2-hydroxy-3-methyl-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 179730
• Molecular Formular: C11H8O3
• Molecular Mass: 188.17942
• Monoisotopic Mass: 188.04734412
• SMILES: C1(=C(C(=O)c2c(C1=O)cccc2)O)C
• Canonical SMILES: CC1=C(O)C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C11H8O3/c1-6-9(12)7-4-2-3-5-8(7)11(14)10(6)13/h2-5,13H,1H3
• InChIKey: LULCPJWUGUVEFU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-methyl-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: 2-hydroxy-3-methyl-1,4-dihydronaphthalene-1,4-dione
• Synonyms: Phthiocol

Database IDs

• CAS Number: 483-55-6
• PubChem SID: 164235640
• PubChem CID: 10221

CALCULATED PROPERTIES

• Acid pKa: 7.9920173
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3698146
• LogD (pH = 7.4): 1.2723063
• Log P: 1.3712108
• Molar Refractivity: 52.5077 cm^3
• Polarizability: 19.295668 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Involvement of calcium channels

Product Information

• Biological Source: Pigment of human tubercle bacillus. Also isol. from Streptococcus faecalis and Asplenium laciniatum
• Application(s): Antibiotic; Antifungal activity; Hemostatic

REFERENCES

• Andersen, R.J. et al., J. Biol. Chem., 1933, 103, 197-201; 1939, 130, 429-430, (isol, synth)
• Fieser, L., J. Biol. Chem., 1940, 133, 391-396, (synth)
• Lichstein, H.C. et al., J. Bacteriol., 1946, 52, 145-146, (props)
• Weygand, F. et al., Chem. Ber., 1957, 90, 1879-1895, (synth)
• Gaultier, N. et al., Acta Cryst., 1965, 19, 919-926, (cryst struct)
• Baum, R.H. et al., J. Biol. Chem., 1965, 240, 3425-3433, (isol)
• Gupta, R.B. et al., Curr. Sci., 1976, 45, 44-46, (isol)
• Bansal, V. et al., Synth. Commun., 1995, 25, 1669-1675, (synth, pmr, ir)
• Kankaria, R.A. et al., Res. J. Chem. Environ., 2000, 4, 71-73, (Phthiocol, activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HMI000