2-[2-(hydroxymethyl)-5-nitro-1H-imidazol-1-yl](2H4)ethan-1-ol

• ChemBase ID: 170919
• Molecular Formular: C6H9N3O4
• Molecular Mass: 187.15336
• Monoisotopic Mass: 187.05930578
• SMILES: c1c(n(c(n1)CO)CCO)[N+](=O)[O-]
• Canonical SMILES: OCCn1c(CO)ncc1[N+](=O)[O-]
• InChI: InChI=1S/C6H9N3O4/c10-2-1-8-5(4-11)7-3-6(8)9(12)13/h3,10-11H,1-2,4H2
• InChIKey: AEHPOYAOLCAMIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(hydroxymethyl)-5-nitro-1H-imidazol-1-yl](^2H₄)ethan-1-ol
• IUPAC Traditional name: 2-[2-(hydroxymethyl)-5-nitroimidazol-1-yl](^2H₄)ethanol
• Synonyms: 2-(Hydroxymethyl-d4)-5-nitro-1H-imidazole-1-ethanol; Metronidazole-OH-d4; 1-2-(Hydroxyethyl-d4)-2-(hydroxymethyl)-5-nitroimidazole; Hydroxymetronidazole-d4; Hydroxy Metronidazole-d4

Database IDs

• CAS Number: 1215071-08-1
• PubChem SID: 164226829
• PubChem CID: 53394718

CALCULATED PROPERTIES

• Acid pKa: 13.817862
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.276603
• LogD (pH = 7.4): -1.276559
• Log P: -1.2765583
• Molar Refractivity: 42.9227 cm^3
• Polarizability: 16.018732 Å^3
• Polar Surface Area: 104.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H948397

A labelled metabolite of Metronidazole (M338880).

REFERENCES

• Haller, I., et al.: Antimicrob. Agents Chemother., 22, 165 (1982)
• Gibson, R., et al.: Clin. Chem., 30, 784 (1982)
• Kuti, J., et al.: Pharmacotherapy, 25, 935 (1982)