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

• ChemBase ID: 167691
• Molecular Formular: C19H12N2O2
• Molecular Mass: 300.31078
• Monoisotopic Mass: 300.08987763
• SMILES: c12c(cc3c(c1C=O)[nH]c1c3cccc1)[nH]c1c2cc(cc1)O
• Canonical SMILES: O=Cc1c2[nH]c3c(c2cc2c1c1cc(O)ccc1[nH]2)cccc3
• InChI: InChI=1S/C19H12N2O2/c22-9-14-18-13-7-10(23)5-6-16(13)20-17(18)8-12-11-3-1-2-4-15(11)21-19(12)14/h1-9,20-21,23H
• InChIKey: UBSNONGPZJJCAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-5H,11H-indolo[3,2-b]carbazole-6-carbaldehyde
• IUPAC Traditional name: 8-hydroxy-5H,11H-indolo[3,2-b]carbazole-6-carbaldehyde
• Synonyms: 5,11-Dihydro-8-hydroxyindolo[3,2-b]carbazole-6-carboxaldehyde

Database IDs

• CAS Number: 549548-25-6
• PubChem SID: 162261824
• PubChem CID: 11392417

CALCULATED PROPERTIES

• Acid pKa: 9.344316
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 3.617401
• LogD (pH = 7.4): 3.612585
• Log P: 3.6174626
• Molar Refractivity: 89.4513 cm^3
• Polarizability: 38.50581 Å^3
• Polar Surface Area: 68.88 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449420

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)