data_336
# 
_chem_comp.id                                    336 
_chem_comp.name                                  4-{2-[4-(3,10-DIBROMO-8-CHLORO-6,11-DIHYDRO-5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN-11-YL)PIPERIDIN-1-YL]-2-OXOETHYL}PIPERIDINE-1-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H31 Br2 Cl N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         SCH66336 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-10-06 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        638.822 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     336 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1O5M 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
336 C1   C1   C  0 1 N N N 187.085 131.704 33.595 -1.127 -1.553 0.496  C1   336 1  
336 C4   C4   C  0 1 N N N 186.548 129.303 32.965 -0.861 0.175  -1.286 C4   336 2  
336 C6   C6   C  0 1 N N N 185.567 129.275 34.129 -0.825 1.283  -0.230 C6   336 3  
336 C9   C9   C  0 1 N N N 185.999 130.184 35.258 -1.688 0.865  0.970  C9   336 4  
336 N12  N12  N  0 1 N N N 186.230 131.544 34.778 -1.218 -0.440 1.450  N12  336 5  
336 C13  C13  C  0 1 N N N 186.704 130.733 32.478 -0.276 -1.110 -0.698 C13  336 6  
336 CL16 CL16 CL 0 0 N N N 182.921 123.634 33.671 -2.966 -1.347 -7.329 CL16 336 7  
336 C17  C17  C  0 1 Y N N 189.329 126.944 30.219 3.617  -0.286 -2.140 C17  336 8  
336 C19  C19  C  0 1 Y N N 183.856 124.974 33.135 -2.109 -0.851 -5.903 C19  336 9  
336 C20  C20  C  0 1 Y N N 185.210 125.090 33.479 -0.837 -1.302 -5.664 C20  336 10 
336 C22  C22  C  0 1 N N N 187.399 126.334 33.402 1.217  -1.652 -4.489 C22  336 11 
336 C25  C25  C  0 1 N N N 188.257 125.994 32.237 2.400  -0.806 -4.137 C25  336 12 
336 C28  C28  C  0 1 Y N N 183.973 127.057 31.900 -1.973 0.407  -3.898 C28  336 13 
336 C29  C29  C  0 1 Y N N 189.449 127.837 29.154 3.851  0.327  -0.932 C29  336 14 
336 C30  C30  C  0 1 Y N N 188.480 128.838 29.003 2.816  1.037  -0.347 C30  336 15 
336 N32  N32  N  0 1 Y N N 187.464 128.931 29.864 1.650  1.074  -0.936 N32  336 16 
336 C33  C33  C  0 1 N N R 186.111 128.357 31.766 -0.034 0.602  -2.500 C33  336 17 
336 C35  C35  C  0 1 Y N N 183.244 125.951 32.348 -2.700 0.006  -4.991 C35  336 18 
336 BR37 BR37 BR 0 0 N N N 190.902 127.677 27.955 5.541  0.206  -0.092 BR37 336 19 
336 BR38 BR38 BR 0 0 N N N 183.097 128.363 30.838 -2.759 1.599  -2.658 BR38 336 20 
336 C39  C39  C  0 1 Y N N 187.314 128.081 30.904 1.384  0.458  -2.108 C39  336 21 
336 C40  C40  C  0 1 Y N N 185.335 127.179 32.240 -0.655 -0.046 -3.674 C40  336 22 
336 C41  C41  C  0 1 Y N N 188.268 127.042 31.122 2.345  -0.184 -2.759 C41  336 23 
336 C42  C42  C  0 1 Y N N 185.943 126.193 33.031 -0.105 -0.916 -4.516 C42  336 24 
336 C43  C43  C  0 1 N N N 185.619 136.469 35.162 -0.645 1.241  6.084  C43  336 25 
336 C46  C46  C  0 1 N N N 185.527 137.585 36.203 -0.175 0.782  7.468  C46  336 26 
336 C49  C49  C  0 1 N N N 185.785 135.094 35.809 -0.545 0.071  5.102  C49  336 27 
336 C51  C51  C  0 1 N N N 186.882 135.078 36.870 -1.455 -1.067 5.568  C51  336 28 
336 N54  N54  N  0 1 N N N 186.624 137.463 37.164 -0.949 -0.403 7.861  N54  336 29 
336 C55  C55  C  0 1 N N N 187.507 138.467 37.390 -1.604 -0.436 9.039  C55  336 30 
336 N56  N56  N  0 1 N N N 188.420 138.108 38.305 -1.645 0.662  9.818  N56  336 31 
336 O57  O57  O  0 1 N N N 187.500 139.572 36.848 -2.157 -1.458 9.398  O57  336 32 
336 C58  C58  C  0 1 N N N 186.726 136.187 37.862 -0.989 -1.554 6.949  C58  336 33 
336 C61  C61  C  0 1 N N N 185.996 133.964 34.806 -0.981 0.535  3.711  C61  336 34 
336 O64  O64  O  0 1 N N N 184.954 132.504 36.398 -0.501 -1.700 3.129  O64  336 35 
336 C65  C65  C  0 1 N N N 185.673 132.596 35.410 -0.882 -0.616 2.744  C65  336 36 
336 H11  1H1  H  0 1 N N N 188.164 131.612 33.860 -2.126 -1.823 0.153  H11  336 37 
336 H12  2H1  H  0 1 N N N 187.082 132.759 33.233 -0.660 -2.412 0.979  H12  336 38 
336 H4   H4   H  0 1 N N N 187.524 128.911 33.336 -1.891 -0.000 -1.593 H4   336 39 
336 H61  1H6  H  0 1 N N N 185.398 128.234 34.490 -1.220 2.205  -0.657 H61  336 40 
336 H62  2H6  H  0 1 N N N 184.532 129.514 33.791 0.202  1.443  0.094  H62  336 41 
336 H91  1H9  H  0 1 N N N 186.890 129.780 35.793 -2.731 0.794  0.663  H91  336 42 
336 H92  2H9  H  0 1 N N N 185.271 130.165 36.103 -1.588 1.604  1.765  H92  336 43 
336 H131 1H13 H  0 0 N N N 187.432 130.790 31.635 0.746  -0.927 -0.368 H131 336 44 
336 H132 2H13 H  0 0 N N N 185.785 131.076 31.948 -0.280 -1.892 -1.457 H132 336 45 
336 H17  H17  H  0 1 N N N 190.083 126.150 30.349 4.404  -0.849 -2.620 H17  336 46 
336 H20  H20  H  0 1 N N N 185.696 124.318 34.099 -0.378 -1.975 -6.374 H20  336 47 
336 H221 1H22 H  0 0 N N N 187.630 127.346 33.810 1.145  -2.463 -3.764 H221 336 48 
336 H222 2H22 H  0 0 N N N 187.661 125.732 34.303 1.388  -2.090 -5.473 H222 336 49 
336 H251 1H25 H  0 0 N N N 187.975 124.996 31.827 2.484  -0.006 -4.873 H251 336 50 
336 H252 2H25 H  0 0 N N N 189.298 125.777 32.574 3.297  -1.423 -4.201 H252 336 51 
336 H30  H30  H  0 1 N N N 188.518 129.574 28.183 2.971  1.555  0.586  H30  336 52 
336 H33  H33  H  0 1 N N N 185.375 128.863 31.099 -0.213 1.672  -2.613 H33  336 53 
336 H35  H35  H  0 1 N N N 182.179 125.849 32.079 -3.713 0.352  -5.136 H35  336 54 
336 H431 1H43 H  0 0 N N N 186.431 136.670 34.425 -1.680 1.577  6.144  H431 336 55 
336 H432 2H43 H  0 0 N N N 184.745 136.488 34.471 -0.015 2.061  5.739  H432 336 56 
336 H461 1H46 H  0 0 N N N 184.532 137.608 36.705 -0.338 1.581  8.192  H461 336 57 
336 H462 2H46 H  0 0 N N N 185.494 138.595 35.732 0.884  0.531  7.429  H462 336 58 
336 H49  H49  H  0 1 N N N 184.809 134.901 36.312 0.485  -0.280 5.061  H49  336 59 
336 H511 1H51 H  0 0 N N N 187.895 135.094 36.403 -2.482 -0.709 5.634  H511 336 60 
336 H512 2H51 H  0 0 N N N 186.937 134.087 37.378 -1.400 -1.890 4.856  H512 336 61 
336 H561 1H56 H  0 0 N N N 189.084 138.863 38.475 -2.189 0.666  10.621 H561 336 62 
336 H562 2H56 H  0 0 N N N 188.426 137.192 38.754 -1.129 1.447  9.578  H562 336 63 
336 H581 1H58 H  0 0 N N N 187.543 136.188 38.621 0.003  -1.995 6.865  H581 336 64 
336 H582 2H58 H  0 0 N N N 185.866 136.016 38.551 -1.690 -2.296 7.330  H582 336 65 
336 H611 1H61 H  0 0 N N N 187.027 133.986 34.382 -0.333 1.345  3.378  H611 336 66 
336 H612 2H61 H  0 0 N N N 185.417 134.140 33.870 -2.012 0.888  3.752  H612 336 67 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
336 C1   N12  SING N N 1  
336 C1   C13  SING N N 2  
336 C1   H11  SING N N 3  
336 C1   H12  SING N N 4  
336 C4   C6   SING N N 5  
336 C4   C13  SING N N 6  
336 C4   C33  SING N N 7  
336 C4   H4   SING N N 8  
336 C6   C9   SING N N 9  
336 C6   H61  SING N N 10 
336 C6   H62  SING N N 11 
336 C9   N12  SING N N 12 
336 C9   H91  SING N N 13 
336 C9   H92  SING N N 14 
336 N12  C65  SING N N 15 
336 C13  H131 SING N N 16 
336 C13  H132 SING N N 17 
336 CL16 C19  SING N N 18 
336 C17  C29  DOUB Y N 19 
336 C17  C41  SING Y N 20 
336 C17  H17  SING N N 21 
336 C19  C20  DOUB Y N 22 
336 C19  C35  SING Y N 23 
336 C20  C42  SING Y N 24 
336 C20  H20  SING N N 25 
336 C22  C25  SING N N 26 
336 C22  C42  SING N N 27 
336 C22  H221 SING N N 28 
336 C22  H222 SING N N 29 
336 C25  C41  SING N N 30 
336 C25  H251 SING N N 31 
336 C25  H252 SING N N 32 
336 C28  C35  DOUB Y N 33 
336 C28  BR38 SING N N 34 
336 C28  C40  SING Y N 35 
336 C29  C30  SING Y N 36 
336 C29  BR37 SING N N 37 
336 C30  N32  DOUB Y N 38 
336 C30  H30  SING N N 39 
336 N32  C39  SING Y N 40 
336 C33  C39  SING N N 41 
336 C33  C40  SING N N 42 
336 C33  H33  SING N N 43 
336 C35  H35  SING N N 44 
336 C39  C41  DOUB Y N 45 
336 C40  C42  DOUB Y N 46 
336 C43  C46  SING N N 47 
336 C43  C49  SING N N 48 
336 C43  H431 SING N N 49 
336 C43  H432 SING N N 50 
336 C46  N54  SING N N 51 
336 C46  H461 SING N N 52 
336 C46  H462 SING N N 53 
336 C49  C51  SING N N 54 
336 C49  C61  SING N N 55 
336 C49  H49  SING N N 56 
336 C51  C58  SING N N 57 
336 C51  H511 SING N N 58 
336 C51  H512 SING N N 59 
336 N54  C55  SING N N 60 
336 N54  C58  SING N N 61 
336 C55  N56  SING N N 62 
336 C55  O57  DOUB N N 63 
336 N56  H561 SING N N 64 
336 N56  H562 SING N N 65 
336 C58  H581 SING N N 66 
336 C58  H582 SING N N 67 
336 C61  C65  SING N N 68 
336 C61  H611 SING N N 69 
336 C61  H612 SING N N 70 
336 O64  C65  DOUB N N 71 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
336 SMILES           ACDLabs              10.04 O=C(N4CCC(C3c1c(Br)cc(Cl)cc1CCc2cc(Br)cnc23)CC4)CC5CCN(C(=O)N)CC5                                                                                                                          
336 InChI            InChI                1.02b InChI=1/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1/f/h31H2 
336 InChIKey         InChI                1.02b DHMTURDWPRKSOA-TYQFRRCBDC                                                                                                                                                                  
336 SMILES_CANONICAL CACTVS               3.341 NC(=O)N1CCC(CC1)CC(=O)N2CCC(CC2)[C@H]3c4ncc(Br)cc4CCc5cc(Cl)cc(Br)c35                                                                                                                      
336 SMILES           CACTVS               3.341 NC(=O)N1CCC(CC1)CC(=O)N2CCC(CC2)[CH]3c4ncc(Br)cc4CCc5cc(Cl)cc(Br)c35                                                                                                                       
336 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1c(cc(c2c1CCc3cc(cnc3[C@@H]2C4CCN(CC4)C(=O)CC5CCN(CC5)C(=O)N)Br)Br)Cl                                                                                                                     
336 SMILES           "OpenEye OEToolkits" 1.5.0 c1c(cc(c2c1CCc3cc(cnc3C2C4CCN(CC4)C(=O)CC5CCN(CC5)C(=O)N)Br)Br)Cl                                                                                                                          
# 
_pdbx_chem_comp_identifier.comp_id           336 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        4-(2-{4-[(11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide 
# 
