N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 76084
• Molecular Formular: C15H21NO6
• Molecular Mass: 311.33034
• Monoisotopic Mass: 311.1368874
• SMILES: O=C(N[C@@H]1[C@@H](O)[C@@H](O)[C@H](O[C@@H]1OCc1ccccc1)CO)C
• Canonical SMILES: OC[C@H]1O[C@H](OCc2ccccc2)[C@@H]([C@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11-,12-,13+,14-,15+/m1/s1
• InChIKey: SKOZFDIGKDPQBO-QMIVOQANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-α-D-galactopyranoside; Benzyl N-Acetyl-α-D-galactosaminide; Benzyl 2-Acetamido-2-deoxy-α-D-galactopyranoside; Benzyl-2-acetamido-2-deoxy-alpha-D-galactopyranosie

Database IDs

• CAS Number: 3554-93-6
• MDL Number: MFCD00057920
• PubChem SID: 162041002
• PubChem CID: 122253

CALCULATED PROPERTIES

• Acid pKa: 12.357337
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.8529751
• LogD (pH = 7.4): -0.8529792
• Log P: -0.8529748
• Molar Refractivity: 76.3885 cm^3
• Polarizability: 30.718012 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 201-203°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Apollo Scientific Ltd - OR1252T

A substrate for N-acetyl-b-D-glucosaminyl transferase. Also an inhibitor of 1-b-3-galactotransferase.

Toronto Research Chemicals - B212520

A substrate for N-acetyl-β-D-glucosaminyltransferase. Also an inhibitor of 1-β-3-galctotransferase. Blocks the apical biosynthetic pathway in polarized HT-29 cells.

REFERENCES

• Delacour, D., et al.: J. Cell Biol., 169, 491 (2005)
• Suzuki, O., et al.: Int. J. Oncol., 26, 1063 (2005)