(3R,4R,5S)-5-(hydroxymethyl)piperidine-3,4-diol

• ChemBase ID: 171789
• Molecular Formular: C6H13NO3
• Molecular Mass: 147.17232
• Monoisotopic Mass: 147.08954328
• SMILES: [C@@H]1([C@H]([C@@H](CNC1)O)O)CO
• Canonical SMILES: OC[C@@H]1CNC[C@H]([C@@H]1O)O
• InChI: InChI=1S/C6H13NO3/c8-3-4-1-7-2-5(9)6(4)10/h4-10H,1-3H2/t4-,5+,6+/m0/s1
• InChIKey: QPYJXFZUIJOGNX-KVQBGUIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,5S)-5-(hydroxymethyl)piperidine-3,4-diol
• IUPAC Traditional name: (3R,4R,5S)-5-(hydroxymethyl)piperidine-3,4-diol
• Synonyms: 5-epi-(3R,4R,5R)-5-(Hydroxymethyl)-3,4-piperidinediol; (3R,4R,5S)-5-(Hydroxymethyl)-3,4-piperidinediol; [3R-(3α,4β,5β)]-5-(Hydroxymethyl)-3,4-piperidinediol; 5-epi-Isofagomine

Database IDs

• CAS Number: 202979-51-9
• PubChem SID: 164227699
• PubChem CID: 10820691

CALCULATED PROPERTIES

• H Donor: 4
• LogD (pH = 5.5): -5.228414
• LogD (pH = 7.4): -3.667671
• Log P: -2.2613895
• Molar Refractivity: 35.4991 cm^3
• Polarizability: 14.5027485 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 13.516852
• H Acceptors: 4

PROPERTIES

Physical Property

• Apperance: Colourless Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I816005

A selective and very strong inhibitor of β-Glucosidase (Ki=0.11uM).

REFERENCES

• Jespersen, T.M., et al.: Tetrahedron, 50, 13499 (1994)
• Bulow, A., et al.: J. Am. Chem. Soc., 122, 8567 (2000)