(2S,3R,4R,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol

• ChemBase ID: 162308
• Molecular Formular: C6H13NO4
• Molecular Mass: 163.17172
• Monoisotopic Mass: 163.0844579
• SMILES: [C@@H]1([C@@H]([C@@H](N[C@H]1CO)CO)O)O
• Canonical SMILES: OC[C@@H]1N[C@H]([C@H]([C@@H]1O)O)CO
• InChI: InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5+,6+/m0/s1
• InChIKey: PFYHYHZGDNWFIF-UNTFVMJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• IUPAC Traditional name: (2S,3R,4R,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• Synonyms: (2S,5S)-Bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine

Database IDs

• CAS Number: 105015-44-9
• PubChem SID: 162256443
• PubChem CID: 11116369

CALCULATED PROPERTIES

• Acid pKa: 13.180374
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.8919373
• LogD (pH = 7.4): -4.375834
• Log P: -2.8857431
• Molar Refractivity: 36.5744 cm^3
• Polarizability: 15.1906805 Å^3
• Polar Surface Area: 92.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Crystalline Solid
• Melting Point: 161-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B445000

A potent and specific glycosidase inhibitor. Shows potential as an antiviral agent.

REFERENCES

• Kessel, D., et al.: Photochem. Photobiol., 55, 397 (1992)