(3R)-3-(sulfoamino)-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

• ChemBase ID: 177784
• Molecular Formular: C16H15F6N5O4S
• Molecular Mass: 487.3768192
• Monoisotopic Mass: 487.07489431
• SMILES: c1(cc(c(cc1F)C[C@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)NS(=O)(=O)O)F)F
• Canonical SMILES: O=C(N1CCn2c(C1)nnc2C(F)(F)F)C[C@H](NS(=O)(=O)O)Cc1cc(F)c(cc1F)F
• InChI: InChI=1S/C16H15F6N5O4S/c17-10-6-12(19)11(18)4-8(10)3-9(25-32(29,30)31)5-14(28)26-1-2-27-13(7-26)23-24-15(27)16(20,21)22/h4,6,9,25H,1-3,5,7H2,(H,29,30,31)/t9-/m1/s1
• InChIKey: AOWQKFDVSZMKPA-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(sulfoamino)-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
• IUPAC Traditional name: (3R)-3-(sulfoamino)-1-[3-(trifluoromethyl)-5H,6H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
• Synonyms: 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]sulfamic Acid; Sitagliptin N-Sulfate

Database IDs

• CAS Number: 940002-57-3
• PubChem SID: 164233694
• PubChem CID: 46782925

CALCULATED PROPERTIES

• Acid pKa: -2.2970662
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.6861395
• LogD (pH = 7.4): -1.6864926
• Log P: -0.05613658
• Molar Refractivity: 97.7787 cm^3
• Polarizability: 36.279175 Å^3
• Polar Surface Area: 117.42 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S491005

A metabolite of Sitagliptin.

REFERENCES

• Beconi, M.G., et al.: Drug Metab. Dispos., 35, 525 (2007)