(2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexanamine

• ChemBase ID: 92020
• Molecular Formular: C20H26BrClN2O7
• Molecular Mass: 521.78664
• Monoisotopic Mass: 520.06119086
• SMILES: NC1CCCCC1.O[C@@H]1[C@@H](O)[C@H](Oc2c[nH]c3c2c(Cl)c(Br)cc3)O[C@@H]([C@H]1O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@@H]1O)O)O.NC1CCCCC1
• InChI: InChI=1S/C14H13BrClNO7.C6H13N/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;7-6-4-2-1-3-5-6/h1-3,9-12,14,17-20H,(H,21,22);6H,1-5,7H2/t9-,10-,11+,12-,14+;/m0./s1
• InChIKey: JXCKZXHCJOVIAV-CYRSAHDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexanamine
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexylamine
• Synonyms: 5-Bromo-4-chloro-3-indolyl-beta-D-glucuronide, cyclohexylammonium salt; X-GlcA; X-glucuronide CHA salt; 5-Bromo-4-chloro-3-indolyl β-D-glucuronide cyclohexylammonium salt; 5-Bromo-4-chloro-1H-indol-3-yl β-D-Glucopyranosiduronic Acid Monosodium Salt; X-GLUC, CHA SALT; 5-Bromo-4-chloro-3-indolyl β-D-glucuronide, Cyclohexylammonium Salt; 5-Bromo-4-chloro-3-indolyl-beta-D-glucuronide cyclohexylamine salt; 5-溴-4-氯-3-吲哚基-β-D-葡萄糖醛酸苷环己基胺盐

Database IDs

• CAS Number: 18656-96-7; 114162-64-0
• MDL Number: MFCD00058543
• PubChem SID: 24892045; 24891524; 24891926; 24850177; 162078718; 24891735
• PubChem CID: 2733578

CALCULATED PROPERTIES

• Acid pKa: 2.9452777
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.3187351
• LogD (pH = 7.4): -2.2872984
• Log P: 1.1934463
• Molar Refractivity: 83.5648 cm^3
• Polarizability: 34.665928 Å^3
• Polar Surface Area: 132.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: tablet; White Solid
• Melting Point: 228-230°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98%; ≥98% (TLC); ≥99.0% (TLC); 98%
• Grade: for molecular biology; Molecular Biology Reagent
• Suitability: suitable as substrate for β-glucuronidase test
• Impurities: DNases, none detected; phosphatases, none detected; proteases, none detected; RNases, none detected
• Empirical Formula (Hill Notation): C14H13BrClNO7 · C6H13N

DETAILS

Apollo Scientific Ltd - OR8238T

Substrate for b-Glucuronidase that is converted by the enzyme into an intense blue prepicitate. It is used for the detection of the Gus gene in bacterial colonies.

Sigma Aldrich - B0522

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

Sigma Aldrich - B6650

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

Sigma Aldrich - B3783

Application
Chromogenic substrate for β-glucuronidase (GUS) gene detection.
Linkage
Similar to B 0522, but produced by Sigma

Sigma Aldrich - B8049

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

Sigma Aldrich - 16666

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

Toronto Research Chemicals - B682380

A substrate for β-Glucuronidase that is converted by the enzyme into an intense blue prepicitate. It is used for the detection of the Gus gene in bacterial colonies, e.g. Escherichia Coli, or for histochemical applications.

REFERENCES

• Jefferson, R.A., et al.: EMBO J, 6, 3901 (1987)
• Frampton, E.W., et al.: J. Food Protection, 51, 402 (1987)
• Watkins, et al.: Environ. Microbiol. , 54, 1874 (1988)