(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-(2H3)methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 170387
• Molecular Formular: C16H20N2O8
• Molecular Mass: 368.3386
• Monoisotopic Mass: 368.12196561
• SMILES: [C@H]1(C[C@H](N(C1=O)C)c1cnccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@@H]2C[C@H](N(C2=O)C)c2cccnc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8-,9+,10-,11-,12+,13-,16+/m0/s1
• InChIKey: WALNNKZUGHYSCT-MGKNELHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-(^2H₃)methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-(^2H₃)methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
• Synonyms: rel-(3R,5S)-1-(Methyl-d3)-2-oxo-5-(3-pyridinyl)-3-pyrrolidinyl β-D-Glucopyranosiduronic Acid; rac-trans-3'-(Hydroxycotinine-d3)-O-glucuronide; rac-trans-3'-Hydroxy Cotinine-d3 O-β-D-Glucuronide (mixture of diastereomers)

Database IDs

• PubChem SID: 164226297
• PubChem CID: 57347715

CALCULATED PROPERTIES

• Acid pKa: 3.2272434
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -4.0141277
• LogD (pH = 7.4): -5.47405
• Log P: -3.2885127
• Molar Refractivity: 83.0098 cm^3
• Polarizability: 33.483665 Å^3
• Polar Surface Area: 149.65 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 165-176°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H924542

A labelled Nicotine metabolite. Carcinogen.

REFERENCES

• Le Marchand, L., et al.: Cancer Res., 58, 4858 (1998)
• Minna, J., et al.: J. Clin. Invest., 111, 31 (1998)
• Bierut, L., et al.: Hum. Mol. Genet., 16, 24 (1998)
• Thorgeirsson, T., et al.: Nature, 452, 638 (1998)