4,16-dimethoxy-10-methyl-9-(2-phenylethyl)-10-azatricyclo[11.4.0.02,7]heptadeca-1(17),2(7),3,5,13,15-hexaen-3-ol

• ChemBase ID: 160841
• Molecular Formular: C27H31NO3
• Molecular Mass: 417.53994
• Monoisotopic Mass: 417.23039386
• SMILES: c1(ccc2c(c1)c1c(CC(N(CC2)C)CCc2ccccc2)ccc(c1O)OC)OC
• Canonical SMILES: COc1ccc2c(c1O)c1cc(OC)ccc1CCN(C(C2)CCc1ccccc1)C
• InChI: InChI=1S/C27H31NO3/c1-28-16-15-20-10-13-23(30-2)18-24(20)26-21(11-14-25(31-3)27(26)29)17-22(28)12-9-19-7-5-4-6-8-19/h4-8,10-11,13-14,18,22,29H,9,12,15-17H2,1-3H3
• InChIKey: IORHSKBXWWSQME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,16-dimethoxy-10-methyl-9-(2-phenylethyl)-10-azatricyclo[11.4.0.0^2,^7]heptadeca-1(17),2(7),3,5,13,15-hexaen-3-ol
• IUPAC Traditional name: 4,16-dimethoxy-10-methyl-9-(2-phenylethyl)-10-azatricyclo[11.4.0.0^2,^7]heptadeca-1(17),2(7),3,5,13,15-hexaen-3-ol
• Synonyms: 6,7,8,9-Tetrahydro-2,12-dimethoxy-7-methyl-6-(2-phenylethyl)-5H-dibenz[d,f]azonin-1-ol; Go 4704; Goe 4704; Asocainol

Database IDs

• CAS Number: 77400-65-8
• PubChem SID: 162254976
• PubChem CID: 71161

CALCULATED PROPERTIES

• Acid pKa: 9.895109
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5560334
• LogD (pH = 7.4): 4.113472
• Log P: 5.3477125
• Molar Refractivity: 126.3476 cm^3
• Polarizability: 50.034977 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A788500

Asocainol (ASOC) belongs to class I antiarrhythmic drugs, i.e., those that exert their action at the level of sodium channels of the myocardial cell membrane.

REFERENCES

• Bakken, G.A., et al.: J. Med. Chem., 43, 4534 (2000)