[(3S,4R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methyl acetate

• ChemBase ID: 159285
• Molecular Formular: C10H17NO7
• Molecular Mass: 263.24448
• Monoisotopic Mass: 263.10050189
• SMILES: [C@@H]1([C@@H](C(C(OC1COC(=O)C)O)NC(=O)C)O)O
• Canonical SMILES: CC(=O)OCC1OC(O)C([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C10H17NO7/c1-4(12)11-7-9(15)8(14)6(18-10(7)16)3-17-5(2)13/h6-10,14-16H,3H2,1-2H3,(H,11,12)/t6?,7?,8-,9-,10?/m1/s1
• InChIKey: BUOUIFKLABWPRZ-CTOGJURTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,4R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methyl acetate
• IUPAC Traditional name: [(3S,4R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-D-glucose 6-Acetate; (N,6-O)-Diacetyl-D-Glucosamine; N-Acetyl-D-Glucosamine 6-Acetate

Database IDs

• CAS Number: 131832-93-4
• PubChem SID: 162253420
• PubChem CID: 71312897

CALCULATED PROPERTIES

• Acid pKa: 11.595095
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.7794495
• LogD (pH = 7.4): -2.779476
• Log P: -2.779449
• Molar Refractivity: 56.1762 cm^3
• Polarizability: 23.252766 Å^3
• Polar Surface Area: 125.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A178205

A diacetylated analogue of D-Glucosamine (G514950) used in the preparation of the active mutant subtilisin BPN' in DMF via site-directed mutagenesis

REFERENCES

• Zhong, Z. et al.: J. AM. Chem. Soc., 113, 683 (1991)