(2S,3R,4S,5R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 153824
• Molecular Formular: C13H13BrClNO5
• Molecular Mass: 378.60302
• Monoisotopic Mass: 376.9665622
• SMILES: c1cc(c(c2c1[nH]cc2O[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)Cl)Br
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)Oc1c[nH]c2c1c(Cl)c(cc2)Br
• InChI: InChI=1S/C13H13BrClNO5/c14-5-1-2-6-9(10(5)15)7(3-16-6)20-13-12(19)11(18)8(4-17)21-13/h1-3,8,11-13,16-19H,4H2/t8-,11-,12-,13-/m1/s1
• InChIKey: RYLVNYDICPAOQR-HUXSOILUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2S,3R,4S,5R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: X β-D-ribofuranoside; X-riboside; 5-Bromo-4-chloro-3-indolyl β-D-ribofuranoside

Database IDs

• CAS Number: 518033-33-5
• MDL Number: MFCD06796946
• PubChem SID: 162247963
• PubChem CID: 10134282

CALCULATED PROPERTIES

• Acid pKa: 12.264376
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.5035065
• LogD (pH = 7.4): 1.5035007
• Log P: 1.5035067
• Molar Refractivity: 77.7349 cm^3
• Polarizability: 32.13556 Å^3
• Polar Surface Area: 94.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -102.0±3.0°, c = 1 in methanol

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% (HPLC)
• Empirical Formula (Hill Notation): C13H13BrClNO5

DETAILS

Sigma Aldrich - 44687

Application
Evaluation of novel beta-ribosidase substrates for the differentiation of Gram-negative bacteria1
Legal Information
Supplied by Glycosynth Limited, U.S. Patent No. 7,323,488, European Patent Nos. 1436411 and 1438424, for use only in internal research conducted by the purchaser. No rights under the aforementioned patents are conveyed which permit the resale, transfer, or use for purposes other than research. Rights under the aforementioned patents, for purposes other than internal research, may be obtained by contacting Glycosynth Limited.