sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 178682
• Molecular Formular: C16H14N3NaO10S
• Molecular Mass: 463.35123
• Monoisotopic Mass: 463.02975894
• SMILES: c1(ccccc1C(=O)Nc1ncc(s1)[N+](=O)[O-])O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Oc2ccccc2C(=O)Nc2ncc(s2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C16H15N3O10S.Na/c20-9-10(21)12(14(24)25)29-15(11(9)22)28-7-4-2-1-3-6(7)13(23)18-16-17-5-8(30-16)19(26)27;/h1-5,9-12,15,20-22H,(H,24,25)(H,17,18,23);/q;+1/p-1/t9-,10-,11+,12-,15+;/m0./s1
• InChIKey: HJXNHPDNJXKILF-MFUMLHGQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate
• Synonyms: 2-[[(5-Nitro-2-thiazolyl)amino]carbonyl]phenyl β-D-Glucopyranosiduronic Acid Monosodium Salt; Tizoxanide Glucuronide Sodium Salt

Database IDs

• CAS Number: 221287-83-8
• PubChem SID: 164234592
• PubChem CID: 71752592

CALCULATED PROPERTIES

• Acid pKa: 2.8873897
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -2.3017216
• LogD (pH = 7.4): -3.2610612
• Log P: 0.2627947
• Molar Refractivity: 107.5876 cm^3
• Polarizability: 37.136887 Å^3
• Polar Surface Area: 207.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol (sparingly); Methanol; Water (sparingly),
• Apperance: Yellow Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T450115

A metabolite of Nitazoxanide (N490100).

REFERENCES

• Honma, K., et al.: Chem. Pharm. Bull., 24, 394 (1976)
• Dubreuil, L., et al.: Antimicrob. Agents Chemother., 40, 2266 (1976)
• Stockis, A., et al.: Int. J. Clin. Pharmacol. Ther., 34, 349 (1976)