data_5CB
# 
_chem_comp.id                                    5CB 
_chem_comp.name                                  N-(5-CHLORO-BENZO[B]THIOPHEN-3-YLMETHYL)-2-[6-CHLORO-OXO-3-(2-PYRIDIN-2-YL-ETHYLAMINO)-2H-PYRAZIN-1-YL]-ACETAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H23 Cl2 N5 O2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-07-04 
_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                        492.421 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5CB 
_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        2BVX 
_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 
5CB O1   O1   O  0 1 N N N 12.211 -13.561 12.593 1.435  0.970  0.289  O1   5CB 1  
5CB CL2  CL2  CL 0 0 N N N 16.350 -8.057  10.951 -6.928 -2.467 1.370  CL2  5CB 2  
5CB CL3  CL3  CL 0 0 N N N 8.496  -13.097 16.031 0.235  -3.730 -1.087 CL3  5CB 3  
5CB C4   C4   C  0 1 Y N N 17.738 -10.405 10.966 -7.907 -0.290 0.102  C4   5CB 4  
5CB C5   C5   C  0 1 Y N N 18.088 -11.672 11.501 -7.805 0.976  -0.438 C5   5CB 5  
5CB C6   C6   C  0 1 Y N N 16.762 -9.593  11.621 -6.794 -0.874 0.694  C6   5CB 6  
5CB C7   C7   C  0 1 Y N N 17.445 -12.095 12.687 -6.602 1.646  -0.383 C7   5CB 7  
5CB C8   C8   C  0 1 Y N N 16.130 -10.039 12.815 -5.592 -0.218 0.754  C8   5CB 8  
5CB C9   C9   C  0 1 Y N N 16.481 -11.307 13.346 -5.451 1.079  0.205  C9   5CB 9  
5CB S10  S10  S  0 1 Y N N 17.639 -13.455 13.498 -6.047 3.238  -0.936 S10  5CB 10 
5CB C11  C11  C  0 1 Y N N 16.587 -13.179 14.679 -4.352 3.143  -0.392 C11  5CB 11 
5CB C12  C12  C  0 1 Y N N 15.989 -11.937 14.501 -4.272 1.932  0.177  C12  5CB 12 
5CB C13  C13  C  0 1 N N N 14.945 -11.358 15.451 -2.973 1.455  0.775  C13  5CB 13 
5CB N14  N14  N  0 1 N N N 13.562 -11.383 14.928 -2.303 0.556  -0.167 N14  5CB 14 
5CB C15  C15  C  0 1 N N N 12.508 -12.195 15.366 -1.116 0.004  0.157  C15  5CB 15 
5CB C16  C16  C  0 1 N N N 11.141 -12.067 14.698 -0.427 -0.922 -0.812 C16  5CB 16 
5CB C17  C17  C  0 1 N N R 9.319  -13.869 14.716 1.412  -2.365 -1.128 C17  5CB 17 
5CB N18  N18  N  0 1 N N N 10.530 -13.327 14.171 0.910  -1.255 -0.303 N18  5CB 18 
5CB C19  C19  C  0 1 N N N 8.790  -15.017 14.208 2.758  -2.826 -0.565 C19  5CB 19 
5CB C20  C20  C  0 1 N N S 11.177 -13.997 13.082 1.771  -0.103 -0.592 C20  5CB 20 
5CB N21  N21  N  0 1 N N N 9.464  -15.729 13.064 3.642  -1.675 -0.395 N21  5CB 21 
5CB C22  C22  C  0 1 N N N 10.585 -15.260 12.533 3.215  -0.467 -0.403 C22  5CB 22 
5CB N23  N23  N  0 1 N N N 11.208 -15.920 11.471 4.123  0.545  -0.232 N23  5CB 23 
5CB C24  C24  C  0 1 N N N 10.594 -16.793 10.446 5.542  0.232  -0.046 C24  5CB 24 
5CB C25  C25  C  0 1 N N N 9.954  -15.943 9.326  6.333  1.531  0.122  C25  5CB 25 
5CB C26  C26  C  0 1 Y N N 7.459  -16.136 9.978  8.733  1.778  -0.525 C26  5CB 26 
5CB C27  C27  C  0 1 Y N N 8.565  -15.353 9.592  7.793  1.209  0.313  C27  5CB 27 
5CB C28  C28  C  0 1 Y N N 6.214  -15.511 10.200 10.074 1.476  -0.340 C28  5CB 28 
5CB N29  N29  N  0 1 Y N N 8.388  -13.962 9.439  8.159  0.392  1.282  N29  5CB 29 
5CB C30  C30  C  0 1 Y N N 6.048  -14.117 10.043 10.419 0.609  0.686  C30  5CB 30 
5CB C31  C31  C  0 1 Y N N 7.144  -13.335 9.659  9.424  0.078  1.483  C31  5CB 31 
5CB O32  O32  O  0 1 N N N 12.667 -12.997 16.266 -0.604 0.252  1.227  O32  5CB 32 
5CB H1   H1   H  0 1 N N N 12.096 -13.448 11.657 2.016  1.709  0.063  H1   5CB 33 
5CB H4   H4   H  0 1 N N N 18.211 -10.054 10.061 -8.846 -0.824 0.065  H4   5CB 34 
5CB H5   H5   H  0 1 N N N 18.825 -12.295 11.016 -8.664 1.440  -0.900 H5   5CB 35 
5CB H8   H8   H  0 1 N N N 15.394 -9.422  13.310 -4.744 -0.697 1.220  H8   5CB 36 
5CB H11  H11  H  0 1 N N N 16.375 -13.858 15.492 -3.574 3.885  -0.496 H11  5CB 37 
5CB H131 1H13 H  0 0 N N N 15.207 -10.300 15.603 -3.175 0.924  1.705  H131 5CB 38 
5CB H132 2H13 H  0 0 N N N 14.966 -11.951 16.377 -2.331 2.312  0.979  H132 5CB 39 
5CB H14  H14  H  0 1 N N N 13.357 -10.751 14.180 -2.713 0.357  -1.023 H14  5CB 40 
5CB H161 1H16 H  0 0 N N N 11.304 -11.429 13.817 -0.334 -0.430 -1.781 H161 5CB 41 
5CB H162 2H16 H  0 0 N N N 10.449 -11.662 15.451 -1.012 -1.835 -0.922 H162 5CB 42 
5CB H117 17H1 H  0 0 N N N 10.082 -13.093 14.474 1.543  -2.026 -2.156 H117 5CB 43 
5CB H19  H19  H  0 1 N N N 7.732  -14.816 13.920 3.215  -3.536 -1.254 H19  5CB 44 
5CB H191 1H19 H  0 0 N N N 8.662  -15.743 15.045 2.601  -3.308 0.400  H191 5CB 45 
5CB H220 20H2 H  0 0 N N N 11.274 -12.935 13.408 1.612  0.215  -1.623 H220 5CB 46 
5CB H23  H23  H  0 1 N N N 11.611 -15.177 10.936 3.826  1.469  -0.233 H23  5CB 47 
5CB H241 1H24 H  0 0 N N N 9.813  -17.405 10.920 5.664  -0.385 0.844  H241 5CB 48 
5CB H242 2H24 H  0 0 N N N 11.371 -17.439 10.010 5.912  -0.309 -0.917 H242 5CB 49 
5CB H251 1H25 H  0 0 N N N 9.812  -16.639 8.486  6.211  2.148  -0.768 H251 5CB 50 
5CB H252 2H25 H  0 0 N N N 10.631 -15.096 9.141  5.963  2.072  0.993  H252 5CB 51 
5CB H26  H26  H  0 1 N N N 7.563  -17.204 10.103 8.428  2.449  -1.314 H26  5CB 52 
5CB H28  H28  H  0 1 N N N 5.368  -16.113 10.497 10.831 1.905  -0.979 H28  5CB 53 
5CB H30  H30  H  0 1 N N N 5.086  -13.659 10.217 11.454 0.351  0.858  H30  5CB 54 
5CB H31  H31  H  0 1 N N N 7.038  -12.268 9.533  9.684  -0.598 2.284  H31  5CB 55 
# 
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 
5CB O1  C20  SING N N 1  
5CB O1  H1   SING N N 2  
5CB CL2 C6   SING N N 3  
5CB CL3 C17  SING N N 4  
5CB C4  C5   SING Y N 5  
5CB C4  C6   DOUB Y N 6  
5CB C4  H4   SING N N 7  
5CB C5  C7   DOUB Y N 8  
5CB C5  H5   SING N N 9  
5CB C6  C8   SING Y N 10 
5CB C7  C9   SING Y N 11 
5CB C7  S10  SING Y N 12 
5CB C8  C9   DOUB Y N 13 
5CB C8  H8   SING N N 14 
5CB C9  C12  SING Y N 15 
5CB S10 C11  SING Y N 16 
5CB C11 C12  DOUB Y N 17 
5CB C11 H11  SING N N 18 
5CB C12 C13  SING N N 19 
5CB C13 N14  SING N N 20 
5CB C13 H131 SING N N 21 
5CB C13 H132 SING N N 22 
5CB N14 C15  SING N N 23 
5CB N14 H14  SING N N 24 
5CB C15 C16  SING N N 25 
5CB C15 O32  DOUB N N 26 
5CB C16 N18  SING N N 27 
5CB C16 H161 SING N N 28 
5CB C16 H162 SING N N 29 
5CB C17 N18  SING N N 30 
5CB C17 C19  SING N N 31 
5CB C17 H117 SING N N 32 
5CB N18 C20  SING N N 33 
5CB C19 N21  SING N N 34 
5CB C19 H19  SING N N 35 
5CB C19 H191 SING N N 36 
5CB C20 C22  SING N N 37 
5CB C20 H220 SING N N 38 
5CB N21 C22  DOUB N N 39 
5CB C22 N23  SING N N 40 
5CB N23 C24  SING N N 41 
5CB N23 H23  SING N N 42 
5CB C24 C25  SING N N 43 
5CB C24 H241 SING N N 44 
5CB C24 H242 SING N N 45 
5CB C25 C27  SING N N 46 
5CB C25 H251 SING N N 47 
5CB C25 H252 SING N N 48 
5CB C26 C27  SING Y N 49 
5CB C26 C28  DOUB Y N 50 
5CB C26 H26  SING N N 51 
5CB C27 N29  DOUB Y N 52 
5CB C28 C30  SING Y N 53 
5CB C28 H28  SING N N 54 
5CB N29 C31  SING Y N 55 
5CB C30 C31  DOUB Y N 56 
5CB C30 H30  SING N N 57 
5CB C31 H31  SING N N 58 
# 
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 
5CB SMILES           ACDLabs              10.04 ClC1N(C(O)C(=NC1)NCCc2ncccc2)CC(=O)NCc3c4cc(Cl)ccc4sc3                                                                                                                                                   
5CB InChI            InChI                1.02b InChI=1/C22H23Cl2N5O2S/c23-15-4-5-18-17(9-15)14(13-32-18)10-27-20(30)12-29-19(24)11-28-21(22(29)31)26-8-6-16-3-1-2-7-25-16/h1-5,7,9,13,19,22,31H,6,8,10-12H2,(H,26,28)(H,27,30)/t19-,22-/m0/s1/f/h26-27H 
5CB InChIKey         InChI                1.02b SOBGXPPOYFFGTK-VHNWYSIIDS                                                                                                                                                                                
5CB SMILES_CANONICAL CACTVS               3.341 O[C@@H]1N(CC(=O)NCc2csc3ccc(Cl)cc23)[C@H](Cl)CN=C1NCCc4ccccn4                                                                                                                                            
5CB SMILES           CACTVS               3.341 O[CH]1N(CC(=O)NCc2csc3ccc(Cl)cc23)[CH](Cl)CN=C1NCCc4ccccn4                                                                                                                                               
5CB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccnc(c1)CCNC2=NCC(N(C2O)CC(=O)NCc3csc4c3cc(cc4)Cl)Cl                                                                                                                                                   
5CB SMILES           "OpenEye OEToolkits" 1.5.0 c1ccnc(c1)CCNC2=NCC(N(C2O)CC(=O)NCc3csc4c3cc(cc4)Cl)Cl                                                                                                                                                   
# 
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 
5CB "SYSTEMATIC NAME" ACDLabs              10.04 N-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-[(2R,6S)-2-chloro-6-hydroxy-5-[(2-pyridin-2-ylethyl)amino]-3,6-dihydropyrazin-1(2H)-yl]acetamide 
5CB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(5-chloro-1-benzothiophen-3-yl)methyl]-2-[6-chloro-2-hydroxy-3-(2-pyridin-2-ylethylamino)-5,6-dihydro-2H-pyrazin-1-yl]ethanamide          
# 
