6-chloro-8-hydroxy-4-[2-(1-hydroxycyclopropyl)ethynyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 167814
• Molecular Formular: C14H9ClF3NO4
• Molecular Mass: 347.6737696
• Monoisotopic Mass: 347.01722011
• SMILES: c1(cc(cc2c1NC(=O)OC2(C#CC1(CC1)O)C(F)(F)F)Cl)O
• Canonical SMILES: O=C1Nc2c(O)cc(cc2C(O1)(C#CC1(O)CC1)C(F)(F)F)Cl
• InChI: InChI=1S/C14H9ClF3NO4/c15-7-5-8-10(9(20)6-7)19-11(21)23-13(8,14(16,17)18)4-3-12(22)1-2-12/h5-6,20,22H,1-2H2,(H,19,21)
• InChIKey: WILFXLMJFSKQRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-8-hydroxy-4-[2-(1-hydroxycyclopropyl)ethynyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: 6-chloro-8-hydroxy-4-[2-(1-hydroxycyclopropyl)ethynyl]-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: 6-Chloro-1,4-dihydro-8-hydroxy-4-[(1-hydroxycyclopropyl)ethynyl]-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; rac 8,14-Dihydroxy Efavirenz

Database IDs

• CAS Number: 1189909-96-3
• PubChem SID: 162261947
• PubChem CID: 46781323

CALCULATED PROPERTIES

• Acid pKa: 7.66455
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.9907203
• LogD (pH = 7.4): 2.8068173
• Log P: 2.9936612
• Molar Refractivity: 74.8513 cm^3
• Polarizability: 27.194727 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: >199°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D452800

A metabolite of Efavirenz (E425000) (secondary metabolism).

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)