(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 169565
• Molecular Formular: C23H29NO9
• Molecular Mass: 463.47766
• Monoisotopic Mass: 463.18423151
• SMILES: c12c3CN(CC[C@@]41C=C[C@@H](C[C@@H]4Oc2c(cc3)OC)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)C
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=C[C@@H](C1)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C23H29NO9/c1-24-8-7-23-6-5-12(31-22-18(27)16(25)17(26)20(33-22)21(28)29)9-14(23)32-19-13(30-2)4-3-11(10-24)15(19)23/h3-6,12,14,16-18,20,22,25-27H,7-10H2,1-2H3,(H,28,29)/t12-,14-,16+,17+,18-,20+,22-,23-/m0/s1
• InChIKey: YWSWSACTOVQVLT-PWLISGMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(1S,12S,14R)-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-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(1S,12S,14R)-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-14-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-yl β-D-Glucopyranosiduronic Acid; Galanthamine β-D-Glucuronide >70%

Database IDs

• CAS Number: 464189-56-8
• PubChem SID: 162263697
• PubChem CID: 71317034

CALCULATED PROPERTIES

• Acid pKa: 2.8902369
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -3.0191827
• LogD (pH = 7.4): -3.0292757
• Log P: -3.0188856
• Molar Refractivity: 114.5856 cm^3
• Polarizability: 45.265514 Å^3
• Polar Surface Area: 138.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >292°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G188515

The major metabolite of Galanthamine (G188500).This compound contains unidentified inorganic impurities.

REFERENCES

• Mihailova, D., et al.: Pharmacology, 32, 301 (1986)
• Bickel, U., et al.: Clin. Pharmacol. Ther., 50, 420 (1986)
• Raskind, M., et al.: Neurology, 54, 2261 (1986)
• Mannens, G.S.J., et al.: Drug Metab. Dispos., 30, 553 (1986)