(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butoxy}oxane-2-carboxylic acid

• ChemBase ID: 174126
• Molecular Formular: C16H23N3O8
• Molecular Mass: 385.36912
• Monoisotopic Mass: 385.14851471
• SMILES: c1(cccnc1)C(CCCN(C)N=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O=NN(CCCC(c1cccnc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C16H23N3O8/c1-19(18-25)7-3-5-10(9-4-2-6-17-8-9)26-16-13(22)11(20)12(21)14(27-16)15(23)24/h2,4,6,8,10-14,16,20-22H,3,5,7H2,1H3,(H,23,24)/t10?,11-,12-,13+,14-,16+/m0/s1
• InChIKey: KNPUXTWHFSLCDT-BBYIEOQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butoxy}oxane-2-carboxylic acid
• Synonyms: 4-(Methylnitrosoamino)-1-(3-pyridinyl)butyl β-D-Glucopyranosiduronic Acid; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol Glucuronide; NNAL-β-O-glucuronide; [4-(Methylnitrosamino)-1-(3-pyridyl)but-1-yl] β-O-D-Glucosiduronic Acid; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol O-β-D-Glucuronide(Mixture of Diastereomers)

Database IDs

• CAS Number: 131119-04-5
• PubChem SID: 164230036
• PubChem CID: 183009

CALCULATED PROPERTIES

• Acid pKa: 3.0514932
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.8030035
• LogD (pH = 7.4): -4.2594934
• Log P: -2.0419738
• Molar Refractivity: 90.2594 cm^3
• Polarizability: 35.462467 Å^3
• Polar Surface Area: 162.01 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - M325720

NNAL glucuronide is a metabolite of NNAL and a major metabolite of nicotine.

REFERENCES

• Ritter, J., et al.: J. Biol. Chem., 265, 7900 (1990)
• Jin, C., et al.: Pharmacol. Exp. Ther., 264, 475 (1990)
• Murata, M., et al.: J. Exp. Med., 197, 1279 (1990)
• Turgeon, D., et al.: Drug Metab. Disp., 31, 670 (1990)