1-[(2R,3R,4S)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-(2H3)methylpyrrolidin-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 175113
• Molecular Formular: C16H20N2O5
• Molecular Mass: 320.3404
• Monoisotopic Mass: 320.13722175
• SMILES: [C@H]1(OC(=C[C@@H]([C@@H]1O)O)C(=O)[O-])[n+]1cccc(c1)[C@@H]1CCCN1C
• Canonical SMILES: O[C@H]1C=C(O[C@H]([C@H]1O)[n+]1cccc(c1)[C@@H]1CCCN1C)C(=O)[O-]
• InChI: InChI=1S/C16H20N2O5/c1-17-6-3-5-11(17)10-4-2-7-18(9-10)15-14(20)12(19)8-13(23-15)16(21)22/h2,4,7-9,11-12,14-15,19-20H,3,5-6H2,1H3/t11-,12-,14+,15+/m0/s1
• InChIKey: IBRSYETXOXCCLW-DDHJSBNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-(^2H₃)methylpyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4S)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-(^2H₃)methylpyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: Nicotine-d3 N-(4-Deoxy-4,5-didehydro)-β-D-glucuronide

Database IDs

• PubChem SID: 164231023
• PubChem CID: 71751006

CALCULATED PROPERTIES

• Acid pKa: 2.705696
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -6.1874833
• LogD (pH = 7.4): -4.673654
• Log P: -6.5240884
• Molar Refractivity: 94.538 cm^3
• Polarizability: 32.138268 Å^3
• Polar Surface Area: 96.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 64-66°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N414255

Labelled Nicotine N-(4-Deoxy-4,5-didehydro)-β-D-glucuronide (N414250). Nicotine-N-(4-deoxy-4,5-didehydro)-β-D-glucuronide is a possible metabolite of Nicotine (N412420).