(2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)(4-13C,4,4,4-2H3)butan-2-ol

• ChemBase ID: 179561
• Molecular Formular: C16H14F3N5O
• Molecular Mass: 350.30312444
• Monoisotopic Mass: 350.11839959
• SMILES: C(C([C@@H](c1ncncc1F)[13CH3])(c1c(cc(cc1)F)F)O)n1cncn1
• Canonical SMILES: Fc1ccc(c(c1)F)C([C@@H](c1ncncc1F)[13CH3])(Cn1cncn1)O
• InChI: InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16-/m1/s1/i1+1
• InChIKey: BCEHBSKCWLPMDN-NCZKGZOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)(4-^1^3C,4,4,4-^2H₃)butan-2-ol
• IUPAC Traditional name: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)(4-^1^3C,4,4,4-^2H₃)butan-2-ol
• Synonyms: (αR,βS)-α-(2,4-Difluorophenyl)-5-fluoro-β-(methyl-13C3)-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol; DRG 0301-13C3; UK-109496-13C3; VRC-13C3; Vfend-13C3; Voriconazol-13C3; Voriconazole-13C3

Database IDs

• PubChem SID: 164235471
• PubChem CID: 71752987

CALCULATED PROPERTIES

• Acid pKa: 12.708208
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8227984
• LogD (pH = 7.4): 1.8230275
• Log P: 1.8230326
• Molar Refractivity: 95.278 cm^3
• Polarizability: 30.731285 Å^3
• Polar Surface Area: 76.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V760003

Labelled Vorizonazole (V760000), used as an antifungal (systemic). An Ergosterol Biosynthesis inhibitor.

REFERENCES

• Sanati, H., et al.: Antimicrob. Ag. Chemother., 41, 2492 (1997)