Compound,SMILES,IC50 (5-LOX enzyme) [µM] #published in Pein et al.4,IC50 (5-LOX PMNL) [µM] #published in Pein et al.4,PAINS
1a,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(C)C(O)=C1C,> 1#,> 3#,
1b,CC1=C2C(CC[C@](C)(O2)CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)=C(C)C(O)=C1,0.75 ± 0.15#,> 3#,
1c,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=CC(O)=C1C,0.91 ± 0.15#,> 3#,
1d,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=CC(O)=C1,0.60 ± 0.25,> 3#,
2,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(Cl)C(O)=C1C([H])=O,> 1,> 3,
3,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(C([H])=O)C(O)=C1,> 1,> 3,
4,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(C([H])=O)C(OCOC)=C1,> 1,> 3,
5,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(C(O)=O)C(O)=C1,> 1,> 3,
6a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=C(C)C(O)=C1C,0.33 ± 0.08#,> 3#,
6b,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=C(C)C(O)=C1,0.19 ± 0.03#,2.11 ± 0.36#,
6c,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=CC(O)=C1C,0.20 ± 0.06#,> 3#,
6d,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=CC(O)=C1,0.17 ± 0.10#,> 3#,
7,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=C(C([H])=O)C(O)=C1,> 1,> 3,
8,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=C(C([H])=O)C(O)=C1Br,> 1,> 3,
9a,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(C)CO)(C)O2)=C(C)C(O)=C1C,0.35 ± 0.04#,0.19 ± 0.05#,
9b,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(C)CO)(C)O2)=CC(O)=C1,0.12 ± 0.04#,0.54 ± 0.18#,
10a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CO)(C)O2)=C(C)C(O)=C1C,0.11 ± 0.01#,0.27 ± 0.10#,
10b,CC1=C2C(CC[C@](C)(O2)CC/C=C(CC/C=C(CC/C=C(CO)\C)\C)\C)=C(C)C(O)=C1,0.09 ± 0.03#,0.38 ± 0.09#,
10c,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CO)(C)O2)=CC(O)=C1,0.15 ± 0.05#,1.26 ± 0.33#,
10d,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/C)(C)O2)=CC(O)=C1C,0.12 ± 0.03#,0.14 ± 0.02#,
10e,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/C)(C)O2)=CC(O)=C1,0.14 ± 0.03#,0.22 ± 0.04#,
11,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/C([H])=O)(C)O2)=CC(O)=C1,0.12 ± 0.05,0.57 ± 0.09,
12a,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(C)C(O)=O)(C)O2)=C(C)C(O)=C1C,0.27 ± 0.01#,0.08 ± 0.00#,
12b,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(C)C(O)=O)(C)O2)=CC(O)=C1,> 1#,2.01 ± 0.59#,
13a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=C(C)C(O)=C1C,0.40 ± 0.08#,0.56 ± 0.18,
13b,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=C(C)C(O)=C1,0.15 ± 0.04#,0.31 ± 0.11#,
13c,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=CC(O)=C1C,0.30 ± 0.10#,0.49 ± 0.03#,
13d,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=CC(O)=C1,0.06 ± 0.01#,0.35 ± 0.07#,
13e,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C(O)=O)/C)(C)O2)=CC(O)=C1,0.18 ± 0.05,0.63 ± 0.18,
14,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C/C(O)=O)(C)O2)=CC(O)=C1,0.44 ± 0.08,2.20 ± 0.14,
15a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCC(O)=O)(C)O2)=C(C)C(O)=C1C,0.44 ± 0.07,0.45 ± 0.12,
15b,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCC(O)=O)(C)O2)=CC(O)=C1,0.47 ± 0.14,2.19 ± 0.40,
16,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C/C(O)=O)(C)O2)=CC(O)=C1,0.92 ± 0.04,> 3,
17,CC1=C2C(CC[C@](CC/C=C/C(O)=O)(C)O2)=CC(O)=C1,> 1,> 3,
18,CC1=C2C(CC[C@](CC/C=C(C)/C(O)=O)(C)O2)=CC(O)=C1,> 1,> 3,
19a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCCC(C)C(O)=O)(C)O2)=C(C)C(O)=C1,0.81 ± 0.08,0.81 ± 0.33,
19b,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCCC(C)C(O)=O)(C)O2)=CC(O)=C1,0.17 ± 0.04#,0.61 ± 0.15,
20,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCCC(C)C(O)=O)(C)O2)=CC(OC)=C1,> 1,n.d.,
21,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCCC(C)C(OC)=O)(C)O2)=CC(O)=C1,0.17 ± 0.01,1.14 ± 0.39,
22,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CCCC(C)C(OC)=O)(C)O2)=CC(OC)=C1,> 1,n.d.,
23,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=C(CN(C)C)C(O)=C1,0.07 ± 0.02,2.06 ± 0.45,mannich_A(296) 
24,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=C(CN(C)C)C(O)=C1CN(C)C,> 1,> 3,mannich_A(296) 
25,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(OC)=O)(C)O2)=C(C(OC)=O)C(O)=C1,> 1,> 3,
26,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(CO)CO)(C)O2)=CC(O)=C1,> 1,> 3,
27a,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C)C(O)=C1C,0.11 ± 0.03,0.04 ± 0.01,
27b,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C)C(O)=C1,0.09 ± 0.02,0.10 ± 0.02,
27c,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=CC(O)=C1C,0.11 ± 0.00#,0.05 ± 0.04,
27d,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=CC(O)=C1,0.15 ± 0.04#,0.43 ± 0.04,
28,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=CC(O)=C1,0.17 ± 0.03,2.30 ± 0.26,
29,CC1=C2C(CC[C@](CC/C=C(CO)/CO)(C)O2)=CC(O)=C1,> 1,> 3,
30,CC1=C2C(CC[C@](C)(O2)CC/C=C(CCC(O)C(C)(CC/C=C(CO)\CO)O)\C)=CC(O)=C1,0.38 ± 0.11,n.d.,
31,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=CC(OC(CCC(O)=O)=O)=C1,0.09 ± 0.03,0.45 ± 0.10,
32,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=CC(OCC(N)=O)=C1,> 1,n.d.,
33,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C)C(O)=C1C([H])=O,0.17 ± 0.05,1.38 ± 0.28,
34,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C([H])=O)C(O)=C1,0.17 ± 0.06,1.81 ± 0.32,
35,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN3CCCC3)C(O)=C1,0.17 ± 0.03,1.90 ± 0.11,mannich_A(296) 
36,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN(C)C)C(O)=C1,0.11 ± 0.02,> 3,mannich_A(296) 
37,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN3CCOCC3)C(O)=C1,0.12 ± 0.03,1.74 ± 0.09,mannich_A(296) 
38,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN3CCCCC3)C(O)=C1,0.11 ± 0.02,1.95 ± 0.07,mannich_A(296) 
39,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN3CCN(C)CC3)C(O)=C1,0.31 ± 0.07,2.03 ± 0.16,mannich_A(296) 
40,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(CN3CCN(C)CC3)C(O)=C1CN4CCN(C)CC4,> 1,> 3,mannich_A(296) 
41,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C)C(O3)=C1C=C(C(C)=O)C3=O,0.63 ± 0.13,1.25 ± 0.20,
42,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C=C3C(C)=O)C(OC3=O)=C1,0.21 ± 0.02,1.44 ± 0.42,
43,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/CO)(C)O2)=C(C=C3C(OCC)=O)C(OC3=O)=C1,0.47 ± 0.14,1.58 ± 0.21,
44,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(O)=C1,0.21 ± 0.14,n.d.,
45,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(OCCCC(O)=O)=C1,> 1,n.d.,
46,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=C(C)C(O)=C1CO,0.09 ± 0.00,0.39 ± 0.18,
47,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=C(C)C(O)=C1C([H])=O,> 1,> 3,
48,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC=C([N+]([O-])=O)C=C4)OC/3)(C)O2)=C(CO)C(O)=C1,0.21 ± 0.13,0.49 ± 0.13,
49,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(CO)/C)(C)O2)=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
50,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C(O)=O)/C)(C)O2)=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
51,CC1=C2C(CC[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)O2)=C(Cl)C(O)=C1,,,
52,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(OC)=O)(C)O2)=CC(O)=C1,,,
53,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(OC)=O)(C)O2)=CC(OC)=C1,,,
54,CC1=C(O[C@@](CC/C=C(CC/C=C(CCC=O)\C)\C)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
55,CC1=C(O[C@@](CC/C=C(CC/C=C(CCC(O)=O)\C)\C)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
56,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C(O)=O)(C)O2)=C(C(O)=O)C(O)=C1,,,
57,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)(C)O2)=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
58,CC1=C(O[C@@](CC/C=C(CC/C=C(CC/C=C/C(OC)=O)\C)\C)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
59,CC1=C(O[C@@](CC/C=C(CC/C=C/C(OC)=O)\C)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
60,CC1=C(O[C@@](CC/C=C/C(OC)=O)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
61,CC1=C(O[C@@](CC/C=C(C)/C(OC)=O)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
62,CC1=C(O[C@@](CC/C=C(C)/CC/C=C(COC(C)=O)/COC(C)=O)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
63,CC1=C(O[C@@](CC/C=C(COC(C)=O)/COC(C)=O)(C)CC2)C2=CC(OS(C3=CC=C(C)C=C3)(=O)=O)=C1,,,
64,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(O)=C1,,,
65,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C(COC(C)=O)/COC(C)=O)(C)O2)=CC(OC(C)=O)=C1,,,
66,CC1=C2C(CC[C@](CCCC(C)CCCC(C)CCCC(COC(C)=O)COC(C)=O)(C)O2)=CC(OC(C)=O)=C1,,,
67,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(OCCCC(OCC)=O)=C1,,,
68,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(OC(CCC(O)=O)=O)=C1,,,
69,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC(OC)=C(OC)C=C4)OC/3)(C)O2)=CC(OCC(N)=O)=C1,,,
70,CC1=C2C(CC[C@](CC/C=C(C)/CC/C=C(C)/CC/C=C3COC(C4=CC=C([N+]([O-])=O)C=C4)OC/3)(C)O2)=CC(O)=C1,,,