data_85A
# 
_chem_comp.id                                    85A 
_chem_comp.name                                  18-CHLORO-2-OXO-17-[(PYRIDIN-4-YLMETHYL)AMINO]-2,3,11,12,13,14-HEXAHYDRO-1H,10H-4,8-(AZENO)-9,15,1,3,6-BENZODIOXATRIAZACYCLOHEPTADECINE-7-CARBONITRILE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 Cl N7 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         7-CHLORO-3-OXO-8-[(PYRIDIN-4-YLMETHYL)-AMINO]-11,17-DIOXA-2,4,20,22-TETRAAZA-TRICYCLO[16.3.1.0*5,10*]DOCOSA-1(21),5(10)6,8,18(22),19-HEXAENE-19-CARBONITRILE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-01 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        479.919 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     85A 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
85A C1   C1   C  0 1 Y N N 3.619  13.766 -3.770 -0.982 -1.881 0.365  C1   85A 1  
85A C2   C2   C  0 1 Y N N 2.423  13.446 -2.935 -1.985 -2.562 1.073  C2   85A 2  
85A C3   C3   C  0 1 Y N N 2.433  13.818 -1.504 -2.798 -1.851 1.981  C3   85A 3  
85A C4   C4   C  0 1 Y N N 3.628  14.496 -0.969 -2.587 -0.473 2.149  C4   85A 4  
85A C5   C5   C  0 1 Y N N 4.742  14.781 -1.803 -1.581 0.188  1.443  C5   85A 5  
85A C6   C6   C  0 1 Y N N 4.769  14.432 -3.205 -0.780 -0.515 0.554  C6   85A 6  
85A N7   N7   N  0 1 N N N 5.851  14.721 -3.987 0.253  0.123  -0.170 N7   85A 7  
85A CL8  CL8  CL 0 0 N N N 6.063  15.566 -1.087 -1.362 1.881  1.710  CL8  85A 8  
85A C9   C9   C  0 1 N N N -4.744 10.534 -0.534 -8.401 -7.062 1.888  C9   85A 9  
85A N10  N10  N  0 1 N N N -5.680 9.951  -0.846 -9.014 -7.967 1.486  N10  85A 10 
85A N11  N11  N  0 1 N N N 1.286  13.520 -0.686 -3.826 -2.549 2.673  N11  85A 11 
85A C12  C12  C  0 1 N N N 0.926  14.025 0.596  -4.531 -2.096 3.779  C12  85A 12 
85A N13  N13  N  0 1 N N N -0.279 13.662 1.116  -5.664 -2.817 4.133  N13  85A 13 
85A O14  O14  O  0 1 N N N 1.631  14.777 1.269  -4.218 -1.115 4.460  O14  85A 14 
85A C15  C15  C  0 1 Y N N -1.351 12.881 0.712  -6.279 -3.912 3.486  C15  85A 15 
85A N16  N16  N  0 1 Y N N -1.438 12.449 -0.663 -5.776 -4.474 2.370  N16  85A 16 
85A C17  C17  C  0 1 Y N N -2.558 11.666 -1.091 -6.463 -5.512 1.844  C17  85A 17 
85A C18  C18  C  0 1 Y N N -3.597 11.316 -0.101 -7.650 -5.954 2.380  C18  85A 18 
85A N19  N19  N  0 1 Y N N -3.481 11.744 1.220  -8.163 -5.406 3.495  N19  85A 19 
85A C20  C20  C  0 1 Y N N -2.392 12.505 1.629  -7.459 -4.389 4.036  C20  85A 20 
85A O21  O21  O  0 1 N N N 1.239  12.808 -3.394 -2.234 -3.910 0.940  O21  85A 21 
85A C22  C22  C  0 1 N N N 1.366  11.556 -4.042 -1.221 -4.677 0.282  C22  85A 22 
85A C23  C23  C  0 1 N N N -1.542 10.089 -4.405 -3.967 -6.101 -0.553 C23  85A 23 
85A C24  C24  C  0 1 N N N -1.753 10.165 -2.868 -4.651 -6.495 0.751  C24  85A 24 
85A O25  O25  O  0 1 N N N -2.535 11.310 -2.483 -6.023 -6.091 0.677  O25  85A 25 
85A C26  C26  C  0 1 N N N 0.505  11.527 -5.319 -1.541 -6.169 0.373  C26  85A 26 
85A C27  C27  C  0 1 N N N -0.781 11.447 -4.463 -2.548 -6.653 -0.677 C27  85A 27 
85A C28  C28  C  0 1 N N N 5.861  15.651 -5.076 1.099  -0.574 -1.087 C28  85A 28 
85A C29  C29  C  0 1 Y N N 7.257  16.121 -5.370 2.142  0.327  -1.684 C29  85A 29 
85A C30  C30  C  0 1 Y N N 7.981  15.603 -6.474 1.870  1.012  -2.856 C30  85A 30 
85A C31  C31  C  0 1 Y N N 9.295  16.075 -6.709 2.865  1.829  -3.366 C31  85A 31 
85A N32  N32  N  0 1 Y N N 9.894  17.013 -5.909 4.077  1.996  -2.791 N32  85A 32 
85A C33  C33  C  0 1 Y N N 9.191  17.508 -4.848 4.298  1.308  -1.648 C33  85A 33 
85A C34  C34  C  0 1 Y N N 7.875  17.091 -4.543 3.370  0.466  -1.058 C34  85A 34 
85A H20  H20  H  0 1 N N N -2.327 12.821 2.660  -7.895 -3.959 4.932  H20  85A 35 
85A H13  H13  H  0 1 N N N -0.429 14.061 2.021  -6.145 -2.477 4.962  H13  85A 36 
85A H11  H11  H  0 1 N N N 0.646  12.859 -1.077 -3.985 -3.505 2.368  H11  85A 37 
85A H4   H4   H  0 1 N N N 3.657  14.780 0.073  -3.212 0.136  2.792  H4   85A 38 
85A H1   H1   H  0 1 N N N 3.624  13.494 -4.815 -0.336 -2.382 -0.348 H1   85A 39 
85A H221 1H22 H  0 0 N N N 2.420  11.393 -4.312 -0.260 -4.509 0.785  H221 85A 40 
85A H222 2H22 H  0 0 N N N 1.024  10.763 -3.361 -1.142 -4.384 -0.771 H222 85A 41 
85A H261 1H26 H  0 0 N N N 0.594  12.395 -5.989 -1.887 -6.424 1.380  H261 85A 42 
85A H262 2H26 H  0 0 N N N 0.697  10.770 -6.093 -0.610 -6.724 0.204  H262 85A 43 
85A H271 1H27 H  0 0 N N N -1.483 12.185 -4.879 -2.166 -6.408 -1.676 H271 85A 44 
85A H272 2H27 H  0 0 N N N -0.440 11.619 -3.431 -2.593 -7.748 -0.630 H272 85A 45 
85A H231 1H23 H  0 0 N N N -2.464 10.043 -5.003 -3.976 -5.011 -0.664 H231 85A 46 
85A H232 2H23 H  0 0 N N N -1.049 9.197  -4.820 -4.564 -6.478 -1.393 H232 85A 47 
85A H241 1H24 H  0 0 N N N -2.279 9.256  -2.541 -4.639 -7.585 0.867  H241 85A 48 
85A H242 2H24 H  0 0 N N N -0.764 10.254 -2.394 -4.120 -6.067 1.609  H242 85A 49 
85A HN7  HN7  H  0 1 N N N 6.534  15.076 -3.348 0.376  1.104  -0.012 HN7  85A 50 
85A H281 1H28 H  0 0 N N N 5.454  15.158 -5.971 0.466  -1.003 -1.871 H281 85A 51 
85A H282 2H28 H  0 0 N N N 5.248  16.522 -4.800 1.561  -1.408 -0.549 H282 85A 52 
85A H34  H34  H  0 1 N N N 7.350  17.505 -3.695 3.607  -0.060 -0.139 H34  85A 53 
85A H33  H33  H  0 1 N N N 9.659  18.248 -4.216 5.277  1.456  -1.203 H33  85A 54 
85A H31  H31  H  0 1 N N N 9.846  15.681 -7.550 2.708  2.390  -4.282 H31  85A 55 
85A H30  H30  H  0 1 N N N 7.538  14.862 -7.123 0.916  0.920  -3.365 H30  85A 56 
# 
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 
85A C1  C6   DOUB Y N 1  
85A C1  C2   SING Y N 2  
85A C1  H1   SING N N 3  
85A C2  C3   DOUB Y N 4  
85A C2  O21  SING N N 5  
85A C3  N11  SING N N 6  
85A C3  C4   SING Y N 7  
85A C4  C5   DOUB Y N 8  
85A C4  H4   SING N N 9  
85A C5  CL8  SING N N 10 
85A C5  C6   SING Y N 11 
85A C6  N7   SING N N 12 
85A N7  C28  SING N N 13 
85A N7  HN7  SING N N 14 
85A C9  N10  TRIP N N 15 
85A C9  C18  SING N N 16 
85A N11 C12  SING N N 17 
85A N11 H11  SING N N 18 
85A C12 N13  SING N N 19 
85A C12 O14  DOUB N N 20 
85A N13 C15  SING N N 21 
85A N13 H13  SING N N 22 
85A C15 C20  DOUB Y N 23 
85A C15 N16  SING Y N 24 
85A N16 C17  DOUB Y N 25 
85A C17 O25  SING N N 26 
85A C17 C18  SING Y N 27 
85A C18 N19  DOUB Y N 28 
85A N19 C20  SING Y N 29 
85A C20 H20  SING N N 30 
85A O21 C22  SING N N 31 
85A C22 C26  SING N N 32 
85A C22 H221 SING N N 33 
85A C22 H222 SING N N 34 
85A C23 C27  SING N N 35 
85A C23 C24  SING N N 36 
85A C23 H231 SING N N 37 
85A C23 H232 SING N N 38 
85A C24 O25  SING N N 39 
85A C24 H241 SING N N 40 
85A C24 H242 SING N N 41 
85A C26 C27  SING N N 42 
85A C26 H261 SING N N 43 
85A C26 H262 SING N N 44 
85A C27 H271 SING N N 45 
85A C27 H272 SING N N 46 
85A C28 C29  SING N N 47 
85A C28 H281 SING N N 48 
85A C28 H282 SING N N 49 
85A C29 C34  DOUB Y N 50 
85A C29 C30  SING Y N 51 
85A C30 C31  DOUB Y N 52 
85A C30 H30  SING N N 53 
85A C31 N32  SING Y N 54 
85A C31 H31  SING N N 55 
85A N32 C33  DOUB Y N 56 
85A C33 C34  SING Y N 57 
85A C33 H33  SING N N 58 
85A C34 H34  SING N N 59 
# 
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 
85A SMILES           ACDLabs              10.04 Clc4cc2c(OCCCCCOc1nc(cnc1C#N)NC(=O)N2)cc4NCc3ccncc3                                                                                                                                      
85A InChI            InChI                1.02b InChI=1/C23H22ClN7O3/c24-16-10-18-20(11-17(16)27-13-15-4-6-26-7-5-15)33-8-2-1-3-9-34-22-19(12-25)28-14-21(30-22)31-23(32)29-18/h4-7,10-11,14,27H,1-3,8-9,13H2,(H2,29,30,31,32)/f/h29,31H 
85A InChIKey         InChI                1.02b ZUEAHWHCYOLVEP-SCXYCHFOCW                                                                                                                                                                
85A SMILES_CANONICAL CACTVS               3.341 Clc1cc2NC(=O)Nc3cnc(C#N)c(OCCCCCOc2cc1NCc4ccncc4)n3                                                                                                                                      
85A SMILES           CACTVS               3.341 Clc1cc2NC(=O)Nc3cnc(C#N)c(OCCCCCOc2cc1NCc4ccncc4)n3                                                                                                                                      
85A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cnccc1CNc2cc3c(cc2Cl)NC(=O)Nc4cnc(c(n4)OCCCCCO3)C#N                                                                                                                                    
85A SMILES           "OpenEye OEToolkits" 1.5.0 c1cnccc1CNc2cc3c(cc2Cl)NC(=O)Nc4cnc(c(n4)OCCCCCO3)C#N                                                                                                                                    
# 
_pdbx_chem_comp_identifier.comp_id           85A 
_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        18-chloro-2-oxo-17-[(pyridin-4-ylmethyl)amino]-2,3,11,12,13,14-hexahydro-1H,10H-4,8-(azeno)-9,15,1,3,6-benzodioxatriazacycloheptadecine-7-carbonitrile 
# 
