7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one

• ChemBase ID: 179770
• Molecular Formular: C19H12O7
• Molecular Mass: 352.29438
• Monoisotopic Mass: 352.05830272
• SMILES: c1(c(=O)oc2c(c1)cc(c(c2)O)OC)Oc1cc2oc(=O)ccc2cc1
• Canonical SMILES: COc1cc2cc(Oc3ccc4c(c3)oc(=O)cc4)c(=O)oc2cc1O
• InChI: InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3
• InChIKey: JRHMMVBOTXEHGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one
• IUPAC Traditional name: daphnoretin; 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one
• Synonyms: Thymelol; Edgeworthin; Daphnoretin

Database IDs

• CAS Number: 2034-69-7
• PubChem SID: 164235680
• PubChem CID: 5281406

CALCULATED PROPERTIES

• Acid pKa: 8.0433235
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.6880329
• LogD (pH = 7.4): 2.6010237
• Log P: 2.689265
• Molar Refractivity: 91.7106 cm^3
• Polarizability: 34.51862 Å^3
• Polar Surface Area: 91.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Pharmacology Properties

• Mechanism of Action: Protein kinase C activator

Product Information

• Biological Source: Constit. of Daphne mezereum and Wikstroemia viridiflora. A common bis-coumarin found in many plants
• Application(s): Anti-HIV-1 and Antifungal activity; Cytostatic

REFERENCES

• Tschesche, R. et al., Annalen, 1963, 662, 113, (struct)
• Tschesche, R. et al., Naturwissenschaften, 1963, 50, 521, (struct)
• Kirkiacharian, B. et al., Bull. Soc. Chim. Fr., 1966, 770, (synth)
• Reisch, J. et al., Planta Med., 1968, 16, 372, (deriv)
• Majumder, P.L. et al., Phytochemistry, 1974, 13, 1929, (Edgeworthin)
• Tandon, S. et al., Phytochemistry, 1977, 16, 1991, (isol)
• Cordell, G.A., J. Nat. Prod., 1984, 47, 84, (pmr, cmr)
• Ulubelen, A. et al., J. Nat. Prod., 1986, 49, 692, (Edgeworthin)
• Chakrabarti, R. et al., Phytochemistry, 1986, 25, 557, (isol)
• Ke, H. et al., Planta Med., 2000, 66, 564-567, (isol, activity)