5-(1,3-benzothiazol-2-yl)-3-ethyl-2-{2-[methyl(phenyl)amino]ethenyl}-1-phenyl-1H-1,3-benzodiazol-3-ium iodide

• ChemBase ID: 153854
• Molecular Formular: C31H27IN4S
• Molecular Mass: 614.54235
• Monoisotopic Mass: 614.10011588
• SMILES: CC[n+]1c2cc(ccc2n(c1/C=C/N(C)c1ccccc1)c1ccccc1)c1nc2ccccc2s1.[I-]
• Canonical SMILES: CC[n+]1c(/C=C/N(c2ccccc2)C)n(c2c1cc(cc2)c1nc2c(s1)cccc2)c1ccccc1.[I-]
• InChI: InChI=1S/C31H27N4S.HI/c1-3-34-28-22-23(31-32-26-16-10-11-17-29(26)36-31)18-19-27(28)35(25-14-8-5-9-15-25)30(34)20-21-33(2)24-12-6-4-7-13-24;/h4-22H,3H2,1-2H3;1H/q+1;/p-1
• InChIKey: NAYRELMNTQSBIN-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1,3-benzothiazol-2-yl)-3-ethyl-2-{2-[methyl(phenyl)amino]ethenyl}-1-phenyl-1H-1,3-benzodiazol-3-ium iodide
• IUPAC Traditional name: 6-(1,3-benzothiazol-2-yl)-1-ethyl-2-{2-[methyl(phenyl)amino]ethenyl}-3-phenyl-1,3-benzodiazol-1-ium iodide
• Synonyms: 5-(2-Benzothiazolyl)-3-ethyl-2-[2-(methylphenylamino)ethenyl]-1-phenyl-1H-benzimidazolium iodide

Database IDs

• CAS Number: 681281-88-9
• MDL Number: MFCD00570739
• PubChem SID: 24724416; 162247993
• PubChem CID: 5719375

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.030211
• LogD (pH = 7.4): 4.0303245
• Log P: 4.030326
• Molar Refractivity: 180.1328 cm^3
• Polarizability: 60.70124 Å^3
• Polar Surface Area: 24.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: orange solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C31H27IN4S

DETAILS

Sigma Aldrich - B2311

Biochem/physiol Actions
5-(2-Benzothiazolyl)-3-ethyl-2-[2-(methylphenylamino)-ethenyl]-1-phenyl-1H-benzimidazolium or Akt Inhibitor IV is a cell-permeable benzimidazole compound that inhibits Akt phosphorylation/activation by targeting the ATP binding site of a kinase upstream of Akt, but downstream of PI3K. Shown to block Akt-mediated FOXO1a nuclear export (IC₅₀ = 0.625μM) and cell proliferation (IC₅₀ < 1.25μM) in 786-O cells. Unlike phosphatidylinositol analog-based Akt inhibitors, this inhibitor does not affect PI3K.