3-azaniumyl-2-oxopropyl 2,6-bis(trifluoromethyl)benzoate 4-methylbenzene-1-sulfonate

• ChemBase ID: 179090
• Molecular Formular: C19H17F6NO6S
• Molecular Mass: 501.3967992
• Monoisotopic Mass: 501.06807759
• SMILES: c1cc(c(c(c1)C(F)(F)F)C(=O)OCC(=O)C[NH3+])C(F)(F)F.c1c(ccc(c1)C)S(=O)(=O)[O-]
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)[O-].[NH3+]CC(=O)COC(=O)c1c(cccc1C(F)(F)F)C(F)(F)F
• InChI: InChI=1S/C12H9F6NO3.C7H8O3S/c13-11(14,15)7-2-1-3-8(12(16,17)18)9(7)10(21)22-5-6(20)4-19;1-6-2-4-7(5-3-6)11(8,9)10/h1-3H,4-5,19H2;2-5H,1H3,(H,8,9,10)
• InChIKey: ZNTJKSNSJAUSMC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-azaniumyl-2-oxopropyl 2,6-bis(trifluoromethyl)benzoate 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: 3-ammonio-2-oxopropyl 2,6-bis(trifluoromethyl)benzoate tosylate
• Synonyms: 2,6-Bis(trifluoromethyl)benzoic Acid 3-Amino-2-oxopropyl Ester 4-Methylbenzenesulfonate; TF3BOK; 2,6-Trifluoromethylbenzyloxy Glycine Methyl Ketone Tosylate

Database IDs

• CAS Number: 1144516-95-9
• PubChem SID: 164235000
• PubChem CID: 71752763

CALCULATED PROPERTIES

• Acid pKa: 15.6096735
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.42298976
• LogD (pH = 7.4): 2.1009781
• Log P: 2.6158988
• Molar Refractivity: 74.3189 cm^3
• Polarizability: 22.913982 Å^3
• Polar Surface Area: 71.01 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T791200

2,6-Trifluoromethylbenzyloxy Glycine Methyl Ketone is used in the synthesis electrophilic glycine analogs. Ubiquitin C-terminal electrophiles are activity-based probes for identification and mechanistic study of Ubiquitin conjugating machinery.

REFERENCES

• Hicke, L., et al.: Nat. Rev. Mol. Cell Biol., 2, 195 (2001)
• Borodovsky, A., et al.: Chem. Biol., 9, 1149 (2001)
• Pickart, C., et al.: Biochim. Biophys. Acta, 1695, 55 (2001)
• Newton, K., et al.: Cancer Invest., 25, 502 (2001)