(2S,4S,5R)-2-{[(3S,4R,6R)-6-[(3,5-dimethyladamantan-1-yl)amino]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 172631
• Molecular Formular: C24H41NO10
• Molecular Mass: 503.58304
• Monoisotopic Mass: 503.27304652
• SMILES: C12(CC3CC(C1)(CC(C2)(C3)C)C)N[C@H]1C([C@H]([C@@H](C(O1)CO)O[C@@H]1OC([C@@H]([C@@H](C1O)O)O)CO)O)O
• Canonical SMILES: OCC1O[C@@H](NC23CC4CC(C3)(CC(C2)(C4)C)C)C([C@H]([C@@H]1O[C@@H]1OC(CO)[C@@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C24H41NO10/c1-22-3-11-4-23(2,8-22)10-24(5-11,9-22)25-20-17(31)16(30)19(13(7-27)33-20)35-21-18(32)15(29)14(28)12(6-26)34-21/h11-21,25-32H,3-10H2,1-2H3/t11?,12?,13?,14-,15-,16+,17?,18?,19+,20+,21-,22?,23?,24?/m0/s1
• InChIKey: IDHWSQNFOHZVMN-GFYLEGOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-{[(3S,4R,6R)-6-[(3,5-dimethyladamantan-1-yl)amino]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5R)-2-{[(3S,4R,6R)-6-[(3,5-dimethyladamantan-1-yl)amino]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: MLA; N-(3,5-Dimethyltricyclo[3.3.1.13,7]dec-1-yl)-4-O-β-D-galactopyranosyl-D-glucopyranosylamine; Memantine Lactose Adduct

Database IDs

• CAS Number: 1159637-28-1
• PubChem SID: 164228541
• PubChem CID: 71434024

CALCULATED PROPERTIES

• Acid pKa: 12.053463
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.584396
• LogD (pH = 7.4): -2.9647331
• Log P: -1.6861756
• Molar Refractivity: 119.3358 cm^3
• Polarizability: 49.445004 Å^3
• Polar Surface Area: 181.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol,; Water
• Apperance: White Solid
• Melting Point: 148-150°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M218010

A lactose adduct of Memantine (M218000). Intermediate in the synthesis of reducing carbohydrate Adamantane amines for use in treating Gram positive or Gram negative bacteria infections.

REFERENCES

• Kustimur, et al.: Chinese Med. J., 116, 633 (2003)