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

• ChemBase ID: 174055
• Molecular Formular: C18H27N3O9
• Molecular Mass: 429.42168
• Monoisotopic Mass: 429.17472946
• SMILES: O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)[n+]1cc(C(=O)CCCN(C)N=O)ccc1.[O-]C(=O)C
• Canonical SMILES: [O-]C(=O)C.OC[C@H]1O[C@@H]([n+]2cccc(c2)C(=O)CCCN(N=O)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H24N3O7.C2H4O2/c1-18(17-25)6-3-5-11(21)10-4-2-7-19(8-10)16-15(24)14(23)13(22)12(9-20)26-16;1-2(3)4/h2,4,7-8,12-16,20,22-24H,3,5-6,9H2,1H3;1H3,(H,3,4)/q+1;/p-1/t12-,13-,14+,15-,16-;/m1./s1
• InChIKey: YWOZFHDTAPJHBJ-DNJQXARPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[methyl(nitroso)amino]butanoyl}-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1λ^5-pyridin-1-ylium acetate
• IUPAC Traditional name: 3-{4-[methyl(nitroso)amino]butanoyl}-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1λ^5-pyridin-1-ylium acetate
• Synonyms: NNK-β-D-glucoside Acetate Salt; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone β-D-Glucoside, Acetate Salt

Database IDs

• PubChem SID: 164229965
• PubChem CID: 71750499

CALCULATED PROPERTIES

• Acid pKa: 11.702219
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -5.7791176
• LogD (pH = 7.4): -5.778479
• Log P: -5.778493
• Molar Refractivity: 91.0672 cm^3
• Polarizability: 35.0903 Å^3
• Polar Surface Area: 143.77 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol,
• Apperance: Orange Solid

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic and Moisture Sensitive

DETAILS

Toronto Research Chemicals - M325770

A glucoside of NNK.