N-[(3R,4R,5S)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl]acetamide

• ChemBase ID: 158924
• Molecular Formular: C7H14N2O3
• Molecular Mass: 174.19766
• Monoisotopic Mass: 174.10044232
• SMILES: [C@@H]1([C@H]([C@@H](NC1)CO)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1NC[C@H]([C@H]1O)NC(=O)C
• InChI: InChI=1S/C7H14N2O3/c1-4(11)9-5-2-8-6(3-10)7(5)12/h5-8,10,12H,2-3H2,1H3,(H,9,11)/t5-,6+,7-/m1/s1
• InChIKey: CIBNSHFFZNRICG-DSYKOEDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-3-yl]acetamide
• Synonyms: N-[(3S,4R,5S)-4-Hydroxy-5-(hydroxymethyl)-3-pyrrolidinyl]acetamide; LABNAc; 2-Acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol

Database IDs

• CAS Number: 944329-24-2
• PubChem SID: 162253059
• PubChem CID: 53235688

CALCULATED PROPERTIES

• Acid pKa: 13.652564
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -5.653144
• LogD (pH = 7.4): -4.3253665
• Log P: -2.5434434
• Molar Refractivity: 41.7132 cm^3
• Polarizability: 16.951561 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A158415

A potent pyrrolidine inhibitor of hexosaminidases.

REFERENCES

• Platt, F., et al.: Biochem. Pharmacol., 56, 421 (1998)
• Cox, T., et al.: Lancet, 355, 1481 (1998)
• Tropak, M., et al.: J. Biol. Chem., 279, 13478 (1998)