7-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol

• ChemBase ID: 4488
• Molecular Formular: C15H10FNO3
• Molecular Mass: 271.2432032
• Monoisotopic Mass: 271.06447141
• SMILES: c1c(c2c(cc1O)nc(o2)c1ccc(c(c1)F)O)C=C
• Canonical SMILES: C=Cc1cc(O)cc2c1oc(n2)c1ccc(c(c1)F)O
• InChI: InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2
• InChIKey: MQIMZDXIAHJKQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol
• IUPAC Traditional name: prinaberel
• Synonyms: 2-(3-FLUORO-4-HYDROXYPHENYL)-7-VINYL-1,3-BENZOXAZOL-5-OL; 7-Ethenyl-2-(3-fluoro-4-hydroxyphenyl)-5-benzoxazolol; 2-(3-Fluoro-4-hydroxyphenyl)-7-vinyl-1,3-benzoxazol-5-ol; 2-(3-Fluoro-4-hydroxyphenyl)-7-vinylbenzoxazol-5-ol; Prinaberel; ERB 041

Database IDs

• CAS Number: 524684-52-4
• PubChem SID: 160967920; 99443303
• PubChem CID: 5388909

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: 3.28
• LOG S: -3.42
• Solubility (Water): 1.03e-01 g/l

JChem

• Log P: 3.616909
• Molar Refractivity: 81.6892 cm^3
• Polarizability: 28.470993 Å^3
• Polar Surface Area: 66.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 7.5252767
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6128473
• LogD (pH = 7.4): 3.3622425

PROPERTIES

Product Information

• Purity: 97%

DETAILS

DrugBank - DB06832

Drug information: experimental

Toronto Research Chemicals - E594500

ERB 041 is a potent ERβ agonist; displays >200-fold selectivity for ERβ over ERα (IC50 values are 5 and 1216 nM for human ERβ and ERα; 3.1 and 620 nM for rat ERβ and ERα; and 3.7 and 750 nM for mouse ERβ and ERα respectively).

REFERENCES

• Harris, et al.: Endocrinology, 144. 4241 (2003)
• Malamas, et al.: J. Med. Chem., 47, 5021 (2003)
• Cvoro, et al.: J. Immunol., 180, 630 (2003)