdb::MsMs 34561 11954044 10128340 C14792 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 <> (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene R07004 Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene PW_R005246