4-[(4-{[tris(2H3)methyl(2H2)phenyl]amino}pyrimidin-2-yl)amino]benzonitrile

• ChemBase ID: 165401
• Molecular Formular: C20H19N5
• Molecular Mass: 329.39836
• Monoisotopic Mass: 329.16404563
• SMILES: c1c(ccc(c1)Nc1nccc(n1)Nc1c(cc(cc1C)C)C)C#N
• Canonical SMILES: N#Cc1ccc(cc1)Nc1nccc(n1)Nc1c(C)cc(cc1C)C
• InChI: InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)
• InChIKey: ILAYIAGXTHKHNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(4-{[tris(^2H₃)methyl(^2H₂)phenyl]amino}pyrimidin-2-yl)amino]benzonitrile
• IUPAC Traditional name: 4-[(4-{[tris(^2H₃)methyl(^2H₂)phenyl]amino}pyrimidin-2-yl)amino]benzonitrile
• Synonyms: 4-[[4-[(2,4,6-Trimethylphenyl-d11)amino]-2-pyrimidinyl]amino]benzonitrile; R 147681-d11; TMC 120-d11; TMC 120R147681-d11; Dapivirine-d11

Database IDs

• PubChem SID: 162259534
• PubChem CID: 71315182

CALCULATED PROPERTIES

• Acid pKa: 12.926171
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.4419494
• LogD (pH = 7.4): 5.5967746
• Log P: 5.5991907
• Molar Refractivity: 100.7994 cm^3
• Polarizability: 37.37458 Å^3
• Polar Surface Area: 73.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D185502

Labelled Dapivirine (D185500). Non-nucleoside Reverse Transcriptase inhibitor. An antiviral agent.

REFERENCES

• Qin, B., et al.: J. Med. Chem., 53, 4906 (2010)
• Woolfson, A., et al.: Int. J. Pharm., 388, 136 (2010)
• Johnson, T., et al.: Eur. J. Pharm. Sci., 39, 203 (2010)