(2S,4S,5R)-2-{[(4-aminophenyl)methyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 159847
• Molecular Formular: C13H19NO5S
• Molecular Mass: 301.35866
• Monoisotopic Mass: 301.09839371
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)SCc1ccc(cc1)N)O)O)O
• Canonical SMILES: OCC1O[C@@H](SCc2ccc(cc2)N)C([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C13H19NO5S/c14-8-3-1-7(2-4-8)6-20-13-12(18)11(17)10(16)9(5-15)19-13/h1-4,9-13,15-18H,5-6,14H2/t9?,10-,11-,12?,13-/m0/s1
• InChIKey: VNOKYKUWHBAQKG-IJTJVXSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-{[(4-aminophenyl)methyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5R)-2-{[(4-aminophenyl)methyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: (4-Aminophenyl)methyl 1-Thio-β-D-galactopyranoside; 4-Aminobenzyl 1-Thio-β-D-galactopryranoside

Database IDs

• CAS Number: 35785-20-7
• PubChem SID: 162253982
• PubChem CID: 46783470

CALCULATED PROPERTIES

• Acid pKa: 12.480158
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.80613023
• LogD (pH = 7.4): -0.7869067
• Log P: -0.7866523
• Molar Refractivity: 76.157 cm^3
• Polarizability: 29.94799 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water (20 mg/0.2 ml)
• Apperance: Light Yellow Solid
• Melting Point: 110-112°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A601750

A thio sugar as a β-galactosidase inhibitor.

REFERENCES

• Hazes, B., et al.: Biochemistry, 36, 11051 (1982)
• Kassis, S., et al.: J. Biol. Chem., 257, 12148 (1982)
• Zhang, R., et al.: J. Mol. Biol., 251, 563 (1982)