3D-QSAR studies of substituted 1-(3, 3-diphenylpropyl)-piperidinyl amides and ureas as CCR5 receptor antagonists
Yogesh D. Aher, Avantika Agrawal, Prasad V. Bharatam and Prabha GargΞ
Supplementary Material
# Name: 1
@<TRIPOS>MOLECULE
1
63 66 4 9 0
SMALL
GAST_HUCK
@<TRIPOS>ATOM
1 C1 -4.047611 1.522460 -1.501143 C.3 1 BENZYL 0.026671
2 C2 -4.502243 2.722025 -0.641087 C.ar 1 BENZYL -0.028845
3 C3 -5.854382 3.084015 -0.704963 C.ar 1 BENZYL -0.058081
4 C4 -6.357933 4.136346 0.064544 C.ar 1 BENZYL -0.068181
5 C5 -5.505033 4.854423 0.905287 C.ar 1 BENZYL -0.068494
6 C6 -4.150470 4.518493 0.962125 C.ar 1 BENZYL -0.068181
7 C7 -3.650982 3.466391 0.188240 C.ar 1 BENZYL -0.058081
8 C -4.964171 0.303971 -1.287217 C.ar 2 PHENYL -0.028845
9 C -5.532351 0.040291 -0.034376 C.ar 2 PHENYL -0.058081
10 C -6.362020 -1.069493 0.149243 C.ar 2 PHENYL -0.068181
11 C -6.629025 -1.928451 -0.919868 C.ar 2 PHENYL -0.068494
12 C -6.064583 -1.673114 -2.172252 C.ar 2 PHENYL -0.068181
13 C -5.235744 -0.562000 -2.353137 C.ar 2 PHENYL -0.058081
14 C14 -2.567620 1.059881 -1.354999 C.3 1 BENZYL -0.018108
15 C15 -2.286478 0.331478 -0.009792 C.3 1 BENZYL 0.002675
16 N16 -0.840028 0.225780 0.324966 N.3 3 CYCLOHEXYL -0.301856
17 C2 0.008821 -0.425585 -0.705482 C.3 3 CYCLOHEXYL 0.000991
18 C3 1.507676 -0.335068 -0.317382 C.3 3 CYCLOHEXYL -0.016868
19 C4 1.743112 -0.991155 1.066931 C.3 3 CYCLOHEXYL 0.046440
20 C5 0.853552 -0.276556 2.109936 C.3 3 CYCLOHEXYL -0.016868
21 C6 -0.633056 -0.348469 1.681133 C.3 3 CYCLOHEXYL 0.000991
22 N22 3.143863 -0.971417 1.515236 N.am 3 CYCLOHEXYL -0.272916
23 C23 4.035561 0.156388 1.223220 C.3 3 CYCLOHEXYL 0.022296
24 F24 8.955768 -2.540391 3.928646 F 4 PHENYL -0.179396
25 C25 3.582024 -2.012776 2.278058 C.2 3 CYCLOHEXYL 0.204375
26 O26 2.819847 -2.877427 2.679078 O.2 3 CYCLOHEXYL -0.386376
27 H1 -4.179570 1.883633 -2.535221 H 1 BENZYL 0.061861
28 C 5.028614 -2.181028 2.693899 C.ar 4 PHENYL 0.045851
29 C 5.324448 -2.446597 4.035249 C.ar 4 PHENYL -0.043719
30 C 6.652365 -2.574232 4.453322 C.ar 4 PHENYL -0.022321
31 C 7.690763 -2.439736 3.528734 C.ar 4 PHENYL 0.137532
32 C 7.399589 -2.200936 2.183465 C.ar 4 PHENYL -0.022321
33 C 6.070374 -2.093024 1.763351 C.ar 4 PHENYL -0.043719
34 H2 -6.530218 2.543447 -1.360575 H 1 BENZYL 0.056063
35 H3 -7.410775 4.395901 0.009195 H 1 BENZYL 0.059991
36 H4 -5.892229 5.669089 1.509828 H 1 BENZYL 0.056079
37 H5 -3.483463 5.078833 1.610562 H 1 BENZYL 0.059991
38 H6 -2.591660 3.253085 0.252656 H 1 BENZYL 0.056063
39 H7 -5.334307 0.692610 0.809695 H 2 PHENYL 0.056063
40 H8 -6.799365 -1.264911 1.123770 H 2 PHENYL 0.059991
41 H9 -7.272668 -2.791209 -0.777659 H 2 PHENYL 0.056079
42 H10 -6.270049 -2.339019 -3.004963 H 2 PHENYL 0.059991
43 H11 -4.801674 -0.377579 -3.330636 H 2 PHENYL 0.056063
44 H12 -1.884860 1.912944 -1.487860 H 1 BENZYL 0.032377
45 H13 -2.367416 0.351468 -2.175914 H 1 BENZYL 0.032377
46 H14 -2.737077 -0.674959 -0.032200 H 1 BENZYL 0.042969
47 H15 -2.781709 0.899197 0.791511 H 1 BENZYL 0.042969
48 H16 -0.089340 0.079343 -1.678321 H 3 CYCLOHEXYL 0.042722
49 H17 -0.293838 -1.477803 -0.834119 H 3 CYCLOHEXYL 0.042722
50 H18 2.131573 -0.841091 -1.072725 H 3 CYCLOHEXYL 0.029980
51 H19 1.780503 0.731007 -0.300075 H 3 CYCLOHEXYL 0.029980
52 H20 1.393778 -2.033685 0.960990 H 3 CYCLOHEXYL 0.055829
53 H21 0.987504 -0.754447 3.094548 H 3 CYCLOHEXYL 0.029980
54 H22 1.155675 0.779018 2.194891 H 3 CYCLOHEXYL 0.029980
55 H23 -0.970137 -1.398478 1.699164 H 3 CYCLOHEXYL 0.042722
56 H24 -1.217961 0.208118 2.432143 H 3 CYCLOHEXYL 0.042722
57 H25 4.864425 0.253983 1.939476 H 3 CYCLOHEXYL 0.048561
58 H26 3.484230 1.105495 1.281664 H 3 CYCLOHEXYL 0.048561
59 H27 4.446702 0.056992 0.207730 H 3 CYCLOHEXYL 0.048561
60 H28 4.518701 -2.551955 4.755388 H 4 PHENYL 0.065935
61 H29 6.882455 -2.776800 5.494191 H 4 PHENYL 0.061628
62 H30 8.210176 -2.102765 1.468813 H 4 PHENYL 0.061628
63 H31 5.850340 -1.949584 0.710855 H 4 PHENYL 0.065935
@<TRIPOS>BOND
1 1 2 1
2 2 3 ar
3 2 7 ar
4 7 6 ar
5 6 5 ar
6 5 4 ar
7 4 3 ar
8 8 9 ar
9 8 13 ar
10 13 12 ar
11 12 11 ar
12 11 10 ar
13 10 9 ar
14 1 8 1
15 1 14 1
16 14 15 1
17 16 17 1
18 16 21 1
19 21 20 1
20 20 19 1
21 19 18 1
22 18 17 1
23 15 16 1
24 19 22 1
25 22 23 1
26 31 24 1
27 22 25 am
28 25 26 2
29 25 28 1
30 28 29 ar
31 33 28 ar
32 32 33 ar
33 32 31 ar
34 31 30 ar
35 30 29 ar
36 1 27 1
37 3 34 1
38 4 35 1
39 5 36 1
40 6 37 1
41 7 38 1
42 9 39 1
43 10 40 1
44 11 41 1
45 12 42 1
46 13 43 1
47 14 44 1
48 14 45 1
49 15 46 1
50 15 47 1
51 17 48 1
52 17 49 1
53 18 50 1
54 18 51 1
55 19 52 1
56 20 53 1
57 20 54 1
58 21 55 1
59 21 56 1
60 23 57 1
61 23 58 1
62 23 59 1
63 29 60 1
64 30 61 1
65 32 62 1
66 33 63 1
@<TRIPOS>SUBSTRUCTURE
1 BENZYL 1 PERM 0 **** **** 2 ROOT
2 PHENYL 8 PERM 0 **** **** 1
3 CYCLOHEXYL 16 PERM 0 **** **** 2
4 PHENYL 28 PERM 0 **** **** 1
@<TRIPOS>ROTATABLE_BOND
1 15 3 1 1 0 1 30 0 359
14 15 9 2 1 0 1 30 0 359
15 14 16 3 1 0 1 30 0 359
16 15 23 4 1 0 1 30 0 359
23 16 18 5 1 0 1 30 0 359
24 21 27 6 1 0 1 30 0 359
@<TRIPOS>ANCHOR_ATOM
1
@<TRIPOS>NORMAL
@<TRIPOS>FF_PBC
FORCE_FIELD_SETUP_FEATURE Force Field Setup information
v1.0 0 0.000000 0.000000 0.000000 0.000000 0.000000 0.000000 NONE 0 0 0 0 1 0 0 0 0 0 0 0 0
@<TRIPOS>SEARCH_OPTS
1 0 1 1 9.999000e+03 0 9.500000e-01 6.500000e-01 8.700000e-01 0 0
------
# Name: 2
@<TRIPOS>MOLECULE
2
65 68 5 9 0
SMALL
GAST_HUCK
@<TRIPOS>ATOM
1 C1 -3.986506 1.454162 -1.481636 C.3 1 BENZYL 0.026671
2 C2 -4.440610 2.689374 -0.673334 C.ar 1 BENZYL -0.028845
3 C3 -5.784145 3.073440 -0.777748 C.ar 1 BENZYL -0.058081
4 C4 -6.286079 4.152796 -0.045529 C.ar 1 BENZYL -0.068181
5 C5 -5.439177 4.878467 0.794776 C.ar 1 BENZYL -0.068494
6 C6 -4.090847 4.525446 0.885123 C.ar 1 BENZYL -0.068181
7 C7 -3.592648 3.447517 0.146762 C.ar 1 BENZYL -0.058081
8 C -4.963398 0.276390 -1.311974 C.ar 2 PHENYL -0.028845
9 C -5.603361 0.041685 -0.088554 C.ar 2 PHENYL -0.058081
10 C -6.494597 -1.025903 0.052104 C.ar 2 PHENYL -0.068181
11 C -6.749382 -1.872612 -1.029781 C.ar 2 PHENYL -0.068494
12 C -6.109369 -1.648966 -2.251495 C.ar 2 PHENYL -0.068181
13 C -5.219571 -0.579783 -2.389672 C.ar 2 PHENYL -0.058081
14 C14 -2.542333 0.928455 -1.232238 C.3 1 BENZYL -0.018108
15 C15 -2.353753 0.276930 0.167327 C.3 1 BENZYL 0.002675
16 N16 -0.911658 0.143702 0.508513 N.3 3 CYCLOHEXYL -0.301856
17 C2 -0.196156 -0.921263 -0.239812 C.3 3 CYCLOHEXYL 0.000992
18 C3 1.332884 -0.816765 -0.015351 C.3 3 CYCLOHEXYL -0.016855
19 C4 1.662939 -0.890019 1.493674 C.3 3 CYCLOHEXYL 0.046534
20 C5 0.885271 0.230847 2.231914 C.3 3 CYCLOHEXYL -0.016855
21 C6 -0.635858 0.090891 1.967589 C.3 3 CYCLOHEXYL 0.000992
22 N22 3.122172 -0.842117 1.671147 N.am 3 CYCLOHEXYL -0.272470
23 C23 3.845116 0.424411 1.832703 C.3 3 CYCLOHEXYL 0.022392
24 N 8.292558 -3.490292 0.243576 N.pl3 5 NO2 0.122181
25 C25 3.806907 -2.018878 1.611112 C.2 3 CYCLOHEXYL 0.204346
26 O26 3.254886 -3.067777 1.320683 O.2 3 CYCLOHEXYL -0.384495
27 O 7.774378 -3.944373 -0.753580 O.2 5 NO2 -0.113153
28 C 6.112528 -2.777307 0.962775 C.ar 4 PHENYL -0.017445
29 C 7.499241 -2.863121 1.154365 C.ar 4 PHENYL 0.136162
30 C 8.047369 -2.283808 2.308256 C.ar 4 PHENYL -0.032755
31 C 7.231077 -1.652628 3.251405 C.ar 4 PHENYL -0.067773
32 C 5.850918 -1.584493 3.049756 C.ar 4 PHENYL -0.055272
33 C 5.292361 -2.121297 1.886295 C.ar 4 PHENYL 0.038532
34 O 9.480810 -3.563543 0.471039 O.2 5 NO2 -0.113153
35 H1 -4.035803 1.802016 -2.527375 H 1 BENZYL 0.061861
36 H2 -6.454801 2.530099 -1.436404 H 1 BENZYL 0.056063
37 H3 -7.333209 4.427539 -0.129652 H 1 BENZYL 0.059991
38 H4 -5.826120 5.712285 1.372624 H 1 BENZYL 0.056079
39 H5 -3.427714 5.092642 1.531564 H 1 BENZYL 0.059991
40 H6 -2.536376 3.225126 0.229923 H 1 BENZYL 0.056063
41 H7 -5.413723 0.684875 0.764402 H 2 PHENYL 0.056063
42 H8 -6.989588 -1.197976 1.003069 H 2 PHENYL 0.059991
43 H9 -7.442085 -2.701645 -0.921397 H 2 PHENYL 0.056079
44 H10 -6.303458 -2.306521 -3.093488 H 2 PHENYL 0.059991
45 H11 -4.726264 -0.420526 -3.343228 H 2 PHENYL 0.056063
46 H12 -1.808191 1.735516 -1.377862 H 1 BENZYL 0.032377
47 H13 -2.339789 0.169880 -2.004795 H 1 BENZYL 0.032377
48 H14 -2.846436 -0.708606 0.206894 H 1 BENZYL 0.042969
49 H15 -2.854615 0.917659 0.907148 H 1 BENZYL 0.042969
50 H16 -0.365743 -0.835153 -1.323115 H 3 CYCLOHEXYL 0.042722
51 H17 -0.554761 -1.913482 0.080827 H 3 CYCLOHEXYL 0.042722
52 H18 1.847729 -1.634736 -0.545884 H 3 CYCLOHEXYL 0.029981
53 H19 1.695235 0.140322 -0.422738 H 3 CYCLOHEXYL 0.029981
54 H20 1.266993 -1.839700 1.895602 H 3 CYCLOHEXYL 0.055846
55 H21 1.095229 0.174472 3.312863 H 3 CYCLOHEXYL 0.029981
56 H22 1.184708 1.226125 1.871136 H 3 CYCLOHEXYL 0.029981
57 H23 -1.017163 -0.853351 2.390293 H 3 CYCLOHEXYL 0.042722
58 H24 -1.136264 0.923218 2.490226 H 3 CYCLOHEXYL 0.042722
59 H25 3.771713 0.765789 2.875983 H 3 CYCLOHEXYL 0.048577
60 H26 3.413105 1.196681 1.180793 H 3 CYCLOHEXYL 0.048577
61 H27 4.906027 0.365295 1.549778 H 3 CYCLOHEXYL 0.048577
62 H28 5.647662 -3.218557 0.087208 H 4 PHENYL 0.056711
63 H29 9.116682 -2.315425 2.491027 H 4 PHENYL 0.055280
64 H30 7.669447 -1.215664 4.143960 H 4 PHENYL 0.059446
65 H31 5.216354 -1.122147 3.798721 H 4 PHENYL 0.055682
@<TRIPOS>BOND
1 1 2 1
2 2 3 ar
3 2 7 ar
4 7 6 ar
5 6 5 ar
6 5 4 ar
7 4 3 ar
8 8 9 ar
9 8 13 ar
10 13 12 ar
11 12 11 ar
12 11 10 ar
13 10 9 ar
14 1 8 1
15 1 14 1
16 14 15 1
17 16 17 1
18 16 21 1
19 21 20 1
20 20 19 1
21 19 18 1
22 18 17 1
23 15 16 1
24 19 22 1
25 22 23 1
26 25 33 1
27 22 25 am
28 25 26 2
29 24 27 2
30 28 29 ar
31 28 33 ar
32 33 32 ar
33 32 31 ar
34 31 30 ar
35 30 29 ar
36 24 34 2
37 29 24 1
38 1 35 1
39 3 36 1
40 4 37 1
41 5 38 1
42 6 39 1
43 7 40 1
44 9 41 1
45 10 42 1
46 11 43 1
47 12 44 1
48 13 45 1
49 14 46 1
50 14 47 1
51 15 48 1
52 15 49 1
53 17 50 1
54 17 51 1
55 18 52 1
56 18 53 1
57 19 54 1
58 20 55 1
59 20 56 1
60 21 57 1
61 21 58 1
62 23 59 1
63 23 60 1
64 23 61 1
65 28 62 1
66 30 63 1
67 31 64 1
68 32 65 1
@<TRIPOS>SUBSTRUCTURE
1 BENZYL 1 PERM 0 **** **** 2 ROOT
2 PHENYL 8 PERM 0 **** **** 1
3 CYCLOHEXYL 16 PERM 0 **** **** 2
4 PHENYL 28 PERM 0 **** **** 2
5 NO2 24 PERM 0 **** **** 1
@<TRIPOS>ROTATABLE_BOND
1 15 3 1 1 0 1 30 0 359
14 15 9 2 1 0 1 30 0 359
15 14 16 3 1 0 1 30 0 359
16 15 23 4 1 0 1 30 0 359
23 16 18 5 1 0 1 30 0 359
24 21 27 6 1 0 1 30 0 359
@<TRIPOS>ANCHOR_ATOM
1
@<TRIPOS>NORMAL
@<TRIPOS>FF_PBC
FORCE_FIELD_SETUP_FEATURE Force Field Setup information
v1.0 0 0.000000 0.000000 0.000000 0.000000 0.000000 0.000000 NONE 0 0 0 0 1 0 0 0 0 0 0 0 0
@<TRIPOS>SEARCH_OPTS
1 0 1 1 9.999000e+03 0 9.500000e-01 6.500000e-01 8.700000e-01 0 0
------
# Name: 3
@<TRIPOS>MOLECULE
3
69 72 4 12 0
SMALL
GAST_HUCK
@<TRIPOS>ATOM
1 C1 -3.993533 1.424478 -1.504481 C.3 1 BENZYL 0.026671
2 C2 -4.423388 2.670368 -0.698573 C.ar 1 BENZYL -0.028845
3 C3 -5.765487 3.064708 -0.780047 C.ar 1 BENZYL -0.058081
4 C4 -6.245918 4.149649 -0.041524 C.ar 1 BENZYL -0.068181
5 C5 -5.378245 4.872356 0.779937 C.ar 1 BENZYL -0.068494
6 C6 -4.030390 4.511822 0.843720 C.ar 1 BENZYL -0.068181
7 C7 -3.554143 3.428046 0.099585 C.ar 1 BENZYL -0.058081
8 C -4.981113 0.258974 -1.311307 C.ar 2 PHENYL -0.028845
9 C -5.606838 0.040460 -0.077470 C.ar 2 PHENYL -0.058081
10 C -6.506644 -1.016918 0.084332 C.ar 2 PHENYL -0.068181
11 C -6.786490 -1.868456 -0.987412 C.ar 2 PHENYL -0.068494
12 C -6.162269 -1.660199 -2.219974 C.ar 2 PHENYL -0.068181
13 C -5.262453 -0.602299 -2.378677 C.ar 2 PHENYL -0.058081
14 C14 -2.551881 0.885969 -1.266333 C.3 1 BENZYL -0.018108