2.02012-05-31 14:22:29 -06002015-06-03 17:19:06 -0600ECMDB20006M2MDB000855(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-dihydrodiol3,4-dihydronaphthalene-3,4-diol<i>cis</i>-1,2-dihydronaphthalene-1,2-diolcis-1,2-Dihydronaphthalene-1,2-diolCis-1,2-dihydroxy-1,2-dihydronaphthaleneC20H25N3O7S451.493451.141320859(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)=OInChI=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/s1HBBDHJOSZGOTBV-XSWJXKHESA-NCytoplasmPeriplasmlogp-1.59logs-3.89solubility5.76e-02 g/llogp-1.7pka_strongest_acidic1.96pka_strongest_basic9.54iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acidaverage_mass451.493mono_mass451.141320859smiles[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)=OformulaC20H25N3O7SinchiInChI=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/s1inchikeyHBBDHJOSZGOTBV-XSWJXKHESA-Npolar_surface_area186.03refractivity114.1polarizability45.87rotatable_bond_count11acceptor_count10donor_count6physiological_charge-2formal_charge0Glutathione metabolismThe 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.
PW000833ec00480MetabolicSpecdb::CMs36471Specdb::CMs48125Specdb::CMs156355Specdb::CMs156476Specdb::CMs156478Specdb::CMs156480Specdb::CMs156482Specdb::CMs156484Specdb::CMs280115Specdb::NmrOneD56992Specdb::NmrOneD56993Specdb::NmrOneD56994Specdb::NmrOneD56995Specdb::NmrOneD56996Specdb::NmrOneD56997Specdb::NmrOneD56998Specdb::NmrOneD56999Specdb::NmrOneD57000Specdb::NmrOneD57001Specdb::NmrOneD57002Specdb::NmrOneD57003Specdb::NmrOneD57004Specdb::NmrOneD57005Specdb::NmrOneD57006Specdb::NmrOneD57007Specdb::NmrOneD57008Specdb::NmrOneD57009Specdb::NmrOneD57010Specdb::NmrOneD57011Specdb::MsMs28001Specdb::MsMs28002Specdb::MsMs28003Specdb::MsMs34559Specdb::MsMs34560Specdb::MsMs345611195404410128340C14792CIS-12-DIHYDRONAPHTHALENE-12-DIOLKanehisa, 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.xml(1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthaleneR07004Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalenePW_R005246