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

• ChemBase ID: 167569
• Molecular Formular: C19H12N2O3
• Molecular Mass: 316.31018
• Monoisotopic Mass: 316.08479225
• SMILES: c12c(cc3c(c1C=O)[nH]c1c3cc(cc1)O)[nH]c1c2cc(cc1)O
• Canonical SMILES: O=Cc1c2[nH]c3c(c2cc2c1c1cc(O)ccc1[nH]2)cc(cc3)O
• InChI: InChI=1S/C19H12N2O3/c22-8-14-18-13-6-10(24)2-4-16(13)20-17(18)7-12-11-5-9(23)1-3-15(11)21-19(12)14/h1-8,20-21,23-24H
• InChIKey: ASRXEXWTTPEQEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 549548-29-0
• PubChem SID: 162261702
• PubChem CID: 11267049

CALCULATED PROPERTIES

• Acid pKa: 8.735921
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): 3.3136468
• LogD (pH = 7.4): 3.2942767
• Log P: 3.3138974
• Molar Refractivity: 91.4322 cm^3
• Polarizability: 39.008156 Å^3
• Polar Surface Area: 89.11 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448920

A dihydroxy 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)