(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]oxane-2-carboxylic acid

• ChemBase ID: 174599
• Molecular Formular: C12H17N3O9
• Molecular Mass: 347.27808
• Monoisotopic Mass: 347.09647914
• SMILES: c1(n(c(nc1)C)CCO[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)[N+](=O)[O-]
• Canonical SMILES: OC(=O)[C@H]1O[C@H](OCCn2c(C)ncc2[N+](=O)[O-])[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C12H17N3O9/c1-5-13-4-6(15(21)22)14(5)2-3-23-12-9(18)7(16)8(17)10(24-12)11(19)20/h4,7-10,12,16-18H,2-3H2,1H3,(H,19,20)/t7-,8-,9+,10-,12+/m1/s1
• InChIKey: KOVNZSSTXZPVCG-GPTQDWHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(2-methyl-5-nitroimidazol-1-yl)ethoxy]oxane-2-carboxylic acid
• Synonyms: 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl β-D-Glucopyranosiduronic Acid; Metronidazole β-D-Glucuronide

Database IDs

• CAS Number: 100495-98-5
• PubChem SID: 164230509
• PubChem CID: 9974956

CALCULATED PROPERTIES

• Acid pKa: 2.6450472
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -4.485157
• LogD (pH = 7.4): -5.3974514
• Log P: -2.5690677
• Molar Refractivity: 73.5012 cm^3
• Polarizability: 29.010132 Å^3
• Polar Surface Area: 180.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M338890

A metabolite of Metronidazole.

REFERENCES

• Kokwaro, G.O., et al.: Biochem. Pharmacol., 45, 1243 (1993)
• Sidelmann, U.G., et al.: Xenobiotica, 26, 709 (1993)