2-(butan-2-yldisulfanyl)-1H-imidazole

• ChemBase ID: 154923
• Molecular Formular: C7H12N2S2
• Molecular Mass: 188.31358
• Monoisotopic Mass: 188.04419039
• SMILES: CCC(C)SSc1[nH]ccn1
• Canonical SMILES: CCC(SSc1ncc[nH]1)C
• InChI: InChI=1S/C7H12N2S2/c1-3-6(2)10-11-7-8-4-5-9-7/h4-6H,3H2,1-2H3,(H,8,9)
• InChIKey: BPBPYQWMFCTCNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(butan-2-yldisulfanyl)-1H-imidazole
• IUPAC Traditional name: 2-(sec-butyldisulfanyl)-1H-imidazole
• Synonyms: 2-[(1-methylpropyl)dithio]-1H-imidazole; PX 12

Database IDs

• CAS Number: 141400-58-0
• MDL Number: MFCD18086851
• PubChem SID: 162249061
• PubChem CID: 219104

CALCULATED PROPERTIES

• Acid pKa: 10.933308
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.69823
• LogD (pH = 7.4): 2.770886
• Log P: 2.7720373
• Molar Refractivity: 50.8676 cm^3
• Polarizability: 20.670696 Å^3
• Polar Surface Area: 28.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >25 mg/mL
• Apperance: off-white to tan powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C7H12N2S2

DETAILS

Sigma Aldrich - M5324

Biochem/physiol Actions
PX-12 inhibits the thioredoxin redox system and HIF-1a activity. PX 12 inhibits hypoxia-induced HIF-1a transcriptional activity (IC50 11 nM) and proliferation of HT29 and MCF-7 tumor cells (IC50 1.9 and 0.9 uM, respectively).