Thiostrepton from Streptomyces azureus

Base Information

• Chemical Name: Thiostrepton from Streptomyces azureus
• CAS No.: 1393-48-2
• Molecular Formula: C72H85 N19 O18 S5
• Molecular Weight: 1665.06
• Hs Code.: 29419090
• European Community (EC) Number: 215-734-9
• ChEMBL ID: CHEMBL1981887
• Metabolomics Workbench ID: 70988
• NCI Thesaurus Code: C187031
• Wikipedia: Thiostrepton
• Mol file: 1393-48-2.mol

Synonyms:Bryamycin;Gargon;Thiactin;Thiostrepton

Chemical Property of Thiostrepton from Streptomyces azureus

Chemical Property:

• Melting Point: 248-257°C (dec.)
• Refractive Index: 1.6700 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 10.43±0.46(Predicted)
• Flash Point: °C
• PSA: 701.00000
• Density: 1.64 g/cm³
• LogP: 4.08640
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO or chloroform
• Water Solubility.: 0.24g/L(28 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 17
• Hydrogen Bond Acceptor Count: 31
• Rotatable Bond Count: 12
• Exact Mass: 1663.4923528
• Heavy Atom Count: 114
• Complexity: 3940

Purity/Quality:

99% ^*data from raw suppliers

Thiostrepton ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)C(=CC)NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
• Isomeric SMILES: CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)/C(=C/C)/NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
• Description: The mammalian transcription factor forkhead box M1 (FoxM1) is induced during G1 phase, with expression continuing through S phase and mitosis. Thiostrepton is a natural peptide thiazole antibiotic that inhibits FoxM1 in mammalian cells, preventing the expression of FoxM1-regulated genes, which includes FoxM1 itself. Through this mechanism, thiostrepton prevents proliferation and induces apoptosis in human cancer cells. These effects correlate with the ability of thiostrepton to act as a proteasome inhibitor.
• Uses: beta-adrenergic agonist Thiostrepton is a macrocyclic antibiotic incorporating thiazoles and other atypical amino acids. Patented in 1961, thiostrepton has been used as an antibiotic and acts by binding to ribosomes to prevent the binding of the EF-G elongation factor and GTP to the 50S ribosomal subunit. Thiostrepton is an inducer of tipA, a gene that controls the bacterial transcription regulators, TipAL and TipAS, that are central regulators in multidrug resistance. Thiostrepton is closely related to siomycin, a recently discovered inhibitor of oncogenic transcription factor, FoxM1. A protein synthesis-inhibiting antibiotic Natural antibiotic derived from Streptomyces.