data_TTX
# 
_chem_comp.id                                    TTX 
_chem_comp.name                                  TENTOXIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H30 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         0 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-01-14 
_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                        414.498 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TTX 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "not provided" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   Y 
_chem_comp.pdbx_model_coordinates_db_code        1KMH 
_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 
TTX C7   C7   C 0 1 N N N 49.435 37.299 61.546 ? ? ? C7   TTX 1  
TTX N1   N1   N 0 1 N N N 49.969 36.038 61.340 ? ? ? N1   TTX 2  
TTX C15  C15  C 0 1 N N N 51.069 35.890 60.591 ? ? ? C15  TTX 3  
TTX C16  C16  C 0 1 N N N 51.702 36.993 60.124 ? ? ? C16  TTX 4  
TTX C17  C17  C 0 1 Y N N 51.359 38.447 60.181 ? ? ? C17  TTX 5  
TTX C22  C22  C 0 1 Y N N 52.256 39.263 59.572 ? ? ? C22  TTX 6  
TTX C21  C21  C 0 1 Y N N 52.148 40.632 59.570 ? ? ? C21  TTX 7  
TTX C20  C20  C 0 1 Y N N 51.108 41.232 60.172 ? ? ? C20  TTX 8  
TTX C19  C19  C 0 1 Y N N 50.190 40.445 60.777 ? ? ? C19  TTX 9  
TTX C18  C18  C 0 1 Y N N 50.311 39.096 60.777 ? ? ? C18  TTX 10 
TTX C6   C6   C 0 1 N N N 48.791 35.315 61.774 ? ? ? C6   TTX 11 
TTX O1   O1   O 0 1 N N N 47.992 35.710 62.891 ? ? ? O1   TTX 12 
TTX C5   C5   C 0 1 N N S 48.093 35.459 60.301 ? ? ? C5   TTX 13 
TTX C4   C4   C 0 1 N N N 46.678 36.001 60.134 ? ? ? C4   TTX 14 
TTX C2   C2   C 0 1 N N N 46.315 37.361 60.617 ? ? ? C2   TTX 15 
TTX C1   C1   C 0 1 N N N 46.582 38.388 59.567 ? ? ? C1   TTX 16 
TTX C3   C3   C 0 1 N N N 44.826 37.383 60.927 ? ? ? C3   TTX 17 
TTX N2   N2   N 0 1 N N N 48.186 34.057 59.783 ? ? ? N2   TTX 18 
TTX C8   C8   C 0 1 N N N 48.839 33.708 58.663 ? ? ? C8   TTX 19 
TTX O2   O2   O 0 1 N N N 48.903 34.493 57.740 ? ? ? O2   TTX 20 
TTX C9   C9   C 0 1 N N S 49.519 32.383 58.520 ? ? ? C9   TTX 21 
TTX C10  C10  C 0 1 N N N 49.043 31.699 57.272 ? ? ? C10  TTX 22 
TTX N3   N3   N 0 1 N N N 49.277 31.547 59.638 ? ? ? N3   TTX 23 
TTX C11  C11  C 0 1 N N N 48.077 30.771 59.746 ? ? ? C11  TTX 24 
TTX C12  C12  C 0 1 N N N 50.107 31.389 60.608 ? ? ? C12  TTX 25 
TTX O3   O3   O 0 1 N N N 49.821 30.628 61.518 ? ? ? O3   TTX 26 
TTX C13  C13  C 0 1 N N N 51.393 32.179 60.612 ? ? ? C13  TTX 27 
TTX N4   N4   N 0 1 N N N 51.045 33.584 60.850 ? ? ? N4   TTX 28 
TTX C14  C14  C 0 1 N N N 51.624 34.694 60.412 ? ? ? C14  TTX 29 
TTX O4   O4   O 0 1 N N N 52.658 34.627 59.805 ? ? ? O4   TTX 30 
TTX H71  1H7  H 0 1 N N N 49.251 37.770 60.552 ? ? ? H71  TTX 31 
TTX H72  2H7  H 0 1 N N N 48.519 37.422 62.170 ? ? ? H72  TTX 32 
TTX H73  3H7  H 0 1 N N N 50.234 37.957 61.960 ? ? ? H73  TTX 33 
TTX H161 1H16 H 0 0 N N N 52.628 36.660 59.627 ? ? ? H161 TTX 34 
TTX H221 1H22 H 0 0 N N N 53.110 38.793 59.056 ? ? ? H221 TTX 35 
TTX H211 1H21 H 0 0 N N N 52.909 41.260 59.077 ? ? ? H211 TTX 36 
TTX H201 1H20 H 0 0 N N N 51.011 42.331 60.170 ? ? ? H201 TTX 37 
TTX H191 1H19 H 0 0 N N N 49.327 40.912 61.280 ? ? ? H191 TTX 38 
TTX H181 1H18 H 0 0 N N N 49.528 38.505 61.281 ? ? ? H181 TTX 39 
TTX H51  1H5  H 0 1 N N N 48.628 36.273 59.759 ? ? ? H51  TTX 40 
TTX H41  1H4  H 0 1 N N N 45.972 35.271 60.593 ? ? ? H41  TTX 41 
TTX H42  2H4  H 0 1 N N N 46.407 35.934 59.055 ? ? ? H42  TTX 42 
TTX H21  1H2  H 0 1 N N N 46.925 37.593 61.521 ? ? ? H21  TTX 43 
TTX H11  1H1  H 0 1 N N N 46.068 38.141 58.609 ? ? ? H11  TTX 44 
TTX H12  2H1  H 0 1 N N N 46.310 39.407 59.929 ? ? ? H12  TTX 45 
TTX H13  3H1  H 0 1 N N N 47.637 38.346 59.209 ? ? ? H13  TTX 46 
TTX H31  1H3  H 0 1 N N N 44.526 36.581 61.642 ? ? ? H31  TTX 47 
TTX H32  2H3  H 0 1 N N N 44.554 38.402 61.289 ? ? ? H32  TTX 48 
TTX H33  3H3  H 0 1 N N N 44.204 37.057 60.061 ? ? ? H33  TTX 49 
TTX HN21 1HN2 H 0 0 N N N 47.758 33.253 60.243 ? ? ? HN21 TTX 50 
TTX H91  1H9  H 0 1 N N N 50.617 32.570 58.458 ? ? ? H91  TTX 51 
TTX H101 1H10 H 0 0 N N N 49.175 32.338 56.368 ? ? ? H101 TTX 52 
TTX H102 2H10 H 0 0 N N N 49.550 30.712 57.165 ? ? ? H102 TTX 53 
TTX H103 3H10 H 0 0 N N N 47.932 31.605 57.243 ? ? ? H103 TTX 54 
TTX H111 1H11 H 0 0 N N N 47.987 30.148 58.826 ? ? ? H111 TTX 55 
TTX H112 2H11 H 0 0 N N N 47.887 30.113 60.626 ? ? ? H112 TTX 56 
TTX H113 3H11 H 0 0 N N N 47.210 31.464 59.641 ? ? ? H113 TTX 57 
TTX H131 1H13 H 0 0 N N N 51.997 32.031 59.687 ? ? ? H131 TTX 58 
TTX H132 2H13 H 0 0 N N N 52.142 31.787 61.339 ? ? ? H132 TTX 59 
TTX HN41 1HN4 H 0 0 N N N 50.247 33.838 61.432 ? ? ? HN41 TTX 60 
# 
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 
TTX C7  N1   SING N N 1  
TTX C7  H71  SING N N 2  
TTX C7  H72  SING N N 3  
TTX C7  H73  SING N N 4  
TTX N1  C15  SING N N 5  
TTX N1  C6   SING N N 6  
TTX C15 C16  DOUB N Z 7  
TTX C15 C14  SING N N 8  
TTX C16 C17  SING N N 9  
TTX C16 H161 SING N N 10 
TTX C17 C22  DOUB Y N 11 
TTX C17 C18  SING Y N 12 
TTX C22 C21  SING Y N 13 
TTX C22 H221 SING N N 14 
TTX C21 C20  DOUB Y N 15 
TTX C21 H211 SING N N 16 
TTX C20 C19  SING Y N 17 
TTX C20 H201 SING N N 18 
TTX C19 C18  DOUB Y N 19 
TTX C19 H191 SING N N 20 
TTX C18 H181 SING N N 21 
TTX C6  O1   DOUB N N 22 
TTX C6  C5   SING N N 23 
TTX C5  C4   SING N N 24 
TTX C5  N2   SING N N 25 
TTX C5  H51  SING N N 26 
TTX C4  C2   SING N N 27 
TTX C4  H41  SING N N 28 
TTX C4  H42  SING N N 29 
TTX C2  C1   SING N N 30 
TTX C2  C3   SING N N 31 
TTX C2  H21  SING N N 32 
TTX C1  H11  SING N N 33 
TTX C1  H12  SING N N 34 
TTX C1  H13  SING N N 35 
TTX C3  H31  SING N N 36 
TTX C3  H32  SING N N 37 
TTX C3  H33  SING N N 38 
TTX N2  C8   SING N N 39 
TTX N2  HN21 SING N N 40 
TTX C8  O2   DOUB N N 41 
TTX C8  C9   SING N N 42 
TTX C9  C10  SING N N 43 
TTX C9  N3   SING N N 44 
TTX C9  H91  SING N N 45 
TTX C10 H101 SING N N 46 
TTX C10 H102 SING N N 47 
TTX C10 H103 SING N N 48 
TTX N3  C11  SING N N 49 
TTX N3  C12  SING N N 50 
TTX C11 H111 SING N N 51 
TTX C11 H112 SING N N 52 
TTX C11 H113 SING N N 53 
TTX C12 O3   DOUB N N 54 
TTX C12 C13  SING N N 55 
TTX C13 N4   SING N N 56 
TTX C13 H131 SING N N 57 
TTX C13 H132 SING N N 58 
TTX N4  C14  SING N N 59 
TTX N4  HN41 SING N N 60 
TTX C14 O4   DOUB N N 61 
# 
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 
TTX SMILES           ACDLabs              10.04 O=C1NC(C(=O)N(/C(C(=O)NCC(=O)N(C)C1C)=C\c2ccccc2)C)CC(C)C                                                                                                                                       
TTX InChI            InChI                1.02b InChI=1/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1/f/h23-24H 
TTX InChIKey         InChI                1.02b SIIRBDOFKDACOK-IOPTVNHMDE                                                                                                                                                                       
TTX SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@@H]1NC(=O)[C@H](C)N(C)C(=O)CNC(=O)C(=C/c2ccccc2)/N(C)C1=O                                                                                                                              
TTX SMILES           CACTVS               3.341 CC(C)C[CH]1NC(=O)[CH](C)N(C)C(=O)CNC(=O)C(=Cc2ccccc2)N(C)C1=O                                                                                                                                   
TTX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1C(=O)N[C@H](C(=O)N(/C(=C\c2ccccc2)/C(=O)NCC(=O)N1C)C)CC(C)C                                                                                                                              
TTX SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(=O)NC(C(=O)N(C(=Cc2ccccc2)C(=O)NCC(=O)N1C)C)CC(C)C                                                                                                                                         
# 
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 
TTX "SYSTEMATIC NAME" ACDLabs              10.04 (3S,6S,12Z)-1,6,7-trimethyl-3-(2-methylpropyl)-12-(phenylmethylidene)-1,4,7,10-tetraazacyclododecane-2,5,8,11-tetrone 
TTX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3S,6S,12Z)-12-benzylidene-1,6,7-trimethyl-3-(2-methylpropyl)-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone          
# 
