6-chloro-4-{2-[(2,2,3,3-2H4)cyclopropyl]ethynyl}-7-hydroxy-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 170498
• Molecular Formular: C14H9ClF3NO3
• Molecular Mass: 331.6743696
• Monoisotopic Mass: 331.02230549
• SMILES: c1c(c(cc2c1NC(=O)OC2(C#CC1CC1)C(F)(F)F)Cl)O
• Canonical SMILES: FC(C1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)c(c2)O)(F)F
• InChI: InChI=1S/C14H9ClF3NO3/c15-9-5-8-10(6-11(9)20)19-12(21)22-13(8,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)
• InChIKey: GZMDZAYFVCXHFM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-4-{2-[(2,2,3,3-^2H₄)cyclopropyl]ethynyl}-7-hydroxy-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: 6-chloro-4-{2-[(2,2,3,3-^2H₄)cyclopropyl]ethynyl}-7-hydroxy-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: 6-Chloro-4-(cyclopropyl-d4-ethynyl)-1,4-dihydro-7-hydroxy-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; rac 7-Hydroxy Efavirenz-d4 (Major)

Database IDs

• PubChem SID: 164226408
• PubChem CID: 46781791

CALCULATED PROPERTIES

• Acid pKa: 7.543819
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.149081
• LogD (pH = 7.4): 3.9201949
• Log P: 4.152961
• Molar Refractivity: 73.3232 cm^3
• Polarizability: 26.482113 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Actetae; Methanol
• Apperance: Off-White Solid
• Melting Point: >194°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941822

An isotope labelled metabolite of Efavirenz (E425000) (minor).A representative lot was 84% d4, 12% d5, 2% d3 and 1% d6.

REFERENCES

• Gorski, J., et al.: Biochem. Pharmacol., 47, 1643 (1994)
• Desta, Z., et al.: J. Pharmacol. Exp. Ther., 285, 428 (1994)
• Langmann, P., et al.: Eur. J. Med. Res., 7, 309 (1994)
• Chang, T., et al.: Drug Metab. Dispos., 31, 7 (1994)