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

• ChemBase ID: 172852
• Molecular Formular: C10H14N2O6S
• Molecular Mass: 290.29296
• Monoisotopic Mass: 290.05725718
• SMILES: S([C@H]1O[C@@H]([C@H](O)[C@@H](O)[C@H]1O)C(=O)O)c1n(ccn1)C
• Canonical SMILES: OC(=O)[C@H]1O[C@H](Sc2nccn2C)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C10H14N2O6S/c1-12-3-2-11-10(12)19-9-6(15)4(13)5(14)7(18-9)8(16)17/h2-7,9,13-15H,1H3,(H,16,17)/t4-,5-,6+,7-,9-/m1/s1
• InChIKey: KENJCTIXBHPRDX-XSEHCYKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(1-methyl-1H-imidazol-2-yl)sulfanyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(1-methylimidazol-2-yl)sulfanyl]oxane-2-carboxylic acid
• Synonyms: 1-Methyl-1H-imidazol-2-yl 1-Thio-β-D-glucopyranosiduronic Acid; Methimazole Glucuronide; Methimazole Thio-β-D-glucuronide

Database IDs

• CAS Number: 39038-19-2
• PubChem SID: 164228762
• PubChem CID: 71750049

CALCULATED PROPERTIES

• Acid pKa: 3.1981723
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.8860471
• LogD (pH = 7.4): -4.346859
• Log P: -2.2974257
• Molar Refractivity: 63.9122 cm^3
• Polarizability: 25.646803 Å^3
• Polar Surface Area: 125.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M260310

A metabolite of Methimazole.

REFERENCES

• Sitar, D.S., et al.: J. Pharmacol. Exp. Ther., 184, 432 (1973)