Basic information
- CAS
6803-19-6- Standard SMILES
N[C@@H](CCC(=O)N[C@@H](CSCc1ccc([N+](=O)[O-])cc1)C(=O)NCC(=O)O)C(=O)O- InChIKey
OAWORKDPTSAMBZ-STQMWFEESA-N- Molecular formula
- C17H22N4O8S
- Average molar mass
- 442.4 g/mol
- Monoisotopic mass
- 442.11583485
Overview
S-(4-nitrobenzyl)glutathione is an S-substituted glutathione in which the thiol hydrogen of glutathione is replaced by a 4-nitrobenzyl group. It is an organic sulfide, a S-substituted glutathione and a C-nitro compound.
Names & identifiers
- Preferred name
- L-gamma-glutamyl-S-((4-nitrophenyl)methyl)-L-cysteinylglycine
- IUPAC
- (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(4-nitrophenyl)methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
- English name
- S-(p-Nitrobenzyl)glutathione
- Molecular formula
- C17H22N4O8S
- Molecular weight
- 442.44
Names & synonyms
s-(p-nitrobenzyl)glutathione6803-19-6S-(4-Nitrobenzyl)glutathioneNSC 131122CHEBI:87407L-gamma-glutamyl-S-[(4-nitrophenyl)methyl]-L-cysteinylglycineL-gamma-Glutamyl-S-((4-nitrophenyl)methyl)-L-cysteinylglycineRefChem:180555(2S)-2-amino-4-(((1R)-1-((carboxymethyl)carbamoyl)-2-(((4-nitrophenyl)methyl)sulfanyl)ethyl)carbamoyl)butanoic acid(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(4-nitrophenyl)methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acidGTBs-(p-nitrobenzyl)-glutathione
Show more names
Glycine, L-γ-glutamyl-S-[(4-nitrophenyl)methyl]-L-cysteinyl-(2R)-2-[[(2S)-2-[[2-[[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)-4-oxanyl]oxy]-1-oxopropyl]amino]-3-methyl-1-oxobutyl]amino]-5-amino-5-oxopentanoic acid
orb1943531SCHEMBL2089788DB03686HY-148208CS-0616363NS00069538T81233L-gamma-glutamyl-S-(4-nitrobenzyl)-L-cysteinylglycine
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 230 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 12
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 634
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- storage temp.
- 2 · 2-8°C
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
Chemistry & industry
Pharmacology
Metabolism/Metabolites4-nitrobenzyl-glutathione is a known human metabolite of 4-nitrobenzyl chloride.
Applications
UsesS-(p-Nitrobenzyl)glutathione is a competitive glutathionase inhibitor. S-(p-Nitrobenzyl)glutathione is converted to the corresponding cysteine derivatives by rat kidney microsomes. S-(p-Nitrobenzyl)glutathione can be used for the research of metabolic breakdown of glutathione by the glutathionase system[1][2].
Suppliers1 total
TargetMol中国（陶术生物）15002134094 · [email protected]
Additional notes
DefinitionChEBI: A glutathione derivative in which the thiol hydrogen of glutathione is replaced by a 4-nitrobenzyl group.
Related reactions
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Compound notes
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