(2S,3S,4S,5R,6S)-6-({2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172298
• Molecular Formular: C29H30ClNO8
• Molecular Mass: 556.0034
• Monoisotopic Mass: 555.16599461
• SMILES: c12n(c(c(c1c1ccccc1)c1ccc(cc1)Cl)CC(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)CC(C2)(C)C
• Canonical SMILES: O=C(Cc1c(c2ccc(cc2)Cl)c(c2n1CC(C2)(C)C)c1ccccc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C29H30ClNO8/c1-29(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(30)11-9-16)18(31(19)14-29)12-20(32)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h3-11,23-26,28,33-35H,12-14H2,1-2H3,(H,36,37)/t23-,24-,25+,26-,28+/m0/s1
• InChIKey: WHKFJCYVPLCOGR-NLMMERCGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetate] β-D-Glucopyranuronic Acid; Licofelone M1 Metabolite; Licofelone Acyl-β-D-glucuronide

Database IDs

• CAS Number: 1033702-58-7
• PubChem SID: 164228208
• PubChem CID: 71749786

CALCULATED PROPERTIES

• Acid pKa: 3.488182
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.7737482
• LogD (pH = 7.4): 0.39789388
• Log P: 3.7767818
• Molar Refractivity: 141.0862 cm^3
• Polarizability: 57.954334 Å^3
• Polar Surface Area: 138.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L397740

M1 metabolite of Licofeline.

REFERENCES

• Laufer, S.A., et al.: J. Med. Chem., 37, 1894 (1994)
• Tries, S., et al.: Inflamm. Res., 51, 135 (1994)
• Moreau, M., et al.: J. Vet. Pharmacol. Ther., 28, 81 (1994)