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

• ChemBase ID: 160425
• Molecular Formular: C18H27NO10S
• Molecular Mass: 449.47268
• Monoisotopic Mass: 449.13556707
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)O[C@H]1[C@@H](C([C@@H](OC1CO)Sc1ccc(cc1)N)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Sc2ccc(cc2)N)C([C@H]([C@@H]1O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C18H27NO10S/c19-7-1-3-8(4-2-7)30-18-15(26)13(24)16(10(6-21)28-18)29-17-14(25)12(23)11(22)9(5-20)27-17/h1-4,9-18,20-26H,5-6,19H2/t9?,10?,11-,12+,13-,14?,15?,16-,17+,18+/m1/s1
• InChIKey: RIQWCPMDWZXHSW-HALRCSOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{[(3S,4R,6S)-6-[(4-aminophenyl)sulfanyl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{[(3S,4R,6S)-6-[(4-aminophenyl)sulfanyl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 4-Aminophenyl 4-O-β-D-Glucopyranosyl-1-thio-β-D-glucopyranoside; APTC; 4-Aminophenyl 1-Thio-β-D-cellobioside

Database IDs

• CAS Number: 68636-51-1
• PubChem SID: 162254560
• PubChem CID: 46780344

CALCULATED PROPERTIES

• Acid pKa: 12.059008
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -2.8168883
• LogD (pH = 7.4): -2.800522
• Log P: -2.8002996
• Molar Refractivity: 103.8337 cm^3
• Polarizability: 41.86322 Å^3
• Polar Surface Area: 195.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pale Yellow Solid
• Melting Point: >210°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A626960

Shown to be a functional affinity ligand for the separation of exo-(cellobiohydrolasees) and endo-(endoglucanases) acting cellulases.

REFERENCES

• Piyachomkwan, K., et al.: Carbohydrate Research, 303, 255 (1997)