data_L20
# 
_chem_comp.id                                    L20 
_chem_comp.name                                  (2S)-1-(1H-INDOL-3-YL)-3-{[5-(3-METHYL-1H-INDAZOL-5-YL)PYRIDIN-3-YL]OXY}PROPAN-2-AMINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H23 N5 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-01-12 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        397.472 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     L20 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2JDR 
_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 
L20 C1   C1   C 0 1 N N N 24.754 5.148  42.808 -1.728 -6.238 11.651 C1   L20 1  
L20 C2   C2   C 0 1 Y N N 23.588 6.049  42.640 -3.092 -5.879 12.078 C2   L20 2  
L20 N3   N3   N 0 1 Y N N 23.555 7.354  42.779 -3.629 -6.485 13.139 N3   L20 3  
L20 N4   N4   N 0 1 Y N N 22.260 7.852  42.540 -4.846 -5.924 13.234 N4   L20 4  
L20 C6   C6   C 0 1 Y N N 21.450 6.779  42.215 -5.106 -4.983 12.274 C6   L20 5  
L20 C7   C7   C 0 1 Y N N 20.105 6.663  41.914 -6.229 -4.189 12.033 C7   L20 6  
L20 C8   C8   C 0 1 Y N N 19.586 5.432  41.635 -6.164 -3.313 10.944 C8   L20 7  
L20 C9   C9   C 0 1 Y N N 20.371 4.261  41.681 -5.024 -3.238 10.138 C9   L20 8  
L20 C10  C10  C 0 1 Y N N 21.716 4.358  42.019 -3.908 -4.046 10.402 C10  L20 9  
L20 C11  C11  C 0 1 Y N N 22.249 5.618  42.268 -3.958 -4.931 11.491 C11  L20 10 
L20 C12  C12  C 0 1 Y N N 19.738 2.922  41.429 -4.992 -2.321 9.024  C12  L20 11 
L20 C13  C13  C 0 1 Y N N 18.775 2.708  40.454 -6.152 -1.980 8.346  C13  L20 12 
L20 N14  N14  N 0 1 Y N N 18.243 1.512  40.299 -6.192 -1.131 7.295  N14  L20 13 
L20 C15  C15  C 0 1 Y N N 18.572 0.495  41.049 -5.012 -0.599 6.907  C15  L20 14 
L20 C16  C16  C 0 1 Y N N 19.503 0.617  42.068 -3.810 -0.881 7.522  C16  L20 15 
L20 O17  O17  O 0 1 N N N 19.738 -0.510 42.779 -2.649 -0.310 7.075  O17  L20 16 
L20 C18  C18  C 0 1 N N N 20.360 -0.617 44.030 -2.755 0.981  6.484  C18  L20 17 
L20 C19  C19  C 0 1 N N S 20.614 -2.120 44.098 -1.464 1.763  6.734  C19  L20 18 
L20 N21  N21  N 0 1 N N N 19.408 -2.891 43.814 -1.527 3.039  6.052  N21  L20 19 
L20 C25  C25  C 0 1 N N N 21.573 -2.555 43.001 -1.204 1.972  8.247  C25  L20 20 
L20 C26  C26  C 0 1 Y N N 22.941 -1.976 43.252 -0.590 0.811  8.923  C26  L20 21 
L20 C27  C27  C 0 1 Y N N 23.849 -2.505 44.109 0.465  0.067  8.444  C27  L20 22 
L20 N28  N28  N 0 1 Y N N 24.986 -1.720 44.082 0.736  -0.916 9.357  N28  L20 23 
L20 C30  C30  C 0 1 Y N N 24.819 -0.661 43.194 -0.127 -0.823 10.426 C30  L20 24 
L20 C31  C31  C 0 1 Y N N 25.639 0.415  42.796 -0.221 -1.605 11.582 C31  L20 25 
L20 C32  C32  C 0 1 Y N N 25.224 1.355  41.863 -1.211 -1.271 12.510 C32  L20 26 
L20 C33  C33  C 0 1 Y N N 23.953 1.240  41.308 -2.071 -0.197 12.288 C33  L20 27 
L20 C34  C34  C 0 1 Y N N 23.121 0.196  41.693 -1.965 0.577  11.127 C34  L20 28 
L20 C35  C35  C 0 1 Y N N 23.532 -0.774 42.643 -0.974 0.259  10.177 C35  L20 29 
L20 C36  C36  C 0 1 Y N N 20.098 1.832  42.261 -3.797 -1.754 8.595  C36  L20 30 
L20 H1C1 1H1C H 0 0 N N N 25.154 5.355  43.828 -1.272 -5.433 11.050 H1C1 L20 31 
L20 H1C2 2H1C H 0 0 N N N 25.546 5.546  42.131 -1.061 -6.432 12.510 H1C2 L20 32 
L20 H1C3 3H1C H 0 0 N N N 24.782 4.040  42.690 -1.712 -7.159 11.042 H1C3 L20 33 
L20 H4   H4   H 0 1 N N N 22.243 8.589  41.835 -5.455 -6.228 13.983 H4   L20 34 
L20 H7   H7   H 0 1 N N N 19.448 7.549  41.896 -7.114 -4.246 12.657 H7   L20 35 
L20 H8   H8   H 0 1 N N N 18.517 5.383  41.368 -7.026 -2.682 10.733 H8   L20 36 
L20 H10  H10  H 0 1 N N N 22.346 3.455  42.088 -3.019 -3.992 9.779  H10  L20 37 
L20 H13  H13  H 0 1 N N N 18.423 3.510  39.784 -7.117 -2.390 8.630  H13  L20 38 
L20 H36  H36  H 0 1 N N N 20.847 1.930  43.065 -2.861 -1.991 9.095  H36  L20 39 
L20 H15  H15  H 0 1 N N N 18.067 -0.460 40.824 -5.072 0.077  6.060  H15  L20 40 
L20 H181 1H18 H 0 0 N N N 19.791 -0.187 44.887 -2.923 0.843  5.411  H181 L20 41 
L20 H182 2H18 H 0 0 N N N 21.257 0.029  44.177 -3.623 1.490  6.916  H182 L20 42 
L20 H19  H19  H 0 1 N N N 21.002 -2.303 45.127 -0.625 1.223  6.279  H19  L20 43 
L20 H211 1H21 H 0 0 N N N 19.001 -2.624 42.918 -2.402 3.527  6.024  H211 L20 44 
L20 H212 2H21 H 0 0 N N N 19.578 -3.896 43.859 -0.763 3.305  5.459  H212 L20 45 
L20 H251 1H25 H 0 0 N N N 21.191 -2.298 41.986 -2.158 2.260  8.734  H251 L20 46 
L20 H252 2H25 H 0 0 N N N 21.603 -3.664 42.888 -0.552 2.861  8.372  H252 L20 47 
L20 H27  H27  H 0 1 N N N 23.691 -3.411 44.718 1.046  0.148  7.536  H27  L20 48 
L20 H28  H28  H 0 1 N N N 25.821 -2.266 43.870 1.465  -1.609 9.262  H28  L20 49 
L20 H31  H31  H 0 1 N N N 26.646 0.526  43.232 0.448  -2.441 11.757 H31  L20 50 
L20 H32  H32  H 0 1 N N N 25.893 2.180  41.567 -1.311 -1.859 13.419 H32  L20 51 
L20 H33  H33  H 0 1 N N N 23.605 1.976  40.563 -2.833 0.044  13.024 H33  L20 52 
L20 H34  H34  H 0 1 N N N 22.118 0.136  41.237 -2.643 1.411  10.968 H34  L20 53 
# 
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 
L20 C1  C2   SING N N 1  
L20 C1  H1C1 SING N N 2  
L20 C1  H1C2 SING N N 3  
L20 C1  H1C3 SING N N 4  
L20 C2  N3   DOUB Y N 5  
L20 C2  C11  SING Y N 6  
L20 N3  N4   SING Y N 7  
L20 N4  C6   SING Y N 8  
L20 N4  H4   SING N N 9  
L20 C6  C7   DOUB Y N 10 
L20 C6  C11  SING Y N 11 
L20 C7  C8   SING Y N 12 
L20 C7  H7   SING N N 13 
L20 C8  C9   DOUB Y N 14 
L20 C8  H8   SING N N 15 
L20 C9  C10  SING Y N 16 
L20 C9  C12  SING N N 17 
L20 C10 C11  DOUB Y N 18 
L20 C10 H10  SING N N 19 
L20 C12 C13  SING Y N 20 
L20 C12 C36  DOUB Y N 21 
L20 C13 N14  DOUB Y N 22 
L20 C13 H13  SING N N 23 
L20 N14 C15  SING Y N 24 
L20 C15 C16  DOUB Y N 25 
L20 C15 H15  SING N N 26 
L20 C16 O17  SING N N 27 
L20 C16 C36  SING Y N 28 
L20 O17 C18  SING N N 29 
L20 C18 C19  SING N N 30 
L20 C18 H181 SING N N 31 
L20 C18 H182 SING N N 32 
L20 C19 N21  SING N N 33 
L20 C19 C25  SING N N 34 
L20 C19 H19  SING N N 35 
L20 N21 H211 SING N N 36 
L20 N21 H212 SING N N 37 
L20 C25 C26  SING N N 38 
L20 C25 H251 SING N N 39 
L20 C25 H252 SING N N 40 
L20 C26 C27  DOUB Y N 41 
L20 C26 C35  SING Y N 42 
L20 C27 N28  SING Y N 43 
L20 C27 H27  SING N N 44 
L20 N28 C30  SING Y N 45 
L20 N28 H28  SING N N 46 
L20 C30 C31  DOUB Y N 47 
L20 C30 C35  SING Y N 48 
L20 C31 C32  SING Y N 49 
L20 C31 H31  SING N N 50 
L20 C32 C33  DOUB Y N 51 
L20 C32 H32  SING N N 52 
L20 C33 C34  SING Y N 53 
L20 C33 H33  SING N N 54 
L20 C34 C35  DOUB Y N 55 
L20 C34 H34  SING N N 56 
L20 C36 H36  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 
L20 SMILES           ACDLabs              10.04 n2c(c1cc(ccc1n2)c5cc(OCC(N)Cc4c3ccccc3nc4)cnc5)C                                                                                                                              
L20 InChI            InChI                1.02b InChI=1/C24H23N5O/c1-15-22-10-16(6-7-24(22)29-28-15)17-9-20(13-26-11-17)30-14-19(25)8-18-12-27-23-5-3-2-4-21(18)23/h2-7,9-13,19,27H,8,14,25H2,1H3,(H,28,29)/t19-/m0/s1/f/h29H 
L20 InChIKey         InChI                1.02b YWTBGJGMTBHQTM-MBJLRDGADQ                                                                                                                                                     
L20 SMILES_CANONICAL CACTVS               3.341 Cc1n[nH]c2ccc(cc12)c3cncc(OC[C@@H](N)Cc4c[nH]c5ccccc45)c3                                                                                                                     
L20 SMILES           CACTVS               3.341 Cc1n[nH]c2ccc(cc12)c3cncc(OC[CH](N)Cc4c[nH]c5ccccc45)c3                                                                                                                       
L20 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c2cc(ccc2[nH]n1)c3cc(cnc3)OC[C@H](Cc4c[nH]c5c4cccc5)N                                                                                                                      
L20 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c2cc(ccc2[nH]n1)c3cc(cnc3)OCC(Cc4c[nH]c5c4cccc5)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 
L20 "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-1-(1H-indol-3-yl)-3-{[5-(3-methyl-1H-indazol-5-yl)pyridin-3-yl]oxy}propan-2-amine 
L20 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-1-(1H-indol-3-yl)-3-[5-(3-methyl-1H-indazol-5-yl)pyridin-3-yl]oxy-propan-2-amine  
# 
