1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 175119
• Molecular Formular: C16H22N2O6
• Molecular Mass: 338.35568
• Monoisotopic Mass: 338.14778643
• SMILES: c1c[n+](cc(c1)[C@@H]1CCCN1C)[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-]
• Canonical SMILES: CN1CCC[C@H]1c1ccc[n+](c1)[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15+/m0/s1
• InChIKey: SAWAIULJDYFLPD-CTTWBBHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: 1-β-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]pyridinium Inner Salt; (S)-1-β-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium Inner Salt; Nicotine N-Glucuronide; NNG; NIC GLUC; Nicotine N-β-D-Glucuronide

Database IDs

• CAS Number: 153536-53-9
• PubChem SID: 164231029
• PubChem CID: 71751013

CALCULATED PROPERTIES

• Acid pKa: 2.5186102
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -6.926464
• LogD (pH = 7.4): -5.4127965
• Log P: -7.2624025
• Molar Refractivity: 94.177 cm^3
• Polarizability: 33.054962 Å^3
• Polar Surface Area: 117.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N424575

Nicotine N-β-D-Glucuronide is a Nicotine (N412420) metabolite in rat brain. Nicotine N-β-D-Glucuronide is used as a Nicotine biomarker in rat brain.

REFERENCES

• Alexandrov, K., et al.: Toxicol. Lett., 198, 63 (2010)
• Huang, L., et al.: J. Neurochem., 109, 826 (2010)
• Quik, M., et al.: Biochem. Pharmacol., 78, 677 (2010)
• Weems, J., et al.: Chem. Res. Toxicol., 23, 696 (2010)