oxiglutatione   Click here for help

GtoPdb Ligand ID: 6835

Synonyms: glutathione disulfide | Navstel®
Approved drug PDB Ligand
oxiglutatione is an approved drug (FDA (2008)-see Comment)
Compound class: Synthetic organic
Comment: The approved drug in this case is Navstel®. Oxiglutatione is listed as the active ingredient. Inhibits glutathione reductase. Note that the chemical structure given by DrugBank has opposite stereochemistry to the INN record and the ChEMBL ligand mapped here.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 10
Rotatable bonds 25
Topological polar surface area 368.24
Molecular weight 612.15
XLogP -6.62
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES O=C(NC(C(=O)NCC(=O)O)CSSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)CCC(C(=O)O)N
Isomeric SMILES N[C@@H](CCC(=O)N[C@@H](CSSC[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 InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(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
InChI Key YPZRWBKMTBYPTK-BJDJZHNGSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2008)-see Comment)
IUPAC Name Click here for help
(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
International Nonproprietary Names Click here for help
INN number INN
6698 oxiglutatione
Synonyms Click here for help
glutathione disulfide | Navstel®
Database Links Click here for help
CAS Registry No. 27025-41-8
ChEMBL Ligand CHEMBL1372
DrugBank Ligand DB03310
DrugCentral Ligand 5130
GtoPdb PubChem SID 178103441
PubChem CID 65359
RCSB PDB Ligand GDS
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SynPHARM 78934 (in complex with glutathione-disulfide reductase)
Wikipedia Oxiglutatione