data_WOL
# 
_chem_comp.id                                    WOL 
_chem_comp.name                                  "12-(pyridin-3-yl)-8alpha,10alpha,13alpha,14beta-androsta-4,11-diene-3,17-dione" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H27 N O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-10-06 
_chem_comp.pdbx_modified_date                    2023-07-28 
_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                        361.477 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     WOL 
_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        8EOH 
_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 
WOL C10  C1  C 0 1 N N R -23.900 13.829 -14.325 1.054  -0.135 0.429  C10  WOL 1  
WOL C13  C2  C 0 1 N N N -23.525 16.493 -14.312 -1.386 0.273  0.107  C13  WOL 2  
WOL C15  C3  C 0 1 N N N -21.011 15.005 -17.051 -1.012 -3.419 0.316  C15  WOL 3  
WOL C17  C4  C 0 1 N N N -21.950 17.315 -16.522 -2.891 -1.816 0.231  C17  WOL 4  
WOL C22  C5  C 0 1 Y N N -23.864 17.851 -13.570 -2.531 1.207  0.100  C22  WOL 5  
WOL C24  C6  C 0 1 Y N N -24.565 20.329 -13.568 -3.989 2.741  1.210  C24  WOL 6  
WOL C01  C7  C 0 1 N N N -26.427 11.377 -11.925 3.907  2.303  -0.375 C01  WOL 7  
WOL C02  C8  C 0 1 N N N -25.663 9.987  -12.324 4.901  1.368  0.285  C02  WOL 8  
WOL C03  C9  C 0 1 N N N -24.419 10.104 -13.310 4.639  -0.069 0.154  C03  WOL 9  
WOL C04  C10 C 0 1 N N N -23.680 11.251 -13.745 3.416  -0.506 -0.145 C04  WOL 10 
WOL C05  C11 C 0 1 N N R -24.166 12.688 -13.157 2.243  0.412  -0.355 C05  WOL 11 
WOL C06  C12 C 0 1 N N N -25.763 12.721 -12.679 2.508  1.851  0.045  C06  WOL 12 
WOL C07  C13 C 0 1 N N N -22.425 11.027 -14.765 3.220  -2.003 -0.296 C07  WOL 13 
WOL C08  C14 C 0 1 N N N -22.059 12.353 -15.683 1.966  -2.443 0.468  C08  WOL 14 
WOL C09  C15 C 0 1 N N S -22.311 13.734 -14.809 0.796  -1.584 0.001  C09  WOL 15 
WOL C11  C16 C 0 1 N N S -22.220 14.927 -15.934 -0.527 -1.994 0.600  C11  WOL 16 
WOL C12  C17 C 0 1 N N R -22.168 16.399 -15.204 -1.604 -1.167 -0.155 C12  WOL 17 
WOL C14  C18 C 0 1 N N N -24.212 15.332 -13.784 -0.158 0.725  0.348  C14  WOL 18 
WOL C16  C19 C 0 1 N N N -21.503 16.398 -17.799 -2.553 -3.286 0.472  C16  WOL 19 
WOL C18  C20 C 0 1 N N N -20.819 16.698 -14.289 -1.393 -1.393 -1.654 C18  WOL 20 
WOL C19  C21 C 0 1 N N N -23.251 13.067 -11.830 1.884  0.398  -1.842 C19  WOL 21 
WOL C23  C22 C 0 1 Y N N -24.259 19.078 -14.338 -2.910 1.876  1.270  C23  WOL 22 
WOL C25  C23 C 0 1 Y N N -24.457 20.312 -12.067 -4.651 2.916  0.009  C25  WOL 23 
WOL C27  C24 C 0 1 Y N N -23.748 17.855 -12.082 -3.248 1.442  -1.073 C27  WOL 24 
WOL N26  N1  N 0 1 Y N N -24.043 19.089 -11.343 -4.268 2.276  -1.079 N26  WOL 25 
WOL O20  O1  O 0 1 N N N -26.051 8.735  -11.832 5.865  1.787  0.890  O20  WOL 26 
WOL O21  O2  O 0 1 N N N -22.101 18.695 -16.532 -3.973 -1.289 0.332  O21  WOL 27 
WOL H101 H1  H 0 0 N N N -24.547 13.613 -15.188 1.352  -0.170 1.476  H101 WOL 28 
WOL H151 H3  H 0 0 N N N -21.012 14.141 -17.731 -0.750 -3.722 -0.698 H151 WOL 29 
WOL H152 H4  H 0 0 N N N -20.018 15.106 -16.588 -0.605 -4.120 1.045  H152 WOL 30 
WOL H241 H6  H 0 0 N N N -24.859 21.231 -14.085 -4.312 3.271  2.094  H241 WOL 31 
WOL H011 H7  H 0 0 N N N -26.359 11.515 -10.836 4.082  3.326  -0.040 H011 WOL 32 
WOL H012 H8  H 0 0 N N N -27.484 11.295 -12.219 4.005  2.246  -1.459 H012 WOL 33 
WOL H031 H9  H 0 0 N N N -24.076 9.165  -13.718 5.441  -0.777 0.300  H031 WOL 34 
WOL H061 H11 H 0 0 N N N -25.871 13.565 -11.982 2.415  1.943  1.128  H061 WOL 35 
WOL H062 H12 H 0 0 N N N -26.363 12.911 -13.581 1.768  2.495  -0.430 H062 WOL 36 
WOL H072 H13 H 0 0 N N N -22.673 10.196 -15.441 3.105  -2.248 -1.352 H072 WOL 37 
WOL H071 H14 H 0 0 N N N -21.538 10.763 -14.170 4.090  -2.524 0.104  H071 WOL 38 
WOL H081 H15 H 0 0 N N N -22.700 12.365 -16.577 1.758  -3.493 0.261  H081 WOL 39 
WOL H082 H16 H 0 0 N N N -21.004 12.304 -15.990 2.120  -2.303 1.538  H082 WOL 40 
WOL H091 H17 H 0 0 N N N -21.599 13.859 -13.980 0.724  -1.633 -1.086 H091 WOL 41 
WOL H111 H18 H 0 0 N N N -23.163 14.894 -16.500 -0.545 -1.787 1.670  H111 WOL 42 
WOL H4   H19 H 0 1 N N N -24.952 15.468 -13.009 -0.032 1.788  0.495  H4   WOL 43 
WOL H162 H21 H 0 0 N N N -20.680 16.865 -18.360 -3.059 -3.911 -0.264 H162 WOL 44 
WOL H161 H22 H 0 0 N N N -22.350 16.213 -18.476 -2.853 -3.578 1.479  H161 WOL 45 
WOL H181 H23 H 0 0 N N N -20.870 16.115 -13.358 -2.277 -1.061 -2.199 H181 WOL 46 
WOL H182 H24 H 0 0 N N N -19.921 16.408 -14.854 -0.525 -0.825 -1.989 H182 WOL 47 
WOL H183 H25 H 0 0 N N N -20.770 17.770 -14.048 -1.228 -2.454 -1.841 H183 WOL 48 
WOL H192 H26 H 0 0 N N N -23.417 12.317 -11.043 1.006  1.023  -2.009 H192 WOL 49 
WOL H191 H27 H 0 0 N N N -22.187 13.076 -12.109 2.721  0.785  -2.422 H191 WOL 50 
WOL H193 H28 H 0 0 N N N -23.541 14.060 -11.456 1.667  -0.623 -2.154 H193 WOL 51 
WOL H231 H29 H 0 0 N N N -24.321 19.061 -15.416 -2.375 1.720  2.195  H231 WOL 52 
WOL H251 H30 H 0 0 N N N -24.686 21.208 -11.508 -5.496 3.587  -0.039 H251 WOL 53 
WOL H271 H31 H 0 0 N N N -23.451 16.961 -11.555 -2.964 0.937  -1.985 H271 WOL 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 
WOL C16 C15  SING N N 1  
WOL C16 C17  SING N N 2  
WOL C15 C11  SING N N 3  
WOL O21 C17  DOUB N N 4  
WOL C17 C12  SING N N 5  
WOL C11 C12  SING N N 6  
WOL C11 C09  SING N N 7  
WOL C08 C09  SING N N 8  
WOL C08 C07  SING N N 9  
WOL C12 C13  SING N N 10 
WOL C12 C18  SING N N 11 
WOL C09 C10  SING N N 12 
WOL C07 C04  SING N N 13 
WOL C23 C22  DOUB Y N 14 
WOL C23 C24  SING Y N 15 
WOL C10 C14  SING N N 16 
WOL C10 C05  SING N N 17 
WOL C13 C14  DOUB N N 18 
WOL C13 C22  SING N N 19 
WOL C04 C03  DOUB N N 20 
WOL C04 C05  SING N N 21 
WOL C22 C27  SING Y N 22 
WOL C24 C25  DOUB Y N 23 
WOL C03 C02  SING N N 24 
WOL C05 C06  SING N N 25 
WOL C05 C19  SING N N 26 
WOL C06 C01  SING N N 27 
WOL C02 C01  SING N N 28 
WOL C02 O20  DOUB N N 29 
WOL C27 N26  DOUB Y N 30 
WOL C25 N26  SING Y N 31 
WOL C10 H101 SING N N 32 
WOL C15 H151 SING N N 33 
WOL C15 H152 SING N N 34 
WOL C24 H241 SING N N 35 
WOL C01 H011 SING N N 36 
WOL C01 H012 SING N N 37 
WOL C03 H031 SING N N 38 
WOL C06 H061 SING N N 39 
WOL C06 H062 SING N N 40 
WOL C07 H072 SING N N 41 
WOL C07 H071 SING N N 42 
WOL C08 H081 SING N N 43 
WOL C08 H082 SING N N 44 
WOL C09 H091 SING N N 45 
WOL C11 H111 SING N N 46 
WOL C14 H4   SING N N 47 
WOL C16 H162 SING N N 48 
WOL C16 H161 SING N N 49 
WOL C18 H181 SING N N 50 
WOL C18 H182 SING N N 51 
WOL C18 H183 SING N N 52 
WOL C19 H192 SING N N 53 
WOL C19 H191 SING N N 54 
WOL C19 H193 SING N N 55 
WOL C23 H231 SING N N 56 
WOL C25 H251 SING N N 57 
WOL C27 H271 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 
WOL SMILES           ACDLabs              12.01 "O=C1CCC2C3CCC4=CC(=O)CCC4(C)C3C=C(c3cccnc3)C21C"                                                                                                                         
WOL InChI            InChI                1.06  "InChI=1S/C24H27NO2/c1-23-10-9-17(26)12-16(23)5-6-18-19-7-8-22(27)24(19,2)20(13-21(18)23)15-4-3-11-25-14-15/h3-4,11-14,18-19,21H,5-10H2,1-2H3/t18-,19-,21-,23-,24+/m0/s1" 
WOL InChIKey         InChI                1.06  XWNGZWLWVUCVNS-ZGJXEWGXSA-N                                                                                                                                               
WOL SMILES_CANONICAL CACTVS               3.385 "C[C@]12CCC(=O)C=C1CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)C(=C[C@H]23)c5cccnc5"                                                                                                   
WOL SMILES           CACTVS               3.385 "C[C]12CCC(=O)C=C1CC[CH]3[CH]4CCC(=O)[C]4(C)C(=C[CH]23)c5cccnc5"                                                                                                          
WOL SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C=C([C@]4([C@H]3CCC4=O)C)c5cccnc5"                                                                                                     
WOL SMILES           "OpenEye OEToolkits" 2.0.7 "CC12CCC(=O)C=C1CCC3C2C=C(C4(C3CCC4=O)C)c5cccnc5"                                                                                                                         
# 
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 
WOL "SYSTEMATIC NAME" ACDLabs              12.01 "12-(pyridin-3-yl)-8alpha,10alpha,13alpha,14beta-androsta-4,11-diene-3,17-dione"                                                            
WOL "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(8~{S},9~{R},10~{R},13~{R},14~{S})-10,13-dimethyl-12-pyridin-3-yl-2,6,7,8,9,14,15,16-octahydro-1~{H}-cyclopenta[a]phenanthrene-3,17-dione" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
WOL "Create component" 2022-10-06 RCSB 
WOL "Initial release"  2023-08-02 RCSB 
# 
