N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide

• ChemBase ID: 178563
• Molecular Formular: C8H8N2O2S2
• Molecular Mass: 228.29132
• Monoisotopic Mass: 228.00271951
• SMILES: c12c(c(=O)n(c1css2)C)NC(=O)C
• Canonical SMILES: CC(=O)Nc1c(=O)n(c2c1ssc2)C
• InChI: InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
• InChIKey: MHMRAFONCSQAIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide
• IUPAC Traditional name: thiolutin
• Synonyms: N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide; 6-Acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one; 3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole; Acetopyrrothin; NSC 3927; Thiolutin

Database IDs

• CAS Number: 87-11-6
• PubChem SID: 164234473
• PubChem CID: 6870

CALCULATED PROPERTIES

• Acid pKa: 12.501974
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.5274867
• LogD (pH = 7.4): -0.52748966
• Log P: -0.5274866
• Molar Refractivity: 60.3465 cm^3
• Polarizability: 22.180225 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T350900

Thiolutin is an antibiotic isolated from several strains of Streptomyces albus. Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases.

REFERENCES

• Seneca, et al.: Antibiot. Chemother., 2, 357 (1952)
• Jimenez, A., et al.: Antimicrob. Agents Chemother., 3, 729 (1952)
• Deb, P.R., et al.: Curr. Sci., 53, 659 (1952)