(3R,4R)-1-[5-(adamantan-1-ylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol

• ChemBase ID: 159537
• Molecular Formular: C22H39NO5
• Molecular Mass: 397.54876
• Monoisotopic Mass: 397.28282335
• SMILES: [C@@H]1([C@@H](C(CN(C1CO)CCCCCOCC12CC3CC(C1)CC(C2)C3)O)O)O
• Canonical SMILES: OCC1N(CCCCCOCC23CC4CC(C3)CC(C2)C4)CC([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15?,16?,17?,18?,19?,20-,21-,22?/m1/s1
• InChIKey: XVYLNHVEAOOEGI-GSPNYCQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-1-[5-(adamantan-1-ylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
• IUPAC Traditional name: (3R,4R)-1-[5-(adamantan-1-ylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-[5-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)pentyl]-3,4,5-piperidinetriol; N-(5-Adamant-1-yl-methoxy)pentyl Deoxynojirimycin

Database IDs

• CAS Number: 216758-20-2
• PubChem SID: 162253672
• PubChem CID: 71313022

CALCULATED PROPERTIES

• Acid pKa: 12.902212
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.7666702
• LogD (pH = 7.4): 0.007187805
• Log P: 0.8981099
• Molar Refractivity: 107.2081 cm^3
• Polarizability: 43.05205 Å^3
• Polar Surface Area: 93.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: Off White Foam

DETAILS

Toronto Research Chemicals - A210000

A powerful inhibitor of the non-lysomal glucoceramidase at nanomolar concentrations. At these low concentrations, the lysosomal glucocerebrosidase and a-glucosidase, the glucoceramide synthetase, and the N-linked glycantrimming a-glucosidases of the endop

REFERENCES

• Jeckel, D., et al.: J. Cell Biol., 117, 259 (1992)
• Kato, A., et al.: J. Med. Chem., 48, 2036 (1992)
• Sakabe, K., et al.: J. Biol. Chem., 285, 34460 (1992)