2-[4-(trifluoromethyl)phenyl]-1H,4H,5H,7H,8H-thiopyrano[4,3-d]pyrimidin-4-one

• ChemBase ID: 179599
• Molecular Formular: C14H11F3N2OS
• Molecular Mass: 312.3101496
• Monoisotopic Mass: 312.05441864
• SMILES: C1SCc2c(C1)[nH]c(nc2=O)c1ccc(cc1)C(F)(F)F
• Canonical SMILES: O=c1nc([nH]c2c1CSCC2)c1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C14H11F3N2OS/c15-14(16,17)9-3-1-8(2-4-9)12-18-11-5-6-21-7-10(11)13(20)19-12/h1-4H,5-7H2,(H,18,19,20)
• InChIKey: KLGQSVMIPOVQAX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(trifluoromethyl)phenyl]-1H,4H,5H,7H,8H-thiopyrano[4,3-d]pyrimidin-4-one
• IUPAC Traditional name: 2-[4-(trifluoromethyl)phenyl]-1H,5H,7H,8H-thiopyrano[4,3-d]pyrimidin-4-one
• Synonyms: 1,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one; NVP-XAV 939; XAV 939

Database IDs

• CAS Number: 284028-89-3
• PubChem SID: 164235509
• PubChem CID: 2726824

CALCULATED PROPERTIES

• Acid pKa: 7.8525004
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.2632604
• LogD (pH = 7.4): 2.1471102
• Log P: 2.2650151
• Molar Refractivity: 76.6214 cm^3
• Polarizability: 27.628622 Å^3
• Polar Surface Area: 41.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - X744000

A tankyrase (TNKS) inhibitor that antagonizes Wnt signaling via stimulation of β-catenin degradation and stabilization of axin. XAV 939 inhibits proliferation of the μ-catenin-dependent colon carcinoma cell line DLD-1.

REFERENCES

• Huang, S. et al.: Nature, 461, 614 (2009)
• Wang, H. et al.: ACS Chem. Biol., 6, 192 (2009)
• Adles, M.E. et al.: Sci. Signal., 91, ec326 (2009)