data_2D9
# 
_chem_comp.id                                    2D9 
_chem_comp.name                                  4-CHLORO-6-(4-{4-[4-(METHYLSULFONYL)BENZYL]PIPERAZIN-1-YL}-1H-PYRAZOL-5-YL)BENZENE-1,3-DIOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H23 Cl N4 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-18 
_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                        462.950 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     2D9 
_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        2CCU 
_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 
2D9 C31  C31  C  0 1 N N N 30.325 3.080  18.589 8.482  1.280  0.588  C31  2D9 1  
2D9 S28  S28  S  0 1 N N N 32.102 2.840  18.483 7.533  -0.186 0.096  S28  2D9 2  
2D9 O29  O29  O  0 1 N N N 32.181 1.358  18.705 7.451  -1.134 1.150  O29  2D9 3  
2D9 O30  O30  O  0 1 N N N 32.415 3.223  17.048 7.816  -0.568 -1.243 O30  2D9 4  
2D9 C25  C25  C  0 1 Y N N 33.055 3.753  19.776 5.882  0.422  -0.012 C25  2D9 5  
2D9 C26  C26  C  0 1 Y N N 33.742 4.972  19.582 5.411  0.934  -1.207 C26  2D9 6  
2D9 C27  C27  C  0 1 Y N N 34.435 5.607  20.651 4.116  1.410  -1.292 C27  2D9 7  
2D9 C24  C24  C  0 1 Y N N 33.120 3.208  21.065 5.057  0.383  1.096  C24  2D9 8  
2D9 C23  C23  C  0 1 Y N N 33.807 3.836  22.124 3.764  0.863  1.012  C23  2D9 9  
2D9 C19  C19  C  0 1 Y N N 34.463 5.056  21.951 3.293  1.376  -0.182 C19  2D9 10 
2D9 C18  C18  C  0 1 N N N 35.222 5.690  23.169 1.881  1.896  -0.274 C18  2D9 11 
2D9 N15  N15  N  0 1 N N N 34.447 6.608  24.087 0.982  0.804  -0.671 N15  2D9 12 
2D9 C16  C16  C  0 1 N N N 33.108 7.014  23.563 -0.388 1.306  -0.507 C16  2D9 13 
2D9 C17  C17  C  0 1 N N N 31.984 6.951  24.611 -1.384 0.180  -0.786 C17  2D9 14 
2D9 C14  C14  C  0 1 N N N 34.460 6.097  25.499 1.163  -0.270 0.314  C14  2D9 15 
2D9 C13  C13  C  0 1 N N N 33.637 6.940  26.524 0.166  -1.396 0.035  C13  2D9 16 
2D9 N12  N12  N  0 1 N N N 32.358 7.414  25.951 -1.204 -0.894 0.198  N12  2D9 17 
2D9 C3   C3   C  0 1 Y N N 31.504 8.257  26.703 -2.064 -1.938 -0.181 C3   2D9 18 
2D9 C2   C2   C  0 1 Y N N 31.169 7.902  27.924 -1.678 -3.208 -0.625 C2   2D9 19 
2D9 N1   N1   N  0 1 Y N N 30.376 8.875  28.398 -2.754 -3.907 -0.885 N1   2D9 20 
2D9 N5   N5   N  0 1 Y N N 30.170 9.795  27.577 -3.881 -3.119 -0.620 N5   2D9 21 
2D9 C4   C4   C  0 1 Y N N 30.858 9.543  26.463 -3.445 -1.900 -0.178 C4   2D9 22 
2D9 C6   C6   C  0 1 Y N N 30.897 10.370 25.302 -4.291 -0.755 0.218  C6   2D9 23 
2D9 C7   C7   C  0 1 Y N N 32.104 10.816 24.805 -5.084 -0.109 -0.731 C7   2D9 24 
2D9 C8   C8   C  0 1 Y N N 32.180 11.620 23.654 -5.873 0.960  -0.358 C8   2D9 25 
2D9 CL20 CL20 CL 0 0 N N N 33.764 12.118 23.154 -6.858 1.764  -1.539 CL20 2D9 26 
2D9 C9   C9   C  0 1 Y N N 31.022 12.010 22.921 -5.880 1.394  0.963  C9   2D9 27 
2D9 O21  O21  O  0 1 N N N 31.094 12.788 21.737 -6.660 2.447  1.324  O21  2D9 28 
2D9 C10  C10  C  0 1 Y N N 29.781 11.566 23.459 -5.096 0.757  1.912  C10  2D9 29 
2D9 C11  C11  C  0 1 Y N N 29.743 10.767 24.618 -4.305 -0.319 1.549  C11  2D9 30 
2D9 O22  O22  O  0 1 N N N 28.544 10.348 25.067 -3.536 -0.945 2.478  O22  2D9 31 
2D9 H311 1H31 H  0 0 N N N 29.812 2.239  18.100 8.371  2.056  -0.170 H311 2D9 32 
2D9 H312 2H31 H  0 0 N N N 30.051 4.019  18.086 8.109  1.650  1.543  H312 2D9 33 
2D9 H313 3H31 H  0 0 N N N 30.023 3.129  19.646 9.534  1.015  0.686  H313 2D9 34 
2D9 H26  H26  H  0 1 N N N 33.741 5.431  18.604 6.054  0.961  -2.074 H26  2D9 35 
2D9 H27  H27  H  0 1 N N N 34.954 6.535  20.463 3.748  1.811  -2.225 H27  2D9 36 
2D9 H24  H24  H  0 1 N N N 32.623 2.268  21.255 5.425  -0.018 2.029  H24  2D9 37 
2D9 H23  H23  H  0 1 N N N 33.826 3.361  23.094 3.120  0.836  1.879  H23  2D9 38 
2D9 H181 1H18 H  0 0 N N N 35.993 6.331  22.716 1.574  2.286  0.696  H181 2D9 39 
2D9 H182 2H18 H  0 0 N N N 35.583 4.855  23.787 1.836  2.692  -1.017 H182 2D9 40 
2D9 H161 1H16 H  0 0 N N N 32.845 6.303  22.766 -0.523 1.666  0.513  H161 2D9 41 
2D9 H162 2H16 H  0 0 N N N 33.183 8.052  23.206 -0.560 2.124  -1.206 H162 2D9 42 
2D9 H171 1H17 H  0 0 N N N 31.715 5.889  24.714 -2.400 0.569  -0.716 H171 2D9 43 
2D9 H172 2H17 H  0 0 N N N 31.161 7.588  24.256 -1.216 -0.214 -1.788 H172 2D9 44 
2D9 H141 1H14 H  0 0 N N N 35.507 6.145  25.833 2.179  -0.659 0.244  H141 2D9 45 
2D9 H142 2H14 H  0 0 N N N 34.036 5.082  25.488 0.994  0.124  1.316  H142 2D9 46 
2D9 H131 1H13 H  0 0 N N N 34.235 7.821  26.799 0.339  -2.214 0.734  H131 2D9 47 
2D9 H132 2H13 H  0 0 N N N 33.418 6.312  27.400 0.302  -1.756 -0.985 H132 2D9 48 
2D9 H2   H2   H  0 1 N N N 31.472 7.005  28.443 -0.661 -3.554 -0.734 H2   2D9 49 
2D9 H5   H5   H  0 1 N N N 29.584 10.591 27.731 -4.806 -3.390 -0.728 H5   2D9 50 
2D9 H7   H7   H  0 1 N N N 33.016 10.540 25.314 -5.079 -0.444 -1.758 H7   2D9 51 
2D9 H21  H21  H  0 1 N N N 31.110 13.710 21.964 -7.517 2.084  1.586  H21  2D9 52 
2D9 H10  H10  H  0 1 N N N 28.858 11.845 22.973 -5.105 1.098  2.937  H10  2D9 53 
2D9 H22  H22  H  0 1 N N N 28.576 10.249 26.011 -4.047 -1.699 2.802  H22  2D9 54 
# 
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 
2D9 C31 S28  SING N N 1  
2D9 C31 H311 SING N N 2  
2D9 C31 H312 SING N N 3  
2D9 C31 H313 SING N N 4  
2D9 S28 O29  DOUB N N 5  
2D9 S28 O30  DOUB N N 6  
2D9 S28 C25  SING N N 7  
2D9 C25 C26  DOUB Y N 8  
2D9 C25 C24  SING Y N 9  
2D9 C26 C27  SING Y N 10 
2D9 C26 H26  SING N N 11 
2D9 C27 C19  DOUB Y N 12 
2D9 C27 H27  SING N N 13 
2D9 C24 C23  DOUB Y N 14 
2D9 C24 H24  SING N N 15 
2D9 C23 C19  SING Y N 16 
2D9 C23 H23  SING N N 17 
2D9 C19 C18  SING N N 18 
2D9 C18 N15  SING N N 19 
2D9 C18 H181 SING N N 20 
2D9 C18 H182 SING N N 21 
2D9 N15 C16  SING N N 22 
2D9 N15 C14  SING N N 23 
2D9 C16 C17  SING N N 24 
2D9 C16 H161 SING N N 25 
2D9 C16 H162 SING N N 26 
2D9 C17 N12  SING N N 27 
2D9 C17 H171 SING N N 28 
2D9 C17 H172 SING N N 29 
2D9 C14 C13  SING N N 30 
2D9 C14 H141 SING N N 31 
2D9 C14 H142 SING N N 32 
2D9 C13 N12  SING N N 33 
2D9 C13 H131 SING N N 34 
2D9 C13 H132 SING N N 35 
2D9 N12 C3   SING N N 36 
2D9 C3  C2   SING Y N 37 
2D9 C3  C4   DOUB Y N 38 
2D9 C2  N1   DOUB Y N 39 
2D9 C2  H2   SING N N 40 
2D9 N1  N5   SING Y N 41 
2D9 N5  C4   SING Y N 42 
2D9 N5  H5   SING N N 43 
2D9 C4  C6   SING N N 44 
2D9 C6  C7   DOUB Y N 45 
2D9 C6  C11  SING Y N 46 
2D9 C7  C8   SING Y N 47 
2D9 C7  H7   SING N N 48 
2D9 C8  CL20 SING N N 49 
2D9 C8  C9   DOUB Y N 50 
2D9 C9  O21  SING N N 51 
2D9 C9  C10  SING Y N 52 
2D9 O21 H21  SING N N 53 
2D9 C10 C11  DOUB Y N 54 
2D9 C10 H10  SING N N 55 
2D9 C11 O22  SING N N 56 
2D9 O22 H22  SING N N 57 
# 
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 
2D9 SMILES           ACDLabs              10.04 Clc1cc(c(O)cc1O)c4nncc4N3CCN(Cc2ccc(cc2)S(=O)(=O)C)CC3                                                                                                                 
2D9 InChI            InChI                1.02b InChI=1/C21H23ClN4O4S/c1-31(29,30)15-4-2-14(3-5-15)13-25-6-8-26(9-7-25)18-12-23-24-21(18)16-10-17(22)20(28)11-19(16)27/h2-5,10-12,27-28H,6-9,13H2,1H3,(H,23,24)/f/h24H 
2D9 InChIKey         InChI                1.02b BDFJIEMVNDLSTB-LQFNOIFHCG                                                                                                                                              
2D9 SMILES_CANONICAL CACTVS               3.341 C[S](=O)(=O)c1ccc(CN2CCN(CC2)c3cn[nH]c3c4cc(Cl)c(O)cc4O)cc1                                                                                                            
2D9 SMILES           CACTVS               3.341 C[S](=O)(=O)c1ccc(CN2CCN(CC2)c3cn[nH]c3c4cc(Cl)c(O)cc4O)cc1                                                                                                            
2D9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CS(=O)(=O)c1ccc(cc1)CN2CCN(CC2)c3cn[nH]c3c4cc(c(cc4O)O)Cl                                                                                                              
2D9 SMILES           "OpenEye OEToolkits" 1.5.0 CS(=O)(=O)c1ccc(cc1)CN2CCN(CC2)c3cn[nH]c3c4cc(c(cc4O)O)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 
2D9 "SYSTEMATIC NAME" ACDLabs              10.04 4-chloro-6-(4-{4-[4-(methylsulfonyl)benzyl]piperazin-1-yl}-1H-pyrazol-5-yl)benzene-1,3-diol       
2D9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-chloro-6-[4-[4-[(4-methylsulfonylphenyl)methyl]piperazin-1-yl]-2H-pyrazol-3-yl]benzene-1,3-diol 
# 
