data_DUO
# 
_chem_comp.id                                    DUO 
_chem_comp.name                                  "4-HYDROXY-2,8-DIMETHYL-1-OXO-6-(4,5,6-TRIMETHOXY-1H-INDOLE-2-CARBONYL)-1,2,3,6,7,8-HEXAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H27 N3 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "DUOCARMYCIN A" 
_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                        509.508 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DUO 
_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        107D 
_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 
DUO N1   N1   N 0 1 N N N 2.577  7.193  -6.269 0.952  -0.489 5.673  N1   DUO 1  
DUO C2   C2   C 0 1 N N R 3.313  5.997  -6.676 -0.480 -0.520 5.999  C2   DUO 2  
DUO C3   C3   C 0 1 N N N 2.561  4.834  -6.150 -1.201 -0.411 4.674  C3   DUO 3  
DUO C4   C4   C 0 1 Y N N 1.401  5.344  -5.381 -0.140 -0.321 3.658  C4   DUO 4  
DUO C5   C5   C 0 1 Y N N 1.446  6.730  -5.489 1.105  -0.372 4.297  C5   DUO 5  
DUO C6   C6   C 0 1 Y N N 0.469  7.528  -4.879 2.266  -0.304 3.519  C6   DUO 6  
DUO C7   C7   C 0 1 Y N N -0.568 6.936  -4.164 2.184  -0.189 2.149  C7   DUO 7  
DUO C8   C8   C 0 1 Y N N -0.633 5.549  -4.055 0.941  -0.138 1.506  C8   DUO 8  
DUO C9   C9   C 0 1 Y N N 0.368  4.782  -4.641 -0.210 -0.204 2.261  C9   DUO 9  
DUO C10  C10  C 0 1 N N N -0.585 2.626  -5.494 -2.248 -1.399 1.444  C10  DUO 10 
DUO C11  C11  C 0 1 N N S 0.143  3.320  -4.353 -1.403 -0.128 1.335  C11  DUO 11 
DUO C12  C12  C 0 1 N N N -0.810 3.459  -3.224 -0.793 -0.009 -0.070 C12  DUO 12 
DUO N13  N13  N 0 1 N N N -1.592 4.667  -3.410 0.656  -0.023 0.139  N13  DUO 13 
DUO C14  C14  C 0 1 N N N -2.793 5.054  -2.672 1.580  0.059  -0.838 C14  DUO 14 
DUO C15  C15  C 0 1 Y N N -3.468 4.291  -1.561 1.161  0.067  -2.245 C15  DUO 15 
DUO C16  C16  C 0 1 Y N N -3.027 3.167  -0.882 1.997  0.041  -3.317 C16  DUO 16 
DUO C17  C17  C 0 1 Y N N -3.982 2.775  0.038  1.201  0.055  -4.487 C17  DUO 17 
DUO C18  C18  C 0 1 Y N N -4.163 1.731  0.943  1.508  0.039  -5.857 C18  DUO 18 
DUO C19  C19  C 0 1 Y N N -5.305 1.598  1.735  0.492  0.067  -6.786 C19  DUO 19 
DUO C20  C20  C 0 1 Y N N -6.291 2.595  1.637  -0.842 0.111  -6.372 C20  DUO 20 
DUO C21  C21  C 0 1 Y N N -6.167 3.641  0.705  -1.159 0.129  -5.025 C21  DUO 21 
DUO C22  C22  C 0 1 Y N N -5.009 3.702  -0.085 -0.141 0.100  -4.071 C22  DUO 22 
DUO N23  N23  N 0 1 Y N N -4.664 4.573  -1.033 -0.146 0.107  -2.693 N23  DUO 23 
DUO O24  O24  O 0 1 N N N -5.453 0.518  2.601  0.788  0.051  -8.114 O24  DUO 24 
DUO C25  C25  C 0 1 N N N -4.866 -0.772 2.317  2.213  0.005  -8.218 C25  DUO 25 
DUO O26  O26  O 0 1 N N N -7.402 2.553  2.470  -1.836 0.138  -7.300 O26  DUO 26 
DUO C27  C27  C 0 1 N N N -8.471 1.666  2.115  -2.017 1.506  -7.672 C27  DUO 27 
DUO O28  O28  O 0 1 N N N -7.156 4.604  0.567  -2.461 0.172  -4.632 O28  DUO 28 
DUO C29  C29  C 0 1 N N N -8.058 4.383  -0.525 -2.864 -1.177 -4.392 C29  DUO 29 
DUO O30  O30  O 0 1 N N N -3.272 6.126  -3.048 2.761  0.129  -0.554 O30  DUO 30 
DUO O31  O31  O 0 1 N N N 0.449  8.903  -4.928 3.485  -0.351 4.121  O31  DUO 31 
DUO O32  O32  O 0 1 N N N 2.819  3.640  -6.331 -2.400 -0.400 4.487  O32  DUO 32 
DUO C33  C33  C 0 1 N N N 3.190  6.017  -8.203 -0.837 -1.838 6.689  C33  DUO 33 
DUO C34  C34  C 0 1 N N N 4.723  5.800  -6.206 -0.839 0.644  6.885  C34  DUO 34 
DUO O35  O35  O 0 1 N N N 4.993  5.927  -5.013 -1.932 1.153  6.801  O35  DUO 35 
DUO O36  O36  O 0 1 N N N 5.748  5.487  -7.087 0.055  1.117  7.767  O36  DUO 36 
DUO C37  C37  C 0 1 N N N 6.101  4.098  -7.115 -0.290 2.240  8.620  C37  DUO 37 
DUO H1   H1   H 0 1 N N N 3.130  7.881  -5.843 1.323  0.357  6.079  H1   DUO 38 
DUO H7   H7   H 0 1 N N N -1.341 7.550  -3.725 3.089  -0.138 1.563  H7   DUO 39 
DUO H101 1H10 H 0 0 N N N -1.546 3.157  -5.429 -3.068 -1.353 0.728  H101 DUO 40 
DUO H102 2H10 H 0 0 N N N 0.036  2.804  -6.385 -1.626 -2.268 1.229  H102 DUO 41 
DUO H103 3H10 H 0 0 N N N -0.053 2.772  -6.463 -2.651 -1.482 2.454  H103 DUO 42 
DUO H11  H11  H 0 1 N N N 1.007  2.801  -3.910 -2.007 0.749  1.564  H11  DUO 43 
DUO H121 1H12 H 0 0 N N N -0.129 3.624  -2.376 -1.099 0.927  -0.537 H121 DUO 44 
DUO H122 2H12 H 0 0 N N N -1.338 2.498  -3.134 -1.095 -0.856 -0.687 H122 DUO 45 
DUO H16  H16  H 0 1 N N N -2.066 2.713  -1.074 3.076  0.008  -3.282 H16  DUO 46 
DUO H18  H18  H 0 1 N N N -3.421 0.959  1.080  2.537  0.005  -6.181 H18  DUO 47 
DUO H23  H23  H 0 1 N N N -5.213 5.315  -1.312 -0.935 0.135  -2.130 H23  DUO 48 
DUO H251 1H25 H 0 0 N N N -4.901 -1.405 3.216  2.500  -0.008 -9.269 H251 DUO 49 
DUO H252 2H25 H 0 0 N N N -3.799 -0.657 2.076  2.641  0.884  -7.736 H252 DUO 50 
DUO H253 3H25 H 0 0 N N N -5.330 -1.319 1.483  2.584  -0.894 -7.728 H253 DUO 51 
DUO H271 1H27 H 0 0 N N N -9.209 1.646  2.930  -2.745 1.570  -8.480 H271 DUO 52 
DUO H272 2H27 H 0 0 N N N -8.093 0.646  1.945  -2.378 2.072  -6.813 H272 DUO 53 
DUO H273 3H27 H 0 0 N N N -8.944 2.040  1.195  -1.066 1.921  -8.007 H273 DUO 54 
DUO H291 1H29 H 0 0 N N N -7.518 4.547  -1.470 -3.928 -1.202 -4.159 H291 DUO 55 
DUO H292 2H29 H 0 0 N N N -8.909 5.078  -0.464 -2.672 -1.777 -5.282 H292 DUO 56 
DUO H293 3H29 H 0 0 N N N -8.428 3.348  -0.482 -2.298 -1.582 -3.553 H293 DUO 57 
DUO H31  H31  H 0 1 N N N 0.657  9.170  -5.823 3.738  -1.284 4.167  H31  DUO 58 
DUO H331 1H33 H 0 0 N N N 3.937  5.343  -8.647 -0.295 -1.913 7.632  H331 DUO 59 
DUO H332 2H33 H 0 0 N N N 3.357  7.045  -8.557 -1.909 -1.868 6.883  H332 DUO 60 
DUO H333 3H33 H 0 0 N N N 2.180  5.686  -8.488 -0.562 -2.672 6.044  H333 DUO 61 
DUO H371 1H37 H 0 0 N N N 6.576  3.839  -8.073 0.555  2.480  9.265  H371 DUO 62 
DUO H372 2H37 H 0 0 N N N 6.796  3.865  -6.295 -0.533 3.104  8.003  H372 DUO 63 
DUO H373 3H37 H 0 0 N N N 5.195  3.483  -7.013 -1.152 1.978  9.234  H373 DUO 64 
# 
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 
DUO N1  C2   SING N N 1  
DUO N1  C5   SING N N 2  
DUO N1  H1   SING N N 3  
DUO C2  C3   SING N N 4  
DUO C2  C33  SING N N 5  
DUO C2  C34  SING N N 6  
DUO C3  C4   SING N N 7  
DUO C3  O32  DOUB N N 8  
DUO C4  C5   DOUB Y N 9  
DUO C4  C9   SING Y N 10 
DUO C5  C6   SING Y N 11 
DUO C6  C7   DOUB Y N 12 
DUO C6  O31  SING N N 13 
DUO C7  C8   SING Y N 14 
DUO C7  H7   SING N N 15 
DUO C8  C9   DOUB Y N 16 
DUO C8  N13  SING N N 17 
DUO C9  C11  SING N N 18 
DUO C10 C11  SING N N 19 
DUO C10 H101 SING N N 20 
DUO C10 H102 SING N N 21 
DUO C10 H103 SING N N 22 
DUO C11 C12  SING N N 23 
DUO C11 H11  SING N N 24 
DUO C12 N13  SING N N 25 
DUO C12 H121 SING N N 26 
DUO C12 H122 SING N N 27 
DUO N13 C14  SING N N 28 
DUO C14 C15  SING N N 29 
DUO C14 O30  DOUB N N 30 
DUO C15 C16  DOUB Y N 31 
DUO C15 N23  SING Y N 32 
DUO C16 C17  SING Y N 33 
DUO C16 H16  SING N N 34 
DUO C17 C18  DOUB Y N 35 
DUO C17 C22  SING Y N 36 
DUO C18 C19  SING Y N 37 
DUO C18 H18  SING N N 38 
DUO C19 C20  DOUB Y N 39 
DUO C19 O24  SING N N 40 
DUO C20 C21  SING Y N 41 
DUO C20 O26  SING N N 42 
DUO C21 C22  DOUB Y N 43 
DUO C21 O28  SING N N 44 
DUO C22 N23  SING Y N 45 
DUO N23 H23  SING N N 46 
DUO O24 C25  SING N N 47 
DUO C25 H251 SING N N 48 
DUO C25 H252 SING N N 49 
DUO C25 H253 SING N N 50 
DUO O26 C27  SING N N 51 
DUO C27 H271 SING N N 52 
DUO C27 H272 SING N N 53 
DUO C27 H273 SING N N 54 
DUO O28 C29  SING N N 55 
DUO C29 H291 SING N N 56 
DUO C29 H292 SING N N 57 
DUO C29 H293 SING N N 58 
DUO O31 H31  SING N N 59 
DUO C33 H331 SING N N 60 
DUO C33 H332 SING N N 61 
DUO C33 H333 SING N N 62 
DUO C34 O35  DOUB N N 63 
DUO C34 O36  SING N N 64 
DUO O36 C37  SING N N 65 
DUO C37 H371 SING N N 66 
DUO C37 H372 SING N N 67 
DUO C37 H373 SING N N 68 
# 
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 
DUO SMILES           ACDLabs              10.04 O=C(N3c2cc(O)c1c(C(=O)C(C(=O)OC)(N1)C)c2C(C)C3)c5cc4cc(OC)c(OC)c(OC)c4n5                                                                                                             
DUO InChI            InChI                1.02b InChI=1/C26H27N3O8/c1-11-10-29(14-9-15(30)20-18(17(11)14)23(31)26(2,28-20)25(33)37-6)24(32)13-7-12-8-16(34-3)21(35-4)22(36-5)19(12)27-13/h7-9,11,27-28,30H,10H2,1-6H3/t11-,26-/m1/s1 
DUO InChIKey         InChI                1.02b WQAYQZWERWNDPV-RPHGYIDUBG                                                                                                                                                            
DUO SMILES_CANONICAL CACTVS               3.341 COC(=O)[C@]1(C)Nc2c(O)cc3N(C[C@@H](C)c3c2C1=O)C(=O)c4[nH]c5c(c4)cc(OC)c(OC)c5OC                                                                                                      
DUO SMILES           CACTVS               3.341 COC(=O)[C]1(C)Nc2c(O)cc3N(C[CH](C)c3c2C1=O)C(=O)c4[nH]c5c(c4)cc(OC)c(OC)c5OC                                                                                                         
DUO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]1CN(c2c1c3c(c(c2)O)N[C@@](C3=O)(C)C(=O)OC)C(=O)c4cc5cc(c(c(c5[nH]4)OC)OC)OC                                                                                                   
DUO SMILES           "OpenEye OEToolkits" 1.5.0 CC1CN(c2c1c3c(c(c2)O)NC(C3=O)(C)C(=O)OC)C(=O)c4cc5cc(c(c(c5[nH]4)OC)OC)OC                                                                                                            
# 
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 
DUO "SYSTEMATIC NAME" ACDLabs              10.04 "methyl (2R,8S)-4-hydroxy-2,8-dimethyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indole-2-carboxylate" 
DUO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (1S,7R)-5-hydroxy-1,7-dimethyl-8-oxo-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-2,6-dihydro-1H-pyrrolo[4,5-e]indole-7-carboxylate"       
# 
