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. 2018 Oct 2;115(10):1931–1941. doi: 10.1016/j.bpj.2018.09.025

Table 1.

IUPAC Name, CAS Number, Abbreviation, and Experimental Logarithmic Anion Permeability through a DPhPC Bilayer Measured at Listed pH, pKa Experimental/Predicted, and Calculated Logarithmic Anionic Bulk Partition Coefficient Hexadecane/Water Khd/w

IUPAC name CAS Abbreviation Log[(Pexp/(cm/s)] pH pKa Log[Khd/wa/(Lw./Lhd)]
tetraphenylboranuide 143-66-8 TPB −0.5b 6 NDc −8.8
2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile 555-60-2 CCCP −3.4 7d 6.09e −14.6
3,5-dibromo-2-(2,4-dibromophenoxy)phenol 79755-43-4 6-OH-BDE47 −5.2 12.5 7.2f −14.8
bis(fluorosulfonyl)azanide 14984-76-0 ND −4.7 7 −1.5f −15.2
2-(2-Methyl-2-propanyl)-4,6-dinitrophenol 1420-07-1 dino2terb −4.0 7 5.1f −16.2
2-butan-2-yl-4,6-dinitrophenol 88-85-7 dinoseb −4.4 7 4.9f −16.6
2,3,4,5,6-pentachlorophenol 87-86-5 PCP −4.4 7 4.8g −16.6
3,5-dibromo-4-hydroxybenzonitrile 1689-84-5 bromoxynil −6.2 7 5.1f −17.5
5-chloro-2-(2,4-dichlorophenoxy)phenol 3380-34-5 triclosan <−5.9h 12 7.7f −17.8
3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxychromen-2-one 81-82-3 coumachlor −6.8 7 5.2f −18.2
4-nitro-2-(trifluoromethyl)-1H-benzimidazole 14689-51-1 ND −6.1 9 7.0f −18.4
3,4-dinitrophenol 577-71-9 3,4-Dnp −7.5 12 5.7f −18.9
2,4,6-tribromophenol 118-79-6 bromol −7.3 9 6.3f −19.0
2,4-dinitrophenol 51-28-5 2,4-Dnp −6.5 7 4.3f −19.2
4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one 81-81-2 warfarin −8.4 7 5.6f −19.9
2-[3-(trifluoromethyl)anilino]benzoic acid 530-78-9 flufenamic acid −6.8 7 3.9f −21.1
3,5-dichlorophenol 591-35-5 3,5-Dcp −7.9 12.5 8.1f −21.8
4-nitrophenol 100-02-7 4-Np −8.9 12 7.1f −22.5
2-[2-(2,6-dichloroanilino)phenyl]acetate 15307-79-6 diclofenac <−8.5h 7 4.0f −23.5
4-octylbenzenesulfonate 6149-03-7 ND <−8i 7 −1.8f −24.9
2-(2-chloro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione 99105-77-8 sulcotrione <−8.7i 7 4.5f −25.2
2-hydroxybenzoic acid 69-72-7 salicylic acid −11 7 2.8f −26.1
9,10-dimethoxyanthracene-2-sulfonate 67580-39-6 ND <−9i 7 −1.7f −26.6
anthracene-9-carboxylic acid 723-62-6 ND <−9i 7 3.2f −27.4
a

COSMOtherm (31), C30_18, COSMOlogic, http://www.cosmologic.de.

b

Voltage step measurement evaluated at t = 0 after voltage application because of UWL limitations; all others evaluated at steady state.

c

ND, no data.

d

At pH 7, for CCCP, canion ≈ 0.9ctot. Correcting for this reduced anion fraction did not significantly change the result for Pexp.

e

From (16).

f

JChem for Office (Excel) was used for pKa calculation, JChem for Office 17.14.0.1746, 2017, ChemAxon (http://www.chemaxon.com).

g

From (42).

h

Only heterodimer signal detected in the experimental limit.

i

No signal detected in the experimental limit.