N-[(2R,3R,4R,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 92007
• Molecular Formular: C16H18BrClN2O6
• Molecular Mass: 449.68092
• Monoisotopic Mass: 448.00367599
• SMILES: CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1Oc1c[nH]c2c1c(Cl)c(Br)cc2
• Canonical SMILES: OC[C@H]1O[C@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C16H18BrClN2O6/c1-6(22)20-13-15(24)14(23)10(5-21)26-16(13)25-9-4-19-8-3-2-7(17)12(18)11(8)9/h2-4,10,13-16,19,21,23-24H,5H2,1H3,(H,20,22)/t10-,13-,14+,15-,16+/m1/s1
• InChIKey: SUWPNTKTZYIFQT-IRHMCKRBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 5-Bromo-4-chloro-3-indolyl-2-acetamido-2-deoxy-alpha-D-galactopyranoside; 5-Bromo-4-chloro-1H-indol-3-yl 2-(Acetylamino)-2-deoxy-α-D-galactopyranoside; 5-Bromo-4-chloro-3-indolyl 2-Acetamido-2-deoxy-α-D-galactopyranoside

Database IDs

• CAS Number: 210110-89-7
• MDL Number: MFCD00269934
• PubChem SID: 162078705
• PubChem CID: 29974819

CALCULATED PROPERTIES

• Acid pKa: 11.129693
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.5851354
• LogD (pH = 7.4): 0.58506465
• Log P: 0.5851365
• Molar Refractivity: 94.7987 cm^3
• Polarizability: 38.90574 Å^3
• Polar Surface Area: 124.04 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >210°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - B682250

A histochemical substrate for a-N-acetyl-galactosaminidase.

REFERENCES

• Zhu, et al.: Gene, 137, 309 (1994)