2-carbamoyl-7-nitro-5-(trifluoromethyl)-1,3-benzothiazol-3-ium-3-olate

• ChemBase ID: 154049
• Molecular Formular: C9H4F3N3O4S
• Molecular Mass: 307.2059696
• Monoisotopic Mass: 306.98746128
• SMILES: c1c(cc(c2c1[n+](c(s2)C(=O)N)[O-])[N+](=O)[O-])C(F)(F)F
• Canonical SMILES: [O-][N+](=O)c1cc(cc2c1sc([n+]2[O-])C(=O)N)C(F)(F)F
• InChI: InChI=1S/C9H4F3N3O4S/c10-9(11,12)3-1-4-6(5(2-3)15(18)19)20-8(7(13)16)14(4)17/h1-2H,(H2,13,16)
• InChIKey: FHFLXKUKCSDMLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-carbamoyl-7-nitro-5-(trifluoromethyl)-1,3-benzothiazol-3-ium-3-olate
• IUPAC Traditional name: 2-carbamoyl-7-nitro-5-(trifluoromethyl)-1,3-benzothiazol-3-ium-3-olate
• Synonyms: 7-Nitro-5-(trifluoromethyl)-2-Benzothiazolecarboxamide 3-oxide; Cyclapolin 9

Database IDs

• CAS Number: 40533-25-3
• MDL Number: MFCD00119343
• PubChem SID: 162248188
• PubChem CID: 2779952

CALCULATED PROPERTIES

• Acid pKa: 9.228344
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.4892664
• LogD (pH = 7.4): 1.4948286
• Log P: 1.4891939
• Molar Refractivity: 61.7973 cm^3
• Polarizability: 22.519934 Å^3
• Polar Surface Area: 114.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble2 mg/mL (Lower concentrations not tested)
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H4F3N3O4S

DETAILS

Sigma Aldrich - C6493

Biochem/physiol Actions
Cyclapolin 9 is a Polo-like kinase (Plk) inhibitor. IC50 is 500 nM; selective against a panel of 20 kinases