(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 131903
• Molecular Formular: C20H25BrClNO11
• Molecular Mass: 570.7696
• Monoisotopic Mass: 569.02995031
• SMILES: c1cc(c(c2c1[nH]cc2O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)Cl)Br
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
• InChI: InChI=1S/C20H25BrClNO11/c21-6-1-2-7-11(12(6)22)8(3-23-7)31-19-17(30)15(28)18(10(5-25)33-19)34-20-16(29)14(27)13(26)9(4-24)32-20/h1-3,9-10,13-20,23-30H,4-5H2/t9-,10-,13-,14+,15-,16-,17-,18-,19-,20+/m1/s1
• InChIKey: TXCDHJGGJYHESA-OIHNOWRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: X-Cellobiose; 5-Bromo-4-chloro-3-indolyl β-D-cellobioside

Database IDs

• CAS Number: 177966-52-8
• MDL Number: MFCD00798387
• PubChem SID: 162226180
• PubChem CID: 12001507

CALCULATED PROPERTIES

• Acid pKa: 11.9339285
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -0.8976641
• LogD (pH = 7.4): -0.89767665
• Log P: -0.89766395
• Molar Refractivity: 116.1107 cm^3
• Polarizability: 48.45692 Å^3
• Polar Surface Area: 194.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

DETAILS

Sigma Aldrich - B6795

Substrates
Chromogenic substrate for certain β-glucosidases