data_ANT
# 
_chem_comp.id                                    ANT 
_chem_comp.name                                  ANTHRAMYCIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C16 H17 N3 O4" 
_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                        315.324 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ANT 
_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        274D 
_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 
ANT C1   C1   C 0 1 N N N 17.704 -0.286 24.981 -0.530 0.762  -1.528 C1   ANT 1  
ANT C2   C2   C 0 1 N N N 17.699 -1.804 25.221 0.486  -0.029 -2.320 C2   ANT 2  
ANT C3   C3   C 0 1 N N N 18.568 -2.132 26.199 1.372  -0.571 -1.461 C3   ANT 3  
ANT N4   N4   N 0 1 N N N 19.348 -0.998 26.625 1.150  -0.216 -0.187 N4   ANT 4  
ANT C5   C5   C 0 1 N N N 20.593 -1.222 27.132 1.929  -0.280 0.939  C5   ANT 5  
ANT O5   O5   O 0 1 N N N 20.785 -2.396 27.576 3.102  -0.600 0.929  O5   ANT 6  
ANT C5A  C5A  C 0 1 Y N N 21.494 -0.064 27.390 1.179  0.086  2.189  C5A  ANT 7  
ANT C6   C6   C 0 1 Y N N 22.885 -0.346 27.532 1.669  0.996  3.112  C6   ANT 8  
ANT C7   C7   C 0 1 Y N N 23.872 0.645  27.772 0.899  1.264  4.232  C7   ANT 9  
ANT C8   C8   C 0 1 Y N N 23.435 2.012  27.896 -0.319 0.625  4.399  C8   ANT 10 
ANT C8M  C8M  C 0 1 N N N 24.492 3.084  28.136 -1.146 0.925  5.622  C8M  ANT 11 
ANT C9   C9   C 0 1 Y N N 22.123 2.340  27.790 -0.792 -0.285 3.471  C9   ANT 12 
ANT C9A  C9A  C 0 1 Y N N 21.124 1.319  27.514 -0.022 -0.560 2.327  C9A  ANT 13 
ANT O9   O9   O 0 1 N N N 21.692 3.642  27.896 -1.993 -0.895 3.656  O9   ANT 14 
ANT N10  N10  N 0 1 N N N 19.840 1.697  27.399 -0.484 -1.439 1.398  N10  ANT 15 
ANT C11  C11  C 0 1 N N S 18.776 1.317  26.563 -1.227 -0.709 0.333  C11  ANT 16 
ANT O11  O11  O 0 1 N Y N 17.886 2.257  26.216 -2.442 -0.156 0.843  O11  ANT 17 
ANT C4A  C4A  C 0 1 N N S 19.046 0.147  25.656 -0.186 0.447  -0.051 C4A  ANT 18 
ANT C12  C12  C 0 1 N N N 16.555 -2.727 24.927 0.505  -0.176 -3.722 C12  ANT 19 
ANT C13  C13  C 0 1 N N N 15.447 -2.134 24.385 -0.449 0.423  -4.480 C13  ANT 20 
ANT C14  C14  C 0 1 N N N 14.326 -2.914 23.807 -0.430 0.276  -5.885 C14  ANT 21 
ANT O14  O14  O 0 1 N N N 14.116 -4.119 24.163 0.441  -0.387 -6.416 O14  ANT 22 
ANT N15  N15  N 0 1 N N N 13.604 -2.103 22.972 -1.377 0.871  -6.638 N15  ANT 23 
ANT H11A 1H1  H 0 0 N N N 17.590 0.023  23.915 -0.423 1.828  -1.727 H11A ANT 24 
ANT H12A 2H1  H 0 0 N N N 16.797 0.252  25.344 -1.541 0.428  -1.764 H12A ANT 25 
ANT H3   H3   H 0 1 N N N 18.630 -3.162 26.588 2.177  -1.222 -1.767 H3   ANT 26 
ANT H6   H6   H 0 1 N N N 23.217 -1.394 27.451 2.622  1.481  2.963  H6   ANT 27 
ANT H7   H7   H 0 1 N N N 24.935 0.364  27.858 1.248  1.968  4.973  H7   ANT 28 
ANT HM81 1HM8 H 0 0 N N N 24.153 4.142  28.232 -1.814 1.761  5.413  HM81 ANT 29 
ANT HM82 2HM8 H 0 0 N N N 25.092 2.809  29.034 -1.735 0.047  5.888  HM82 ANT 30 
ANT HM83 3HM8 H 0 0 N N N 25.265 3.019  27.335 -0.487 1.185  6.451  HM83 ANT 31 
ANT HO9  HO9  H 0 1 N N N 20.773 3.871  27.821 -1.820 -1.712 4.144  HO9  ANT 32 
ANT HN   HN   H 0 1 N N N 19.896 2.707  27.273 -1.154 -2.032 1.864  HN   ANT 33 
ANT H11  H11  H 0 1 N N N 18.066 0.810  27.258 -1.424 -1.357 -0.520 H11  ANT 34 
ANT HO1  HO1  H 0 1 N N N 17.166 2.000  25.650 -3.021 -0.900 1.054  HO1  ANT 35 
ANT H4A  H4A  H 0 1 N N N 19.833 0.379  24.902 -0.200 1.310  0.614  H4A  ANT 36 
ANT H12  H12  H 0 1 N N N 16.529 -3.815 25.105 1.278  -0.765 -4.193 H12  ANT 37 
ANT H13  H13  H 0 1 N N N 15.457 -1.031 24.413 -1.222 1.012  -4.009 H13  ANT 38 
ANT HN51 1HN5 H 0 0 N N N 13.772 -1.138 22.687 -1.364 0.770  -7.602 HN51 ANT 39 
ANT HN52 2HN5 H 0 0 N N N 12.833 -2.639 22.574 -2.071 1.400  -6.214 HN52 ANT 40 
# 
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 
ANT C1  C2   SING N N 1  
ANT C1  C4A  SING N N 2  
ANT C1  H11A SING N N 3  
ANT C1  H12A SING N N 4  
ANT C2  C3   DOUB N N 5  
ANT C2  C12  SING N N 6  
ANT C3  N4   SING N N 7  
ANT C3  H3   SING N N 8  
ANT N4  C5   SING N N 9  
ANT N4  C4A  SING N N 10 
ANT C5  O5   DOUB N N 11 
ANT C5  C5A  SING N N 12 
ANT C5A C6   DOUB Y N 13 
ANT C5A C9A  SING Y N 14 
ANT C6  C7   SING Y N 15 
ANT C6  H6   SING N N 16 
ANT C7  C8   DOUB Y N 17 
ANT C7  H7   SING N N 18 
ANT C8  C8M  SING N N 19 
ANT C8  C9   SING Y N 20 
ANT C8M HM81 SING N N 21 
ANT C8M HM82 SING N N 22 
ANT C8M HM83 SING N N 23 
ANT C9  C9A  DOUB Y N 24 
ANT C9  O9   SING N N 25 
ANT C9A N10  SING N N 26 
ANT O9  HO9  SING N N 27 
ANT N10 C11  SING N N 28 
ANT N10 HN   SING N N 29 
ANT C11 O11  SING N N 30 
ANT C11 C4A  SING N N 31 
ANT C11 H11  SING N N 32 
ANT O11 HO1  SING N N 33 
ANT C4A H4A  SING N N 34 
ANT C12 C13  DOUB N E 35 
ANT C12 H12  SING N N 36 
ANT C13 C14  SING N N 37 
ANT C13 H13  SING N N 38 
ANT C14 O14  DOUB N N 39 
ANT C14 N15  SING N N 40 
ANT N15 HN51 SING N N 41 
ANT N15 HN52 SING N N 42 
# 
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 
ANT SMILES           ACDLabs              10.04 O=C(N)\C=C\C3=CN2C(=O)c1c(c(O)c(cc1)C)NC(O)C2C3                                                                                                                
ANT InChI            InChI                1.02b InChI=1/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15-/m0/s1/f/h17H2 
ANT InChIKey         InChI                1.02b VGQOVCHZGQWAOI-OIEQIIICDO                                                                                                                                      
ANT SMILES_CANONICAL CACTVS               3.341 Cc1ccc2C(=O)N3C=C(C[C@H]3[C@H](O)Nc2c1O)\C=C\C(N)=O                                                                                                            
ANT SMILES           CACTVS               3.341 Cc1ccc2C(=O)N3C=C(C[CH]3[CH](O)Nc2c1O)C=CC(N)=O                                                                                                                
ANT SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1ccc2c(c1O)N[C@H]([C@@H]3CC(=CN3C2=O)\C=C\C(=O)N)O                                                                                                           
ANT SMILES           "OpenEye OEToolkits" 1.5.0 Cc1ccc2c(c1O)NC(C3CC(=CN3C2=O)C=CC(=O)N)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 
ANT "SYSTEMATIC NAME" ACDLabs              10.04 (2E)-3-[(11S,11aS)-9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-yl]prop-2-enamide 
ANT "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (E)-3-[(6S,6aS)-4,6-dihydroxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[5,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide           
# 
