NAV

S-benzylglutathione

Identification

Generic Name
S-benzylglutathione
DrugBank Accession Number
DB03602
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 397.446
Monoisotopic: 397.130756173
Chemical Formula
C17H23N3O6S
Synonyms
  • S-benzyl-glutathione
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULactoylglutathione lyaseNot AvailableHumans
UGlutathione S-transferase A1Not 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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group
show 28 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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)carbamoyl]ethyl]carbamoyl}butanoic acid
SMILES
[H]N([H])[C@@H](CCC(=O)N([H])[C@@H](CSCC1=CC=CC=C1)C(=O)N([H])CC(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
445707
PubChem Substance
46507389
ChemSpider
393264
ZINC
ZINC000003874918
PDBe Ligand
GSB
PDB Entries
1fro / 1guh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.116 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.9Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.81Chemaxon
pKa (Strongest Basic)9.31Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area158.82 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity98.43 m3·mol-1Chemaxon
Polarizability40.51 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/MSsplash10-0fba-1189000000-a353dce96d5e6212db05
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0c03-1690000000-557d815dd4da63d72cd0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gw0-7893000000-0d02b9a0a9f4d0d8a3f4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-0940000000-1a73b624390350887c0a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-4910000000-3ad02d709b6382dba374
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9100000000-97660ad28150db18fb25
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.56822
predicted
DeepCCS 1.0 (2019)
[M+H]+184.94975
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.33447
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lactoylglutathione lyase
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details2. Glutathione S-transferase A1
Kind
Protein
Organism
Humans
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

Details1. Glutathione S-transferase A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
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
References
  1. Sinning I, Kleywegt GJ, Cowan SW, Reinemer P, Dirr HW, Huber R, Gilliland GL, Armstrong RN, Ji X, Board PG, et al.: Structure determination and refinement of human alpha class glutathione transferase A1-1, and a comparison with the Mu and Pi class enzymes. J Mol Biol. 1993 Jul 5;232(1):192-212. doi: 10.1006/jmbi.1993.1376. [Article]
  2. Ramsay EE, Dilda PJ: Glutathione S-conjugates as prodrugs to target drug-resistant tumors. Front Pharmacol. 2014 Aug 11;5:181. doi: 10.3389/fphar.2014.00181. eCollection 2014. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52