9-(2H-1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one

• ChemBase ID: 179728
• Molecular Formular: C21H16O7
• Molecular Mass: 380.34754
• Monoisotopic Mass: 380.08960285
• SMILES: c12c(c(c3c(c1O)cc(c(c3)OC)OC)c1cc3c(OCO3)cc1)C(=O)OC2
• Canonical SMILES: COc1cc2c(c3ccc4c(c3)OCO4)c3C(=O)OCc3c(c2cc1OC)O
• InChI: InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3
• InChIKey: VMEJANRODATDOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-(2H-1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one
• IUPAC Traditional name: 9-(2H-1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one
• Synonyms: Diphyllin

Database IDs

• CAS Number: 22055-22-7
• PubChem SID: 164235638
• PubChem CID: 100492

CALCULATED PROPERTIES

• Acid pKa: 8.062737
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1677995
• LogD (pH = 7.4): 3.0842338
• Log P: 3.1689777
• Molar Refractivity: 98.8985 cm^3
• Polarizability: 40.568504 Å^3
• Polar Surface Area: 83.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Potent V-ATPase inhibitor

Product Information

• Biological Source: Lignan from roots of Diphylleia grayi, leaves of Cleistanthus collinus, Justicia procumbens and Haplophyllum hispanicum
• Application(s): Cytotoxin; Regulator of osteoclastic resorption lacunae and bone resorption

REFERENCES

• Horii, Z. et al., Chem. Comm., 1968, 653, (struct)
• Govindachari, T.R. et al., Tetrahedron, 1969, 25, 2815, (isol, struct)
• Okigawa, M. et al., Tetrahedron, 1970, 26, 4301, (isol)
• Stevenson, R. et al., J.O.C., 1971, 36, 3450; 3453, (synth)
• Arnold, B.J. et al., J.C.S. Perkin 1, 1973, 1266, (synth)
• Horii, Z. et al., Chem. Pharm. Bull., 1977, 25, 1803, (synth)
• Anjaneyulu, A.S.R. et al., Indian J. Chem., Sect. B, 1977, 15, 10, (isol, struct)
• Momose, T. et al., Chem. Pharm. Bull., 1978, 26, 3195, (synth)
• Gonzalez, A.G. et al., Planta Med., 1979, 36, 200-203, (Diphyllinins)
• Fukamiya, N. et al., J. Nat. Prod., 1986, 49, 348
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMV375