1-methyl-3-nitro-5H-pyrido[4,3-b]indole

• ChemBase ID: 175216
• Molecular Formular: C12H9N3O2
• Molecular Mass: 227.21876
• Monoisotopic Mass: 227.06947654
• SMILES: c1ccc2c(c1)c1c([nH]2)cc(nc1C)[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1nc(C)c2c(c1)[nH]c1c2cccc1
• InChI: InChI=1S/C12H9N3O2/c1-7-12-8-4-2-3-5-9(8)14-10(12)6-11(13-7)15(16)17/h2-6,14H,1H3
• InChIKey: MVHWCKZQGXOVJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-3-nitro-5H-pyrido[4,3-b]indole
• IUPAC Traditional name: 1-methyl-3-nitro-5H-pyrido[4,3-b]indole
• Synonyms: 1-Methyl-3-nitro-5H-pyrido[4,3-b]indole; Nitro-Trp-P-2; 3-Nitro-1-methyl-5H-pyrido[4,3-b]indole

Database IDs

• CAS Number: 75567-58-7
• PubChem SID: 164231126
• PubChem CID: 5487760

CALCULATED PROPERTIES

• Acid pKa: 12.527597
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.539023
• LogD (pH = 7.4): 2.5390222
• Log P: 2.539025
• Molar Refractivity: 63.545 cm^3
• Polarizability: 25.793262 Å^3
• Polar Surface Area: 74.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N493985

A highly mutagenic metabolite of 3-Amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) (A618001); mutagen-carcinogen product towards Salmonella typhimurium TA 98.

REFERENCES

• Saito, K., et al.: Carcinogenesis, 4, 1547 (1983)
• Hashimoto, Y., et al.: Biochem. Biophysical Res. Communications, 96, 355 (1983)