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

• ChemBase ID: 166501
• Molecular Formular: C22H27NO9
• Molecular Mass: 449.45108
• Monoisotopic Mass: 449.16858145
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)O)O)O)Oc1c2c3c(CN(CC[C@@]43C=C[C@@H](C[C@@H]4O2)O)C)cc1
• Canonical SMILES: O[C@H]1C=C[C@@]23[C@H](C1)Oc1c3c(ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CN(CC2)C
• InChI: InChI=1S/C22H27NO9/c1-23-7-6-22-5-4-11(24)8-13(22)31-18-12(3-2-10(9-23)14(18)22)30-21-17(27)15(25)16(26)19(32-21)20(28)29/h2-5,11,13,15-17,19,21,24-27H,6-9H2,1H3,(H,28,29)/t11-,13-,15-,16-,17+,19-,21+,22-/m0/s1
• InChIKey: XDVUICJRQISSRL-KTEHNTIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-9-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6(17),7,9,15-tetraen-9-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-6-hydroxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-3-yl β-D-Glucopyranosiduronic Acid; O-Desmethyl Galanthamine β-D-Glucuronide

Database IDs

• CAS Number: 464189-54-6
• PubChem SID: 162260634
• PubChem CID: 10321476

CALCULATED PROPERTIES

• Acid pKa: 2.6465857
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.6620257
• LogD (pH = 7.4): -3.672584
• Log P: -3.6619906
• Molar Refractivity: 109.8344 cm^3
• Polarizability: 43.370373 Å^3
• Polar Surface Area: 149.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292033

A metabolite of Galanthamine ((G188500).

REFERENCES

• 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)
• Mannens, G., et al.: Drug Metab. Dispos., 30, 553 (2002)