(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(5-iodo-1H-indol-3-yl)oxy]oxane-3,4,5-triol

• ChemBase ID: 155744
• Molecular Formular: C14H16INO6
• Molecular Mass: 421.18441
• Monoisotopic Mass: 421.00223524
• SMILES: c1cc2c(cc1I)c(c[nH]2)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2cc(I)cc3)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H16INO6/c15-6-1-2-8-7(3-6)9(4-16-8)21-14-13(20)12(19)11(18)10(5-17)22-14/h1-4,10-14,16-20H,5H2/t10-,11+,12+,13-,14-/m1/s1
• InChIKey: XNKCQUZRJVDUFR-MBJXGIAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(5-iodo-1H-indol-3-yl)oxy]oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(5-iodo-1H-indol-3-yl)oxy]oxane-3,4,5-triol
• Synonyms: Purple-β-D-Gal; 5-Iodo-3-indolyl-β -D-galactopyranoside

Database IDs

• MDL Number: MFCD00798400
• PubChem SID: 162249882; 24896110
• PubChem CID: 10310015

CALCULATED PROPERTIES

• Acid pKa: 12.199882
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.4293188
• LogD (pH = 7.4): 0.429312
• Log P: 0.42931888
• Molar Refractivity: 84.6323 cm^3
• Polarizability: 34.999374 Å^3
• Polar Surface Area: 115.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H16INO6

DETAILS

Sigma Aldrich - I7154

Application
Chromogenic substrate for β-galactosidase that produces a purple precipitate.