(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({[(2R)-4-oxo-4-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl]carbamoyl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 177781
• Molecular Formular: C23H23F6N5O9
• Molecular Mass: 627.4472392
• Monoisotopic Mass: 627.13999666
• SMILES: c1(cc(c(cc1F)C[C@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)NC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)F)F
• Canonical SMILES: O=C(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)N[C@H](Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F
• InChI: InChI=1S/C23H23F6N5O9/c24-10-6-12(26)11(25)4-8(10)3-9(30-22(41)43-20-17(38)15(36)16(37)18(42-20)19(39)40)5-14(35)33-1-2-34-13(7-33)31-32-21(34)23(27,28)29/h4,6,9,15-18,20,36-38H,1-3,5,7H2,(H,30,41)(H,39,40)/t9-,15+,16+,17-,18+,20+/m1/s1
• InChIKey: GKDZQUQEXZXGMZ-KUVPMCASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({[(2R)-4-oxo-4-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl]carbamoyl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({[(2R)-4-oxo-4-[3-(trifluoromethyl)-5H,6H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl]carbamoyl}oxy)oxane-2-carboxylic acid
• Synonyms: 1-[N-[(1R)-3-[5,6-Dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-3-oxo-1-[(2,4,5-trifluorophenyl)methyl]propyl]carbamate] β-D-Glucopyranuronic Acid; Sitagliptin Carbamoyl β-D-Glucuronide

Database IDs

• CAS Number: 940002-59-5
• PubChem SID: 164233691
• PubChem CID: 71752203

CALCULATED PROPERTIES

• Acid pKa: 3.2779167
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.6031182
• LogD (pH = 7.4): -3.8292475
• Log P: -0.3983336
• Molar Refractivity: 126.0915 cm^3
• Polarizability: 47.743668 Å^3
• Polar Surface Area: 196.57 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 167-169°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - S490995

A metabolite of Sitagliptin.

REFERENCES

• Zander, M., et al.: Lancet, 359, 824 (2002)
• Kim, D., et al.: J. Med. Chem., 48, 141 (2002)
• Bergman, A., et al.: Clin. Ther., 28, 55 (2002)
• Drucker, D., et al.: Cell Metab., 3, 153 (2002)
• Vincent, S., et al.: Drug Metab. Dispos., 35 (2002)