1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{4-[methyl(nitroso)amino]butanoyl}-1λ5-pyridin-1-ylium

• ChemBase ID: 174057
• Molecular Formular: C16H21N3O8
• Molecular Mass: 383.35324
• Monoisotopic Mass: 383.13286465
• SMILES: O1[C@H]([C@H]([C@H]([C@@H]([C@@H]1C(=O)[O-])O)O)O)[n+]1cc(C(=O)CCCN(C)N=O)ccc1
• Canonical SMILES: O=NN(CCCC(=O)c1ccc[n+](c1)[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C16H21N3O8/c1-18(17-26)6-3-5-10(20)9-4-2-7-19(8-9)15-13(23)11(21)12(22)14(27-15)16(24)25/h2,4,7-8,11-15,21-23H,3,5-6H2,1H3/t11-,12-,13+,14-,15+/m0/s1
• InChIKey: OCZWZVHMLRFHQX-SBJFKYEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{4-[methyl(nitroso)amino]butanoyl}-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-{4-[methyl(nitroso)amino]butanoyl}-1λ^5-pyridin-1-ylium
• Synonyms: NNK-N-β-D-Glucuronide; 1-β-D-Glucopyranuronosyl-3-[4-(methylnitrosoamino)-1-oxobutyl]pyridinium; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone N-β-D-Glucuronide

Database IDs

• CAS Number: 350508-26-8
• PubChem SID: 164229967
• PubChem CID: 71750501

CALCULATED PROPERTIES

• Acid pKa: 2.5675523
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -5.6878996
• LogD (pH = 7.4): -5.68771
• Log P: -5.664582
• Molar Refractivity: 101.7717 cm^3
• Polarizability: 34.96329 Å^3
• Polar Surface Area: 163.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pink Solid
• Melting Point: 118-124°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M325780

A metabolite of N'-Nitrosonornicotine.

REFERENCES

• Caldwell, W.S., et al.: Chem. Res. Toxicol.., 5, 280 (1992)
• Chiu, S.H., et al.: Drug Metab. Dispos., 26, 838 (1992)
• Tukey, R., et al.: Annu. Rev. Pharmacol. Toxicol., 40, 581 (1992)