2,2-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

• ChemBase ID: 179837
• Molecular Formular: C14H13NO2
• Molecular Mass: 227.25852
• Monoisotopic Mass: 227.09462866
• SMILES: c12c(c3c([nH]c1=O)cccc3)OC(C=C2)(C)C
• Canonical SMILES: O=c1[nH]c2ccccc2c2c1C=CC(O2)(C)C
• InChI: InChI=1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)
• InChIKey: PXNMNABLQWUMCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one
• IUPAC Traditional name: 2,2-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one
• Synonyms: Flindersine

Database IDs

• CAS Number: 523-64-8
• PubChem SID: 164235747
• PubChem CID: 68230

CALCULATED PROPERTIES

• Acid pKa: 12.6127825
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.8141465
• LogD (pH = 7.4): 1.814144
• Log P: 1.8141466
• Molar Refractivity: 69.1688 cm^3
• Polarizability: 25.070282 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Leukotriene antagonist

Product Information

• Biological Source: Alkaloid from Flindersia australis, Haplophyllum perforatum and several other spp. (Flindersiaceae, Rutaceae)
• Application(s): Antifungal

REFERENCES

• Robertson, A.V., Aust. J. Chem., 1963, 16, 451, (pmr)
• Lavie, D. et al., Tetrahedron, 1968, 24, 3011, (ms)
• Brown, R.F.C. et al., Aust. J. Chem., 1954, 7, 348, (isol, uv, struct)