Ezatiostat - ≥99% , CAS No.168682-53-9

CAS: 168682-53-9 Cat. No.: E414463 Molecular Weight: 529.65

GRADE & PURITY ≥99%

Synonyms

Q27095680 | NCGC00263221-01 | NCGC00263221-05 | TER 199 | Ezatiostat | Ezatiostat [INN] | Ezatiostat(TER199; TLK199) | SCHEMBL420400 | Glycine, L-gamma-glutamyl-S-(phenylmethyl)-L-cysteinyl-2-phenyl-, diethyl ester, (2R)- | J-690234 | TLK199 | TLK-199 | e

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Ezatiostat Ezatiostat (TER199, TLK199, Telintra), a tripeptide analog of glutathione, is a peptidomimetic inhibitor of Glutathione S-transferase P1-1 (GSTP1-1) . Ezatiostat activates c-Jun NH2 terminal kinase (JNK1) and ERK1/ERK2 and induces apoptosis .

Targets

GSTP1-1 ; JNK1 ; ERK1/ERK2

In vitro

Selection of a resistant clone of an HL60 tumor cell line through chronic exposure to Ezatiostat (TLK199) results in cells with elevated activities of c-Jun NH2 terminal kinase (JNK1) and ERK1/ERK2, and allows the cells to proliferate under stress conditions that induced high levels of apoptosis in the wild type cells.

In vivo

Ezatiostat (TLK199) stimulates both lymphocyte production and bone marrow progenitor (colony-forming unitgranulocyte macrophage) proliferation, but only in GST_π^+/+ and not in GST_π^-/- animals.

Cell Research(from reference)

Cell lines：Human myeloid leukemic cells (HL60) 

Concentrations：2.5 μM - 50 μM 

Incubation Time：8 h, 24 h 

Specifications

Synonyms

Q27095680 | NCGC00263221-01 | NCGC00263221-05 | TER 199 | Ezatiostat | Ezatiostat [INN] | Ezatiostat(TER199; TLK199) | SCHEMBL420400 | Glycine, L-gamma-glutamyl-S-(phenylmethyl)-L-cysteinyl-2-phenyl-, diethyl ester, (2R)- | J-690234 | TLK199 | TLK-199 | e

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Ezatiostat (TER199, TLK199, Telintra), a tripeptide analog of glutathione, is a peptidomimetic inhibitor of Glutathione S-transferase P1-1 (GSTP1-1). Ezatiostat activates c-Jun NH2 terminal kinase (JNK1) and ERK1/ERK2 and induces apoptosis.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Product Properties

• ALogP: 0.745
• hba_count: 7
• HBD Count: 3
• Rotatable Bond: 18

Names and Identifiers

• Pubchem Sid: 488195303
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195303
• Canonical Smiles: CCOC(=O)C(CCC(=O)NC(CSCC1=CC=CC=C1)C(=O)NC(C2=CC=CC=C2)C(=O)OCC)N
• IUPAC Name: ethyl (2S)-2-amino-5-[[(2R)-3-benzylsulfanyl-1-[[(1R)-2-ethoxy-2-oxo-1-phenylethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate
• InChIKey: GWEJFLVSOGNLSS-WPFOTENUSA-N
• INCHI: 1S/C27H35N3O6S/c1-3-35-26(33)21(28)15-16-23(31)29-22(18-37-17-19-11-7-5-8-12-19)25(32)30-24(27(34)36-4-2)20-13-9-6-10-14-20/h5-14,21-22,24H,3-4,15-18,28H2,1-2H3,(H,29,31)(H,30,32)/t21-,22-,24+/m0/s1
• Isomeric SMILES: CCOC(=O)[C@H](CCC(=O)N[C@@H](CSCC1=CC=CC=C1)C(=O)N[C@H](C2=CC=CC=C2)C(=O)OCC)N
• Molecular Weight: 529.65
• Reaxy-Rn: 32132532
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=32132532&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Glutamine and derivatives Alpha amino acid esters N-acyl-alpha amino acids and derivatives Alpha amino acid amides Cysteine and derivatives Fatty acid esters N-acyl amines Dicarboxylic acids and derivatives Benzene and substituted derivatives Carboxylic acid esters Secondary carboxylic acid amides Sulfenyl compounds Dialkylthioethers Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds Organopnictogen compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-oligopeptide - Glutamine or derivatives - Alpha-amino acid ester - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Cysteine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Fatty acid ester - Fatty amide - N-acyl-amine - Fatty acyl - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Benzenoid - Carboxamide group - Amino acid or derivatives - Secondary carboxylic acid amide - Carboxylic acid ester - Thioether - Sulfenyl compound - Dialkylthioether - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Carbonyl group - Primary amine - Hydrocarbon derivative - Amine - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• 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.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 100 mg/mL (155.35 mM); Ethanol: 15 mg/mL (23.3 mM); Water: Insoluble
• DMSO(mg / mL) Max Solubility: 100
• DMSO(mM) Max Solubility: 155.359112588749
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 529.600 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 17
• Exact Mass: 529.225 Da
• Monoisotopic Mass: 529.225 Da
• Topological Polar Surface Area: 162.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 725.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1