Identification
NameS-Benzyl-Glutathione
Accession NumberDB03602  (EXPT01647)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 397.446
Monoisotopic: 397.130756173
Chemical FormulaC17H23N3O6S
InChI KeyXYJWEQWNNKNSFU-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][C@](N)(CCC(O)=N[C@@]([H])(CSCC1=CC=CC=C1)C(O)=NCC(O)=O)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Lactoylglutathione lyaseProteinunknownNot AvailableHumanQ04760 details
Glutathione S-transferase A1ProteinunknownNot AvailableHumanP08263 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentOligopeptides
Alternative ParentsGamma-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
SubstituentsAlpha-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
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot 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. Required for normal osteoclastogenesis.
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 August 02, 2017 16:53