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

• ChemBase ID: 131165
• Molecular Formular: C16H18BrClN2O6
• Molecular Mass: 449.68092
• Monoisotopic Mass: 448.00367599
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1c[nH]c2c1c(c(cc2)Br)Cl)CO)O)O
• 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-XZINFULNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,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-β-D-glucopyranoside; X-GlcNAc; 5-Bromo-4-chloro-3-indolyl N-acetyl-β-D-glucosaminide; X-glucosaminide; 5-Bromo-4-chloro-3-indolyl-N-acetyl-β-D-glucosaminide

Database IDs

• CAS Number: 4264-82-8; 5609-91-6
• MDL Number: MFCD00040631
• PubChem SID: 162225443; 24850171; 24891682
• PubChem CID: 2733915

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: DMF: soluble; DMSO: soluble
• Melting Point: 240 °C(lit.)

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: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C16H18BrClN2O6

DETAILS

Sigma Aldrich - B3041

Substrates
Histochemical substrate for N-acetylglucosaminidase.

Sigma Aldrich - 16659

Application
chromophoric substrate für N-Acetyl-β-D-glucosaminidase