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

• ChemBase ID: 169540
• Molecular Formular: C15H19N3O7
• Molecular Mass: 353.32726
• Monoisotopic Mass: 353.12229996
• SMILES: [C@H]1([C@@H](C(/C(=N/OC(=O)Nc2ccccc2)/OC1CO)NC(=O)C)O)O
• Canonical SMILES: OCC1O/C(=N\OC(=O)Nc2ccccc2)/C([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+/m0/s1
• InChIKey: PBLNJFVQMUMOJY-AYYVYFISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2Z,4R,5R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• IUPAC Traditional name: [(2Z,4R,5R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• Synonyms: 2-(Acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-D-galactonimidic Acid δ-Lactone; Gal-PUGNAc; Galacto-PUGNAc

Database IDs

• CAS Number: 1145878-98-3
• PubChem SID: 162263672
• PubChem CID: 71317024

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

DETAILS

Toronto Research Chemicals - G153200

Galacto-PUGNAc is a highly selective inhibitor for β-hexosaminidases HEXA and HEXB is cell-permeable. Galacto-PUGNAc is able to modulate the activity of HEXA and HEXB in tissue culture, increasing ganglioside GM2 levels in neuroblastoma cells

REFERENCES

• Stubbs, K.A. et al.: Angew. Chem. Int. Ed., 48, 1300 (2009)