(2S,3S,4S,5R,6S)-6-({2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179672
• Molecular Formular: C21H22ClNO9
• Molecular Mass: 467.85368
• Monoisotopic Mass: 467.09830897
• SMILES: c1c(c(n(c1CC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C(=O)c1ccc(cc1)Cl)C
• Canonical SMILES: O=C(Cc1cc(c(n1C)C(=O)c1ccc(cc1)Cl)C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H22ClNO9/c1-9-7-12(23(2)14(9)15(25)10-3-5-11(22)6-4-10)8-13(24)31-21-18(28)16(26)17(27)19(32-21)20(29)30/h3-7,16-19,21,26-28H,8H2,1-2H3,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: FNGKIZYZSHHXJZ-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate] β-D-Glucopyranuronic Acid; Zomepirac Glucuronide; Zomepirac Acyl-1-O-β-D-glucuronide; Zomepirac Acyl-O-β-D-glucuronide

Database IDs

• CAS Number: 75871-31-7
• PubChem SID: 164235582
• PubChem CID: 64760

CALCULATED PROPERTIES

• Acid pKa: 3.138583
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.9511849
• LogD (pH = 7.4): -2.0720603
• Log P: 1.3835821
• Molar Refractivity: 109.4962 cm^3
• Polarizability: 43.185947 Å^3
• Polar Surface Area: 155.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >133°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - Z675010

An unstable metabolite of the nonsteroidal anti-inflammatory drug (NSAID) Zomepirac (Z675000) that is capable of reacting with endogenous proteins to form potentially toxic covalent ZP-protein adducts.

REFERENCES

• King, A.R. et al.: J. Phamacol. Toxicol. Meth., 36, 131 (1996)
• Olsen, J. et al.: Chem. Res. Toxicol., 18, 1729 (1996)
• O’Neill, P.J. et al.: J. Clin. Pharmacol., 22, 470 (1996)