sodium (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 131682
• Molecular Formular: C14H12BrClNNaO7
• Molecular Mass: 444.59435
• Monoisotopic Mass: 442.93833569
• SMILES: c1cc(c(c2c1[nH]cc2O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)[O-])O)O)O)Cl)Br.[Na+]
• Canonical SMILES: [O-]C(=O)[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C14H13BrClNO7.Na/c15-4-1-2-5-7(8(4)16)6(3-17-5)23-14-11(20)9(18)10(19)12(24-14)13(21)22;/h1-3,9-12,14,17-20H,(H,21,22);/q;+1/p-1/t9-,10-,11+,12-,14+;/m0./s1
• InChIKey: IBLSVGDGSKUDCT-CYRSAHDMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: BC-Indicator; X-GlcA; X-glucuronide; 5-Bromo-4-chloro-3-indolyl β-D-glucuronide sodium salt

Database IDs

• CAS Number: 129541-41-9
• MDL Number: MFCD00135782
• PubChem SID: 24891703; 24886828; 162225959; 24891832; 24892057
• PubChem CID: 23664774

CALCULATED PROPERTIES

• Acid pKa: 2.9452777
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.3187351
• LogD (pH = 7.4): -2.2872984
• Log P: 1.1934463
• Molar Refractivity: 94.4019 cm^3
• Polarizability: 34.548016 Å^3
• Polar Surface Area: 135.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: tablet

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: ≥97.0% (HPLC); ≥98%; ≥98% (TLC)
• Empirical Formula (Hill Notation): C14H12BrClNNaO7

DETAILS

Sigma Aldrich - B8174

Application
Chromogenic substrate for β-glucuronidase (GUS) gene detection.
Quantity
Contains 10 mg substrate per tablet

Sigma Aldrich - B4782

Application
Chromogenic substrate for β-glucuronidase (GUS) gene detection.

Sigma Aldrich - B5285

Application
Chromogenic substrate for β-glucuronidase (GUS) gene detection.

Sigma Aldrich - 75439

Application
Chromogenic substrate for β-glucuronidase (GUS) gene detection.
Other Notes
Used as β-glucuronidase substrate for a nonradioactive enzyme assay