(3S)-3-amino-1-[3-(trifluoromethyl)(5,5,6,6-2H4)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; phosphoperoxol

• ChemBase ID: 177788
• Molecular Formular: C16H16F6N5O5P
• Molecular Mass: 503.2929202
• Monoisotopic Mass: 503.07932459
• SMILES: c1(cc(c(cc1F)C[C@@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)N)F)F.P(=O)(=O)OO
• Canonical SMILES: N[C@@H](Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F.OOP(=O)=O
• InChI: InChI=1S/C16H15F6N5O.HO4P/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;1-4-5(2)3/h4,6,9H,1-3,5,7,23H2;1H/t9-;/m0./s1
• InChIKey: MSUBASJQSBTRGJ-FVGYRXGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-1-[3-(trifluoromethyl)(5,5,6,6-^2H₄)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; phosphoperoxol
• IUPAC Traditional name: (3S)-3-amino-1-[3-(trifluoromethyl)(5,5,6,6-^2H₄)-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one; phosphoperoxol
• Synonyms: 7-[(3S)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine Phosphate; (S)-Sitagliptin Phosphate; ent-Sitagliptin-d4 Phosphate

Database IDs

• PubChem SID: 164233698
• PubChem CID: 71752207

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.583009
• LogD (pH = 7.4): -0.13560155
• Log P: 1.2572163
• Molar Refractivity: 87.4946 cm^3
• Polarizability: 31.481646 Å^3
• Polar Surface Area: 77.04 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S491027

Labelled ent-Sitagliptin Phosphate (S491025). ent-Sitagliptin Phosphate is the S-isomer of Sitagliptin Phosphate (S491000), as an impurity.

REFERENCES

• Edmondson, S., et al.: Drug Data Report, 25, 245 (2003)