3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

• ChemBase ID: 126862
• Molecular Formular: C16H10O5
• Molecular Mass: 282.2476
• Monoisotopic Mass: 282.05282342
• SMILES: COc1c2c(cc(c1C=O)O)C(=O)c1ccccc1C2=O
• Canonical SMILES: COc1c2C(=O)c3ccccc3C(=O)c2cc(c1C=O)O
• InChI: InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3
• InChIKey: IPDMWUNUULAXLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
• IUPAC Traditional name: damnacanthal
• Synonyms: 3-Hydroxy-1-methoxyanthraquinone-2-aldehyde; Damnacanthal; 9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde; 9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthraldehyde; 3-Hydroxy-1-methoxy-2-anthraquinonecarboxaldehyde; Damnacanthal

Database IDs

• CAS Number: 477-84-9
• PubChem SID: 162221189
• PubChem CID: 2948
• CHEMBL: 212948
• Chemspider ID: 2843
• Wikipedia Title: Damnacanthal

CALCULATED PROPERTIES

• Acid pKa: 6.4352384
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.772725
• LogD (pH = 7.4): 1.8447931
• Log P: 2.8199718
• Molar Refractivity: 76.1791 cm^3
• Polarizability: 28.350613 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Orange powder
• Boiling Point: 532°C
• Density: 1.461 g/mL

DETAILS

Toronto Research Chemicals - D134800

Damnacanthal-induced anti-inflammation is associated with inhibition of NF-κB activity. Damnacanthal is used in the treatment of inflammatory-related diseases.

REFERENCES

• Hiramatsu, et al.: Cancer Lett., 73, 161 (1993)
• Faltynek, et al.: Biochemistry, 34, 12404 (1993)
• Aoki, et al.: Eur. J. Pharmacol., 387, 119 (1993)