(2S,3R,4S,5S,6S)-2-(4-nitrophenoxy)-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]sulfanyl}methyl)oxane-3,4,5-triol

• ChemBase ID: 4351
• Molecular Formular: C17H23NO11S
• Molecular Mass: 449.42962
• Monoisotopic Mass: 449.09918156
• SMILES: O[C@@H]1CO[C@H](SC[C@H]2O[C@@H](Oc3ccc(cc3)[N+](=O)[O-])[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](CS[C@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O[C@H]([C@@H]([C@H]1O)O)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C17H23NO11S/c19-9-5-27-17(15(24)11(9)20)30-6-10-12(21)13(22)14(23)16(29-10)28-8-3-1-7(2-4-8)18(25)26/h1-4,9-17,19-24H,5-6H2/t9-,10-,11+,12-,13+,14-,15-,16-,17-/m1/s1
• InChIKey: HQYVHBCTLFPWRQ-ZMFOIVQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6S)-2-(4-nitrophenoxy)-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]sulfanyl}methyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S,6S)-2-(4-nitrophenoxy)-6-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]sulfanyl}methyl)oxane-3,4,5-triol
• Synonyms: 4-NITROPHENYL-(6-S-ALPHA-D-XYLOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE

Database IDs

• PubChem SID: 160967783; 46509046
• PubChem CID: 6102810

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.044815
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.3475984
• LogD (pH = 7.4): -1.3476082
• Log P: -1.3475983
• Molar Refractivity: 100.2822 cm^3
• Polarizability: 40.241524 Å^3
• Polar Surface Area: 194.89 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.85
• LOG S: -1.51
• Solubility (Water): 1.40e+01 g/l

DETAILS

DrugBank - DB04807

Drug information: experimental