1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol

• ChemBase ID: 73965
• Molecular Formular: C17H18Br2N2O
• Molecular Mass: 426.14562
• Monoisotopic Mass: 423.97858721
• SMILES: n1(c2c(cc(cc2)Br)c2c1ccc(c2)Br)CC(CN(C)C)O
• Canonical SMILES: CN(CC(Cn1c2ccc(cc2c2c1ccc(c2)Br)Br)O)C
• InChI: InChI=1S/C17H18Br2N2O/c1-20(2)9-13(22)10-21-16-5-3-11(18)7-14(16)15-8-12(19)4-6-17(15)21/h3-8,13,22H,9-10H2,1-2H3
• InChIKey: XUBJEDZHBUPBKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol
• IUPAC Traditional name: (S)-wiskostatin; @(S)-wiskostatin
• Synonyms: 1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol; Wiskostatin; 1-(3,6-Dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol

Database IDs

• CAS Number: 253449-04-6
• MDL Number: MFCD00218393
• PubChem SID: 162038884
• PubChem CID: 2775510

CALCULATED PROPERTIES

• Acid pKa: 14.425322
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.996491
• LogD (pH = 7.4): 2.5453162
• Log P: 4.2403765
• Molar Refractivity: 97.5961 cm^3
• Polarizability: 39.690147 Å^3
• Polar Surface Area: 28.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >26 mg/mL
• Apperance: white powder
• Melting Point: 153-155°C

Safety Information

• Storage Warning: Toxic/Keep Cold
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H413
• GHS Precautionary statements: P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 97%
• Empirical Formula (Hill Notation): C17H18Br2N2O

DETAILS

Sigma Aldrich - W2270

Biochem/physiol Actions
Wiskostatin is a selective inhibitor of N-WASP, a ubiquitously expressed member of the Wiskott-Aldrich Syndrome protein (WASp) family that regulates actin polymerization. Wiskostatin inhibits actin-dependent cellular functions, including migration, transmembrane transport and phagocytosis.