3-nitro-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide

• ChemBase ID: 2516
• Molecular Formular: C13H16N2O9
• Molecular Mass: 344.27414
• Monoisotopic Mass: 344.0855801
• SMILES: NC(=O)c1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(c1)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(cc(c2)C(=O)N)[N+](=O)[O-])[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H16N2O9/c14-12(20)5-1-6(15(21)22)3-7(2-5)23-13-11(19)10(18)9(17)8(4-16)24-13/h1-3,8-11,13,16-19H,4H2,(H2,14,20)/t8-,9-,10+,11-,13-/m1/s1
• InChIKey: BYSXBFJVGIOFBO-BZNQNGANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-nitro-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
• IUPAC Traditional name: 3-nitro-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamide
• Synonyms: 5-Aminocarbonyl-3-Nitrophenyl-Alpha-D-Galactopyranose

Database IDs

• PubChem SID: 46508310; 160965966
• PubChem CID: 46936498

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.137775
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.8077632
• LogD (pH = 7.4): -1.8077691
• Log P: -1.8077631
• Molar Refractivity: 76.5864 cm^3
• Polarizability: 29.611504 Å^3
• Polar Surface Area: 188.29 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.31
• LOG S: -1.62
• Solubility (Water): 8.34e+00 g/l

DETAILS

DrugBank - DB02802

Drug information: experimental