2.0 2012-07-30 14:55:12 -0600 2015-06-03 17:21:04 -0600 ECMDB21283 M2MDB001689 Selenodiglutathione Selenodiglutathione 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. Selenium compounds like selenite (SeO3(2-) may form a covalent adduct with glutathione (GSH) in the form of selenodiglutathione (GS-Se-SG), which is assumed to be important in the metabolism of selenium. GS-Se-SG to be a very efficient oxidant of reduced thioredoxin from E. coli [PMID:1569062] GSSeSG C20H32N6O12S2Se 691.59 692.068483726 (2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid (2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}selanyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid 33944-90-0 N[C@@H](CCC(=O)N[C@@H](CS[Se]SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O InChI=1S/C20H32N6O12S2Se/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-41-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 GJEZZQVPWMCGSB-BJDJZHNGSA-N Cytosol logp -3.47 ALOGPS logs -2.75 ALOGPS solubility 1.23e+00 g/l ALOGPS logp -11 ChemAxon pka_strongest_acidic 0.94 ChemAxon pka_strongest_basic 9.61 ChemAxon iupac (2S)-2-amino-4-{[(1R)-2-[({[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}selanyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid ChemAxon average_mass 691.59 ChemAxon mono_mass 692.068483726 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CS[Se]SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C20H32N6O12S2Se ChemAxon inchi InChI=1S/C20H32N6O12S2Se/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-41-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 ChemAxon inchikey GJEZZQVPWMCGSB-BJDJZHNGSA-N ChemAxon polar_surface_area 317.64 ChemAxon refractivity 149.77 ChemAxon polarizability 59.38 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 14 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Selenium metabolism The selenium metabolism begins with the introduction of selenate and selenite to the cytosol through a sulphate permease system. Once in the cell, selenate can be reduced to selenite through nitrate reductases A and Z. Selenite then interacts with glutathione and 2 hydrogen ions resulting in the release of 2 water molecules, a hydroxide molecule, a glutathione disulfide and a selenodiglutathione. The latter compound then reacts with NADPH+H resulting in the release of a NADP, a glutathione and a glutathioselenol. Glutathiolselenol can then be oxidize resulting in a a glutathiolselenol ion which can then interact with a water molecule resulting in a release of glutathion and selenium Glutathiolselenol can also react with NADPH and hydrogen ion resulting in a release of glutathione, NADP, a hydroxide molecule and a hydrogen selenide. This compound can react in a reversible reaction by being oxidized resulting in a hydrogen selenide ion . This compound can then be phosphorylated by interacting with an ATP and releasing a AMP, a phosphate and a selenophosphate. PW001894 Metabolic Specdb::CMs 1084195 Specdb::NmrOneD 300625 Specdb::NmrOneD 300626 Specdb::NmrOneD 300627 Specdb::NmrOneD 300628 Specdb::NmrOneD 300629 Specdb::NmrOneD 300630 Specdb::NmrOneD 300631 Specdb::NmrOneD 300632 Specdb::NmrOneD 300633 Specdb::NmrOneD 300634 Specdb::NmrOneD 300635 Specdb::NmrOneD 300636 Specdb::NmrOneD 300637 Specdb::NmrOneD 300638 Specdb::NmrOneD 300639 Specdb::NmrOneD 300640 Specdb::NmrOneD 300641 Specdb::NmrOneD 300642 Specdb::NmrOneD 300643 Specdb::NmrOneD 300644 Specdb::MsMs 29150 Specdb::MsMs 29151 Specdb::MsMs 29152 Specdb::MsMs 35708 Specdb::MsMs 35709 Specdb::MsMs 35710 Specdb::MsMs 3608860 Specdb::MsMs 3608861 Specdb::MsMs 3608862 Specdb::MsMs 3609742 Specdb::MsMs 3609743 Specdb::MsMs 3609744 108069 97171 C18870 CPD-13908 Bjornstedt, M., Kumar, S., Holmgren, A. (1992). "Selenodiglutathione is a highly efficient oxidant of reduced thioredoxin and a substrate for mammalian thioredoxin reductase." J Biol Chem 267:8030-8034. 1569062 Thioredoxin-1 P0AA25 THIO_ECOLI trxA http://ecmdb.ca/proteins/P0AA25.xml Selenite + Glutathione + Hydrogen ion > Selenodiglutathione + Glutathione disulfide + Water RXN-12864