(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-9,14-diol

• ChemBase ID: 166500
• Molecular Formular: C16H19NO3
• Molecular Mass: 273.32696
• Monoisotopic Mass: 273.13649347
• SMILES: C1[C@H]2[C@@]3(C=C[C@@H]1O)c1c(CN(CC3)C)ccc(c1O2)O
• Canonical SMILES: O[C@H]1C=C[C@@]23[C@H](C1)Oc1c3c(ccc1O)CN(CC2)C
• InChI: InChI=1S/C16H19NO3/c1-17-7-6-16-5-4-11(18)8-13(16)20-15-12(19)3-2-10(9-17)14(15)16/h2-5,11,13,18-19H,6-9H2,1H3/t11-,13-,16-/m0/s1
• InChIKey: OYSGWKOGUVOGFQ-RBOXIYTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraene-9,14-diol
• IUPAC Traditional name: sanguinine
• Synonyms: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol; 10-Methyl-galantham-1-ene-3β,6-diol; Sanguinine; O-Demethylgalanthamine; O-Desmethyl Galanthamine

Database IDs

• CAS Number: 60755-80-8
• PubChem SID: 162260633
• PubChem CID: 443722

CALCULATED PROPERTIES

• Acid pKa: 9.854485
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.1343658
• LogD (pH = 7.4): -0.5019612
• Log P: 0.69227046
• Molar Refractivity: 77.8226 cm^3
• Polarizability: 29.735287 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 227-230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292030

A metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor.

REFERENCES

• Mannens, G., et al.: Drug Metab. Dispos., 30, 553 (2002)
• Farlow, M., et al.: Clin. Pharmacokinet., 42, 1383 (2002)
• Cisar, P., et al.: J. Pharm. Biomed. Anal., 37, 1059 (2002)
• Geerts, H., et al.: Brain Res., 1033, 186 (2002)