(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 179497
• Molecular Formular: C23H33N3O8
• Molecular Mass: 479.52342
• Monoisotopic Mass: 479.22676503
• SMILES: C1[C@]2(C[C@]3(C[C@@H]1C[C@@H](C2)C3)NCC(=O)N1CCC[C@H]1C#N)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: N#C[C@@H]1CCCN1C(=O)CN[C@]12C[C@@H]3C[C@H](C1)C[C@](C2)(C3)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H33N3O8/c24-9-14-2-1-3-26(14)15(27)10-25-22-5-12-4-13(6-22)8-23(7-12,11-22)34-21-18(30)16(28)17(29)19(33-21)20(31)32/h12-14,16-19,21,25,28-30H,1-8,10-11H2,(H,31,32)/t12-,13+,14-,16-,17-,18+,19-,21-,22+,23-/m0/s1
• InChIKey: PSIDBGKCTWXOHS-VUHWNEFDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1s,3r,5R,7S)-3-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)adamantan-1-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (2S)-1-[2-[(3-Hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-pyrrolidinecarbonitrileO-β-D-Glucopyranosiduronic Acid; Vildagliptin O-Glucuronide; Vildagliptin β-D-Glucuronide

Database IDs

• CAS Number: 1147403-03-9
• PubChem SID: 164235407
• PubChem CID: 71752941

CALCULATED PROPERTIES

• Acid pKa: 3.346729
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.1418943
• LogD (pH = 7.4): -4.143939
• Log P: -4.1402965
• Molar Refractivity: 114.2798 cm^3
• Polarizability: 46.017567 Å^3
• Polar Surface Area: 172.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V305020

A metabolite of Vildagliptin.

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)