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

• ChemBase ID: 154387
• Molecular Formular: C9H10N2O2S2
• Molecular Mass: 242.3179
• Monoisotopic Mass: 242.01836957
• SMILES: CCC(=O)Nc1c2sscc2n(c1=O)C
• Canonical SMILES: CCC(=O)Nc1c(=O)n(c2c1ssc2)C
• InChI: InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
• InChIKey: UGZYFXMSMFMTSM-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}propanamide
• IUPAC Traditional name: aureothricin
• Synonyms: Aureothricin; Farcinicin; N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-B]Pyrrol-6-yl); Propiopyvothine; Thiolutin

Database IDs

• CAS Number: 87-11-6
• MDL Number: MFCD07370147
• PubChem SID: 162248526
• PubChem CID: 68460

CALCULATED PROPERTIES

• Acid pKa: 12.470644
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.1730492
• LogD (pH = 7.4): 0.17304596
• Log P: 0.17304923
• Molar Refractivity: 64.9734 cm^3
• Polarizability: 24.010756 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble5 mg/mL

Safety Information

• RTECS: JP1355000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: from Streptomyces luteosporeus
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C8H8N2O2S2

DETAILS

Sigma Aldrich - T3450

Biochem/physiol Actions
Sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases. It was found to inhibit in vitro RNA synthesis directed by all three yeast RNA polymerases (I, II, and III). Thiolutin is also an inhibitor of mannan and glucan formation in Saccharomyces cerevisiae and used for the analysis of mRNA stability. Studies have shown that thiolutin inhibits adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin and thus suppresses tumor cell-induced angiogenesis in vivo.