S-(4-nitrobenzyl)glutathione

Identification

Name
S-(4-nitrobenzyl)glutathione
Accession Number
DB03686  (EXPT01653)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • S-(p-nitrobenzyl)glutathione
Categories
UNII
Not Available
CAS number
6803-19-6
Weight
Average: 442.444
Monoisotopic: 442.11583439
Chemical Formula
C17H22N4O8S
InChI Key
OAWORKDPTSAMBZ-STQMWFEESA-N
InChI
InChI=1S/C17H22N4O8S/c18-12(17(26)27)5-6-14(22)20-13(16(25)19-7-15(23)24)9-30-8-10-1-3-11(4-2-10)21(28)29/h1-4,12-13H,5-9,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t12-,13-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(4-nitrophenyl)methyl]sulfanyl}ethyl]carbamoyl}butanoic acid
SMILES
N[C@@H](CCC(=O)N[C@@H](CSCC1=CC=C(C=C1)[N+]([O-])=O)C(=O)NCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase PNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
97538
PubChem Substance
46508527
ChemSpider
88035
ChEBI
87407
ZINC
ZINC000003874914
PDBe Ligand
GTB
PDB Entries
1glq / 1gti / 1k0c / 2oac / 2oad / 2qmc / 2vo4 / 2ycd / 3o76 / 5agy

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-3ChemAxon
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area201.96 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity104.75 m3·mol-1ChemAxon
Polarizability43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5651
Blood Brain Barrier+0.6315
Caco-2 permeable-0.6368
P-glycoprotein substrateSubstrate0.5488
P-glycoprotein inhibitor INon-inhibitor0.9213
P-glycoprotein inhibitor IINon-inhibitor0.993
Renal organic cation transporterNon-inhibitor0.9343
CYP450 2C9 substrateNon-substrate0.8612
CYP450 2D6 substrateNon-substrate0.8187
CYP450 3A4 substrateNon-substrate0.6491
CYP450 1A2 substrateNon-inhibitor0.9007
CYP450 2C9 inhibitorNon-inhibitor0.7166
CYP450 2D6 inhibitorNon-inhibitor0.8768
CYP450 2C19 inhibitorNon-inhibitor0.7309
CYP450 3A4 inhibitorNon-inhibitor0.9371
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9653
Ames testAMES toxic0.7206
CarcinogenicityNon-carcinogens0.8103
BiodegradationNot ready biodegradable0.7901
Rat acute toxicity2.5268 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8633
hERG inhibition (predictor II)Non-inhibitor0.7716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Glutamine and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / Nitrobenzenes / Nitroaromatic compounds / Dicarboxylic acids and derivatives / N-acyl amines
show 13 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Cysteine or derivatives / Alpha-amino acid / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives
show 37 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
C-nitro compound, glutathione derivative, organic sulfide (CHEBI:87407)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 19:12

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