data_99A
# 
_chem_comp.id                                    99A 
_chem_comp.name                                  "N-{(3-endo)-8-[5-(benzylcarbamoyl)pyridin-2-yl]-8-azabicyclo[3.2.1]oct-3-yl}-2,5-dimethylbenzene-1,4-dicarboxamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H33 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-06-05 
_chem_comp.pdbx_modified_date                    2014-09-05 
_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                        511.615 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     99A 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4AWP 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
99A C15  C15  C 0 1 N N N 2.823  -0.195 -0.895  4.808  2.984  1.792  C15  99A 1  
99A C8   C8   C 0 1 Y N N 2.906  -1.732 -1.079  5.395  1.895  0.931  C8   99A 2  
99A C9   C9   C 0 1 Y N N 2.549  -2.503 0.034   6.742  1.898  0.638  C9   99A 3  
99A C10  C10  C 0 1 Y N N 2.556  -3.907 -0.097  7.285  0.889  -0.158 C10  99A 4  
99A C14  C14  C 0 1 N N N 2.269  -4.720 1.162   8.732  0.892  -0.472 C14  99A 5  
99A O2   O2   O 0 1 N N N 3.176  -5.466 1.547   9.200  0.029  -1.188 O2   99A 6  
99A N2   N2   N 0 1 N N N 1.090  -4.528 1.758   9.530  1.852  0.036  N2   99A 7  
99A C11  C11  C 0 1 Y N N 2.941  -4.547 -1.306  6.464  -0.122 -0.659 C11  99A 8  
99A C13  C13  C 0 1 N N N 3.005  -6.071 -1.526  7.051  -1.211 -1.520 C13  99A 9  
99A C12  C12  C 0 1 Y N N 3.239  -3.776 -2.396  5.118  -0.125 -0.367 C12  99A 10 
99A C7   C7   C 0 1 Y N N 3.238  -2.389 -2.306  4.576  0.880  0.435  C7   99A 11 
99A C6   C6   C 0 1 N N N 3.660  -1.584 -3.547  3.130  0.874  0.754  C6   99A 12 
99A O1   O1   O 0 1 N N N 3.134  -1.585 -4.668  2.663  1.733  1.476  O1   99A 13 
99A N1   N1   N 0 1 N N N 4.763  -0.936 -3.209  2.332  -0.086 0.245  N1   99A 14 
99A C5   C5   C 0 1 N N N 5.531  0.051  -3.963  0.902  -0.093 0.562  C5   99A 15 
99A C30  C30  C 0 1 N N N 7.065  0.268  -3.682  0.542  -1.404 1.266  C30  99A 16 
99A C4   C4   C 0 1 N N N 4.879  0.944  -5.035  0.093  0.038  -0.732 C4   99A 17 
99A C1   C1   C 0 1 N N R 5.091  2.354  -4.449  0.311  -1.222 -1.585 C1   99A 18 
99A C2   C2   C 0 1 N N N 4.734  2.419  -2.941  1.831  -1.503 -1.633 C2   99A 19 
99A C3   C3   C 0 1 N N N 6.008  2.098  -2.128  2.107  -2.392 -0.402 C3   99A 20 
99A C29  C29  C 0 1 N N S 7.072  1.751  -3.200  0.729  -2.567 0.278  C29  99A 21 
99A N3   N3   N 0 1 N N N 6.586  2.457  -4.340  -0.250 -2.371 -0.825 N3   99A 22 
99A C16  C16  C 0 1 Y N N 7.425  2.989  -5.330  -1.506 -2.069 -0.325 C16  99A 23 
99A C17  C17  C 0 1 Y N N 8.824  2.970  -5.149  -1.952 -2.697 0.837  C17  99A 24 
99A C18  C18  C 0 1 Y N N 9.649  3.440  -6.144  -3.193 -2.396 1.328  C18  99A 25 
99A N5   N5   N 0 1 Y N N 6.889  3.424  -6.475  -2.265 -1.184 -0.956 N5   99A 26 
99A C28  C28  C 0 1 Y N N 7.665  3.885  -7.446  -3.465 -0.867 -0.518 C28  99A 27 
99A C19  C19  C 0 1 Y N N 9.050  3.914  -7.310  -3.978 -1.460 0.637  C19  99A 28 
99A C20  C20  C 0 1 N N N 9.876  4.501  -8.443  -5.323 -1.104 1.127  C20  99A 29 
99A O3   O3   O 0 1 N N N 9.319  4.968  -9.438  -5.759 -1.622 2.137  O3   99A 30 
99A N4   N4   N 0 1 N N N 11.210 4.597  -8.200  -6.068 -0.203 0.456  N4   99A 31 
99A C21  C21  C 0 1 N N N 12.117 5.229  -9.179  -7.404 0.150  0.943  C21  99A 32 
99A C22  C22  C 0 1 Y N N 12.419 4.393  -10.422 -8.021 1.169  0.020  C22  99A 33 
99A C23  C23  C 0 1 Y N N 13.058 5.059  -11.481 -8.778 0.755  -1.060 C23  99A 34 
99A C24  C24  C 0 1 Y N N 13.381 4.392  -12.665 -9.344 1.690  -1.907 C24  99A 35 
99A C25  C25  C 0 1 Y N N 13.107 3.026  -12.755 -9.154 3.039  -1.672 C25  99A 36 
99A C26  C26  C 0 1 Y N N 12.486 2.333  -11.696 -8.399 3.453  -0.591 C26  99A 37 
99A C27  C27  C 0 1 Y N N 12.147 3.009  -10.515 -7.836 2.519  0.257  C27  99A 38 
99A H151 H151 H 0 0 N N N 3.796  0.187  -0.553  4.360  3.748  1.156  H151 99A 39 
99A H152 H152 H 0 0 N N N 2.561  0.275  -1.854  4.045  2.560  2.444  H152 99A 40 
99A H153 H153 H 0 0 N N N 2.052  0.044  -0.147  5.596  3.432  2.397  H153 99A 41 
99A H9   H9   H 0 1 N N N 2.276  -2.035 0.968   7.377  2.681  1.026  H9   99A 42 
99A H21N H21N H 0 0 N N N 0.872  -5.015 2.604   9.156  2.541  0.608  H21N 99A 43 
99A H22N H22N H 0 0 N N N 0.425  -3.898 1.358   10.478 1.854  -0.169 H22N 99A 44 
99A H131 H131 H 0 0 N N N 2.025  -6.434 -1.870  7.503  -1.973 -0.885 H131 99A 45 
99A H132 H132 H 0 0 N N N 3.768  -6.300 -2.285  6.263  -1.662 -2.123 H132 99A 46 
99A H133 H133 H 0 0 N N N 3.268  -6.567 -0.580  7.812  -0.787 -2.175 H133 99A 47 
99A H12  H12  H 0 1 N N N 3.478  -4.250 -3.337  4.483  -0.909 -0.754 H12  99A 48 
99A H1   H1   H 0 1 N N N 5.124  -1.155 -2.303  2.705  -0.772 -0.330 H1   99A 49 
99A H301 H301 H 0 0 N N N 7.433  -0.413 -2.900  1.195  -1.548 2.126  H301 99A 50 
99A H302 H302 H 0 0 N N N 7.665  0.137  -4.594  -0.497 -1.369 1.595  H302 99A 51 
99A H41C H41C H 0 0 N N N 5.383  0.835  -6.007  -0.965 0.139  -0.493 H41C 99A 52 
99A H42C H42C H 0 0 N N N 3.809  0.715  -5.149  0.429  0.916  -1.285 H42C 99A 53 
99A H29  H29  H 0 1 N N N 8.078  2.066  -2.886  0.629  -3.538 0.763  H29  99A 54 
99A HA   HA   H 0 1 N N N 4.625  3.153  -5.044  -0.122 -1.124 -2.580 HA   99A 55 
99A H21C H21C H 0 0 N N N 4.374  3.427  -2.687  2.089  -2.034 -2.549 H21C 99A 56 
99A H22C H22C H 0 0 N N N 3.951  1.682  -2.712  2.391  -0.572 -1.561 H22C 99A 57 
99A H31C H31C H 0 0 N N N 6.322  2.970  -1.536  2.501  -3.359 -0.713 H31C 99A 58 
99A H32C H32C H 0 0 N N N 5.837  1.242  -1.458  2.803  -1.897 0.274  H32C 99A 59 
99A H17  H17  H 0 1 N N N 9.246  2.587  -4.231  -1.323 -3.413 1.345  H17  99A 60 
99A H18  H18  H 0 1 N N N 10.723 3.442  -6.026  -3.561 -2.869 2.227  H18  99A 61 
99A H28  H28  H 0 1 N N N 7.214  4.245  -8.359  -4.058 -0.142 -1.056 H28  99A 62 
99A H4   H4   H 0 1 N N N 11.583 4.234  -7.346  -5.720 0.210  -0.349 H4   99A 63 
99A H211 H211 H 0 0 N N N 11.658 6.173  -9.507  -8.029 -0.742 0.969  H211 99A 64 
99A H212 H212 H 0 0 N N N 13.070 5.441  -8.672  -7.326 0.569  1.946  H212 99A 65 
99A H23  H23  H 0 1 N N N 13.304 6.106  -11.378 -8.926 -0.299 -1.243 H23  99A 66 
99A H27  H27  H 0 1 N N N 11.687 2.482  -9.692  -7.249 2.842  1.104  H27  99A 67 
99A H24  H24  H 0 1 N N N 13.832 4.921  -13.492 -9.934 1.366  -2.751 H24  99A 68 
99A H25  H25  H 0 1 N N N 13.376 2.490  -13.653 -9.596 3.769  -2.334 H25  99A 69 
99A H26  H26  H 0 1 N N N 12.271 1.279  -11.794 -8.250 4.507  -0.409 H26  99A 70 
99A H5   H5   H 0 1 N N N 5.769  -0.705 -4.726  0.672  0.747  1.219  H5   99A 71 
# 
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 
99A C15 C8   SING N N 1  
99A C8  C9   SING Y N 2  
99A C8  C7   DOUB Y N 3  
99A C9  C10  DOUB Y N 4  
99A C10 C14  SING N N 5  
99A C10 C11  SING Y N 6  
99A C14 O2   DOUB N N 7  
99A C14 N2   SING N N 8  
99A C11 C13  SING N N 9  
99A C11 C12  DOUB Y N 10 
99A C12 C7   SING Y N 11 
99A C7  C6   SING N N 12 
99A C6  O1   DOUB N N 13 
99A C6  N1   SING N N 14 
99A N1  C5   SING N N 15 
99A C5  C30  SING N N 16 
99A C5  C4   SING N N 17 
99A C30 C29  SING N N 18 
99A C4  C1   SING N N 19 
99A C1  C2   SING N N 20 
99A C1  N3   SING N N 21 
99A C2  C3   SING N N 22 
99A C3  C29  SING N N 23 
99A C29 N3   SING N N 24 
99A N3  C16  SING N N 25 
99A C16 C17  SING Y N 26 
99A C16 N5   DOUB Y N 27 
99A C17 C18  DOUB Y N 28 
99A C18 C19  SING Y N 29 
99A N5  C28  SING Y N 30 
99A C28 C19  DOUB Y N 31 
99A C19 C20  SING N N 32 
99A C20 O3   DOUB N N 33 
99A C20 N4   SING N N 34 
99A N4  C21  SING N N 35 
99A C21 C22  SING N N 36 
99A C22 C23  SING Y N 37 
99A C22 C27  DOUB Y N 38 
99A C23 C24  DOUB Y N 39 
99A C24 C25  SING Y N 40 
99A C25 C26  DOUB Y N 41 
99A C26 C27  SING Y N 42 
99A C15 H151 SING N N 43 
99A C15 H152 SING N N 44 
99A C15 H153 SING N N 45 
99A C9  H9   SING N N 46 
99A N2  H21N SING N N 47 
99A N2  H22N SING N N 48 
99A C13 H131 SING N N 49 
99A C13 H132 SING N N 50 
99A C13 H133 SING N N 51 
99A C12 H12  SING N N 52 
99A N1  H1   SING N N 53 
99A C30 H301 SING N N 54 
99A C30 H302 SING N N 55 
99A C4  H41C SING N N 56 
99A C4  H42C SING N N 57 
99A C29 H29  SING N N 58 
99A C1  HA   SING N N 59 
99A C2  H21C SING N N 60 
99A C2  H22C SING N N 61 
99A C3  H31C SING N N 62 
99A C3  H32C SING N N 63 
99A C17 H17  SING N N 64 
99A C18 H18  SING N N 65 
99A C28 H28  SING N N 66 
99A N4  H4   SING N N 67 
99A C21 H211 SING N N 68 
99A C21 H212 SING N N 69 
99A C23 H23  SING N N 70 
99A C27 H27  SING N N 71 
99A C24 H24  SING N N 72 
99A C25 H25  SING N N 73 
99A C26 H26  SING N N 74 
99A C5  H5   SING N N 75 
# 
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 
99A SMILES           ACDLabs              12.01 "O=C(N)c1c(cc(c(c1)C)C(=O)NC5CC4N(c3ncc(C(=O)NCc2ccccc2)cc3)C(CC4)C5)C" 
99A InChI            InChI                1.03  
"InChI=1S/C30H33N5O3/c1-18-13-26(19(2)12-25(18)28(31)36)30(38)34-22-14-23-9-10-24(15-22)35(23)27-11-8-21(17-32-27)29(37)33-16-20-6-4-3-5-7-20/h3-8,11-13,17,22-24H,9-10,14-16H2,1-2H3,(H2,31,36)(H,33,37)(H,34,38)/t22-,23+,24-" 
99A InChIKey         InChI                1.03  CHQGBLRVADDSPY-BKFWDETESA-N 
99A SMILES_CANONICAL CACTVS               3.385 "Cc1cc(c(C)cc1C(N)=O)C(=O)NC2C[C@H]3CC[C@@H](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5" 
99A SMILES           CACTVS               3.385 "Cc1cc(c(C)cc1C(N)=O)C(=O)NC2C[CH]3CC[CH](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5" 
99A SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "Cc1cc(c(cc1C(=O)NC2C[C@H]3CC[C@@H](C2)N3c4ccc(cn4)C(=O)NCc5ccccc5)C)C(=O)N" 
99A SMILES           "OpenEye OEToolkits" 1.9.2 "Cc1cc(c(cc1C(=O)NC2CC3CCC(C2)N3c4ccc(cn4)C(=O)NCc5ccccc5)C)C(=O)N" 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
99A "SYSTEMATIC NAME" ACDLabs              12.01 "N-{(3-endo)-8-[5-(benzylcarbamoyl)pyridin-2-yl]-8-azabicyclo[3.2.1]oct-3-yl}-2,5-dimethylbenzene-1,4-dicarboxamide"           
99A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "2,5-dimethyl-N1-[(1R,5S)-8-[5-[(phenylmethyl)carbamoyl]pyridin-2-yl]-8-azabicyclo[3.2.1]octan-3-yl]benzene-1,4-dicarboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
99A "Create component"  2012-06-05 EBI  
99A "Initial release"   2012-08-24 RCSB 
99A "Modify descriptor" 2014-09-05 RCSB 
# 
