3-methylbutyl 7,8-dimethyl-4,5-dioxo-4H,5H,6H-pyrano[3,2-c]quinoline-2-carboxylate

• ChemBase ID: 177398
• Molecular Formular: C20H21NO5
• Molecular Mass: 355.38444
• Monoisotopic Mass: 355.14197278
• SMILES: c1c(c(c2c(c1)c1c(c(=O)[nH]2)c(=O)cc(o1)C(=O)OCCC(C)C)C)C
• Canonical SMILES: CC(CCOC(=O)c1cc(=O)c2c(o1)c1ccc(c(c1[nH]c2=O)C)C)C
• InChI: InChI=1S/C20H21NO5/c1-10(2)7-8-25-20(24)15-9-14(22)16-18(26-15)13-6-5-11(3)12(4)17(13)21-19(16)23/h5-6,9-10H,7-8H2,1-4H3,(H,21,23)
• InChIKey: NFQIAEMCQGTTIR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylbutyl 7,8-dimethyl-4,5-dioxo-4H,5H,6H-pyrano[3,2-c]quinoline-2-carboxylate
• IUPAC Traditional name: repirinast
• Synonyms: 4H-Pyrano[3,2-c]quinoline-2-carboxylic acid, 5,6-dihydro-7,8-dimethyl-4,5-dioxo-, 3-methylbutyl Ester; MY 5116; Romet; Repirinast

Database IDs

• CAS Number: 73080-51-0
• PubChem SID: 164233308
• PubChem CID: 5050

CALCULATED PROPERTIES

• Acid pKa: 12.209828
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.5819979
• LogD (pH = 7.4): 3.5819917
• Log P: 3.581998
• Molar Refractivity: 100.4912 cm^3
• Polarizability: 36.82946 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R144560

Antiallergic.

REFERENCES

• Phillipps, G., et al.: J. Med. Chem., 37, 3717 (1994)
• Tronde, A., et al.: J. Pharm. Sci., 92, 1216 (1994)