data_A53
# 
_chem_comp.id                                    A53 
_chem_comp.name                                  5-{5-[(S)-2-AMINO-3-(1H-INDOL-3-YL)-PROPOXYL]-PYRIDIN-3-YL}-3-[1-(1H-PYRROL-2-YL)-METH-(Z)-YLIDENE]-1,3-DIHYDRO-INDOL-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H25 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-04-05 
_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                        475.541 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A53 
_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        ? 
_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 
A53 C1   C1   C 0 1 Y N N -1.512 8.854  -19.498 8.010   -1.339 0.125  C1   A53 1  
A53 C2   C2   C 0 1 Y N N -0.524 7.951  -19.404 8.979   -1.372 -0.867 C2   A53 2  
A53 C3   C3   C 0 1 Y N N 0.666  8.433  -20.119 10.189  -1.687 -0.247 C3   A53 3  
A53 C4   C4   C 0 1 Y N N 0.412  9.637  -20.652 9.950   -1.849 1.079  C4   A53 4  
A53 N5   N5   N 0 1 Y N N -0.973 9.968  -20.288 8.631   -1.640 1.318  N5   A53 5  
A53 C6   C6   C 0 1 N N N -2.871 8.733  -18.938 6.641   -1.056 -0.055 C6   A53 6  
A53 C7   C7   C 0 1 N N N -4.065 9.603  -19.212 6.169   0.228  0.142  C7   A53 7  
A53 C8   C8   C 0 1 N N N -4.237 10.815 -20.087 6.942   1.413  0.534  C8   A53 8  
A53 N9   N9   N 0 1 N N N -5.497 11.236 -19.979 6.096   2.454  0.614  N9   A53 9  
A53 C10  C10  C 0 1 Y N N -6.245 10.445 -19.099 4.796   2.076  0.306  C10  A53 10 
A53 C11  C11  C 0 1 Y N N -5.376 9.389  -18.587 4.775   0.706  0.005  C11  A53 11 
A53 O12  O12  O 0 1 N N N -3.367 11.316 -20.784 8.141   1.447  0.749  O12  A53 12 
A53 C13  C13  C 0 1 Y N N -7.627 10.436 -18.610 3.609   2.801  0.258  C13  A53 13 
A53 C14  C14  C 0 1 Y N N -8.109 9.474  -17.695 2.428   2.179  -0.083 C14  A53 14 
A53 C15  C15  C 0 1 Y N N -7.281 8.448  -17.195 2.406   0.816  -0.383 C15  A53 15 
A53 C16  C16  C 0 1 Y N N -5.937 8.423  -17.644 3.583   0.077  -0.333 C16  A53 16 
A53 C17  C17  C 0 1 Y N N -7.801 7.405  -16.213 1.128   0.156  -0.750 C17  A53 17 
A53 C18  C18  C 0 1 Y N N -9.168 7.299  -15.850 1.091   -0.801 -1.761 C18  A53 18 
A53 N19  N19  N 0 1 Y N N -9.621 6.353  -14.969 -0.041  -1.390 -2.090 N19  A53 19 
A53 C20  C20  C 0 1 Y N N -8.752 5.471  -14.403 -1.176  -1.103 -1.484 C20  A53 20 
A53 C21  C21  C 0 1 Y N N -7.373 5.489  -14.695 -1.225  -0.161 -0.466 C21  A53 21 
A53 C22  C22  C 0 1 Y N N -6.919 6.476  -15.610 -0.057  0.489  -0.089 C22  A53 22 
A53 O23  O23  O 0 1 N N N -6.551 4.537  -14.064 -2.402  0.125  0.151  O23  A53 23 
A53 C24  C24  C 0 1 N N N -5.887 3.594  -14.907 -3.399  -0.695 -0.461 C24  A53 24 
A53 C25  C25  C 0 1 N N S -6.683 2.286  -14.922 -4.756  -0.420 0.191  C25  A53 25 
A53 C26  C26  C 0 1 N N N -5.789 1.086  -15.284 -5.799  -1.385 -0.376 C26  A53 26 
A53 N27  N27  N 0 1 N N N -7.791 2.422  -15.870 -5.163  0.963  -0.091 N27  A53 27 
A53 C28  C28  C 0 1 Y N N -5.650 0.163  -14.085 -7.105  -1.197 0.352  C28  A53 28 
A53 C29  C29  C 0 1 Y N N -6.701 -0.444 -13.383 -7.541  -1.907 1.405  C29  A53 29 
A53 N30  N30  N 0 1 Y N N -6.203 -1.200 -12.376 -8.770  -1.451 1.799  N30  A53 30 
A53 C31  C31  C 0 1 Y N N -4.817 -1.134 -12.359 -9.164  -0.411 0.988  C31  A53 31 
A53 C32  C32  C 0 1 Y N N -4.426 -0.271 -13.446 -8.136  -0.202 0.050  C32  A53 32 
A53 C33  C33  C 0 1 Y N N -3.846 -1.718 -11.545 -10.297 0.395  0.947  C33  A53 33 
A53 C34  C34  C 0 1 Y N N -2.466 -1.460 -11.780 -10.403 1.380  -0.010 C34  A53 34 
A53 C35  C35  C 0 1 Y N N -2.075 -0.606 -12.851 -9.388  1.578  -0.936 C35  A53 35 
A53 C36  C36  C 0 1 Y N N -3.070 -0.011 -13.679 -8.267  0.798  -0.915 C36  A53 36 
A53 H2   H2   H 0 1 N N N -0.593 7.009  -18.880 8.827   -1.181 -1.919 H2   A53 37 
A53 H3   H3   H 0 1 N N N 1.601  7.900  -20.202 11.146  -1.789 -0.737 H3   A53 38 
A53 H4   H4   H 0 1 N N N 1.091  10.243 -21.234 10.691  -2.103 1.823  H4   A53 39 
A53 HN5  HN5  H 0 1 N N N -1.462 10.805 -20.535 8.198   -1.695 2.184  HN5  A53 40 
A53 H6   H6   H 0 1 N N N -3.027 7.919  -18.246 5.960   -1.842 -0.346 H6   A53 41 
A53 HN9  HN9  H 0 1 N N N -5.865 12.026 -20.470 6.360   3.356  0.855  HN9  A53 42 
A53 H13  H13  H 0 1 N N N -8.306 11.198 -18.965 3.614   3.856  0.488  H13  A53 43 
A53 H14  H14  H 0 1 N N N -9.138 9.526  -17.370 1.512   2.751  -0.117 H14  A53 44 
A53 H16  H16  H 0 1 N N N -5.289 7.645  -17.268 3.572   -0.979 -0.560 H16  A53 45 
A53 H18  H18  H 0 1 N N N -9.877 7.989  -16.284 2.000   -1.064 -2.281 H18  A53 46 
A53 H20  H20  H 0 1 N N N -9.131 4.735  -13.709 -2.082  -1.610 -1.785 H20  A53 47 
A53 H22  H22  H 0 1 N N N -5.868 6.519  -15.853 -0.063  1.227  0.699  H22  A53 48 
A53 H241 1H24 H 0 0 N N N -4.873 3.406  -14.524 -3.138  -1.745 -0.328 H241 A53 49 
A53 H242 2H24 H 0 0 N N N -5.820 3.996  -15.929 -3.454  -0.466 -1.525 H242 A53 50 
A53 H25  H25  H 0 1 N N N -7.080 2.092  -13.915 -4.676  -0.563 1.269  H25  A53 51 
A53 H261 1H26 H 0 0 N N N -4.794 1.451  -15.577 -5.943  -1.182 -1.437 H261 A53 52 
A53 H262 2H26 H 0 0 N N N -6.244 0.532  -16.119 -5.454  -2.410 -0.246 H262 A53 53 
A53 H271 1H27 H 0 0 N N N -7.679 3.266  -16.395 -5.223  1.049  -1.094 H271 A53 54 
A53 H272 2H27 H 0 0 N N N -8.656 2.453  -15.370 -6.101  1.067  0.266  H272 A53 55 
A53 H29  H29  H 0 1 N N N -7.750 -0.326 -13.611 -7.001  -2.718 1.872  H29  A53 56 
A53 H30  H30  H 0 1 N N N -6.756 -1.731 -11.735 -9.286  -1.808 2.538  H30  A53 57 
A53 H33  H33  H 0 1 N N N -4.142 -2.367 -10.735 -11.092 0.248  1.664  H33  A53 58 
A53 H34  H34  H 0 1 N N N -1.716 -1.911 -11.147 -11.283 2.004  -0.040 H34  A53 59 
A53 H35  H35  H 0 1 N N N -1.029 -0.410 -13.034 -9.486  2.355  -1.680 H35  A53 60 
A53 H36  H36  H 0 1 N N N -2.778 0.642  -14.488 -7.482  0.957  -1.639 H36  A53 61 
# 
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 
A53 C1  C2   DOUB Y N 1  
A53 C1  N5   SING Y N 2  
A53 C1  C6   SING N N 3  
A53 C2  C3   SING Y N 4  
A53 C2  H2   SING N N 5  
A53 C3  C4   DOUB Y N 6  
A53 C3  H3   SING N N 7  
A53 C4  N5   SING Y N 8  
A53 C4  H4   SING N N 9  
A53 N5  HN5  SING N N 10 
A53 C6  C7   DOUB N Z 11 
A53 C6  H6   SING N N 12 
A53 C7  C8   SING N N 13 
A53 C7  C11  SING N N 14 
A53 C8  N9   SING N N 15 
A53 C8  O12  DOUB N N 16 
A53 N9  C10  SING N N 17 
A53 N9  HN9  SING N N 18 
A53 C10 C11  DOUB Y N 19 
A53 C10 C13  SING Y N 20 
A53 C11 C16  SING Y N 21 
A53 C13 C14  DOUB Y N 22 
A53 C13 H13  SING N N 23 
A53 C14 C15  SING Y N 24 
A53 C14 H14  SING N N 25 
A53 C15 C16  DOUB Y N 26 
A53 C15 C17  SING N N 27 
A53 C16 H16  SING N N 28 
A53 C17 C18  SING Y N 29 
A53 C17 C22  DOUB Y N 30 
A53 C18 N19  DOUB Y N 31 
A53 C18 H18  SING N N 32 
A53 N19 C20  SING Y N 33 
A53 C20 C21  DOUB Y N 34 
A53 C20 H20  SING N N 35 
A53 C21 C22  SING Y N 36 
A53 C21 O23  SING N N 37 
A53 C22 H22  SING N N 38 
A53 O23 C24  SING N N 39 
A53 C24 C25  SING N N 40 
A53 C24 H241 SING N N 41 
A53 C24 H242 SING N N 42 
A53 C25 C26  SING N N 43 
A53 C25 N27  SING N N 44 
A53 C25 H25  SING N N 45 
A53 C26 C28  SING N N 46 
A53 C26 H261 SING N N 47 
A53 C26 H262 SING N N 48 
A53 N27 H271 SING N N 49 
A53 N27 H272 SING N N 50 
A53 C28 C29  DOUB Y N 51 
A53 C28 C32  SING Y N 52 
A53 C29 N30  SING Y N 53 
A53 C29 H29  SING N N 54 
A53 N30 C31  SING Y N 55 
A53 N30 H30  SING N N 56 
A53 C31 C32  DOUB Y N 57 
A53 C31 C33  SING Y N 58 
A53 C32 C36  SING Y N 59 
A53 C33 C34  DOUB Y N 60 
A53 C33 H33  SING N N 61 
A53 C34 C35  SING Y N 62 
A53 C34 H34  SING N N 63 
A53 C35 C36  DOUB Y N 64 
A53 C35 H35  SING N N 65 
A53 C36 H36  SING N N 66 
# 
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 
A53 SMILES           ACDLabs              10.04 O=C3C(=C\c1cccn1)/c2cc(ccc2N3)c6cc(OCC(N)Cc5c4ccccc4nc5)cnc6                                                                                                                                                 
A53 InChI            InChI                1.02b InChI=1/C29H25N5O2/c30-21(10-20-15-33-27-6-2-1-5-24(20)27)17-36-23-11-19(14-31-16-23)18-7-8-28-25(12-18)26(29(35)34-28)13-22-4-3-9-32-22/h1-9,11-16,21,32-33H,10,17,30H2,(H,34,35)/b26-13-/t21-/m0/s1/f/h34H 
A53 InChIKey         InChI                1.02b DQMKXCKXZQEVJU-NZRJPFKMDE                                                                                                                                                                                    
A53 SMILES_CANONICAL CACTVS               3.341 N[C@H](COc1cncc(c1)c2ccc3NC(=O)\C(=C/c4[nH]ccc4)c3c2)Cc5c[nH]c6ccccc56                                                                                                                                       
A53 SMILES           CACTVS               3.341 N[CH](COc1cncc(c1)c2ccc3NC(=O)C(=Cc4[nH]ccc4)c3c2)Cc5c[nH]c6ccccc56                                                                                                                                          
A53 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)C[C@@H](COc3cc(cnc3)c4ccc5c(c4)/C(=C/c6ccc[nH]6)/C(=O)N5)N                                                                                                                               
A53 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)CC(COc3cc(cnc3)c4ccc5c(c4)C(=Cc6ccc[nH]6)C(=O)N5)N                                                                                                                                       
# 
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 
A53 "SYSTEMATIC NAME" ACDLabs              10.04 (3Z)-5-(5-{[(2S)-2-amino-3-(1H-indol-3-yl)propyl]oxy}pyridin-3-yl)-3-(1H-pyrrol-2-ylmethylidene)-1,3-dihydro-2H-indol-2-one 
A53 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3Z)-5-[5-[(2S)-2-amino-3-(1H-indol-3-yl)propoxy]pyridin-3-yl]-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2-one                 
# 
