(1R,3R,5S)-2-{2-amino-2-[(1r,3R,5S,7r)-3,5-dihydroxyadamantan-1-yl](1,2-13C2)acetyl}(6-13C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile

• ChemBase ID: 171297
• Molecular Formular: C18H25N3O3
• Molecular Mass: 334.38736451
• Monoisotopic Mass: 334.19965619
• SMILES: N1([13C](=O)[13CH](N)[C@@]23C[C@H]4C[C@@](C2)(C[C@@](C3)(C4)O)O)[C@H](C[C@H]2[C@@H]1[13CH2]2)C#N
• Canonical SMILES: N#C[C@H]1C[C@H]2[C@@H](N1[13C](=O)[13CH]([C@]13C[C@H]4C[C@@](C3)(C[C@@](C1)(C4)O)O)N)[13CH2]2
• InChI: InChI=1S/C18H25N3O3/c19-6-12-1-11-2-13(11)21(12)15(22)14(20)16-3-10-4-17(23,7-16)9-18(24,5-10)8-16/h10-14,23-24H,1-5,7-9,20H2/t10-,11-,12-,13+,14?,16-,17+,18-/m1/s1/i2+1,14+1,15+1
• InChIKey: GAWUJFVQGSLSSZ-QTUTTZCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S)-2-{2-amino-2-[(1r,3R,5S,7r)-3,5-dihydroxyadamantan-1-yl](1,2-^1^3C₂)acetyl}(6-^1^3C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• IUPAC Traditional name: (1R,3R,5S)-2-{2-amino-2-[(1r,3R,5S,7r)-3,5-dihydroxyadamantan-1-yl](1,2-^1^3C₂)acetyl}(6-^1^3C)-2-azabicyclo[3.1.0]hexane-3-carbonitrile
• Synonyms: (1S,3S,5S)-2-[(2S)-2-amino-2-(3,5-dihydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-Azabicyclo[3.1.0]hexane-3-carbonitrile-13C3; BMS 510849-13C3; Hydroxy Saxagliptin-13C3

Database IDs

• PubChem SID: 164227207
• PubChem CID: 71749337

CALCULATED PROPERTIES

• Acid pKa: 14.357703
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.5188432
• LogD (pH = 7.4): -1.8764465
• Log P: -1.4675356
• Molar Refractivity: 85.6298 cm^3
• Polarizability: 34.104446 Å^3
• Polar Surface Area: 110.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953467

A labelled metabolite of Saxagliptin (S143500).

REFERENCES

• Patel, C. et al.: J. Clinic. Pharmacol., 50, 1211 (2010)
• Feng, J., et al.: J. Med. Chem., 50, 2297 (2010)
• :Rosenstock, J., et al.: Diabetes Obes. Metab., 10, 376 (2010)