data_TAC
# 
_chem_comp.id                                    TAC 
_chem_comp.name                                  TETRACYCLINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H24 N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        444.435 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TAC 
_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        2TRT 
_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 
TAC C1   C1   C 0 1 N N N 19.610 34.121 34.372 ? ? ? C1   TAC 1  
TAC O1   O1   O 0 1 N N N 19.077 34.444 33.289 ? ? ? O1   TAC 2  
TAC C2   C2   C 0 1 N N N 19.130 33.015 35.144 ? ? ? C2   TAC 3  
TAC C21  C21  C 0 1 N N N 18.027 32.231 34.740 ? ? ? C21  TAC 4  
TAC O21  O21  O 0 1 N N N 17.794 31.108 35.280 ? ? ? O21  TAC 5  
TAC N21  N21  N 0 1 N N N 17.216 32.601 33.694 ? ? ? N21  TAC 6  
TAC C3   C3   C 0 1 N N N 19.912 32.601 36.224 ? ? ? C3   TAC 7  
TAC O3   O3   O 0 1 N N N 19.877 31.291 36.646 ? ? ? O3   TAC 8  
TAC C4   C4   C 0 1 N N S 21.048 33.404 36.693 ? ? ? C4   TAC 9  
TAC N4   N4   N 0 1 N N N 21.918 32.680 37.671 ? ? ? N4   TAC 10 
TAC C42  C42  C 0 1 N N N 22.763 33.612 38.526 ? ? ? C42  TAC 11 
TAC C43  C43  C 0 1 N N N 22.893 31.871 36.835 ? ? ? C43  TAC 12 
TAC C41  C41  C 0 1 N N S 21.414 34.733 36.060 ? ? ? C41  TAC 13 
TAC C5   C5   C 0 1 N N N 20.421 35.869 36.469 ? ? ? C5   TAC 14 
TAC C51  C51  C 0 1 N N S 20.828 37.175 35.810 ? ? ? C51  TAC 15 
TAC C6   C6   C 0 1 N N S 19.916 38.382 36.010 ? ? ? C6   TAC 16 
TAC C62  C62  C 0 1 N N N 19.582 38.717 37.446 ? ? ? C62  TAC 17 
TAC O6   O6   O 0 1 N N N 18.691 38.027 35.339 ? ? ? O6   TAC 18 
TAC C61  C61  C 0 1 Y N N 20.509 39.630 35.336 ? ? ? C61  TAC 19 
TAC C7   C7   C 0 1 Y N N 20.100 40.902 35.733 ? ? ? C7   TAC 20 
TAC C8   C8   C 0 1 Y N N 20.616 42.046 35.111 ? ? ? C8   TAC 21 
TAC C9   C9   C 0 1 Y N N 21.486 41.935 34.067 ? ? ? C9   TAC 22 
TAC C10  C10  C 0 1 Y N N 21.857 40.673 33.595 ? ? ? C10  TAC 23 
TAC O10  O10  O 0 1 N N N 22.754 40.616 32.456 ? ? ? O10  TAC 24 
TAC C1A  C1A  C 0 1 Y N N 21.375 39.499 34.229 ? ? ? C1A  TAC 25 
TAC C11  C11  C 0 1 N N N 21.652 38.216 33.698 ? ? ? C11  TAC 26 
TAC O11  O11  O 0 1 N N N 22.346 38.119 32.669 ? ? ? O11  TAC 27 
TAC C1B  C1B  C 0 1 N N N 21.298 37.050 34.359 ? ? ? C1B  TAC 28 
TAC C12  C12  C 0 1 N N N 21.585 35.785 33.864 ? ? ? C12  TAC 29 
TAC O12  O12  O 0 1 N N N 22.289 35.615 32.654 ? ? ? O12  TAC 30 
TAC C1C  C1C  C 0 1 N N S 21.097 34.507 34.537 ? ? ? C1C  TAC 31 
TAC O1C  O1C  O 0 1 N N N 21.893 33.427 34.044 ? ? ? O1C  TAC 32 
TAC HN21 1HN2 H 0 0 N N N 17.403 33.504 33.259 ? ? ? HN21 TAC 33 
TAC HN22 2HN2 H 0 0 N N N 16.419 32.034 33.402 ? ? ? HN22 TAC 34 
TAC HO3  HO3  H 0 1 N N N 20.409 31.009 37.380 ? ? ? HO3  TAC 35 
TAC H4   H4   H 0 1 N N N 20.747 34.350 37.200 ? ? ? H4   TAC 36 
TAC H421 1H42 H 0 0 N N N 23.411 33.072 39.255 ? ? ? H421 TAC 37 
TAC H422 2H42 H 0 0 N N N 23.368 34.296 37.887 ? ? ? H422 TAC 38 
TAC H423 3H42 H 0 0 N N N 22.123 34.363 39.044 ? ? ? H423 TAC 39 
TAC H431 1H43 H 0 0 N N N 23.541 31.331 37.564 ? ? ? H431 TAC 40 
TAC H432 2H43 H 0 0 N N N 22.397 31.199 36.095 ? ? ? H432 TAC 41 
TAC H433 3H43 H 0 0 N N N 23.463 32.482 36.097 ? ? ? H433 TAC 42 
TAC H41  H41  H 0 1 N N N 22.455 35.016 36.340 ? ? ? H41  TAC 43 
TAC H51A 1H5  H 0 0 N N N 19.362 35.599 36.245 ? ? ? H51A TAC 44 
TAC H52  2H5  H 0 1 N N N 20.332 35.968 37.576 ? ? ? H52  TAC 45 
TAC H51  H51  H 0 1 N N N 21.725 37.417 36.425 ? ? ? H51  TAC 46 
TAC H621 1H62 H 0 0 N N N 18.915 39.598 37.592 ? ? ? H621 TAC 47 
TAC H622 2H62 H 0 0 N N N 19.149 37.824 37.955 ? ? ? H622 TAC 48 
TAC H623 3H62 H 0 0 N N N 20.519 38.846 38.035 ? ? ? H623 TAC 49 
TAC HO6  HO6  H 0 1 N N N 18.123 38.778 35.463 ? ? ? HO6  TAC 50 
TAC H7   H7   H 0 1 N N N 19.361 41.004 36.546 ? ? ? H7   TAC 51 
TAC H8   H8   H 0 1 N N N 20.331 43.056 35.450 ? ? ? H8   TAC 52 
TAC H9   H9   H 0 1 N N N 21.885 42.855 33.609 ? ? ? H9   TAC 53 
TAC HO1  HO1  H 0 1 N N N 23.006 39.758 32.135 ? ? ? HO1  TAC 54 
TAC HO2  HO2  H 0 1 N N N 22.485 34.749 32.315 ? ? ? HO2  TAC 55 
TAC HOC  HOC  H 0 1 N N N 22.807 33.664 34.145 ? ? ? HOC  TAC 56 
# 
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 
TAC C1  O1   DOUB N N 1  
TAC C1  C2   SING N N 2  
TAC C1  C1C  SING N N 3  
TAC C2  C21  SING N N 4  
TAC C2  C3   DOUB N N 5  
TAC C21 O21  DOUB N N 6  
TAC C21 N21  SING N N 7  
TAC N21 HN21 SING N N 8  
TAC N21 HN22 SING N N 9  
TAC C3  O3   SING N N 10 
TAC C3  C4   SING N N 11 
TAC O3  HO3  SING N N 12 
TAC C4  N4   SING N N 13 
TAC C4  C41  SING N N 14 
TAC C4  H4   SING N N 15 
TAC N4  C42  SING N N 16 
TAC N4  C43  SING N N 17 
TAC C42 H421 SING N N 18 
TAC C42 H422 SING N N 19 
TAC C42 H423 SING N N 20 
TAC C43 H431 SING N N 21 
TAC C43 H432 SING N N 22 
TAC C43 H433 SING N N 23 
TAC C41 C5   SING N N 24 
TAC C41 C1C  SING N N 25 
TAC C41 H41  SING N N 26 
TAC C5  C51  SING N N 27 
TAC C5  H51A SING N N 28 
TAC C5  H52  SING N N 29 
TAC C51 C6   SING N N 30 
TAC C51 C1B  SING N N 31 
TAC C51 H51  SING N N 32 
TAC C6  C62  SING N N 33 
TAC C6  O6   SING N N 34 
TAC C6  C61  SING N N 35 
TAC C62 H621 SING N N 36 
TAC C62 H622 SING N N 37 
TAC C62 H623 SING N N 38 
TAC O6  HO6  SING N N 39 
TAC C61 C7   DOUB Y N 40 
TAC C61 C1A  SING Y N 41 
TAC C7  C8   SING Y N 42 
TAC C7  H7   SING N N 43 
TAC C8  C9   DOUB Y N 44 
TAC C8  H8   SING N N 45 
TAC C9  C10  SING Y N 46 
TAC C9  H9   SING N N 47 
TAC C10 O10  SING N N 48 
TAC C10 C1A  DOUB Y N 49 
TAC O10 HO1  SING N N 50 
TAC C1A C11  SING N N 51 
TAC C11 O11  DOUB N N 52 
TAC C11 C1B  SING N N 53 
TAC C1B C12  DOUB N N 54 
TAC C12 O12  SING N N 55 
TAC C12 C1C  SING N N 56 
TAC O12 HO2  SING N N 57 
TAC C1C O1C  SING N N 58 
TAC O1C HOC  SING N N 59 
# 
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 
TAC SMILES           ACDLabs              10.04 O=C3C2=C(O)C1(O)C(=O)C(=C(O)C(N(C)C)C1CC2C(O)(c4cccc(O)c34)C)C(=O)N                                                                                                                                       
TAC InChI            InChI                1.02b InChI=1/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1/f/h23H2 
TAC InChIKey         InChI                1.02b OFVLGDICTFRJMM-PZOPXDMEDB                                                                                                                                                                                 
TAC SMILES_CANONICAL CACTVS               3.341 CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(N)=O)C(=O)c4c(O)cccc4[C@@]3(C)O                                                                                                                     
TAC SMILES           CACTVS               3.341 CN(C)[CH]1[CH]2C[CH]3C(=C(O)[C]2(O)C(=O)C(=C1O)C(N)=O)C(=O)c4c(O)cccc4[C]3(C)O                                                                                                                            
TAC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O                                                                                                                       
TAC SMILES           "OpenEye OEToolkits" 1.5.0 CC1(c2cccc(c2C(=O)C3=C(C4(C(CC31)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O                                                                                                                                       
# 
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 
TAC "SYSTEMATIC NAME" ACDLabs              10.04 (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide 
TAC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4aS,5aS,6S,12aS)-4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide                
# 
