1-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S,4R)-4-hydroxy-1-(2H3)methyl-5-oxopyrrolidin-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 170384
• Molecular Formular: C16H20N2O8
• Molecular Mass: 368.3386
• Monoisotopic Mass: 368.12196561
• SMILES: [C@H]1(C[C@H](N(C1=O)C)c1c[n+](ccc1)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)[O-])O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@H](O[C@@H]([C@@H]1O)[n+]1cccc(c1)[C@@H]1C[C@H](C(=O)N1C)O)C(=O)[O-]
• InChI: InChI=1S/C16H20N2O8/c1-17-8(5-9(19)14(17)23)7-3-2-4-18(6-7)15-12(22)10(20)11(21)13(26-15)16(24)25/h2-4,6,8-13,15,19-22H,5H2,1H3/t8-,9+,10+,11+,12-,13+,15-/m0/s1
• InChIKey: RQZAUCJAFHEEEZ-LXAYBOCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S,4R)-4-hydroxy-1-(^2H₃)methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S,4R)-4-hydroxy-1-(^2H₃)methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: 1-β-D-Glucopyranuronosyl-3-[(2S,4R)-4-hydroxy-1-(methyl-d3)-5-oxo-2-pyrrolidinyl]pyridinium Inner Salt; trans-3'-Hydroxycotinine-N-glucuronide-d3; trans-3'-Hydroxy Cotinine-d3 N-β-D-Glucuronidesee H924535

Database IDs

• PubChem SID: 164226294
• PubChem CID: 71748949

CALCULATED PROPERTIES

• Acid pKa: 2.846223
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -6.99908
• LogD (pH = 7.4): -6.9997625
• Log P: -6.7702813
• Molar Refractivity: 95.2511 cm^3
• Polarizability: 33.52752 Å^3
• Polar Surface Area: 154.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 188-189°C (dec.)

DETAILS

Toronto Research Chemicals - H924532

It is a major labelled metabolite of Nicotine in humans. Carcinogen.

REFERENCES

• Byrd, G., et al.: Drug Metab. Dispos., 20, 192 (1992)
• Benowitz, N., et al.: Br. J. Clin. Pharmacol., 51, 53 (1992)
• Hanioka, N., et al.: Xenobiotica, 31, 687 (1992)
• Ethell, B., et al.: Biochem. Pharmacol., 65, 1441 (1992)
• Yamanaka, H., et al.: Eur. J.