Table 2.
Compounda | Added Ring Substituentsb |
pKac | SASA (Å2)d |
---|---|---|---|
n-Butyl parabens BuP |
None | 8.78 | 412.14 |
2a | 2,3,5,6-tetrafluoro | 3.73 | 434.90 |
2b | 3,5-dichloro | 5.28 | 465.74 |
2c | 3,5-dibromo | 5.30 | 483.57 |
2d | 3-bromo | 7.03 | 447.79 |
2e | 3,5-diiodo | 4.69 | 508.60 |
2f | 3-iodo | 6.68 | 460.43 |
2g | 3,5-dimethyl | 8.94 | 471.89 |
2h | 3,5-di-tert-butyl | 9.50 | 601.17 |
2i | 3,5-dihydroxy | 7.51 | 431.45 |
2j | 3,5-dimethoxy | 8.68 | 506.35 |
2k | 3,5-dinitro | 2.96 | 482.96 |
n-Octyl parabens OcP |
None | 9.08 | 529.01 |
3e | 3,5-diiodo | 5.08 | 625.49 |
3g | 3,5-dimethyl | 9.27 | 588.38 |
3i | 3,5-dihydroxy | 7.90 | 548.40 |
3k | 3,5-dinitro | 3.87 | 599.88 |
Established ERa agonist E2 |
None | 10.31 | 457.02 |
Parent n-butyl and n-octyl paraben and 17β-estradiol (E2) names from Group A (Fig. 2; Table 1). Ring-substituted paraben names from Fig. 3 (Bergquist et al., 2018).
4-position in each case occupied by a hydroxyl group.
Most acidic pKa computed with ADMET_Predictor 9.0.d
Solvent-accessible surface area computed with ADMET_Predictor 9.0.