2-hydroxy-5H,11H-indolo[3,2-b]carbazole-6-carbaldehyde

• ChemBase ID: 167690
• Molecular Formular: C19H12N2O2
• Molecular Mass: 300.31078
• Monoisotopic Mass: 300.08987763
• SMILES: c12c(cc3c(c1C=O)[nH]c1c3cc(cc1)O)[nH]c1c2cccc1
• Canonical SMILES: O=Cc1c2[nH]c3c(c2cc2c1c1ccccc1[nH]2)cc(cc3)O
• InChI: InChI=1S/C19H12N2O2/c22-9-14-18-11-3-1-2-4-15(11)20-17(18)8-13-12-7-10(23)5-6-16(12)21-19(13)14/h1-9,20-21,23H
• InChIKey: HGKLUBYTXRQWNO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-5H,11H-indolo[3,2-b]carbazole-6-carbaldehyde
• IUPAC Traditional name: 2-hydroxy-5H,11H-indolo[3,2-b]carbazole-6-carbaldehyde
• Synonyms: 5,11-Dihydro-2-hydroxyindolo[3,2-b]carbazole-6-carboxaldehyde

Database IDs

• CAS Number: 549548-26-7
• PubChem SID: 162261823
• PubChem CID: 11324039

CALCULATED PROPERTIES

• Acid pKa: 8.853291
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 3.6172714
• LogD (pH = 7.4): 3.6025324
• Log P: 3.6174626
• Molar Refractivity: 89.4513 cm^3
• Polarizability: 38.505814 Å^3
• Polar Surface Area: 68.88 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449415

A hydroxy metabolite of aryl hydrocarbon receptor (AhR) ligand Formylindolocarbazole (FICZ): a photoproduct of Tryptophan (T947200).

REFERENCES

• Bergander, L. et al.: Drug Metab. Disp., 31, 233 (2003)
• Wincent, E. et al.: J. Biol. Chem., 284, 2690 (2003)
• Bergander, L. et al.: Chem.-Biol. Inter., 149, 151 (2003)