(4S)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 170499
• Molecular Formular: C14H9ClF3NO3
• Molecular Mass: 331.6743696
• Monoisotopic Mass: 331.02230549
• SMILES: c1(cc(cc2c1NC(=O)O[C@]2(C#CC1CC1)C(F)(F)F)Cl)O
• Canonical SMILES: O=C1Nc2c(O)cc(cc2[C@@](O1)(C#CC1CC1)C(F)(F)F)Cl
• InChI: InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1
• InChIKey: OOVOMPCQLMFEDT-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: 6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; 8-Hydroxyefavirenz; rac 8-Hydroxy Efavirenz

Database IDs

• CAS Number: 205754-32-1
• PubChem SID: 164226409
• PubChem CID: 487643

CALCULATED PROPERTIES

• Acid pKa: 7.664554
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.15002
• LogD (pH = 7.4): 3.9661188
• Log P: 4.152961
• Molar Refractivity: 73.3232 cm^3
• Polarizability: 26.467903 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941825

A metabolite of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor.

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)