data_TBO
# 
_chem_comp.id                                    TBO 
_chem_comp.name                                  5-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                         "TBO 8; TIBO R86183" 
_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                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        321.868 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TBO 
_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        1HNV 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
TBO N1   N1   N  0 1 Y N N 143.797 -25.826 72.385 -0.859 0.055  3.659  N1   TBO 1  
TBO C1A  C1A  C  0 1 Y N N 144.360 -26.315 73.632 -1.551 0.114  2.453  C1A  TBO 2  
TBO C2   C2   C  0 1 Y N N 144.715 -24.849 71.878 0.454  -0.075 3.379  C2   TBO 3  
TBO S2   S2   S  0 1 N N N 144.579 -23.975 70.447 1.670  -0.573 4.477  S2   TBO 4  
TBO N3   N3   N  0 1 Y N N 145.765 -24.753 72.771 0.642  0.249  2.104  N3   TBO 5  
TBO C3A  C3A  C  0 1 Y N N 145.501 -25.650 73.793 -0.604 0.128  1.422  C3A  TBO 6  
TBO C4   C4   C  0 1 N N N 147.009 -24.192 72.366 1.801  0.785  1.407  C4   TBO 7  
TBO C5   C5   C  0 1 N N S 147.441 -23.148 73.333 2.014  0.076  0.100  C5   TBO 8  
TBO N6   N6   N  0 1 N N N 147.386 -23.517 74.749 1.164  0.543  -0.947 N6   TBO 9  
TBO C7   C7   C  0 1 N N N 147.600 -24.919 74.962 -0.056 -0.230 -1.062 C7   TBO 10 
TBO C7A  C7A  C  0 1 Y N N 146.292 -25.634 74.946 -0.976 -0.035 0.122  C7A  TBO 11 
TBO C8   C8   C  0 1 Y N N 145.857 -26.395 76.067 -2.342 -0.022 -0.182 C8   TBO 12 
TBO CL8  CL8  CL 0 0 N N N 146.762 -26.359 77.579 -2.854 -0.173 -1.834 CL8  TBO 13 
TBO C9   C9   C  0 1 Y N N 144.649 -27.131 75.965 -3.287 0.109  0.815  C9   TBO 14 
TBO C10  C10  C  0 1 Y N N 143.884 -27.094 74.729 -2.902 0.173  2.139  C10  TBO 15 
TBO C11  C11  C  0 1 N N N 148.876 -23.093 73.047 3.470  0.269  -0.329 C11  TBO 16 
TBO C12  C12  C  0 1 N N N 147.790 -22.587 75.878 1.902  0.357  -2.203 C12  TBO 17 
TBO C13  C13  C  0 1 N N N 146.560 -22.201 76.683 1.018  0.727  -3.365 C13  TBO 18 
TBO C14  C14  C  0 1 N N N 146.435 -21.828 77.944 0.862  -0.108 -4.362 C14  TBO 19 
TBO C15  C15  C  0 1 N N N 145.002 -21.501 78.168 -0.147 0.185  -5.441 C15  TBO 20 
TBO C16  C16  C  0 1 N N N 147.627 -21.745 78.864 1.692  -1.364 -4.429 C16  TBO 21 
TBO HN1  HN1  H  0 1 N N N 142.845 -25.472 72.483 -1.251 0.100  4.545  HN1  TBO 22 
TBO H41  1H4  H  0 1 N N N 147.790 -24.973 72.220 2.685  0.660  2.031  H41  TBO 23 
TBO H42  2H4  H  0 1 N N N 146.969 -23.802 71.322 1.645  1.847  1.217  H42  TBO 24 
TBO H5   H5   H  0 1 N N N 146.798 -22.244 73.213 1.833  -0.988 0.247  H5   TBO 25 
TBO H71  1H7  H  0 1 N N N 148.323 -25.349 74.230 0.200  -1.286 -1.139 H71  TBO 26 
TBO H72  2H7  H  0 1 N N N 148.176 -25.119 75.895 -0.581 0.070  -1.969 H72  TBO 27 
TBO H9   H9   H  0 1 N N N 144.310 -27.722 76.832 -4.334 0.163  0.558  H9   TBO 28 
TBO H10  H10  H  0 1 N N N 142.941 -27.657 74.623 -3.641 0.268  2.921  H10  TBO 29 
TBO H111 1H11 H  0 0 N N N 149.199 -22.310 73.772 4.131  -0.009 0.491  H111 TBO 30 
TBO H112 2H11 H  0 0 N N N 149.418 -24.065 73.113 3.680  -0.359 -1.194 H112 TBO 31 
TBO H113 3H11 H  0 0 N N N 149.148 -22.905 71.982 3.636  1.314  -0.590 H113 TBO 32 
TBO H121 1H12 H  0 0 N N N 148.591 -23.024 76.517 2.787  0.994  -2.202 H121 TBO 33 
TBO H122 2H12 H  0 0 N N N 148.348 -21.695 75.509 2.206  -0.685 -2.295 H122 TBO 34 
TBO H13  H13  H  0 1 N N N 145.540 -22.189 76.262 0.512  1.681  -3.377 H13  TBO 35 
TBO H151 1H15 H  0 0 N N N 144.896 -21.186 79.232 -0.134 -0.616 -6.179 H151 TBO 36 
TBO H152 2H15 H  0 0 N N N 144.609 -20.744 77.448 -1.141 0.256  -5.000 H152 TBO 37 
TBO H153 3H15 H  0 0 N N N 144.315 -22.334 77.889 0.103  1.129  -5.926 H153 TBO 38 
TBO H161 1H16 H  0 0 N N N 147.521 -21.430 79.928 2.292  -1.452 -3.523 H161 TBO 39 
TBO H162 2H16 H  0 0 N N N 148.141 -22.734 78.848 1.035  -2.230 -4.514 H162 TBO 40 
TBO H163 3H16 H  0 0 N N N 148.384 -21.082 78.384 2.349  -1.320 -5.297 H163 TBO 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 
TBO N1  C1A  SING Y N 1  
TBO N1  C2   SING Y N 2  
TBO N1  HN1  SING N N 3  
TBO C1A C3A  DOUB Y N 4  
TBO C1A C10  SING Y N 5  
TBO C2  S2   DOUB N N 6  
TBO C2  N3   SING Y N 7  
TBO N3  C3A  SING Y N 8  
TBO N3  C4   SING N N 9  
TBO C3A C7A  SING Y N 10 
TBO C4  C5   SING N N 11 
TBO C4  H41  SING N N 12 
TBO C4  H42  SING N N 13 
TBO C5  N6   SING N N 14 
TBO C5  C11  SING N N 15 
TBO C5  H5   SING N N 16 
TBO N6  C7   SING N N 17 
TBO N6  C12  SING N N 18 
TBO C7  C7A  SING N N 19 
TBO C7  H71  SING N N 20 
TBO C7  H72  SING N N 21 
TBO C7A C8   DOUB Y N 22 
TBO C8  CL8  SING N N 23 
TBO C8  C9   SING Y N 24 
TBO C9  C10  DOUB Y N 25 
TBO C9  H9   SING N N 26 
TBO C10 H10  SING N N 27 
TBO C11 H111 SING N N 28 
TBO C11 H112 SING N N 29 
TBO C11 H113 SING N N 30 
TBO C12 C13  SING N N 31 
TBO C12 H121 SING N N 32 
TBO C12 H122 SING N N 33 
TBO C13 C14  DOUB N N 34 
TBO C13 H13  SING N N 35 
TBO C14 C15  SING N N 36 
TBO C14 C16  SING N N 37 
TBO C15 H151 SING N N 38 
TBO C15 H152 SING N N 39 
TBO C15 H153 SING N N 40 
TBO C16 H161 SING N N 41 
TBO C16 H162 SING N N 42 
TBO 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 
TBO SMILES           ACDLabs              10.04 S=C2Nc1ccc(Cl)c3c1N2CC(N(C3)C\C=C(/C)C)C                                                                                             
TBO InChI            InChI                1.02b InChI=1/C16H20ClN3S/c1-10(2)6-7-19-9-12-13(17)4-5-14-15(12)20(8-11(19)3)16(21)18-14/h4-6,11H,7-9H2,1-3H3,(H,18,21)/t11-/m0/s1/f/h18H 
TBO InChIKey         InChI                1.02b ZNFFMCYSMBXZQU-FPCLSXBCDO                                                                                                            
TBO SMILES_CANONICAL CACTVS               3.341 C[C@H]1CN2C(=S)Nc3ccc(Cl)c(CN1CC=C(C)C)c23                                                                                           
TBO SMILES           CACTVS               3.341 C[CH]1CN2C(=S)Nc3ccc(Cl)c(CN1CC=C(C)C)c23                                                                                            
TBO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1CN2c3c(ccc(c3C[N@]1CC=C(C)C)Cl)NC2=S                                                                                          
TBO SMILES           "OpenEye OEToolkits" 1.5.0 CC1CN2c3c(ccc(c3CN1CC=C(C)C)Cl)NC2=S                                                                                                 
# 
_pdbx_chem_comp_identifier.comp_id           TBO 
_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)-8-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 
# 
