data_QMN
# 
_chem_comp.id                                    QMN 
_chem_comp.name                                  "ethyl (9S)-9-[3-(1H-benzimidazol-2-yloxy)phenyl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylate" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H24 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2014-09-05 
_chem_comp.pdbx_modified_date                    2014-11-14 
_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                        468.504 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     QMN 
_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        4UZD 
_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 
QMN C1   C1   C 0 1 N N S 58.274 -10.128 44.410 1.096  1.211  0.825  C1   QMN 1  
QMN N2   N2   N 0 1 N N N 58.277 -11.463 41.863 3.682  0.685  -0.434 N2   QMN 2  
QMN C3   C3   C 0 1 Y N N 57.484 -11.984 42.850 3.009  -0.352 0.197  C3   QMN 3  
QMN C4   C4   C 0 1 Y N N 57.496 -11.407 44.158 1.757  -0.139 0.820  C4   QMN 4  
QMN C5   C5   C 0 1 Y N N 56.647 -12.178 44.921 1.354  -1.305 1.345  C5   QMN 5  
QMN N6   N6   N 0 1 Y N N 56.133 -13.160 44.137 2.290  -2.258 1.082  N6   QMN 6  
QMN C7   C7   C 0 1 Y N N 56.645 -13.063 42.868 3.327  -1.678 0.366  C7   QMN 7  
QMN C8   C8   C 0 1 N N N 59.091 -9.671  43.205 2.091  2.268  0.394  C8   QMN 8  
QMN C9   C9   C 0 1 N N N 59.106 -10.381 42.039 3.269  1.974  -0.194 C9   QMN 9  
QMN C10  C10  C 0 1 N N N 59.935 -10.000 40.853 4.210  3.074  -0.631 C10  QMN 10 
QMN C11  C11  C 0 1 N N N 60.404 -8.550  40.828 4.080  4.269  0.315  C11  QMN 11 
QMN C12  C12  C 0 1 N N N 60.803 -8.030  42.196 2.626  4.751  0.280  C12  QMN 12 
QMN C13  C13  C 0 1 N N N 59.858 -8.420  43.303 1.724  3.605  0.641  C13  QMN 13 
QMN O14  O14  O 0 1 N N N 59.780 -7.706  44.291 0.649  3.838  1.159  O14  QMN 14 
QMN C15  C15  C 0 1 N N N 56.256 -14.018 41.843 4.493  -2.330 -0.101 C15  QMN 15 
QMN O16  O16  O 0 1 N N N 55.437 -14.898 42.038 5.333  -1.704 -0.720 O16  QMN 16 
QMN O17  O17  O 0 1 N N N 56.893 -13.778 40.674 4.674  -3.646 0.141  O17  QMN 17 
QMN C18  C18  C 0 1 N N N 56.685 -14.726 39.579 5.874  -4.238 -0.360 C18  QMN 18 
QMN C19  C19  C 0 1 N N N 55.682 -14.206 38.645 5.902  -5.723 0.009  C19  QMN 19 
QMN C20  C20  C 0 1 Y N N 57.342 -9.042  44.958 -0.070 1.201  -0.130 C20  QMN 20 
QMN C21  C21  C 0 1 Y N N 56.956 -9.071  46.293 -1.344 1.459  0.335  C21  QMN 21 
QMN C22  C22  C 0 1 Y N N 55.760 -8.481  46.693 -2.418 1.449  -0.544 C22  QMN 22 
QMN C23  C23  C 0 1 Y N N 54.986 -7.776  45.790 -2.207 1.181  -1.889 C23  QMN 23 
QMN C24  C24  C 0 1 Y N N 55.431 -7.644  44.489 -0.930 0.923  -2.349 C24  QMN 24 
QMN C25  C25  C 0 1 Y N N 56.601 -8.262  44.079 0.138  0.939  -1.472 C25  QMN 25 
QMN C26  C26  C 0 1 Y N N 58.945 -5.713  51.442 -7.887 -2.371 0.386  C26  QMN 26 
QMN C27  C27  C 0 1 Y N N 58.048 -6.104  52.443 -6.851 -3.222 0.031  C27  QMN 27 
QMN C28  C28  C 0 1 Y N N 56.971 -6.937  52.159 -5.588 -2.726 -0.205 C28  QMN 28 
QMN C29  C29  C 0 1 Y N N 58.778 -6.140  50.131 -7.666 -1.015 0.508  C29  QMN 29 
QMN C30  C30  C 0 1 Y N N 57.684 -6.948  49.849 -6.401 -0.498 0.275  C30  QMN 30 
QMN C31  C31  C 0 1 Y N N 56.783 -7.350  50.841 -5.348 -1.355 -0.086 C31  QMN 31 
QMN N32  N32  N 0 1 Y N N 55.725 -8.059  50.273 -4.242 -0.583 -0.248 N32  QMN 32 
QMN C33  C33  C 0 1 Y N N 56.008 -8.064  48.989 -4.543 0.669  -0.016 C33  QMN 33 
QMN N34  N34  N 0 1 Y N N 57.167 -7.415  48.654 -5.862 0.777  0.311  N34  QMN 34 
QMN O35  O35  O 0 1 N N N 55.255 -8.654  48.010 -3.673 1.702  -0.089 O35  QMN 35 
QMN H1   H1   H 0 1 N N N 58.995 -10.352 45.210 0.739  1.436  1.829  H1   QMN 36 
QMN HN2  HN2  H 0 1 N N N 58.252 -11.895 40.961 4.425  0.505  -1.030 HN2  QMN 37 
QMN H5   H5   H 0 1 N N N 56.427 -12.027 45.967 0.435  -1.464 1.889  H5   QMN 38 
QMN HN6  HN6  H 0 1 N N N 55.478 -13.852 44.440 2.240  -3.188 1.351  HN6  QMN 39 
QMN H10  H10  H 0 1 N N N 60.825 -10.646 40.838 5.235  2.705  -0.609 H10  QMN 40 
QMN H10A H10A H 0 0 N N N 59.337 -10.180 39.948 3.959  3.385  -1.645 H10A QMN 41 
QMN H11  H11  H 0 1 N N N 61.273 -8.475  40.158 4.342  3.966  1.329  H11  QMN 42 
QMN H11A H11A H 0 0 N N N 59.587 -7.924  40.440 4.741  5.071  -0.013 H11A QMN 43 
QMN H12  H12  H 0 1 N N N 61.800 -8.425  42.438 2.492  5.561  0.998  H12  QMN 44 
QMN H12A H12A H 0 0 N N N 60.845 -6.932  42.149 2.382  5.106  -0.722 H12A QMN 45 
QMN H18  H18  H 0 1 N N N 57.634 -14.879 39.045 5.906  -4.133 -1.444 H18  QMN 46 
QMN H18A H18A H 0 0 N N N 56.337 -15.685 39.990 6.737  -3.739 0.080  H18A QMN 47 
QMN H19  H19  H 0 1 N N N 55.534 -14.926 37.827 5.039  -6.223 -0.431 H19  QMN 48 
QMN H19A H19A H 0 0 N N N 54.731 -14.054 39.176 6.817  -6.175 -0.373 H19A QMN 49 
QMN H19B H19B H 0 0 N N N 56.028 -13.247 38.231 5.870  -5.829 1.093  H19B QMN 50 
QMN H21  H21  H 0 1 N N N 57.587 -9.554  47.024 -1.506 1.667  1.382  H21  QMN 51 
QMN H23  H23  H 0 1 N N N 54.049 -7.336  46.097 -3.041 1.172  -2.576 H23  QMN 52 
QMN H24  H24  H 0 1 N N N 54.862 -7.054  43.786 -0.766 0.714  -3.396 H24  QMN 53 
QMN H25  H25  H 0 1 N N N 56.942 -8.136  43.062 1.136  0.742  -1.834 H25  QMN 54 
QMN H26  H26  H 0 1 N N N 59.777 -5.071  51.692 -8.873 -2.772 0.564  H26  QMN 55 
QMN H27  H27  H 0 1 N N N 58.195 -5.753  53.454 -7.036 -4.282 -0.061 H27  QMN 56 
QMN H28  H28  H 0 1 N N N 56.297 -7.256  52.940 -4.786 -3.395 -0.481 H28  QMN 57 
QMN H29  H29  H 0 1 N N N 59.475 -5.854  49.357 -8.477 -0.357 0.784  H29  QMN 58 
QMN HN34 HN34 H 0 0 N N N 57.556 -7.303  47.740 -6.336 1.595  0.528  HN34 QMN 59 
# 
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 
QMN C1  C4   SING N N 1  
QMN C1  C8   SING N N 2  
QMN C1  C20  SING N N 3  
QMN N2  C3   SING N N 4  
QMN N2  C9   SING N N 5  
QMN C3  C4   SING Y N 6  
QMN C3  C7   DOUB Y N 7  
QMN C4  C5   DOUB Y N 8  
QMN C5  N6   SING Y N 9  
QMN N6  C7   SING Y N 10 
QMN C7  C15  SING N N 11 
QMN C8  C9   DOUB N N 12 
QMN C8  C13  SING N N 13 
QMN C9  C10  SING N N 14 
QMN C10 C11  SING N N 15 
QMN C11 C12  SING N N 16 
QMN C12 C13  SING N N 17 
QMN C13 O14  DOUB N N 18 
QMN C15 O16  DOUB N N 19 
QMN C15 O17  SING N N 20 
QMN O17 C18  SING N N 21 
QMN C18 C19  SING N N 22 
QMN C20 C21  DOUB Y N 23 
QMN C20 C25  SING Y N 24 
QMN C21 C22  SING Y N 25 
QMN C22 C23  DOUB Y N 26 
QMN C22 O35  SING N N 27 
QMN C23 C24  SING Y N 28 
QMN C24 C25  DOUB Y N 29 
QMN C26 C27  DOUB Y N 30 
QMN C26 C29  SING Y N 31 
QMN C27 C28  SING Y N 32 
QMN C28 C31  DOUB Y N 33 
QMN C29 C30  DOUB Y N 34 
QMN C30 C31  SING Y N 35 
QMN C30 N34  SING Y N 36 
QMN C31 N32  SING Y N 37 
QMN N32 C33  DOUB Y N 38 
QMN C33 N34  SING Y N 39 
QMN C33 O35  SING N N 40 
QMN C1  H1   SING N N 41 
QMN N2  HN2  SING N N 42 
QMN C5  H5   SING N N 43 
QMN N6  HN6  SING N N 44 
QMN C10 H10  SING N N 45 
QMN C10 H10A SING N N 46 
QMN C11 H11  SING N N 47 
QMN C11 H11A SING N N 48 
QMN C12 H12  SING N N 49 
QMN C12 H12A SING N N 50 
QMN C18 H18  SING N N 51 
QMN C18 H18A SING N N 52 
QMN C19 H19  SING N N 53 
QMN C19 H19A SING N N 54 
QMN C19 H19B SING N N 55 
QMN C21 H21  SING N N 56 
QMN C23 H23  SING N N 57 
QMN C24 H24  SING N N 58 
QMN C25 H25  SING N N 59 
QMN C26 H26  SING N N 60 
QMN C27 H27  SING N N 61 
QMN C28 H28  SING N N 62 
QMN C29 H29  SING N N 63 
QMN N34 HN34 SING N N 64 
# 
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 
QMN SMILES           ACDLabs              12.01 "O=C(OCC)c3c2NC1=C(C(=O)CCC1)C(c2cn3)c6cc(Oc5nc4ccccc4n5)ccc6"                                                                                                                                          
QMN InChI            InChI                1.03  "InChI=1S/C27H24N4O4/c1-2-34-26(33)25-24-17(14-28-25)22(23-20(29-24)11-6-12-21(23)32)15-7-5-8-16(13-15)35-27-30-18-9-3-4-10-19(18)31-27/h3-5,7-10,13-14,22,28-29H,2,6,11-12H2,1H3,(H,30,31)/t22-/m0/s1" 
QMN InChIKey         InChI                1.03  YXMQIWJYPNBZJS-QFIPXVFZSA-N                                                                                                                                                                             
QMN SMILES_CANONICAL CACTVS               3.385 "CCOC(=O)c1[nH]cc2[C@H](c3cccc(Oc4[nH]c5ccccc5n4)c3)C6=C(CCCC6=O)Nc12"                                                                                                                                  
QMN SMILES           CACTVS               3.385 "CCOC(=O)c1[nH]cc2[CH](c3cccc(Oc4[nH]c5ccccc5n4)c3)C6=C(CCCC6=O)Nc12"                                                                                                                                   
QMN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CCOC(=O)c1c2c(c[nH]1)[C@@H](C3=C(N2)CCCC3=O)c4cccc(c4)Oc5[nH]c6ccccc6n5"                                                                                                                               
QMN SMILES           "OpenEye OEToolkits" 1.7.6 "CCOC(=O)c1c2c(c[nH]1)C(C3=C(N2)CCCC3=O)c4cccc(c4)Oc5[nH]c6ccccc6n5"                                                                                                                                    
# 
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 
QMN "SYSTEMATIC NAME" ACDLabs              12.01 "ethyl (9S)-9-[3-(1H-benzimidazol-2-yloxy)phenyl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylate"       
QMN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "ethyl (9S)-9-[3-(1H-benzimidazol-2-yloxy)phenyl]-8-oxidanylidene-2,4,5,6,7,9-hexahydropyrrolo[3,4-b]quinoline-3-carboxylate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
QMN "Create component" 2014-09-05 EBI  
QMN "Initial release"  2014-11-19 RCSB 
# 
