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

• ChemBase ID: 175496
• Molecular Formular: C15H19N3O7
• Molecular Mass: 353.32726
• Monoisotopic Mass: 353.12229996
• SMILES: O1[C@H]([C@H]([C@H]([C@@H]([C@@H]1C(=O)[O-])O)O)O)[n+]1cc(ccc1)C1N(CCC1)N=O
• Canonical SMILES: O=NN1CCCC1c1ccc[n+](c1)[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H19N3O7/c19-10-11(20)13(15(22)23)25-14(12(10)21)17-5-1-3-8(7-17)9-4-2-6-18(9)16-24/h1,3,5,7,9-14,19-21H,2,4,6H2/t9?,10-,11-,12+,13-,14+/m0/s1
• InChIKey: PSNAJRIZSDTBSS-GCRVBOBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-(1-nitrosopyrrolidin-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-(1-nitrosopyrrolidin-2-yl)-1λ^5-pyridin-1-ylium
• Synonyms: NNN-β-D-Glucuronide; Pirydyl-N-β-D-Glucopyranuronosyl-N’-Nitrosonornicotine; 1-β-D-Glucopyranuronosyl-3[(2RS)-1-nitroso-2-pyrrolidinyl]-pyridinium; N'-Nitrosonornicotine N-β-D-Glucuronide (Mixture Of Diastereomers) X Hydrate

Database IDs

• CAS Number: 350508-25-7
• PubChem SID: 164231406
• PubChem CID: 71751141

CALCULATED PROPERTIES

• Acid pKa: 2.59277
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -5.2552185
• LogD (pH = 7.4): -5.255562
• Log P: -5.1952333
• Molar Refractivity: 94.2394 cm^3
• Polarizability: 32.299377 Å^3
• Polar Surface Area: 146.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

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

DETAILS

Toronto Research Chemicals - N535010

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)