IAM Chromatographic Models of Skin Permeation
Abstract
:1. Introduction
(steroids, n = 16, R2 = 0.99, R2adj. = 0.98, F = 229.0, p < 0.01, se = 0.18)
(structurally diverse compounds, n = 60, R2 = 0.87, R2adj. = 0.85, F = 70.9, p < 0.01, se = 0.40)
(n = 32, R2 = 0.74)
(n = 10, R2 = 0.94)
2. Results and Discussion
(n = 160, R2 = 0.46, R2adj. = 0.45, MSE = 0.32, F = 132.7, p < 0.01, se = 0.57)
(n = 32, R2 = 0.26)
- Generating a well-fitting model based on a relatively large number of independent variables selected by forward stepwise multiple regression;
- Validation of the model using two randomly selected subsets of compounds, namely a training set (n = 120) and a test set (n = 40);
- Validation of the initial model using experimental log Kpexp data for a subset of compounds (n = 20);
- Analysis of every step of multiple stepwise regression in order to eliminate redundant independent variables; and
- Building a new model based on a reduced set of independent variables and its validation as described above.
(n = 160, R2 = 0.96, R2adj. = 0.92, MSE = 0.043, F = 216.6, p < 0.01, se = 0.21)
(n = 120, R2 = 0.95, R2adj. = 0.94, MSE = 0.032, F = 210.5, p < 0.01, se = 0.18)
(n = 160, R2 = 0.91, R2adj. = 0.91, MSE = 0.052, F = 538.9, p < 0.01, se = 0.23)
(n = 160, R2 = 0.87, R2adj. = 0.87, MSE = 0.078, F = 524.7, p < 0.01, se = 0.28)
(n = 160, R2 = 0.85, R2adj. = 0.85, MSE = 0.088, F = 452.8, p < 0.01, se = 0.30)
(n = 120, R2 = 0.93, R2adj. = 0.93, MSE = 0.042, F = 490.7, p < 0.01, se = 0.21)
(n = 120, R2 = 0.90, R2adj. = 0.89, MSE = 0.060, F = 500.1, p < 0.01, se = 0.25)
(n = 120, R2 = 0.87, R2adj. = 0.86, MSE = 0.077, F = 375.2, p < 0.01, se = 0.28)
3. Materials and Methods
3.1. IAM Chromatography
3.2. Calculated Molecular Descriptors
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No. | CAS No. | log kIAM | log KpEPI | log Kp(9) | log Kp(11) | log Kp(12) | log Kp(13) | log Kpexp | |
---|---|---|---|---|---|---|---|---|---|
1 | 103-84-4 | acetanilide | 0.48 | −2.79 | −2.91 | −2.83 | −2.92 | −2.69 | |
2 | 98-86-2 | acetophenone | 0.76 | −2.43 | −2.42 | −2.43 | −2.55 | −2.33 | |
3 | 95-55-6 | 2-aminophenol | 0.28 | −3.01 | −2.97 | −3.01 | −2.89 | −3.11 | |
4 | 100-66-3 | anisole | 1.06 | −2.01 | −2.08 | −2.07 | −2.19 | −2.03 | |
5 | 100-52-7 | benzaldehyde | 0.63 | −2.42 | −2.52 | −2.47 | −2.58 | −2.39 | |
6 | 55-21-0 | benzamide | 0.12 | −3.06 | −3.13 | −3.14 | −3.10 | −3.13 | |
7 | 71-43-2 | benzene | 0.96 | −1.83 | −1.98 | −1.95 | −2.10 | −1.91 | |
8 | 100-47-0 | benzonitrile | 0.77 | −2.35 | −2.43 | −2.41 | −2.41 | −2.45 | |
9 | 100-51-6 | benzyl alcohol | 0.35 | −2.68 | −2.58 | −2.67 | −2.77 | −2.59 | |
10 | 92-52-4 | biphenyl | 2.88 | −1.01 | −1.01 | −0.93 | −1.03 | −0.94 | |
11 | 90-11-9 | 1-bromonaphtalene | 2.90 | −1.27 | −1.12 | −0.92 | −1.04 | −0.93 | |
12 | 591-20-8 | 3-bromophenol | 1.71 | −2.03 | −1.81 | −1.75 | −1.68 | −1.91 | |
13 | 104-54-1 | cinnamyl alcohol | 1.02 | −2.26 | −2.43 | −2.39 | −2.52 | −2.25 | |
14 | 91-64-5 | coumarin | 0.99 | −2.70 | −2.55 | −2.40 | −2.44 | −2.38 | |
15 | 108-94-1 | cyclohexanone | 0.08 | −2.82 | −2.79 | −2.80 | −2.94 | −2.67 | |
16 | 84-66-2 | diethyl phtalate | 1.63 | −2.44 | −2.37 | −2.50 | −2.39 | −2.54 | |
17 | 576-26-1 | 2,6-dimethylphenol | 1.25 | −1.92 | −2.11 | −2.12 | −2.15 | −2.14 | |
18 | 623-05-2 | 4-hydroxybenzyl alcohol | 0.12 | −3.34 | −3.10 | −3.10 | −3.08 | −3.08 | |
19 | 95-48-7 | 2-methylphenol | 1.02 | −2.12 | −2.21 | −2.21 | −2.23 | −2.25 | −1.80 |
20 | 106-44-5 | 4-methylphenol | 1.02 | −2.12 | −2.21 | −2.22 | −2.23 | −2.26 | −1.76 |
21 | 91-20-3 | naphtalene | 2.47 | −1.33 | −1.25 | −1.12 | −1.22 | −1.15 | |
22 | 90-15-3 | 1-naphthol | 2.08 | −1.72 | −1.76 | −1.64 | −1.62 | −1.72 | |
23 | 135-19-3 | 2-naphthol | 1.93 | −1.82 | −1.88 | −1.75 | −1.76 | −1.79 | −1.55 |
24 | 88-74-4 | 2-nitroaniline | 1.13 | −2.35 | −2.72 | −2.70 | −2.24 | −3.16 | |
25 | 100-01-6 | 4-nitroaniline | 1.01 | −2.66 | −2.78 | −2.78 | −2.35 | −3.22 | |
26 | 98-95-3 | nitrobenzene | 1.04 | −2.27 | −2.49 | −2.44 | −2.20 | −2.72 | |
27 | 619-73-8 | 4-nitrobenzyl alcohol | 0.72 | −2.83 | −3.03 | −2.98 | −2.67 | −3.26 | |
28 | 627-05-4 | 1-nitrobutane | 0.42 | −2.41 | −2.70 | −2.80 | −2.59 | −3.03 | |
29 | 99-99-0 | 4-nitrotoluene | 1.35 | −2.00 | −2.34 | −2.29 | −2.05 | −2.56 | |
30 | 108-95-2 | phenol | 0.68 | −2.36 | −2.38 | −2.38 | −2.40 | −2.42 | −2.09 |
31 | 60-12-8 | 2-phenylethanol | 0.53 | −2.59 | −2.63 | −2.65 | −2.79 | −2.50 | |
32 | 92-69-3 | 4-phenylphenol | 2.56 | −1.63 | −1.44 | −1.39 | −1.37 | −1.47 | |
33 | 108-88-3 | toluene | 1.40 | −1.51 | −1.71 | −1.70 | −1.83 | −1.69 | |
34 | 106-48-9 | 4-chlorophenol | 1.48 | −1.94 | −1.89 | −1.87 | −1.81 | −2.02 | −1.44 |
35 | 271-89-6 | 2,3-benzofuran | 1.50 | −1.69 | −1.83 | −1.85 | −1.89 | −1.88 | |
36 | 526-75-0 | 2,3-dimethylphenol | 1.44 | −1.84 | −1.96 | −1.98 | −1.98 | −2.04 | |
37 | 105-67-9 | 2,4-dimethylphenol | 1.46 | −1.96 | −1.96 | −1.96 | −1.96 | −2.03 | |
38 | 91-23-6 | 2-nitroanisole | 1.09 | −2.51 | −2.66 | −2.61 | −2.34 | −2.87 | |
39 | 95-51-2 | 2-chloroaniline | 1.21 | −2.26 | −2.16 | −2.17 | −2.12 | −2.27 | |
40 | 99-09-2 | 3-nitroaniline | 0.93 | −2.67 | −2.85 | −2.85 | −2.42 | −3.26 | |
41 | 539-03-7 | 4-chloroacetanilide | 1.27 | −2.37 | −2.45 | −2.32 | −2.35 | −2.29 | |
42 | 106-47-8 | 4-chloroaniline | 1.16 | −2.30 | −2.21 | −2.21 | −2.17 | −2.29 | |
43 | 62-53-3 | aniline | 0.35 | −2.73 | −2.69 | −2.73 | −2.77 | −2.70 | |
44 | 60-80-0 | antipyrine | 0.22 | −3.61 | −3.48 | −3.20 | −3.55 | −2.72 | |
45 | 119-61-9 | benzophenone | 2.06 | −1.71 | −1.88 | −1.79 | −1.92 | −1.67 | |
46 | 120-51-4 | benzyl benzoate | 2.71 | −1.36 | −1.64 | −1.50 | −1.51 | −1.51 | |
47 | 108-86-1 | bromobenzene | 1.75 | −1.70 | −1.57 | −1.49 | −1.59 | −1.51 | |
48 | 68411-44-9 | butylbenzene | 2.78 | −0.52 | −0.84 | −0.90 | −0.96 | −0.99 | |
49 | 495-40-9 | butyrophenone | 1.56 | −1.80 | −1.95 | −1.99 | −2.08 | −1.92 | |
50 | 58-08-2 | caffeine | −0.17 | −3.94 | −4.24 | −3.71 | −3.78 | −3.47 | |
51 | 108-90-7 | chlorobenzene | 1.58 | −1.55 | −1.60 | −1.57 | −1.67 | −1.59 | |
52 | 50-22-6 | corticosterone | 1.69 | −3.46 | −3.26 | −3.25 | −3.30 | −2.92 | |
53 | 53-06-5 | cortisone | 1.29 | −3.85 | −3.75 | −3.72 | −3.67 | −3.44 | |
54 | 50-28-2 | estradiol | 2.65 | −1.67 | −2.05 | −1.96 | −2.03 | −1.80 | −2.28 |
55 | 50-27-1 | estriol | 1.66 | −2.80 | −3.06 | −2.93 | −2.98 | −2.68 | |
56 | 100-41-4 | ethylbenzene | 1.81 | −1.31 | −1.46 | −1.48 | −1.59 | −1.48 | |
57 | 110-00-9 | furan | 0.32 | −2.30 | −2.38 | −2.42 | −2.46 | −2.48 | |
58 | 106-24-1 | geraniol | 1.80 | −1.36 | −1.74 | −1.91 | −1.98 | −1.86 | |
59 | 1671-75-6 | heptanophenone | 2.99 | −1.13 | −1.00 | −1.16 | −1.18 | −1.20 | |
60 | 50-23-7 | hydrocortisone | 1.30 | −3.77 | −3.79 | −3.76 | −3.70 | −3.50 | −3.92 |
61 | 108-39-4 | 3-methylphenol | 1.05 | −2.11 | −2.19 | −2.19 | −2.20 | −2.24 | |
62 | 93-58-3 | methyl benzoate | 1.11 | −2.16 | −2.30 | −2.29 | −2.29 | −2.32 | |
63 | 150-68-5 | monuron | 1.24 | −2.63 | −2.78 | −2.51 | −2.60 | −2.37 | |
64 | 123-35-3 | myrcene | 3.01 | −0.69 | −0.56 | −0.77 | −0.82 | −0.87 | |
65 | 95-53-4 | o-toluidine | 0.65 | −2.53 | −2.51 | −2.49 | −2.63 | −2.37 | |
66 | 93-55-0 | propiophenone | 1.16 | −2.10 | −2.17 | −2.21 | −2.32 | −2.12 | |
67 | 103-65-1 | propylbenzene | 2.29 | −1.03 | −1.16 | −1.20 | −1.28 | −1.24 | |
68 | 106-42-3 | p-xylene | 1.83 | −1.31 | −1.46 | −1.46 | −1.57 | −1.47 | |
69 | 289-95-2 | pyrimidine | −0.50 | −3.52 | −3.28 | −3.22 | −3.31 | −3.13 | |
70 | 120-80-9 | pyrocatechol | 0.49 | −2.84 | −2.75 | −2.76 | −2.63 | −2.90 | |
71 | 109-97-7 | pyrrole | 0.18 | −2.68 | −2.64 | −2.59 | −2.65 | −2.60 | |
72 | 91-22-5 | quinoline | 2.07 | −2.18 | −1.68 | −1.51 | −1.53 | −1.59 | |
73 | 108-46-3 | resorcinol | 0.40 | −2.89 | −2.83 | −2.82 | −2.71 | −2.95 | −3.62 |
74 | 62-56-6 | thiourea | −0.77 | −3.95 | −3.87 | −3.96 | −3.45 | −4.43 | |
75 | 89-83-8 | thymol | 2.19 | −1.45 | −1.52 | −1.57 | −1.55 | −1.66 | −1.28 |
76 | 1009-14-9 | valerophenone | 2.01 | −1.62 | −1.63 | −1.73 | −1.80 | −1.70 | |
77 | 109-66-0 | pentane | 2.28 | −0.96 | −0.89 | −0.95 | −0.87 | −1.24 | |
78 | 75-09-2 | dichloromethane | 0.22 | −2.45 | −2.30 | −2.34 | −2.49 | −2.28 | |
79 | 67-66-3 | chloroform | 0.62 | −2.17 | −2.12 | −2.12 | −2.26 | −2.08 | |
80 | 56-23-5 | carbon tetrachloride | 1.61 | −1.79 | −1.48 | −1.46 | −1.50 | −1.58 | |
81 | 1300-21-6 | 1,2-dichloroethane | 0.34 | −2.38 | −2.28 | −2.33 | −2.51 | −2.22 | |
82 | 79-34-5 | 1,1,2,2-tetrachloroethane | 1.28 | −2.16 | −1.77 | −1.78 | −1.93 | −1.75 | |
83 | 109-69-3 | 1-chlorobutane | 1.05 | −1.57 | −1.76 | −1.87 | −1.99 | −1.86 | |
84 | 60-29-7 | diethyl ether | −0.06 | −2.63 | −2.69 | −2.74 | −2.91 | −2.60 | −2.80 |
85 | 111-43-3 | dipropyl ether | 0.78 | −2.03 | −2.16 | −2.26 | −2.41 | −2.17 | |
86 | 79-20-9 | methyl acetate | −0.66 | −3.10 | −3.23 | −3.27 | −3.33 | −3.22 | |
87 | 141-78-6 | ethyl acetate | −0.25 | −2.82 | −2.98 | −3.04 | −3.08 | −3.01 | |
88 | 123-86-4 | butyl acetate | 0.62 | −2.27 | −2.24 | −2.55 | −2.55 | −2.57 | |
89 | 75-05-8 | acetonitrile | −0.70 | −3.26 | −3.13 | −3.17 | −3.19 | −3.19 | |
90 | 107-12-0 | propionitrile | −0.35 | −3.01 | −2.96 | −2.98 | −3.00 | −3.01 | |
91 | 64-17-5 | ethanol | −0.62 | −3.27 | −3.09 | −3.10 | −3.16 | −3.08 | −3.10 |
92 | 71-23-8 | 1-propanol | −0.42 | −2.97 | −2.99 | −3.03 | −3.11 | −2.98 | −2.92 |
93 | 75-65-0 | 2-methyl-2-propanol | 0.37 | −2.99 | −2.51 | −2.52 | −2.52 | −2.58 | |
94 | 71-41-0 | 1-pentanol | 0.33 | −2.30 | −2.53 | −2.62 | −2.68 | −2.60 | −2.22 |
95 | 75-85-4 | 2-methyl-2-butanol | −0.08 | −2.51 | −2.88 | −2.93 | −3.05 | −2.81 | |
96 | 111-27-3 | 1-hexanol | 0.83 | −2.03 | −2.21 | −2.33 | −2.36 | −2.35 | −1.89 |
97 | 64-18-6 | formic acid | −0.65 | −3.42 | −3.18 | −3.21 | −3.06 | −3.42 | |
98 | 64-19-7 | acetic acid | −0.68 | −3.25 | −3.29 | −3.31 | −3.21 | −3.43 | −3.21 |
99 | 79-09-4 | propionic acid | −0.08 | −3.00 | −2.89 | −2.94 | −2.80 | −3.13 | |
100 | 107-92-6 | butanoic acid | 0.38 | −2.77 | −2.59 | −2.67 | −2.51 | −2.89 | |
101 | 109-99-9 | tetrahydrofuran | −0.18 | −2.90 | −2.89 | −2.79 | −2.96 | −2.66 | |
102 | 93-89-0 | ethyl benzoate | 1.48 | −1.89 | −2.08 | −2.09 | −2.08 | −2.13 | |
103 | 88-73-3 | 1-chloro-2-nitrobenzene | 1.44 | −2.20 | −2.20 | −2.22 | −1.98 | −2.52 | |
104 | 140-29-4 | phenylacetonitrile | 0.82 | −2.43 | −2.45 | −2.44 | −2.48 | −2.42 | |
105 | 91-59-8 | 2-naphthylamine | 1.77 | −2.09 | −2.08 | −1.96 | −1.97 | −1.98 | |
106 | 108-43-0 | 3-chlorophenol | 1.70 | −1.87 | −1.73 | −1.71 | −1.61 | −1.91 | |
107 | 99-04-7 | 3-methylbenzoic acid | 1.43 | −2.00 | −2.17 | −2.15 | −1.99 | −2.36 | |
108 | 100-02-7 | 4-nitrophenol | 1.28 | −2.32 | −2.52 | −2.49 | −2.04 | −2.97 | −2.25 |
109 | 17849-38-6 | 4-chlorobenzyl alcohol | 1.06 | −2.30 | −2.29 | −2.26 | −2.32 | −2.23 | |
110 | 541-73-1 | 1,3-dichlorobenzene | 2.48 | −1.28 | −1.04 | −0.98 | −0.99 | −1.14 | |
111 | 108-67-8 | 1,3,5-trimethylbenzene | 2.61 | −1.21 | −0.98 | −0.96 | −1.00 | −1.07 | |
112 | 142-82-5 | heptane | 3.20 | −0.27 | −0.30 | −0.41 | −0.29 | −0.78 | |
113 | 110-54-3 | hexane | 1.97 | −0.70 | −1.17 | −1.26 | −1.28 | −1.40 | |
114 | 103-90-2 | acetaminophen | 0.38 | −3.35 | −3.24 | −3.13 | −3.07 | −3.12 | |
115 | 66085-59-4 | nimodipine | 3.06 | −3.13 | −2.88 | −2.90 | −2.45 | −3.07 | |
116 | 57-83-0 | progesterone | 2.98 | −2.00 | −1.88 | −1.85 | −2.05 | −1.52 | |
117 | 19387-91-8 | tinidazole | 0.26 | −4.42 | −4.15 | −3.99 | −3.63 | −4.14 | |
118 | 106-49-0 | p-toluidine | 1.15 | −2.48 | −2.18 | −2.21 | −2.17 | −2.30 | |
119 | 90-41-5 | 2-aminobiphenyl | 2.13 | −1.87 | −1.82 | −1.81 | −1.83 | −1.80 | |
120 | 103-69-5 | N-ethylaniline | 1.06 | −2.05 | −2.29 | −2.23 | −2.40 | −2.08 | |
121 | 86-55-5 | 1-naphthoic acid | 2.13 | −1.71 | −1.99 | −1.85 | −1.72 | −2.01 | |
122 | 103-82-2 | phenylacetic acid | 0.76 | −2.63 | −2.68 | −2.64 | −2.58 | −2.70 | |
123 | 1878-65-5 | 3-chlorophenylacetic acid | 1.47 | −2.37 | −2.24 | −2.20 | −2.07 | −2.34 | |
124 | 1821-12-1 | 4-phenylbutanoic acid | 1.52 | −2.12 | −2.20 | −2.23 | −2.15 | −2.32 | |
125 | 103-29-7 | 1,2-diphenylethane | 3.77 | −0.64 | −0.53 | −0.42 | −0.49 | −0.49 | |
126 | 58-22-0 | testosterone | 2.23 | −2.22 | −2.38 | −2.31 | −2.51 | −1.96 | |
127 | 78-93-3 | 2-butanone | −0.38 | −3.02 | −2.91 | −3.02 | −3.16 | −2.90 | −2.95 |
128 | 110-86-1 | pyridine | 0.32 | −2.82 | −2.56 | −2.52 | −2.62 | −2.47 | |
129 | 123-07-9 | 4-ethylphenol | 1.54 | −1.78 | −1.88 | −1.90 | −1.89 | −1.99 | −1.46 |
130 | 645-56-7 | 4-propylphenol | 2.02 | −1.44 | −1.57 | −1.62 | −1.58 | −1.75 | |
131 | 1638-22-8 | 4-butylphenol | 2.51 | −1.22 | −1.24 | −1.33 | −1.26 | −1.50 | |
132 | 371-41-5 | 4-fluorophenol | 0.96 | −2.26 | −2.14 | −2.18 | −2.15 | −2.29 | |
133 | 106-41-2 | 4-bromophenol | 1.81 | −2.05 | −1.74 | −1.67 | −1.59 | −1.85 | −1.44 |
134 | 540-38-5 | 4-iodophenol | 2.10 | −2.11 | −1.65 | −1.54 | −1.47 | −1.71 | |
135 | 103-79-7 | benzyl methyl ketone | 0.38 | −2.60 | −2.76 | −2.78 | −3.01 | −2.52 | |
136 | 72509-76-3 | felodipine | 3.47 | −2.40 | −1.91 | −1.86 | −1.74 | −1.84 | |
137 | 63675-72-9 | nisoldipine | 3.26 | −2.82 | −2.53 | −2.56 | −2.09 | −2.80 | |
138 | 103890-78-4 | lacidipine | 4.00 | −1.91 | −2.04 | −2.23 | −2.11 | −2.06 | |
139 | 738-70-5 | trimethoprim | 0.95 | −3.83 | −4.05 | −3.88 | −3.59 | −3.87 | |
140 | 50-24-8 | prednisolone | 1.65 | −3.75 | −3.54 | −3.50 | −3.38 | −3.32 | |
141 | 50-78-2 | acetylsalicylic acid | 0.82 | −3.03 | −3.01 | −2.98 | −2.73 | −3.16 | |
142 | 65-85-0 | benzoic acid | 1.05 | −2.25 | −2.38 | −2.36 | −2.21 | −2.56 | |
143 | 140-65-8 | pramocaine | 2.56 | −2.17 | −2.04 | −2.02 | −2.25 | −1.67 | |
144 | 67-64-1 | acetone | −0.75 | −3.29 | −3.13 | −3.22 | −3.37 | −3.09 | −3.21 |
145 | 123-30-8 | 4-aminophenol | −0.20 | −3.39 | −3.33 | −3.36 | −3.32 | −3.35 | |
146 | 93-60-7 | methyl nicotinate | 0.27 | −3.02 | −3.04 | −3.00 | −2.99 | −2.98 | |
147 | 68-12-2 | N,N-dimethylformamide | −0.47 | −3.89 | −3.11 | −3.11 | −3.22 | −3.01 | |
148 | 26839-75-8 | timolol | 0.90 | −3.36 | −3.82 | −3.97 | −3.69 | −3.94 | |
149 | 2180-92-9 | bupivacaine | 1.88 | −2.16 | −2.56 | −2.61 | −2.98 | −2.04 | |
150 | 721-50-6 | prilocaine | 0.99 | −2.64 | −3.01 | −3.01 | −3.20 | −2.66 | |
151 | 29122-68-7 | atenolol | 0.65 | −4.19 | −3.71 | −3.80 | −3.70 | −3.64 | |
152 | 525-66-6 | propranolol | 2.20 | −1.95 | −1.90 | −2.30 | −2.43 | −2.05 | |
153 | 321-97-1 | pseudoephedrine | 0.36 | −2.98 | −3.07 | −3.11 | −3.30 | −2.81 | |
154 | 37517-30-9 | acebutolol | 1.57 | −3.56 | −3.42 | −3.48 | −3.43 | −3.23 | |
155 | 13655-52-2 | alprenolol | 2.08 | −2.14 | −2.16 | −2.33 | −2.43 | −2.11 | |
156 | 37350-58-6 | metoprolol | 1.21 | −3.06 | −3.00 | −3.10 | −3.27 | −2.72 | |
157 | 6452-71-7 | oxprenolol | 1.55 | −2.90 | −2.62 | −2.84 | −2.96 | −2.55 | |
158 | 18559-94-9 | albuterol | 0.48 | −3.73 | −3.61 | −3.70 | −3.68 | −3.50 | |
159 | 54910-89-3 | fluoxetine | 2.98 | −2.00 | −1.50 | −1.54 | −1.74 | −1.28 | |
160 | 52-53-9 | verapamil | 2.76 | −2.84 | −2.94 | −2.98 | −3.38 | −2.19 |
PSA | FRB | HA | VM | α | EHOMO | ELUMO | Sa | ||
---|---|---|---|---|---|---|---|---|---|
1 | Acetanilide | 29.1 | 1 | 2 | 122.5 | 16.07 | −8.82 | −0.03 | 312.2 |
2 | Acetophenone | 17.1 | 1 | 1 | 121.0 | 14.38 | −10.00 | −0.44 | 293.2 |
3 | 2-aminophenol | 46.3 | 2 | 2 | 90.1 | 12.83 | −8.10 | 0.52 | 264.6 |
4 | Anisole | 9.2 | 1 | 1 | 113.4 | 13.05 | −9.11 | 0.35 | 283.9 |
5 | Benzaldehyde | 17.1 | 1 | 1 | 101.1 | 13.08 | −10.05 | −0.48 | 266.7 |
6 | Benzamide | 43.1 | 1 | 2 | 108.1 | 13.95 | −9.72 | −0.36 | 286.2 |
7 | Benzene | 0.0 | 0 | 0 | 89.4 | 10.41 | −9.75 | 0.40 | 241.1 |
8 | Benzonitrile | 23.8 | 0 | 1 | 100.0 | 12.42 | −10.10 | −0.58 | 271.7 |
9 | Benzyl alcohol | 20.2 | 2 | 1 | 109.3 | 12.09 | −9.58 | 0.33 | 281.5 |
10 | Biphenyl | 0.0 | 0 | 0 | 154.7 | 20.16 | −8.92 | −0.36 | 345.0 |
11 | 1-bromonaphtalene | 0.0 | 0 | 0 | 139.7 | 20.53 | −8.99 | −0.65 | 328.6 |
12 | 3-bromophenol | 20.2 | 1 | 1 | 104.1 | 14.20 | −9.41 | −0.13 | 282.5 |
13 | Cinnamyl alcohol | 20.2 | 3 | 1 | 127.9 | 17.32 | −8.95 | −0.15 | 329.7 |
14 | Coumarin | 26.3 | 0 | 2 | 117.1 | 15.76 | −9.45 | −0.99 | 305.5 |
15 | Cyclohexanone | 17.1 | 0 | 1 | 103.0 | 11.02 | −10.48 | 0.85 | 256.1 |
16 | Diethyl phtalate | 52.6 | 6 | 4 | 198.2 | 23.42 | −10.24 | −0.93 | 407.7 |
17 | 2,6-dimethylphenol | 20.2 | 1 | 1 | 120.4 | 14.98 | −8.96 | 0.29 | 296.7 |
18 | 4-hydroxybenzyl alcohol | 40.5 | 3 | 2 | 101.7 | 13.71 | −9.06 | 0.31 | 291.5 |
19 | 2-methylphenol | 20.2 | 1 | 1 | 104.1 | 13.07 | −9.06 | 0.28 | 275.6 |
20 | 4-methylphenol | 20.2 | 1 | 1 | 104.1 | 13.07 | −8.95 | 0.33 | 274.0 |
21 | Naphtalene | 0.0 | 0 | 0 | 123.6 | 17.48 | −8.84 | −0.41 | 299.8 |
22 | 1-naphthol | 20.2 | 1 | 1 | 122.0 | 18.23 | −8.54 | −0.36 | 308.8 |
23 | 2-naphthol | 20.2 | 1 | 1 | 122.0 | 18.23 | −8.72 | −0.45 | 311.6 |
24 | 2-nitroaniline | 71.8 | 2 | 4 | 103.6 | 14.68 | −8.75 | −0.82 | 306.6 |
25 | 4-nitroaniline | 71.8 | 2 | 4 | 103.6 | 14.68 | −9.00 | −0.78 | 291.6 |
26 | Nitrobenzene | 45.8 | 1 | 3 | 101.3 | 13.00 | −10.60 | −1.14 | 273.3 |
27 | 4-nitrobenzyl alcohol | 66.1 | 3 | 4 | 115.1 | 15.56 | −10.52 | −1.13 | 315.5 |
28 | 1-nitrobutane | 45.8 | 3 | 3 | 107.3 | 10.55 | −12.01 | 0.06 | 275.0 |
29 | 4-nitrotoluene | 45.8 | 1 | 3 | 117.6 | 14.91 | −10.47 | −1.11 | 299.3 |
30 | Phenol | 20.2 | 1 | 1 | 87.9 | 11.15 | −9.18 | 0.29 | 248.4 |
31 | 2-phenylethanol | 20.2 | 3 | 1 | 119.8 | 14.80 | −9.55 | 0.29 | 312.0 |
32 | 4-phenylphenol | 20.2 | 2 | 1 | 153.2 | 20.90 | −8.64 | −0.34 | 355.8 |
33 | Toluene | 0.0 | 0 | 0 | 105.7 | 12.32 | −9.44 | 0.45 | 265.6 |
34 | 4-chlorophenol | 20.2 | 1 | 1 | 99.8 | 13.09 | −9.01 | 0.05 | 272.4 |
35 | 2,3-benzofuran | 13.1 | 0 | 1 | 106.3 | 14.43 | −9.07 | −0.15 | 216.7 |
36 | 2,3-dimethylphenol | 20.2 | 1 | 1 | 120.4 | 14.98 | −9.00 | 0.29 | 293.8 |
37 | 2,4-dimethylphenol | 20.2 | 1 | 1 | 120.4 | 14.98 | −8.86 | 0.31 | 301.2 |
38 | 2-nitroanisole | 55.1 | 2 | 4 | 125.3 | 15.65 | −10.29 | −0.89 | 316.0 |
39 | 2-chloroaniline | 26.0 | 1 | 1 | 103.7 | 14.03 | −8.17 | 0.31 | 277.6 |
40 | 3-nitroaniline | 71.8 | 2 | 4 | 103.6 | 14.68 | −9.28 | −1.06 | 291.8 |
41 | 4-chloroacetanilide | 29.1 | 1 | 2 | 134.5 | 18.01 | −8.67 | −0.06 | 341.5 |
42 | 4-chloroaniline | 26.0 | 1 | 1 | 103.7 | 14.03 | −8.11 | 0.38 | 282.0 |
43 | Aniline | 26.0 | 1 | 1 | 91.7 | 12.09 | −8.07 | 0.62 | 257.9 |
44 | Antipyrine | 23.6 | 1 | 3 | 162.8 | 21.63 | −9.04 | −0.33 | 383.0 |
45 | Benzophenone | 17.1 | 2 | 1 | 167.6 | 22.22 | −9.94 | −0.67 | 374.7 |
46 | Benzyl benzoate | 26.3 | 4 | 2 | 188.0 | 24.78 | −9.61 | −0.34 | 438.6 |
47 | Bromobenzene | 0.0 | 0 | 0 | 105.6 | 13.46 | −9.81 | −0.05 | 273.0 |
48 | Butylbenzene | 0.0 | 3 | 0 | 155.3 | 17.87 | −9.51 | 0.36 | 357.3 |
49 | Butyrophenone | 17.1 | 3 | 1 | 154.0 | 18.06 | −9.99 | −0.09 | 363.0 |
50 | Caffeine | 53.5 | 0 | 6 | 133.4 | 19.97 | −8.89 | −0.49 | 364.0 |
51 | Chlorobenzene | 0.0 | 0 | 0 | 101.4 | 12.36 | −9.39 | 0.06 | 264.1 |
52 | Corticosterone | 74.6 | 4 | 4 | 284.3 | 37.27 | −10.21 | −0.15 | 531.3 |
53 | Cortisone | 91.7 | 4 | 5 | 280.3 | 37.33 | −10.09 | −0.07 | 533.8 |
54 | Estradiol | 40.5 | 2 | 2 | 232.6 | 31.52 | −8.86 | −0.35 | 468.3 |
55 | Estriol | 60.7 | 3 | 3 | 229.6 | 32.15 | −8.88 | 0.34 | 481.2 |
56 | Ethylbenzene | 0.0 | 1 | 0 | 122.3 | 14.19 | −9.51 | 0.38 | 294.0 |
57 | Furan | 13.1 | 0 | 1 | 72.2 | 7.35 | −9.38 | 0.61 | 208.2 |
58 | Geraniol | 20.2 | 5 | 1 | 177.9 | 19.71 | −9.33 | 0.99 | 397.4 |
59 | Heptanophenone | 17.1 | 6 | 1 | 203.5 | 23.57 | −10.00 | −0.42 | 438.5 |
60 | Hydrocortisone | 94.8 | 5 | 5 | 281.4 | 37.89 | −10.25 | −0.18 | 542.9 |
61 | 3-methylphenol | 20.2 | 1 | 1 | 104.1 | 13.07 | −9.09 | 0.29 | 275.6 |
62 | Methyl benzoate | 26.3 | 2 | 2 | 127.3 | 15.07 | −10.11 | −0.46 | 314.4 |
63 | Monuron | 32.2 | 1 | 3 | 158.2 | 21.32 | −9.13 | −0.20 | 387.9 |
64 | Myrcene | 0.0 | 4 | 0 | 177.0 | 18.86 | −9.28 | 0.29 | 374.8 |
65 | o-toluidine | 16.0 | 1 | 1 | 108.0 | 14.00 | −7.99 | 0.59 | 276.9 |
66 | Propiophenone | 17.1 | 2 | 1 | 137.5 | 16.22 | −9.99 | −0.42 | 322.0 |
67 | Propylbenzene | 0.0 | 2 | 0 | 138.8 | 16.03 | −9.51 | 0.37 | 326.6 |
68 | p-xylene | 0.0 | 0 | 0 | 122.0 | 14.23 | −9.18 | 0.36 | 289.8 |
69 | Pyrimidine | 25.8 | 0 | 2 | 75.9 | 8.89 | −10.29 | −0.41 | 226.2 |
70 | Pyrocatechol | 40.5 | 2 | 2 | 86.3 | 11.90 | −9.07 | 0.26 | 257.3 |
71 | Pyrrole | 15.8 | 0 | 1 | 67.8 | 8.20 | −8.93 | 1.11 | 216.7 |
72 | Quinoline | 12.9 | 0 | 1 | 116.8 | 16.72 | −9.24 | −0.65 | 297.7 |
73 | Resorcinol | 40.5 | 2 | 2 | 86.3 | 11.90 | −9.06 | 0.27 | 259.6 |
74 | Thiourea | 88.7 | 0 | 2 | 29.9 | 7.26 | −8.62 | −0.27 | 212.2 |
75 | Thymol | 20.2 | 2 | 1 | 154.2 | 18.69 | −9.00 | 0.28 | 346.2 |
76 | Valerophenone | 17.1 | 4 | 1 | 170.5 | 19.89 | −9.99 | −0.42 | 379.6 |
77 | Pentane | 0.0 | 2 | 0 | 111.1 | 10.00 | −11.30 | 3.45 | 266.9 |
78 | Dichloromethane | 0.0 | 0 | 0 | 67.8 | 6.49 | −10.48 | 0.52 | 199.3 |
79 | Chloroform | 0.0 | 0 | 0 | 79.6 | 8.40 | −10.88 | −0.12 | 224.5 |
80 | Carbon tetrachloride | 0.0 | 0 | 0 | 90.6 | 10.32 | −10.99 | −0.63 | 244.2 |
81 | 1,2-dichloroethane | 0.0 | 1 | 0 | 84.3 | 8.33 | −10.69 | 0.54 | 231.1 |
82 | 1,1,2,2,-tetrachloroethane | 0.0 | 1 | 0 | 107.8 | 12.14 | −10.74 | 0.02 | 267.0 |
83 | 1-chlorobutane | 0.0 | 2 | 0 | 106.0 | 10.08 | −10.31 | 1.23 | 264.9 |
84 | Diethyl ether | 9.2 | 2 | 1 | 100.9 | 8.85 | −10.48 | 2.86 | 260.9 |
85 | Dipropyl ether | 9.2 | 4 | 1 | 133.9 | 12.52 | −10.49 | 2.76 | 317.2 |
86 | Methyl acetate | 26.3 | 1 | 2 | 81.5 | 7.03 | −11.26 | 1.02 | 228.3 |
87 | Ethyl acetate | 26.3 | 2 | 2 | 98.0 | 8.83 | −11.24 | 1.06 | 263.0 |
88 | Butyl acetate | 26.3 | 4 | 2 | 131.0 | 12.54 | −11.25 | 1.05 | 232.4 |
89 | Acetonitrile | 23.8 | 0 | 1 | 54.9 | 4.45 | −12.33 | 1.40 | 176.4 |
90 | Propionitrile | 23.8 | 0 | 1 | 71.4 | 6.29 | −12.01 | 1.42 | 211.9 |
91 | Ethanol | 20.2 | 1 | 1 | 59.1 | 5.09 | −10.90 | 3.33 | 191.0 |
92 | 1-propanol | 20.2 | 2 | 1 | 75.6 | 6.93 | −10.88 | 3.23 | 220.6 |
93 | 2-methyl-2-propanol | 20.2 | 1 | 1 | 92.1 | 8.75 | −11.28 | 3.26 | 244.4 |
94 | 1-pentanol | 20.2 | 4 | 1 | 108.6 | 10.60 | −10.89 | 3.11 | 281.4 |
95 | 2-methyl-2-butanol | 20.2 | 2 | 1 | 108.6 | 10.59 | −11.13 | 3.17 | 264.1 |
96 | 1-hexanol | 20.2 | 5 | 1 | 125.1 | 12.44 | −10.89 | 3.09 | 313.0 |
97 | Formic acid | 37.3 | 0 | 2 | 39.9 | 3.33 | −11.57 | 0.97 | 158.3 |
98 | Acetic acid | 37.3 | 0 | 2 | 56.2 | 5.11 | −11.43 | 0.93 | 192.8 |
99 | Propionic acid | 37.3 | 1 | 2 | 72.7 | 6.94 | −11.31 | 0.96 | 222.4 |
100 | Butanoic acid | 37.3 | 2 | 2 | 89.2 | 8.78 | −11.34 | 0.97 | 249.1 |
101 | Tetrahydrofuran | 9.2 | 0 | 1 | 79.8 | 7.95 | −10.28 | 3.29 | 225.0 |
102 | Ethyl benzoate | 26.3 | 3 | 2 | 143.8 | 16.91 | −10.08 | −0.43 | 348.2 |
103 | 2-chloro-1-nitrobenzene | 45.8 | 3 | 3 | 113.2 | 14.94 | −9.94 | −1.27 | 290.8 |
104 | Phenylacetonitrile | 23.8 | 1 | 1 | 115.7 | 14.16 | −9.99 | −0.09 | 300.7 |
105 | 2-naphthylamine | 26.0 | 1 | 1 | 125.8 | 19.16 | −7.92 | −0.21 | 319.6 |
106 | 3-chlorophenol | 20.2 | 1 | 1 | 99.8 | 13.09 | −9.24 | −0.01 | 272.6 |
107 | 3-methylbenzoic acid | 37.3 | 1 | 2 | 118.2 | 15.07 | −9.82 | −0.49 | 304.5 |
108 | 4-nitrophenol | 66.1 | 2 | 4 | 99.7 | 13.75 | −10.17 | −1.08 | 283.4 |
109 | 4-chlorobenzyl alcohol | 20.2 | 2 | 1 | 115.2 | 14.91 | −9.28 | 0.02 | 306.2 |
110 | 1,3-dichlorobenzene | 0.0 | 0 | 0 | 113.3 | 14.29 | −9.42 | −0.19 | 288.6 |
111 | 1,3,5-trimethylbenzene | 0.0 | 0 | 0 | 138.3 | 16.15 | −9.28 | 0.44 | 320.3 |
112 | Heptane | 0.0 | 4 | 0 | 144.1 | 13.67 | −11.27 | 3.30 | 327.7 |
113 | Hexane | 0.0 | 3 | 0 | 127.6 | 11.83 | −11.28 | 3.36 | 297.7 |
114 | Acetaminophen | 49.3 | 1 | 3 | 121.0 | 16.81 | −8.56 | −0.02 | 323.6 |
115 | Nimodipine | 119.7 | 10 | 9 | 345.0 | 42.87 | −9.21 | −0.66 | 682.0 |
116 | Progesterone | 34.1 | 1 | 2 | 289.0 | 36.06 | −10.14 | −0.10 | 514.8 |
117 | Tinidazole | 101.2 | 5 | 7 | 172.4 | 23.36 | −10.47 | −1.21 | 432.8 |
118 | p-toluidine | 26.0 | 1 | 1 | 108.0 | 14.00 | −7.95 | 0.64 | 285.0 |
119 | 2-aminobiphenyl | 26.0 | 2 | 1 | 157.0 | 21.84 | −7.98 | −0.21 | 356.8 |
120 | N-ethylaniline | 12.0 | 2 | 1 | 125.4 | 16.05 | −8.50 | 0.45 | 322.8 |
121 | 1-naphthoic acid | 37.3 | 1 | 2 | 136.1 | 20.23 | −9.13 | −0.97 | 334.0 |
122 | Phenylacetic acid | 37.3 | 2 | 2 | 116.9 | 14.81 | −9.81 | 0.22 | 313.7 |
123 | 3-chlorophenylacetic acid | 37.3 | 2 | 2 | 128.8 | 16.75 | −9.52 | −0.20 | 337.0 |
124 | 4-phenylbutanoic acid | 37.3 | 4 | 2 | 149.9 | 18.49 | −9.67 | 0.21 | 372.0 |
125 | 1,2-diphenylethane | 0.0 | 2 | 0 | 183.0 | 23.90 | −9.48 | 0.32 | 402.0 |
126 | Testosterone | 37.3 | 1 | 2 | 257.0 | 32.95 | −10.12 | −0.09 | 477.5 |
127 | 2-butanone | 17.1 | 1 | 1 | 91.7 | 8.17 | −10.65 | 0.83 | 239.1 |
128 | Pyridine | 12.9 | 0 | 1 | 82.7 | 9.65 | −10.10 | 0.01 | 231.9 |
129 | 4-ethylphenol | 20.2 | 2 | 1 | 120.7 | 14.94 | −9.00 | 0.32 | 305.7 |
130 | 4-propylphenol | 20.2 | 3 | 1 | 137.2 | 16.78 | −9.00 | 0.32 | 335.7 |
131 | 4-butylphenol | 20.2 | 4 | 1 | 153.7 | 18.61 | −8.99 | 0.32 | 360.8 |
132 | 4-fluorophenol | 20.2 | 1 | 1 | 92.1 | 11.15 | −9.27 | −0.06 | 254.4 |
133 | 4-bromophenol | 20.2 | 1 | 1 | 104.1 | 14.20 | −9.31 | −0.03 | 283.6 |
134 | 4-iodophenol | 20.2 | 1 | 1 | 109.9 | 16.27 | −8.84 | −0.41 | 289.8 |
135 | Benzyl methyl ketone | 17.1 | 2 | 1 | 135.9 | 16.04 | −9.71 | 0.07 | 320.4 |
136 | Felodipine | 64.6 | 6 | 5 | 300.8 | 37.97 | −8.87 | −0.18 | 588.5 |
137 | Nisoldipine | 110.5 | 8 | 8 | 322.2 | 40.34 | −9.15 | −0.73 | 628.4 |
138 | Lacidipine | 90.9 | 11 | 7 | 404.0 | 50.26 | −8.91 | −1.29 | 706.6 |
139 | Trimethoprin | 105.5 | 5 | 7 | 231.9 | 31.82 | −8.73 | −0.07 | 519.0 |
140 | Prednisolone | 94.8 | 5 | 5 | 274.7 | 37.85 | −10.07 | −0.42 | 527.4 |
141 | Acetylsalicylic acid | 63.6 | 3 | 4 | 139.6 | 17.65 | −10.19 | −0.54 | 355.9 |
142 | Benzoic acid | 37.3 | 1 | 2 | 102.0 | 13.15 | −10.13 | −0.53 | 278.6 |
143 | Pramocaine | 30.9 | 9 | 4 | 284.6 | 33.45 | −8.78 | 0.24 | 595.7 |
144 | Acetone | 17.1 | 0 | 1 | 75.2 | 6.33 | −10.76 | 0.80 | 206.7 |
145 | 4-aminophenol | 46.3 | 2 | 2 | 90.1 | 12.83 | −7.84 | 0.46 | 267.6 |
146 | Methyl nicotinate | 39.2 | 2 | 3 | 120.6 | 14.32 | −10.44 | −0.80 | 310.4 |
147 | N,N-dimethylformamide | 20.3 | 0 | 2 | 82.6 | 7.87 | −9.26 | 1.36 | 228.9 |
148 | Timolol | 108.0 | 8 | 7 | 258.5 | 32.57 | −9.24 | −1.05 | 520.8 |
149 | Bupivacaine | 32.3 | 5 | 3 | 279.2 | 35.13 | −7.46 | −0.40 | 514.1 |
150 | Prilocaine | 41.1 | 5 | 3 | 214.0 | 26.73 | −9.23 | 0.18 | 449.6 |
151 | Atenolol | 84.6 | 9 | 5 | 236.7 | 29.44 | −9.30 | −0.03 | 541.0 |
152 | Propranolol | 41.5 | 7 | 3 | 237.2 | 31.31 | −8.62 | −0.43 | 307.7 |
153 | Pseudoefedrine | 32.3 | 4 | 2 | 162.7 | 19.88 | −9.44 | 0.29 | 371.4 |
154 | Acebutolol | 87.7 | 11 | 6 | 300.7 | 37.55 | −9.15 | −0.43 | 642.5 |
155 | Alprenolol | 41.5 | 9 | 3 | 247.5 | 29.75 | −9.12 | 0.26 | 506.5 |
156 | Metoprolol | 50.7 | 10 | 4 | 258.7 | 30.55 | −9.00 | −0.27 | 569.8 |
157 | Oxprenolol | 50.7 | 10 | 4 | 255.2 | 30.45 | −9.21 | 0.12 | 496.3 |
158 | Albuterol | 72.7 | 8 | 4 | 207.6 | 26.86 | −8.97 | 0.16 | 474.7 |
159 | Fluoxetine | 21.3 | 6 | 2 | 266.7 | 31.67 | −9.44 | −0.39 | 541.6 |
160 | Verapamil | 64.0 | 13 | 6 | 429.4 | 52.28 | −8.78 | −0.95 | 817.4 |
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Sobańska, A.W.; Brzezińska, E. IAM Chromatographic Models of Skin Permeation. Molecules 2022, 27, 1893. https://doi.org/10.3390/molecules27061893
Sobańska AW, Brzezińska E. IAM Chromatographic Models of Skin Permeation. Molecules. 2022; 27(6):1893. https://doi.org/10.3390/molecules27061893
Chicago/Turabian StyleSobańska, Anna W., and Elżbieta Brzezińska. 2022. "IAM Chromatographic Models of Skin Permeation" Molecules 27, no. 6: 1893. https://doi.org/10.3390/molecules27061893