3-amino-8-azido-5-ethyl-6-phenylphenanthridin-5-ium bromide

• ChemBase ID: 158627
• Molecular Formular: C21H18BrN5
• Molecular Mass: 420.30512
• Monoisotopic Mass: 419.0745576
• SMILES: CC[n+]1c2cc(ccc2c2ccc(cc2c1c1ccccc1)N=[N+]=[N-])N.[Br-]
• Canonical SMILES: [N-]=[N+]=Nc1ccc2c(c1)c(c1ccccc1)[n+](c1c2ccc(c1)N)CC.[Br-]
• InChI: InChI=1S/C21H17N5.BrH/c1-2-26-20-12-15(22)8-10-18(20)17-11-9-16(24-25-23)13-19(17)21(26)14-6-4-3-5-7-14;/h3-13,22H,2H2,1H3;1H
• InChIKey: GHUXAYLZEGLXDA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-8-azido-5-ethyl-6-phenylphenanthridin-5-ium bromide
• IUPAC Traditional name: 3-amino-8-azido-5-ethyl-6-phenylphenanthridin-5-ium bromide
• Synonyms: 3-Amino-8-azido-5-ethyl-6-phenylphenanthridinium bromide; Ethidium monoazide bromide; Ethidium bromide monoazide

Database IDs

• CAS Number: 58880-05-0
• MDL Number: MFCD01708677
• PubChem SID: 162252763
• PubChem CID: 2762649

CALCULATED PROPERTIES

• Acid pKa: 18.710388
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.22198655
• LogD (pH = 7.4): 0.22199202
• Log P: 0.33603773
• Molar Refractivity: 107.5847 cm^3
• Polarizability: 42.825974 Å^3
• Polar Surface Area: 59.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; ethanol: soluble
• Apperance: orange solid

Safety Information

• RTECS: SF7941850
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C21H18BrN5

DETAILS

Sigma Aldrich - E2028

Biochem/physiol Actions
Photoactive stain covalently binds to nucleic acids in solution and in cells with damaged membranes.
Used to footprint drug binding sites on DNA, detect non-viable cells, identify ethidium binding sites on DNA and tRNA, and selectively inactivate gene expression.
Packaging
5 mg in glass bottle