(2S,3R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-(2-chloro-4-nitrophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 156706
• Molecular Formular: C18H24ClNO13
• Molecular Mass: 497.83506
• Monoisotopic Mass: 497.09361751
• SMILES: c1cc(c(cc1[N+](=O)[O-])Cl)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2Cl)[N+](=O)[O-])[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O)O
• InChI: InChI=1S/C18H24ClNO13/c19-7-3-6(20(28)29)1-2-8(7)30-17-15(27)13(25)16(10(5-22)32-17)33-18-14(26)12(24)11(23)9(4-21)31-18/h1-3,9-18,21-27H,4-5H2/t9-,10-,11+,12+,13-,14-,15-,16-,17-,18+/m1/s1
• InChIKey: RFGBZYLCQCJGOG-MUKCROHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-(2-chloro-4-nitrophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-(2-chloro-4-nitrophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 2-Chloro-4-nitrophenyl-β-D-lactoside

Database IDs

• CAS Number: 120583-41-7
• MDL Number: MFCD00037473
• PubChem SID: 24855492; 162250843
• PubChem CID: 16211722

CALCULATED PROPERTIES

• Acid pKa: 11.934085
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -1.8251946
• LogD (pH = 7.4): -1.8252071
• Log P: -1.8251944
• Molar Refractivity: 104.7261 cm^3
• Polarizability: 42.464115 Å^3
• Polar Surface Area: 224.35 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥90% (HPCE)
• Empirical Formula (Hill Notation): C18H24ClNO13

DETAILS

Sigma Aldrich - 25589

Other Notes
Substrate for the determination of cellobiohydrolase I1,2