(1S,12S,14S)-14-hydroxy-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-4-ium-4-olate

• ChemBase ID: 168047
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 303.14705816
• SMILES: C1[C@H]2[C@@]3(C=C[C@H]1O)c1c(C[N+](CC3)(C)[O-])ccc(c1O2)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@]3(C=C[C@H](C1)O)CC[N+](C2)([O-])C
• InChI: InChI=1S/C17H21NO4/c1-18(20)8-7-17-6-5-12(19)9-14(17)22-16-13(21-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14+,17+,18?/m1/s1
• InChIKey: LROQBKNDGTWXET-XWKQXMNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,14S)-14-hydroxy-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-4-ium-4-olate
• IUPAC Traditional name: (1S,12S,14S)-14-hydroxy-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-4-ium-4-olate
• Synonyms: (4aS,6S,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol 11-Oxide; Epi-galanthamine N-Oxide

Database IDs

• CAS Number: 366485-18-9
• PubChem SID: 162262179
• PubChem CID: 26491230

CALCULATED PROPERTIES

• Acid pKa: 14.810369
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.038566273
• LogD (pH = 7.4): 0.038666327
• Log P: 0.03866762
• Molar Refractivity: 84.3498 cm^3
• Polarizability: 31.798489 Å^3
• Polar Surface Area: 65.57 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E588035

A metabolite of Epigalanthamine (E588025).

REFERENCES

• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1991)
• Mannens, G.S.J., et al.: Drug Metab. Dispos., 30, 553 (1991)