data_C2D
# 
_chem_comp.id                                    C2D 
_chem_comp.name                                  6-CHLORO-1-(2-{[(5-CHLORO-1-BENZOTHIEN-3-YL)METHYL]AMINO}ETHYL)-3-[(2-PYRIDIN-2-YLETHYL)AMINO]-1,4-DIHYDROPYRAZIN-2-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H31 Cl2 N5 O S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-07-27 
_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                        484.485 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     C2D 
_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        2BXT 
_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 
C2D O1   O1   O  0 1 N N N 12.172 -13.121 13.027 2.336 1.312  -3.641 O1   C2D 1  
C2D CL2  CL2  CL 0 0 N N N 16.423 -8.334  11.004 2.457 6.927  1.555  CL2  C2D 2  
C2D CL3  CL3  CL 0 0 N N N 8.138  -12.637 15.979 4.811 1.160  -7.701 CL3  C2D 3  
C2D C4   C4   C  0 1 Y N N 17.740 -10.733 11.480 4.295 8.741  0.779  C4   C2D 4  
C2D C5   C5   C  0 1 Y N N 17.906 -11.974 12.189 5.417 9.169  0.067  C5   C2D 5  
C2D C6   C6   C  0 1 Y N N 16.674 -9.836  11.828 3.841 7.435  0.666  C6   C2D 6  
C2D C7   C7   C  0 1 Y N N 16.991 -12.303 13.235 6.083 8.252  -0.770 C7   C2D 7  
C2D C8   C8   C  0 1 Y N N 15.781 -10.180 12.868 4.504 6.527  -0.164 C8   C2D 8  
C2D C9   C9   C  0 1 Y N N 15.953 -11.411 13.556 5.645 6.930  -0.900 C9   C2D 9  
C2D S10  S10  S  0 1 Y N N 16.895 -13.627 14.204 7.478 8.549  -1.738 S10  C2D 10 
C2D C11  C11  C  0 1 Y N N 15.610 -13.112 15.026 7.504 6.949  -2.324 C11  C2D 11 
C2D C12  C12  C  0 1 Y N N 15.154 -11.870 14.581 6.483 6.209  -1.800 C12  C2D 12 
C2D C13  C13  C  0 1 N N N 13.972 -11.057 15.070 6.273 4.764  -2.150 C13  C2D 13 
C2D N14  N14  N  0 1 N N N 13.267 -11.618 16.240 5.399 4.604  -3.313 N14  C2D 14 
C2D C15  C15  C  0 1 N N N 11.917 -12.265 16.135 5.231 3.220  -3.663 C15  C2D 15 
C2D C16  C16  C  0 1 N N N 10.932 -11.761 15.044 4.343 3.045  -4.884 C16  C2D 16 
C2D C17  C17  C  0 1 N N S 9.020  -13.419 14.713 3.491 1.459  -6.519 C17  C2D 17 
C2D N18  N18  N  0 1 N N N 10.315 -12.920 14.347 4.153 1.641  -5.230 N18  C2D 18 
C2D C19  C19  C  0 1 N N N 8.490  -14.480 14.063 2.501 0.293  -6.567 C19  C2D 19 
C2D C20  C20  C  0 1 N N R 11.060 -13.540 13.328 3.587 0.861  -4.133 C20  C2D 20 
C2D N21  N21  N  0 1 N N N 9.266  -15.155 12.964 2.952 -0.858 -5.781 N21  C2D 21 
C2D C22  C22  C  0 1 N N N 10.470 -14.721 12.617 3.451 -0.580 -4.616 C22  C2D 22 
C2D N23  N23  N  0 1 N N N 11.194 -15.327 11.605 3.878 -1.556 -3.750 N23  C2D 23 
C2D C24  C24  C  0 1 N N N 10.861 -16.497 10.746 3.791 -2.938 -4.117 C24  C2D 24 
C2D C25  C25  C  0 1 N N N 10.125 -16.074 9.449  4.295 -3.864 -3.016 C25  C2D 25 
C2D C26  C26  C  0 1 N N N 7.709  -16.151 10.264 4.053 -4.672 -0.644 C26  C2D 26 
C2D C27  C27  C  0 1 N N R 8.797  -15.426 9.758  3.494 -3.733 -1.722 C27  C2D 27 
C2D C28  C28  C  0 1 N N N 6.504  -15.472 10.552 3.216 -4.613 0.630  C28  C2D 28 
C2D N29  N29  N  0 1 N N N 8.657  -14.042 9.563  2.084 -4.038 -1.996 N29  C2D 29 
C2D C30  C30  C  0 1 N N N 6.375  -14.091 10.341 1.743 -4.846 0.314  C30  C2D 30 
C2D C31  C31  C  0 1 N N N 7.462  -13.367 9.837  1.260 -3.913 -0.794 C31  C2D 31 
C2D H1   H1   H  0 1 N N N 12.226 -13.013 12.085 2.172 0.834  -2.812 H1   C2D 32 
C2D H4   H4   H  0 1 N N N 18.421 -10.475 10.682 3.783 9.452  1.423  H4   C2D 33 
C2D H5   H5   H  0 1 N N N 18.711 -12.647 11.934 5.765 10.193 0.161  H5   C2D 34 
C2D H8   H8   H  0 1 N N N 14.975 -9.513  13.137 4.146 5.503  -0.249 H8   C2D 35 
C2D H11  H11  H  0 1 N N N 15.152 -13.666 15.832 8.268 6.638  -3.024 H11  C2D 36 
C2D H131 1H13 H  0 0 N N N 13.243 -11.044 14.246 7.228 4.279  -2.377 H131 C2D 37 
C2D H132 2H13 H  0 0 N N N 14.346 -10.062 15.352 5.822 4.219  -1.315 H132 C2D 38 
C2D H14  H14  H  0 1 N N N 13.873 -12.328 16.599 4.490 5.027  -3.094 H14  C2D 39 
C2D H151 1H15 H  0 0 N N N 11.421 -12.019 17.086 4.785 2.721  -2.797 H151 C2D 40 
C2D H152 2H15 H  0 0 N N N 12.096 -13.330 15.927 6.227 2.799  -3.831 H152 C2D 41 
C2D H161 1H16 H  0 0 N N N 11.482 -11.149 14.314 4.768 3.544  -5.761 H161 C2D 42 
C2D H162 2H16 H  0 0 N N N 10.143 -11.157 15.516 3.351 3.465  -4.691 H162 C2D 43 
C2D H117 17H1 H  0 0 N N N 8.984  -14.501 14.978 2.977 2.367  -6.854 H117 C2D 44 
C2D H19  H19  H  0 1 N N N 8.206  -15.250 14.818 1.526 0.615  -6.177 H19  C2D 45 
C2D H191 1H19 H  0 0 N N N 7.493  -14.184 13.660 2.323 -0.030 -7.599 H191 C2D 46 
C2D H220 20H2 H  0 0 N N N 12.084 -13.225 13.019 4.288 0.875  -3.290 H220 C2D 47 
C2D H23  H23  H  0 1 N N N 11.315 -14.588 10.942 4.240 -1.247 -2.883 H23  C2D 48 
C2D H241 1H24 H  0 0 N N N 10.194 -17.160 11.316 4.395 -3.068 -5.020 H241 C2D 49 
C2D H242 2H24 H  0 0 N N N 11.795 -17.007 10.470 2.748 -3.153 -4.370 H242 C2D 50 
C2D H251 1H25 H  0 0 N N N 9.941  -16.974 8.844  4.227 -4.900 -3.366 H251 C2D 51 
C2D H252 2H25 H  0 0 N N N 10.753 -15.355 8.902  5.352 -3.660 -2.807 H252 C2D 52 
C2D H26  H26  H  0 1 N N N 8.038  -16.700 11.177 5.090 -4.400 -0.413 H26  C2D 53 
C2D H261 1H26 H  0 0 N N N 7.487  -16.995 9.570  4.072 -5.704 -1.018 H261 C2D 54 
C2D H227 27H2 H  0 0 N N N 8.694  -16.439 9.304  3.578 -2.693 -1.384 H227 C2D 55 
C2D H28  H28  H  0 1 N N N 6.235  -15.684 11.613 3.338 -3.631 1.104  H28  C2D 56 
C2D H281 1H28 H  0 0 N N N 5.681  -15.982 9.999  3.569 -5.363 1.346  H281 C2D 57 
C2D H30  H30  H  0 1 N N N 5.493  -13.912 9.683  1.596 -5.890 0.007  H30  C2D 58 
C2D H301 1H30 H  0 0 N N N 6.041  -13.615 11.292 1.142 -4.691 1.217  H301 C2D 59 
C2D H31  H31  H  0 1 N N N 7.679  -12.518 10.526 0.222 -4.155 -1.049 H31  C2D 60 
C2D H311 1H31 H  0 0 N N N 7.137  -12.824 8.919  1.263 -2.873 -0.446 H311 C2D 61 
C2D HN1  HN1  H  0 1 N N N 9.343  -13.619 10.155 2.011 -4.992 -2.353 HN1  C2D 62 
# 
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 
C2D O1  C20  SING N N 1  
C2D O1  H1   SING N N 2  
C2D CL2 C6   SING N N 3  
C2D CL3 C17  SING N N 4  
C2D C4  C5   SING Y N 5  
C2D C4  C6   DOUB Y N 6  
C2D C4  H4   SING N N 7  
C2D C5  C7   DOUB Y N 8  
C2D C5  H5   SING N N 9  
C2D C6  C8   SING Y N 10 
C2D C7  C9   SING Y N 11 
C2D C7  S10  SING Y N 12 
C2D C8  C9   DOUB Y N 13 
C2D C8  H8   SING N N 14 
C2D C9  C12  SING Y N 15 
C2D S10 C11  SING Y N 16 
C2D C11 C12  DOUB Y N 17 
C2D C11 H11  SING N N 18 
C2D C12 C13  SING N N 19 
C2D C13 N14  SING N N 20 
C2D C13 H131 SING N N 21 
C2D C13 H132 SING N N 22 
C2D N14 C15  SING N N 23 
C2D N14 H14  SING N N 24 
C2D C15 C16  SING N N 25 
C2D C15 H151 SING N N 26 
C2D C15 H152 SING N N 27 
C2D C16 N18  SING N N 28 
C2D C16 H161 SING N N 29 
C2D C16 H162 SING N N 30 
C2D C17 N18  SING N N 31 
C2D C17 C19  SING N N 32 
C2D C17 H117 SING N N 33 
C2D N18 C20  SING N N 34 
C2D C19 N21  SING N N 35 
C2D C19 H19  SING N N 36 
C2D C19 H191 SING N N 37 
C2D C20 C22  SING N N 38 
C2D C20 H220 SING N N 39 
C2D N21 C22  DOUB N N 40 
C2D C22 N23  SING N N 41 
C2D N23 C24  SING N N 42 
C2D N23 H23  SING N N 43 
C2D C24 C25  SING N N 44 
C2D C24 H241 SING N N 45 
C2D C24 H242 SING N N 46 
C2D C25 C27  SING N N 47 
C2D C25 H251 SING N N 48 
C2D C25 H252 SING N N 49 
C2D C26 C27  SING N N 50 
C2D C26 C28  SING N N 51 
C2D C26 H26  SING N N 52 
C2D C26 H261 SING N N 53 
C2D C27 N29  SING N N 54 
C2D C27 H227 SING N N 55 
C2D C28 C30  SING N N 56 
C2D C28 H28  SING N N 57 
C2D C28 H281 SING N N 58 
C2D N29 C31  SING N N 59 
C2D C30 C31  SING N N 60 
C2D C30 H30  SING N N 61 
C2D C30 H301 SING N N 62 
C2D C31 H31  SING N N 63 
C2D C31 H311 SING N N 64 
C2D HN1 N29  SING N N 65 
# 
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 
C2D SMILES           ACDLabs              10.04 ClC1N(C(O)C(=NC1)NCCC2NCCCC2)CCNCc3c4cc(Cl)ccc4sc3                                                                                                                                                        
C2D InChI            InChI                1.02b InChI=1/C22H31Cl2N5OS/c23-16-4-5-19-18(11-16)15(14-31-19)12-25-9-10-29-20(24)13-28-21(22(29)30)27-8-6-17-3-1-2-7-26-17/h4-5,11,14,17,20,22,25-26,30H,1-3,6-10,12-13H2,(H,27,28)/t17-,20-,22?/m1/s1/f/h27H 
C2D InChIKey         InChI                1.02b YHTGPUXGIBWHPN-JUDOIHQGDT                                                                                                                                                                                 
C2D SMILES_CANONICAL CACTVS               3.341 O[C@H]1N(CCNCc2csc3ccc(Cl)cc23)[C@@H](Cl)CN=C1NCC[C@H]4CCCCN4                                                                                                                                             
C2D SMILES           CACTVS               3.341 O[CH]1N(CCNCc2csc3ccc(Cl)cc23)[CH](Cl)CN=C1NCC[CH]4CCCCN4                                                                                                                                                 
C2D SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)c(cs2)CNCCN3C(CN=C(C3O)NCCC4CCCCN4)Cl                                                                                                                                                        
C2D SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1Cl)c(cs2)CNCCN3C(CN=C(C3O)NCCC4CCCCN4)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 
C2D "SYSTEMATIC NAME" ACDLabs              10.04 (2R,6S)-6-chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2R)-piperidin-2-yl]ethyl}amino)-1,2,5,6-tetrahydropyrazin-2-ol 
C2D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-chloro-1-[2-[(5-chloro-1-benzothiophen-3-yl)methylamino]ethyl]-3-(2-piperidin-2-ylethylamino)-5,6-dihydro-2H-pyrazin-2-ol                       
# 
