3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]-1λ5-pyridin-1-ylium chloride

• ChemBase ID: 160960
• Molecular Formular: C24H27ClN2O9
• Molecular Mass: 522.93218
• Monoisotopic Mass: 522.14050813
• SMILES: c1(c[n+](ccc1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)OC)[C@H]1N(C(=O)[C@@H](C1)OC(=O)c1ccccc1)C.[Cl-]
• Canonical SMILES: COC(=O)[C@H]1O[C@H]([n+]2cccc(c2)[C@@H]2C[C@H](C(=O)N2C)OC(=O)c2ccccc2)[C@@H]([C@@H]([C@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C24H27N2O9.ClH/c1-25-15(11-16(21(25)30)34-23(31)13-7-4-3-5-8-13)14-9-6-10-26(12-14)22-19(29)17(27)18(28)20(35-22)24(32)33-2;/h3-10,12,15-20,22,27-29H,11H2,1-2H3;1H/q+1;/p-1/t15-,16+,17+,18+,19-,20+,22-;/m0./s1
• InChIKey: QDQCGNBMVBWZHX-RTFOJYQCSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]-1λ^5-pyridin-1-ylium chloride
• IUPAC Traditional name: 3-[(2S,4R)-4-(benzoyloxy)-1-methyl-5-oxopyrrolidin-2-yl]-1-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]-1λ^5-pyridin-1-ylium chloride
• Synonyms: trans-3'-Benzoyloxy-1-(methyl)-5-(2-pyridinyl)-2-pyrrolidinone N-β-D-Glucuronide Methyl Ester Chloride; trans-3'-Benzoyloxy Cotinine N-β-D-Glucuronide Methyl Ester Chloride

Database IDs

• PubChem SID: 162255095
• PubChem CID: 71313557

CALCULATED PROPERTIES

• Acid pKa: 11.689726
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.129087
• LogD (pH = 7.4): -4.129065
• Log P: -4.1290874
• Molar Refractivity: 119.0051 cm^3
• Polarizability: 47.1704 Å^3
• Polar Surface Area: 146.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Semi-Solid

DETAILS

Toronto Research Chemicals - B208170

Used in the preparation of Cotinine derivatives, metabolites of Nicotine in humans.

REFERENCES

• Byrd, G., et al.: Drug Metab. Dispos., 20, 192 (1992)
• Benowitz, N., et al.: Br. J. Clin. Pharmacol., 51, 53 (1992)
• Hanioka, N., et al.: Xenobiotica, 31, 687 (1992)
• Ethell, B., et al.: Biochem. Pharmacol., 65, 1441 (1992)
• Yamanaka, H., et al.: Eur. J.