[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate

• ChemBase ID: 158901
• Molecular Formular: C15H19N3O7
• Molecular Mass: 353.32726
• Monoisotopic Mass: 353.12229996
• SMILES: O1/C(=N\OC(=O)Nc2ccccc2)/[C@H]([C@H]([C@@H]([C@@H]1CO)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1O/C(=N\OC(=O)Nc2ccccc2)/[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1
• InChIKey: PBLNJFVQMUMOJY-JXZOILRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• IUPAC Traditional name: [(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• Synonyms: PugNAc; 2-(Acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-D-gluconimidic Acid δ-Lactone; (Z)-PugNAc; O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate

Database IDs

• CAS Number: 132489-69-1
• PubChem SID: 162253036
• PubChem CID: 9576811

CALCULATED PROPERTIES

• Acid pKa: 11.714825
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.0063037
• LogD (pH = 7.4): -1.0063224
• Log P: -1.0063033
• Molar Refractivity: 84.254 cm^3
• Polarizability: 32.771984 Å^3
• Polar Surface Area: 149.71 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Ethanol; Hot Methanol
• Apperance: White to Off-White Solid
• Melting Point: 172-175°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A157250

An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B.

REFERENCES

• Baji, H., et al,: Eur. J. Med. Chem., 30, 617 (1995)
• Vaaje-Kolstad, G., et al.: J. Biol. Chem., 279, 3612 (1995)
• Perreira, M., et al.: Bioorg. Med. Chem., 14, 837 (2006).