5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-2-ol

• ChemBase ID: 170958
• Molecular Formular: C10H14N2O
• Molecular Mass: 178.23096
• Monoisotopic Mass: 178.11061308
• SMILES: c1c(ncc(c1)[C@@H]1CCCN1C)O
• Canonical SMILES: CN1CCC[C@H]1c1ccc(nc1)O
• InChI: InChI=1S/C10H14N2O/c1-12-6-2-3-9(12)8-4-5-10(13)11-7-8/h4-5,7,9H,2-3,6H2,1H3,(H,11,13)/t9-/m0/s1
• InChIKey: ATRCOGLZUCICIV-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-2-ol
• IUPAC Traditional name: l-6-hydroxynicotine
• Synonyms: 5-[(2S)-1-Methyl-2-pyrrolidinyl]-2(1H)-pyridinone; (-)-5-(1-Methyl-2-pyrrolidinyl)-2-pyridinol; 6-Hydroxynicotine; L-6-Hydroxynicotine; (S)-6-Hydroxy Nicotine

Database IDs

• CAS Number: 10516-09-3
• PubChem SID: 164226868
• PubChem CID: 439383

CALCULATED PROPERTIES

• Acid pKa: 11.173196
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3710574
• LogD (pH = 7.4): 0.38932124
• Log P: 1.453427
• Molar Refractivity: 51.9494 cm^3
• Polarizability: 20.036787 Å^3
• Polar Surface Area: 36.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948555

(S)-6-Hydroxy Nicotinev is a metabolite of Nicotine (N412450), a carcinogen agent.

REFERENCES

• Balint, R., et al.: J. Biol. Chem., 262, 11026 (1987)
• Adams, M., et al.: Anal. Biochem., 266, 77 (1987)
• Roessner, U., et al.: Plant Physiol., 127, 749 (1987)
• Born, S., et al.: Drug Metab. Dispos., 30, 483 (1987)