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

• ChemBase ID: 172678
• Molecular Formular: C10H19NO5S
• Molecular Mass: 265.32656
• Monoisotopic Mass: 265.09839371
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)SCC)NC(=O)C)O)O
• Canonical SMILES: CCS[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1NC(=O)C)O)O
• InChI: InChI=1S/C10H19NO5S/c1-3-17-10-7(11-5(2)13)9(15)8(14)6(4-12)16-10/h6-10,12,14-15H,3-4H2,1-2H3,(H,11,13)/t6-,7-,8+,9-,10+/m1/s1
• InChIKey: GLDKHCZSFYJVMF-SPFKKGSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5R,6R)-2-(ethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5R,6R)-2-(ethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Ethyl 2-Acetamido-2-deoxy-1-thio-β-D-galactopyranoside; 2-Mercaptoethyl 2-(Acetylamino)-2-deoxy-β-D-galactopyranoside

Database IDs

• CAS Number: 95074-13-8
• PubChem SID: 164228588
• PubChem CID: 71749967

CALCULATED PROPERTIES

• Acid pKa: 12.612356
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.613427
• LogD (pH = 7.4): -1.6134292
• Log P: -1.6134267
• Molar Refractivity: 62.6939 cm^3
• Polarizability: 25.392435 Å^3
• Polar Surface Area: 99.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225250

Antispasmodic.

REFERENCES

• Wolfrom, M.L., et al.: J. Am. Chem. Soc., 81, 3474 (1959)