methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-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: 177786
• Molecular Formular: C30H31F6N5O12
• Molecular Mass: 767.5838592
• Monoisotopic Mass: 767.18734078
• 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]1OC(=O)C)OC(=O)C)OC(=O)C)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]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C30H31F6N5O12/c1-12(42)49-22-23(50-13(2)43)25(51-14(3)44)27(52-24(22)26(46)48-4)53-29(47)37-16(7-15-8-18(32)19(33)10-17(15)31)9-21(45)40-5-6-41-20(11-40)38-39-28(41)30(34,35)36/h8,10,16,22-25,27H,5-7,9,11H2,1-4H3,(H,37,47)/t16-,22+,23+,24+,25-,27+/m1/s1
• InChIKey: LANXKLFMZPYHFM-DFHOWEQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-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-tris(acetyloxy)-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] Tri-O-acetyl-β-D-glucopyranuronic Acid Methyl Ester; Sitagliptin Carbamoyl Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164233696
• PubChem CID: 71752205

CALCULATED PROPERTIES

• Acid pKa: 12.151075
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 1.0709302
• LogD (pH = 7.4): 1.0709298
• Log P: 1.0709367
• Molar Refractivity: 158.3151 cm^3
• Polarizability: 61.257545 Å^3
• Polar Surface Area: 203.78 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - S491020

Protected Sitagliptin metabolite.