(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6-one

• ChemBase ID: 174603
• Molecular Formular: C17H23NO3
• Molecular Mass: 289.36942
• Monoisotopic Mass: 289.1677936
• SMILES: C1C(=O)C[C@H]2[C@@](C1)(CCN2C)c1cc(c(cc1)OC)OC
• Canonical SMILES: COc1ccc(cc1OC)[C@]12CCC(=O)C[C@@H]2N(CC1)C
• InChI: InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m0/s1
• InChIKey: DAHIQPJTGIHDGO-IRXDYDNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6-one
• IUPAC Traditional name: mesembrine
• Synonyms: (3aS,7aS)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one; 4α,9α-Mesembrine; (3aS-cis)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-Indol-6-one; (-)-Mesembranone; (-)-Mesembrine; Mesembranone; Mesembrin; Mesembrine

Database IDs

• CAS Number: 24880-43-1
• PubChem SID: 164230513
• PubChem CID: 394162

CALCULATED PROPERTIES

• Acid pKa: 17.841991
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.5912654
• LogD (pH = 7.4): 1.182849
• Log P: 2.0540318
• Molar Refractivity: 81.6492 cm^3
• Polarizability: 32.076374 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M338950

An alkaloid used in preparing Channa, a drug of Southwest Africa. A serotonin-uptake inhibitor; occurs naturally as the (-)-form.

REFERENCES

• Oh-Ishi, K., et al.: Chem. Pharm. Bull., 18, 299 (1970)