(1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6,8,10(17)-trien-14-ol

• ChemBase ID: 172446
• Molecular Formular: C17H23NO3
• Molecular Mass: 289.36942
• Monoisotopic Mass: 289.1677936
• SMILES: C1[C@@H](C[C@@H]2Oc3c(ccc4c3[C@@]2(C1)CCN(C4)C)OC)O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@]3(CC[C@@H](C1)O)CCN(C2)C
• InChI: InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1
• InChIKey: GJRMHIXYLGOZSE-JDFRZJQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6,8,10(17)-trien-14-ol
• IUPAC Traditional name: lycoramine
• Synonyms: (4aS,6S,8aR)-4a,5,7,8,9,10,11,12-Octahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol; Dihydrogalanthamine; 1,2-Dihydrogalanthamine; Lycoramine

Database IDs

• CAS Number: 21133-52-8
• PubChem SID: 164228356
• PubChem CID: 443723

CALCULATED PROPERTIES

• Acid pKa: 15.173409
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.789063
• LogD (pH = 7.4): -0.1596928
• Log P: 1.369057
• Molar Refractivity: 81.3423 cm^3
• Polarizability: 31.813795 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L487600

One of the minor alkaloids of Lycoris radiata, a highly efficient, selective and sensitive acetylcholinesterase inhibitor. An analog of Galanthamine (G188500).

REFERENCES

• Friess, S.L., et al.: Toxicol. Appl. Pharmacol., 3, 347 (1961)
• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1961)
• Harvey, A.L., et al.: Pharmacol. Ther., 68, 113 (1961)