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. Author manuscript; available in PMC: 2019 May 1.
Published in final edited form as: Comput Toxicol. 2018 Nov 28;10:1–16. doi: 10.1016/j.comtox.2018.11.003

Table 2.

Group B ligands and their computed pKa and SASA values.

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
a

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).

b

4-position in each case occupied by a hydroxyl group.

c

Most acidic pKa computed with ADMET_Predictor 9.0.d

d

Solvent-accessible surface area computed with ADMET_Predictor 9.0.