lithium(1+) ion (2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)pyrrolidine-2-carboxylate

• ChemBase ID: 179496
• Molecular Formular: C17H25LiN2O4
• Molecular Mass: 328.3324
• Monoisotopic Mass: 328.19743684
• SMILES: C1[C@]2(C[C@]3(C[C@@H]1C[C@@H](C2)C3)NCC(=O)N1CCC[C@H]1C(=O)[O-])O.[Li+]
• Canonical SMILES: [O-]C(=O)[C@@H]1CCCN1C(=O)CN[C@]12C[C@@H]3C[C@H](C1)C[C@](C2)(C3)O.[Li+]
• InChI: InChI=1S/C17H26N2O4.Li/c20-14(19-3-1-2-13(19)15(21)22)9-18-16-5-11-4-12(6-16)8-17(23,7-11)10-16;/h11-13,18,23H,1-10H2,(H,21,22);/q;+1/p-1/t11-,12+,13-,16+,17-;/m0./s1
• InChIKey: BEOLPNQOPQSVHF-BJSMUCKRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion (2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)pyrrolidine-2-carboxylate
• IUPAC Traditional name: lithium(1+) ion (2S)-1-(2-{[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]amino}acetyl)pyrrolidine-2-carboxylate
• Synonyms: N-(3-Hydroxytricyclo[3.3.1.13,7]dec-1-yl)glycyl- L-proline Lithium Salt Hydrate; Vildagliptin Carboxylic Acid Lithium Salt Hydrate

Database IDs

• PubChem SID: 164235406
• PubChem CID: 71752940

CALCULATED PROPERTIES

• Acid pKa: 3.3724902
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.7493455
• LogD (pH = 7.4): -2.7556329
• Log P: -2.7477665
• Molar Refractivity: 93.8569 cm^3
• Polarizability: 32.937202 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: >182°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - V305015

The major metabolite of Vildagliptin (V305000).

REFERENCES

• Reimer, M.K., et al.: Eur. J. Endocrinol., 146, 717 (2002)
• Villhauer, E.B., et al.: J. Med. Chem., 46, 2774 (2002)
• Ahren, B., et al.: J. Clin. Endocrinol. Metab., 85, 2078 (2002)
• He, H., et al.: Drug Metab. Dispos., 37, 545 (2002)