data_BI3
# 
_chem_comp.id                                    BI3 
_chem_comp.name                                  3-[1-(3-AMINOPROPYL)-1H-INDOL-3-YL]-4-(1H-INDOL-3-YL)-1H-PYRROLE-2,5-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H20 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "INHIBITOR OF 3-PHOSPHOINOSITIDE DEPENDENT PROTEIN KINASE-1" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-12-16 
_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                        384.431 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BI3 
_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        1UU9 
_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 
BI3 NBC  NBC  N 0 1 N N N 22.616 83.356 28.211 1.788  2.107  6.512  NBC  BI3 1  
BI3 CBB  CBB  C 0 1 N N N 23.440 82.339 27.539 2.288  1.310  5.384  CBB  BI3 2  
BI3 CBA  CBA  C 0 1 N N N 22.536 81.321 26.839 1.143  1.036  4.406  CBA  BI3 3  
BI3 CAY  CAY  C 0 1 N N N 23.328 80.394 25.912 1.664  0.205  3.232  CAY  BI3 4  
BI3 NAH  NAH  N 0 1 Y N N 24.113 79.360 26.606 0.569  -0.056 2.295  NAH  BI3 5  
BI3 CAW  CAW  C 0 1 Y N N 25.365 79.531 27.037 0.235  0.741  1.245  CAW  BI3 6  
BI3 CAE  CAE  C 0 1 Y N N 23.719 78.090 26.704 -0.268 -1.151 2.349  CAE  BI3 7  
BI3 CAF  CAF  C 0 1 Y N N 22.555 77.404 26.367 -0.356 -2.239 3.210  CAF  BI3 8  
BI3 CAA  CAA  C 0 1 Y N N 22.496 76.024 26.539 -1.327 -3.197 3.011  CAA  BI3 9  
BI3 CAB  CAB  C 0 1 Y N N 23.595 75.340 27.054 -2.224 -3.086 1.959  CAB  BI3 10 
BI3 CAC  CAC  C 0 1 Y N N 24.749 76.037 27.400 -2.156 -2.013 1.097  CAC  BI3 11 
BI3 CAD  CAD  C 0 1 Y N N 24.818 77.417 27.224 -1.180 -1.037 1.287  CAD  BI3 12 
BI3 CAG  CAG  C 0 1 Y N N 25.830 78.343 27.425 -0.827 0.205  0.580  CAG  BI3 13 
BI3 CAI  CAI  C 0 1 N N N 27.179 78.179 27.746 -1.492 0.761  -0.610 CAI  BI3 14 
BI3 CAT  CAT  C 0 1 N N N 27.950 77.116 27.284 -2.636 1.696  -0.634 CAT  BI3 15 
BI3 OAZ  OAZ  O 0 1 N N N 27.576 76.155 26.615 -3.199 2.152  0.340  OAZ  BI3 16 
BI3 NAU  NAU  N 0 1 N N N 29.197 77.360 27.683 -2.944 1.965  -1.914 NAU  BI3 17 
BI3 CAV  CAV  C 0 1 N N N 29.316 78.495 28.372 -2.127 1.297  -2.746 CAV  BI3 18 
BI3 OAX  OAX  O 0 1 N N N 30.357 78.972 28.825 -2.166 1.335  -3.960 OAX  BI3 19 
BI3 CAJ  CAJ  C 0 1 N N N 28.034 79.035 28.434 -1.174 0.507  -1.939 CAJ  BI3 20 
BI3 CAK  CAK  C 0 1 Y N N 27.726 80.217 29.111 -0.104 -0.370 -2.442 CAK  BI3 21 
BI3 CAM  CAM  C 0 1 Y N N 26.563 80.720 29.678 1.285  0.017  -2.743 CAM  BI3 22 
BI3 CAP  CAP  C 0 1 Y N N 25.322 80.159 29.971 1.995  1.211  -2.653 CAP  BI3 23 
BI3 CAQ  CAQ  C 0 1 Y N N 24.318 80.939 30.539 3.325  1.243  -3.015 CAQ  BI3 24 
BI3 CAR  CAR  C 0 1 Y N N 24.546 82.284 30.820 3.957  0.091  -3.460 CAR  BI3 25 
BI3 CAS  CAS  C 0 1 Y N N 25.786 82.849 30.536 3.267  -1.098 -3.547 CAS  BI3 26 
BI3 CAN  CAN  C 0 1 Y N N 26.784 82.061 29.971 1.925  -1.151 -3.187 CAN  BI3 27 
BI3 NAO  NAO  N 0 1 Y N N 28.040 82.306 29.594 0.993  -2.168 -3.167 NAO  BI3 28 
BI3 CAL  CAL  C 0 1 Y N N 28.610 81.213 29.080 -0.206 -1.700 -2.725 CAL  BI3 29 
BI3 HBC1 1HBC H 0 0 N N N 22.326 84.329 28.113 1.529  3.008  6.138  HBC1 BI3 30 
BI3 HBC2 2HBC H 0 0 N N N 22.605 83.936 29.050 2.572  2.263  7.127  HBC2 BI3 31 
BI3 HBB1 1HBB H 0 0 N N N 24.158 81.851 28.239 3.079  1.859  4.873  HBB1 BI3 32 
BI3 HBB2 2HBB H 0 0 N N N 24.180 82.794 26.840 2.683  0.364  5.755  HBB2 BI3 33 
BI3 HBA1 1HBA H 0 0 N N N 21.705 81.826 26.293 0.353  0.486  4.917  HBA1 BI3 34 
BI3 HBA2 2HBA H 0 0 N N N 21.935 80.739 27.576 0.748  1.981  4.036  HBA2 BI3 35 
BI3 HAY1 1HAY H 0 0 N N N 23.984 80.990 25.236 2.455  0.755  2.721  HAY1 BI3 36 
BI3 HAY2 2HAY H 0 0 N N N 22.651 79.927 25.160 2.060  -0.739 3.602  HAY2 BI3 37 
BI3 HAW  HAW  H 0 1 N N N 25.917 80.486 27.067 0.736  1.660  0.978  HAW  BI3 38 
BI3 HAF  HAF  H 0 1 N N N 21.685 77.951 25.966 0.336  -2.336 4.033  HAF  BI3 39 
BI3 HAA  HAA  H 0 1 N N N 21.580 75.473 26.268 -1.390 -4.043 3.680  HAA  BI3 40 
BI3 HAB  HAB  H 0 1 N N N 23.551 74.246 27.188 -2.980 -3.844 1.815  HAB  BI3 41 
BI3 HAC  HAC  H 0 1 N N N 25.614 75.493 27.816 -2.856 -1.929 0.279  HAC  BI3 42 
BI3 HAU  HAU  H 0 1 N N N 29.982 76.741 27.482 -3.659 2.555  -2.198 HAU  BI3 43 
BI3 HAP  HAP  H 0 1 N N N 25.134 79.094 29.753 1.506  2.110  -2.307 HAP  BI3 44 
BI3 HAQ  HAQ  H 0 1 N N N 23.337 80.489 30.768 3.877  2.169  -2.951 HAQ  BI3 45 
BI3 HAR  HAR  H 0 1 N N N 23.747 82.899 31.266 4.999  0.127  -3.740 HAR  BI3 46 
BI3 HAS  HAS  H 0 1 N N N 25.976 83.913 30.757 3.769  -1.989 -3.895 HAS  BI3 47 
BI3 HAO  HAO  H 0 1 N N N 28.503 83.209 29.686 1.167  -3.085 -3.431 HAO  BI3 48 
BI3 HAL  HAL  H 0 1 N N N 29.641 81.146 28.694 -1.102 -2.293 -2.616 HAL  BI3 49 
# 
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 
BI3 NBC CBB  SING N N 1  
BI3 NBC HBC1 SING N N 2  
BI3 NBC HBC2 SING N N 3  
BI3 CBB CBA  SING N N 4  
BI3 CBB HBB1 SING N N 5  
BI3 CBB HBB2 SING N N 6  
BI3 CBA CAY  SING N N 7  
BI3 CBA HBA1 SING N N 8  
BI3 CBA HBA2 SING N N 9  
BI3 CAY NAH  SING N N 10 
BI3 CAY HAY1 SING N N 11 
BI3 CAY HAY2 SING N N 12 
BI3 NAH CAW  SING Y N 13 
BI3 NAH CAE  SING Y N 14 
BI3 CAW CAG  DOUB Y N 15 
BI3 CAW HAW  SING N N 16 
BI3 CAE CAF  SING Y N 17 
BI3 CAE CAD  DOUB Y N 18 
BI3 CAF CAA  DOUB Y N 19 
BI3 CAF HAF  SING N N 20 
BI3 CAA CAB  SING Y N 21 
BI3 CAA HAA  SING N N 22 
BI3 CAB CAC  DOUB Y N 23 
BI3 CAB HAB  SING N N 24 
BI3 CAC CAD  SING Y N 25 
BI3 CAC HAC  SING N N 26 
BI3 CAD CAG  SING Y N 27 
BI3 CAG CAI  SING N N 28 
BI3 CAI CAT  SING N N 29 
BI3 CAI CAJ  DOUB N N 30 
BI3 CAT OAZ  DOUB N N 31 
BI3 CAT NAU  SING N N 32 
BI3 NAU CAV  SING N N 33 
BI3 NAU HAU  SING N N 34 
BI3 CAV OAX  DOUB N N 35 
BI3 CAV CAJ  SING N N 36 
BI3 CAJ CAK  SING N N 37 
BI3 CAK CAM  SING Y N 38 
BI3 CAK CAL  DOUB Y N 39 
BI3 CAM CAP  SING Y N 40 
BI3 CAM CAN  DOUB Y N 41 
BI3 CAP CAQ  DOUB Y N 42 
BI3 CAP HAP  SING N N 43 
BI3 CAQ CAR  SING Y N 44 
BI3 CAQ HAQ  SING N N 45 
BI3 CAR CAS  DOUB Y N 46 
BI3 CAR HAR  SING N N 47 
BI3 CAS CAN  SING Y N 48 
BI3 CAS HAS  SING N N 49 
BI3 CAN NAO  SING Y N 50 
BI3 NAO CAL  SING Y N 51 
BI3 NAO HAO  SING N N 52 
BI3 CAL HAL  SING N N 53 
# 
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 
BI3 SMILES           ACDLabs              10.04 O=C5C(c2c1ccccc1nc2)=C(c4c3ccccc3n(c4)CCCN)C(=O)N5                                                                                                                   
BI3 InChI            InChI                1.02b InChI=1/C23H20N4O2/c24-10-5-11-27-13-17(15-7-2-4-9-19(15)27)21-20(22(28)26-23(21)29)16-12-25-18-8-3-1-6-14(16)18/h1-4,6-9,12-13,25H,5,10-11,24H2,(H,26,28,29)/f/h26H 
BI3 InChIKey         InChI                1.02b APYXQTXFRIDSGE-HXTKINSTCL                                                                                                                                            
BI3 SMILES_CANONICAL CACTVS               3.341 NCCCn1cc(c2ccccc12)C3=C(C(=O)NC3=O)c4c[nH]c5ccccc45                                                                                                                  
BI3 SMILES           CACTVS               3.341 NCCCn1cc(c2ccccc12)C3=C(C(=O)NC3=O)c4c[nH]c5ccccc45                                                                                                                  
BI3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)C3=C(C(=O)NC3=O)c4cn(c5c4cccc5)CCCN                                                                                                              
BI3 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)C3=C(C(=O)NC3=O)c4cn(c5c4cccc5)CCCN                                                                                                              
# 
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 
BI3 "SYSTEMATIC NAME" ACDLabs              10.04 3-[1-(3-aminopropyl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione 
BI3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[1-(3-aminopropyl)indol-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione         
# 
