(2S,3S,4S,5R,6S)-6-[(6-bromonaphthalen-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 131428
• Molecular Formular: C16H15BrO7
• Molecular Mass: 399.1901
• Monoisotopic Mass: 398.00011482
• SMILES: c1cc(cc2c1cc(cc2)Br)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2ccc3c(c2)ccc(c3)Br)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H15BrO7/c17-9-3-1-8-6-10(4-2-7(8)5-9)23-16-13(20)11(18)12(19)14(24-16)15(21)22/h1-6,11-14,16,18-20H,(H,21,22)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: TYDGGWYIJKMLEO-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(6-bromonaphthalen-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(6-bromonaphthalen-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-Bromo-2-naphthyl β-D-glucopyranosiduronic acid; 6-Bromo-2-naphthyl β-D-glucuronide

Database IDs

• CAS Number: 22720-35-0
• EC Number: 245-176-1
• MDL Number: MFCD00046453
• PubChem SID: 162225706
• PubChem CID: 89804

CALCULATED PROPERTIES

• Acid pKa: 3.3744962
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.6318252
• LogD (pH = 7.4): -1.9291122
• Log P: 1.4801164
• Molar Refractivity: 84.1237 cm^3
• Polarizability: 34.84014 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - B6519

Substrates
A histochemical substrate for β-D-glucuronidase.