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

• ChemBase ID: 160676
• Molecular Formular: C6H13NO4
• Molecular Mass: 163.17172
• Monoisotopic Mass: 163.0844579
• SMILES: [C@@H]1(C([C@H](N[C@H]1CO)CO)O)O
• Canonical SMILES: OC[C@@H]1N[C@@H](C([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-AMVSKUEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• IUPAC Traditional name: (2S,3S,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• Synonyms: (2R,3R,4R,5S)-3,4-Dihydroxy-2,5-pyrrolidinedimethanol; 2,5-Anhydro-2,5-imino-D-glucitol; 2,5-Anhydro-2,5-imino-D-glucitol

Database IDs

• CAS Number: 132295-44-4
• PubChem SID: 162254811
• PubChem CID: 71313423

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

• Solubility: Methanol (sparingly); Water,
• Apperance: White Solid
• Melting Point: 139-142°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A648300

Many pyrrolidines are powerful inhibitors of glycohydrolases, enzymes responsible for cleavage of glycosidic bonds, glycoprotein processing and the gastrointestinal breakdown of dietary carbohydrates. These compounds are charged at physiological pH and

REFERENCES

• Fellows, L.E., et al.: J. Chem. Brit., 287, (1987)
• Elbein, A.D.: Annu. Rev. Biochem., 56, 497 (1987)
• Fleet, G.W., et al.: J. Chem. Brit., 287, (1989) Baxter, E.W., et al.: J. Org. Chem., 59, 3175 (1987)
• Tyms, A.S. et al. Lancet 1025, (1987)
• Spearman,