methyl (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-carboxylate

• ChemBase ID: 177785
• Molecular Formular: C24H25F6N5O9
• Molecular Mass: 641.4738192
• Monoisotopic Mass: 641.15564673
• 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)OC)F)F
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)N[C@H](Cc2cc(F)c(cc2F)F)CC(=O)N2CCn3c(C2)nnc3C(F)(F)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H25F6N5O9/c1-42-20(40)19-17(38)16(37)18(39)21(43-19)44-23(41)31-10(4-9-5-12(26)13(27)7-11(9)25)6-15(36)34-2-3-35-14(8-34)32-33-22(35)24(28,29)30/h5,7,10,16-19,21,37-39H,2-4,6,8H2,1H3,(H,31,41)/t10-,16+,17+,18-,19+,21+/m1/s1
• InChIKey: LKUJSWXRTBRCAD-TZKQNKSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (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-carboxylate
• IUPAC Traditional name: methyl (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-carboxylate
• 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 Methyl Ester; Sitagliptin Carbamoyl β-D-Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164233695
• PubChem CID: 71752204

CALCULATED PROPERTIES

• Acid pKa: 11.772213
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.25244612
• LogD (pH = 7.4): -0.2524568
• Log P: -0.25243953
• Molar Refractivity: 130.8606 cm^3
• Polarizability: 49.736774 Å^3
• Polar Surface Area: 185.57 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - S491010

Protected Sitagliptin metabolite.