S-Benzyl-Glutathione

Identification

Name
S-Benzyl-Glutathione
Accession Number
DB03602  (EXPT01647)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 397.446
Monoisotopic: 397.130756173
Chemical Formula
C17H23N3O6S
InChI Key
XYJWEQWNNKNSFU-STQMWFEESA-N
InChI
InChI=1S/C17H23N3O6S/c18-12(17(25)26)6-7-14(21)20-13(16(24)19-8-15(22)23)10-27-9-11-4-2-1-3-5-11/h1-5,12-13H,6-10,18H2,(H,19,24)(H,20,21)(H,22,23)(H,25,26)/t12-,13-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-2-(benzylsulfanyl)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES
[H][[email protected]](N)(CCC(O)=N[[email protected]@]([H])(CSCC1=CC=CC=C1)C(O)=NCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULactoylglutathione lyaseNot AvailableHuman
UGlutathione S-transferase A1Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
445707
PubChem Substance
46507389
ChemSpider
393264
HET
GSB
PDB Entries
1fro / 1guh

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
Water Solubility0.0801 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.3ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.8 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.47 m3·mol-1ChemAxon
Polarizability40.68 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7306
Blood Brain Barrier+0.5795
Caco-2 permeable-0.7604
P-glycoprotein substrateSubstrate0.6015
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9965
Renal organic cation transporterNon-inhibitor0.903
CYP450 2C9 substrateNon-substrate0.8784
CYP450 2D6 substrateNon-substrate0.8239
CYP450 3A4 substrateNon-substrate0.7597
CYP450 1A2 substrateNon-inhibitor0.9572
CYP450 2C9 inhibitorNon-inhibitor0.9466
CYP450 2D6 inhibitorNon-inhibitor0.9145
CYP450 2C19 inhibitorNon-inhibitor0.9281
CYP450 3A4 inhibitorNon-inhibitor0.8931
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.993
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.9412
BiodegradationNot ready biodegradable0.6825
Rat acute toxicity1.8241 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.973
hERG inhibition (predictor II)Non-inhibitor0.9164
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 / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / N-acyl amines / Amino acids
show 9 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Alpha-amino acid amide / Cysteine or derivatives / Alpha-amino acid / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives
show 28 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B. Requ...
Gene Name
GLO1
Uniprot ID
Q04760
Uniprot Name
Lactoylglutathione lyase
Molecular Weight
20777.515 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:16