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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Search Google for chemical match using the InChIKey YPZRWBKMTBYPTK-BJDJZHNGSA-N
Search Google for chemicals with the same backbone YPZRWBKMTBYPTK
Search PubMed clinical trials oxiglutatione
Search PubMed titles oxiglutatione
Search PubMed titles/abstracts oxiglutatione
SynPHARM 78934 (in complex with glutathione-disulfide reductase)
UniChem Compound Search for chemical match using the InChIKey YPZRWBKMTBYPTK-BJDJZHNGSA-N
UniChem Connectivity Search for chemical match using the InChIKey YPZRWBKMTBYPTK-BJDJZHNGSA-N
Wikipedia Oxiglutatione