4,8-dimethoxyfuro[2,3-b]quinolin-7-ol

• ChemBase ID: 179740
• Molecular Formular: C13H11NO4
• Molecular Mass: 245.23074
• Monoisotopic Mass: 245.06880784
• SMILES: c12nc3c(c(c1ccc(c2OC)O)OC)cco3
• Canonical SMILES: COc1c(O)ccc2c1nc1occc1c2OC
• InChI: InChI=1S/C13H11NO4/c1-16-11-7-3-4-9(15)12(17-2)10(7)14-13-8(11)5-6-18-13/h3-6,15H,1-2H3
• InChIKey: LJKPBWHZRNQEMO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,8-dimethoxyfuro[2,3-b]quinolin-7-ol
• IUPAC Traditional name: 4,8-dimethoxyfuro[2,3-b]quinolin-7-ol; haplopine
• Synonyms: 7-Hydroxy-8-methoxydictamnine; Haplopine

Database IDs

• CAS Number: 5876-17-5
• PubChem SID: 164235650
• PubChem CID: 165368

CALCULATED PROPERTIES

• Acid pKa: 7.841514
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.0365283
• LogD (pH = 7.4): 1.9057435
• Log P: 2.038578
• Molar Refractivity: 63.6803 cm^3
• Polarizability: 26.300278 Å^3
• Polar Surface Area: 64.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Product Information

• Biological Source: Alkaloid from Haplophyllum robustum, Zanthoxylum cuspidatum, Monnieria trifolia and Melicope lasioneura (Rutaceae)
• Application(s): Antiaggregant; Hypotensive; Sedative

REFERENCES

• Fakhrutdinova, I.M. et al., Khim. Prir. Soedin., 1965, 1, 107; Chem. Nat. Compd. (Engl. Transl.), 1965, 1, 83, (isol, struct)
• Faizutdinova, Z.S. et al., Khim. Prir. Soedin., 1967, 3, 260; Chem. Nat. Compd. (Engl. Transl.), 1967, 3, 218, (ms)
• Collins, J.F. et al., J.C.S. Perkin 1, 1973, 94-97, (synth)
• Narasimhan, N.S. et al., Tetrahedron, 1974, 30, 4153-4157, (synth, uv, ir, pmr)
• Chang, P.T.O. et al., J. Nat. Prod., 1976, 39, 134, (isol, ir, uv, ms, pmr)