(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl]amino}oxane-2-carboxylic acid

• ChemBase ID: 172629
• Molecular Formular: C18H29NO6
• Molecular Mass: 355.42596
• Monoisotopic Mass: 355.19948765
• SMILES: [C@]12(C[C@H]3C[C@@](C1)(C[C@@](C2)(C3)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](N[C@]23C[C@H]4C[C@@](C3)(C[C@@](C2)(C4)C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H29NO6/c1-16-3-9-4-17(2,6-16)8-18(5-9,7-16)19-14-12(22)10(20)11(21)13(25-14)15(23)24/h9-14,19-22H,3-8H2,1-2H3,(H,23,24)/t9-,10-,11-,12+,13-,14+,16+,17-,18-/m0/s1
• InChIKey: HYFLKMZNQYTCMY-ILGSKIEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl]amino}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl]amino}oxane-2-carboxylic acid
• Synonyms: 3,5-Dimethyltricyclo[3.3.1.13,7]decan-1-amine β-D-Glucuronide; Memantine N-β-D-Glucuronide

Database IDs

• PubChem SID: 164228539
• PubChem CID: 71749947

CALCULATED PROPERTIES

• Acid pKa: 3.5729065
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.0700064
• LogD (pH = 7.4): -2.0840688
• Log P: -2.06763
• Molar Refractivity: 86.7899 cm^3
• Polarizability: 35.660942 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 123-125°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M218005

A glucuronide metabolite of Memantine (M218000).