(2H3)methyl (1R,2R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

• ChemBase ID: 175604
• Molecular Formular: C9H15NO3
• Molecular Mass: 185.2203
• Monoisotopic Mass: 185.10519335
• SMILES: [C@@H]12CC[C@@H](N1)[C@H]([C@H](C2)O)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1[C@@H](O)C[C@H]2N[C@@H]1CC2
• InChI: InChI=1S/C9H15NO3/c1-13-9(12)8-6-3-2-5(10-6)4-7(8)11/h5-8,10-11H,2-4H2,1H3/t5-,6+,7-,8+/m0/s1
• InChIKey: DTIRBMVDLCFJDP-FKSUSPILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (^2H₃)methyl (1R,2R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: (^2H₃)methyl (1R,2R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: 1R,2R,3S,5S)-3-Hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl-d3 Ester; [1R-(exo,exo)]-3-Hydroxy-8-Azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl-d3 Ester; Norecgonine Methyl-d3 Ester; Nor Ecgonine Methyl-d3 Ester

Database IDs

• PubChem SID: 164231514
• PubChem CID: 71751186

CALCULATED PROPERTIES

• Acid pKa: 14.596194
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.7894814
• LogD (pH = 7.4): -2.8215601
• Log P: -0.5962398
• Molar Refractivity: 46.0437 cm^3
• Polarizability: 18.802631 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N674012

A labelled metabolite of Cocaine (C633500).Controlled substance.

REFERENCES

• Brzezinski, M., et al.: Drug Metab. Dispos., 25, 1089 (1997)
• Larsen, N., et al.: J. Mol. Biol., 311, 9 (1997)
• Paula, S., et al.: J. Med. Chem., 47, 133 (1997)