data_TRB
# 
_chem_comp.id                                    TRB 
_chem_comp.name                                  4-CHLORO-8-METHYL-7-(3-METHYL-BUT-2-ENYL)-6,7,8,9-TETRAHYDRO-2H-2,7,9A-TRIAZA-BENZO[CD]AZULENE-1-THIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H20 Cl N3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         9-CL-TIBO 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   OBS 
_chem_comp.pdbx_replaced_by                      TB9 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        321.868 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TRB 
_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        1REV 
_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 
TRB N1   N1   N  0 1 Y N N 0.898  -37.311 18.514 0.385  0.022  3.454  N1   TRB 1  
TRB C1A  C1A  C  0 1 Y N N 0.284  -37.130 19.703 -0.627 0.052  2.501  C1A  TRB 2  
TRB C2   C2   C  0 1 Y N N 2.142  -37.757 18.770 1.565  -0.071 2.805  C2   TRB 3  
TRB S2   S2   S  0 1 N N N 3.302  -38.059 17.578 3.061  -0.525 3.503  S2   TRB 4  
TRB N3   N3   N  0 1 Y N N 2.350  -37.879 20.114 1.366  0.249  1.532  N3   TRB 5  
TRB C3A  C3A  C  0 1 Y N N 1.211  -37.493 20.725 -0.021 0.086  1.240  C3A  TRB 6  
TRB C4   C4   C  0 1 N N N 3.622  -38.384 20.632 2.256  0.815  0.529  C4   TRB 7  
TRB C5   C5   C  0 1 N N S 3.536  -38.992 22.039 2.102  0.103  -0.784 C5   TRB 8  
TRB N6   N6   N  0 1 N N N 3.019  -38.021 23.005 0.971  0.537  -1.539 N6   TRB 9  
TRB C7   C7   C  0 1 N N N 1.567  -38.160 23.125 -0.206 -0.275 -1.297 C7   TRB 10 
TRB C7A  C7A  C  0 1 Y N N 0.823  -37.372 22.074 -0.749 -0.098 0.103  C7A  TRB 11 
TRB C8   C8   C  0 1 Y N N -0.432 -36.899 22.389 -2.143 -0.127 0.207  C8   TRB 12 
TRB C9   C9   C  0 1 Y N N -1.325 -36.553 21.397 -2.762 -0.015 1.435  C9   TRB 13 
TRB CL9  CL9  CL 0 0 N N N -2.861 -36.001 21.838 -4.496 0.018  1.527  CL9  TRB 14 
TRB C10  C10  C  0 1 Y N N -0.980 -36.661 20.066 -2.012 0.069  2.593  C10  TRB 15 
TRB C11  C11  C  0 1 N N N 2.733  -40.282 22.009 3.365  0.335  -1.617 C11  TRB 16 
TRB C12  C12  C  0 1 N N N 3.777  -36.876 23.537 1.320  0.363  -2.955 C12  TRB 17 
TRB C13  C13  C  0 1 N N N 3.008  -36.158 24.602 0.126  0.696  -3.812 C13  TRB 18 
TRB C14  C14  C  0 1 N N N 3.491  -35.202 25.375 -0.284 -0.152 -4.721 C14  TRB 19 
TRB C15  C15  C  0 1 N N N 2.642  -34.548 26.423 -1.571 0.100  -5.462 C15  TRB 20 
TRB C16  C16  C  0 1 N N N 4.894  -34.709 25.255 0.531  -1.382 -5.026 C16  TRB 21 
TRB HN1  HN1  H  0 1 N N N 0.886  -36.476 17.927 0.265  0.062  4.416  HN1  TRB 22 
TRB H41  1H4  H  0 1 N N N 4.069  -39.114 19.919 3.286  0.719  0.870  H41  TRB 23 
TRB H42  2H4  H  0 1 N N N 4.399  -37.585 20.600 2.019  1.870  0.395  H42  TRB 24 
TRB H5   H5   H  0 1 N N N 4.563  -39.254 22.383 2.004  -0.965 -0.592 H5   TRB 25 
TRB H71  1H7  H  0 1 N N N 1.263  -39.232 23.111 0.049  -1.324 -1.446 H71  TRB 26 
TRB H72  2H7  H  0 1 N N N 1.221  -37.889 24.149 -0.979 0.002  -2.013 H72  TRB 27 
TRB H8   H8   H  0 1 N N N -0.725 -36.796 23.447 -2.742 -0.238 -0.684 H8   TRB 28 
TRB H10  H10  H  0 1 N N N -1.713 -36.373 19.293 -2.496 0.147  3.555  H10  TRB 29 
TRB H111 1H11 H  0 0 N N N 2.670  -40.723 23.030 4.243  0.082  -1.023 H111 TRB 30 
TRB H112 2H11 H  0 0 N N N 1.724  -40.133 21.558 3.334  -0.292 -2.506 H112 TRB 31 
TRB H113 3H11 H  0 0 N N N 3.140  -41.007 21.266 3.416  1.383  -1.913 H113 TRB 32 
TRB H121 1H12 H  0 0 N N N 4.784  -37.186 23.899 2.146  1.027  -3.210 H121 TRB 33 
TRB H122 2H12 H  0 0 N N N 4.093  -36.182 22.723 1.618  -0.670 -3.132 H122 TRB 34 
TRB H13  H13  H  0 1 N N N 1.951  -36.358 24.848 -0.391 1.633  -3.675 H13  TRB 35 
TRB H151 1H15 H  0 0 N N N 3.049  -33.741 27.075 -1.746 -0.706 -6.173 H151 TRB 36 
TRB H152 2H15 H  0 0 N N N 1.721  -34.159 25.928 -2.397 0.145  -4.752 H152 TRB 37 
TRB H153 3H15 H  0 0 N N N 2.228  -35.347 27.080 -1.502 1.047  -5.998 H153 TRB 38 
TRB H161 1H16 H  0 0 N N N 5.301  -33.902 25.907 1.370  -1.443 -4.333 H161 TRB 39 
TRB H162 2H16 H  0 0 N N N 5.570  -35.590 25.346 -0.093 -2.269 -4.919 H162 TRB 40 
TRB H163 3H16 H  0 0 N N N 5.053  -34.399 24.195 0.907  -1.324 -6.048 H163 TRB 41 
# 
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 
TRB N1  C1A  SING Y N 1  
TRB N1  C2   SING Y N 2  
TRB N1  HN1  SING N N 3  
TRB C1A C3A  DOUB Y N 4  
TRB C1A C10  SING Y N 5  
TRB C2  S2   DOUB N N 6  
TRB C2  N3   SING Y N 7  
TRB N3  C3A  SING Y N 8  
TRB N3  C4   SING N N 9  
TRB C3A C7A  SING Y N 10 
TRB C4  C5   SING N N 11 
TRB C4  H41  SING N N 12 
TRB C4  H42  SING N N 13 
TRB C5  N6   SING N N 14 
TRB C5  C11  SING N N 15 
TRB C5  H5   SING N N 16 
TRB N6  C7   SING N N 17 
TRB N6  C12  SING N N 18 
TRB C7  C7A  SING N N 19 
TRB C7  H71  SING N N 20 
TRB C7  H72  SING N N 21 
TRB C7A C8   DOUB Y N 22 
TRB C8  C9   SING Y N 23 
TRB C8  H8   SING N N 24 
TRB C9  CL9  SING N N 25 
TRB C9  C10  DOUB Y N 26 
TRB C10 H10  SING N N 27 
TRB C11 H111 SING N N 28 
TRB C11 H112 SING N N 29 
TRB C11 H113 SING N N 30 
TRB C12 C13  SING N N 31 
TRB C12 H121 SING N N 32 
TRB C12 H122 SING N N 33 
TRB C13 C14  DOUB N N 34 
TRB C13 H13  SING N N 35 
TRB C14 C15  SING N N 36 
TRB C14 C16  SING N N 37 
TRB C15 H151 SING N N 38 
TRB C15 H152 SING N N 39 
TRB C15 H153 SING N N 40 
TRB C16 H161 SING N N 41 
TRB C16 H162 SING N N 42 
TRB C16 H163 SING N N 43 
# 
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 
TRB SMILES           ACDLabs              10.04 S=C2N3c1c(cc(Cl)cc1N2)CN(C(C3)C)C\C=C(/C)C                                                                                               
TRB InChI            InChI                1.02b InChI=1/C16H20ClN3S/c1-10(2)4-5-19-9-12-6-13(17)7-14-15(12)20(8-11(19)3)16(21)18-14/h4,6-7,11H,5,8-9H2,1-3H3,(H,18,21)/t11-/m0/s1/f/h18H 
TRB InChIKey         InChI                1.02b RCSLUNOLLUVOOG-FPCLSXBCDT                                                                                                                
TRB SMILES_CANONICAL CACTVS               3.341 C[C@H]1CN2C(=S)Nc3cc(Cl)cc(CN1CC=C(C)C)c23                                                                                               
TRB SMILES           CACTVS               3.341 C[CH]1CN2C(=S)Nc3cc(Cl)cc(CN1CC=C(C)C)c23                                                                                                
TRB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1CN2c3c(cc(cc3NC2=S)Cl)CN1CC=C(C)C                                                                                                 
TRB SMILES           "OpenEye OEToolkits" 1.5.0 CC1CN2c3c(cc(cc3NC2=S)Cl)CN1CC=C(C)C                                                                                                     
# 
_pdbx_chem_comp_identifier.comp_id           TRB 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        (5S)-9-chloro-5-methyl-6-(3-methylbut-2-en-1-yl)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione 
# 
