data_DSA
# 
_chem_comp.id                                    DSA 
_chem_comp.name                                  "4-HYDROXY-8-METHYL-6-(4,5,6-TRIMETHOXY-1H-INDOLE-2-CARBONYL)-3,6,7,8-TETRAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H25 N3 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(+)DUOCARMYCIN SA" 
_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                        479.482 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DSA 
_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        1DSM 
_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 
DSA C20  C20  C 0 1 Y N N -0.601  0.580  1.758  1.155  -0.047 -4.212 C20  DSA 1  
DSA C21  C21  C 0 1 Y N N -1.094  0.502  0.427  -0.189 -0.005 -3.799 C21  DSA 2  
DSA C22  C22  C 0 1 Y N N -0.235  0.339  -0.680 -1.205 -0.045 -4.754 C22  DSA 3  
DSA C23  C23  C 0 1 Y N N 1.150   0.241  -0.453 -0.886 -0.127 -6.098 C23  DSA 4  
DSA C24  C24  C 0 1 Y N N 1.659   0.245  0.860  0.449  -0.169 -6.508 C24  DSA 5  
DSA C25  C25  C 0 1 Y N N 0.790   0.450  1.953  1.464  -0.130 -5.579 C25  DSA 6  
DSA C18  C18  C 0 1 Y N N -2.884  0.678  1.839  1.112  0.082  -1.974 C18  DSA 7  
DSA C19  C19  C 0 1 Y N N -1.739  0.748  2.644  1.950  0.014  -3.043 C19  DSA 8  
DSA C16  C16  C 0 1 N N N -4.323  0.682  2.162  1.529  0.157  -0.568 C16  DSA 9  
DSA C6   C6   C 0 1 Y N N -8.568  0.421  3.867  2.229  0.037  3.798  C6   DSA 10 
DSA C7   C7   C 0 1 Y N N -7.337  0.374  3.204  2.138  0.077  2.424  C7   DSA 11 
DSA C8   C8   C 0 1 Y N N -6.175  0.841  3.867  0.890  0.073  1.783  C8   DSA 12 
DSA C11  C11  C 0 1 N N N -4.027  1.395  4.575  -0.844 0.087  0.200  C11  DSA 13 
DSA C10  C10  C 0 1 N N R -4.924  1.737  5.771  -1.452 0.033  1.611  C10  DSA 14 
DSA C13  C13  C 0 1 N N N -4.758  0.748  6.948  -2.324 1.264  1.864  C13  DSA 15 
DSA C9   C9   C 0 1 Y N N -6.225  1.357  5.144  -0.259 0.028  2.540  C9   DSA 16 
DSA C26  C26  C 0 1 N N N -0.706  -0.951 -2.617 -2.888 -1.347 -4.055 C26  DSA 17 
DSA C27  C27  C 0 1 N N N 2.395   1.423  -2.077 -2.084 1.174  -7.471 C27  DSA 18 
DSA C5   C5   C 0 1 Y N N -8.637  1.025  5.131  1.071  -0.008 4.575  C5   DSA 19 
DSA C4   C4   C 0 1 Y N N -7.455  1.504  5.764  -0.184 -0.013 3.940  C4   DSA 20 
DSA C3   C3   C 0 1 Y N N -7.865  2.068  7.045  -1.163 -0.069 4.961  C3   DSA 21 
DSA C2   C2   C 0 1 Y N N -9.246  1.884  7.137  -0.515 -0.087 6.156  C2   DSA 22 
DSA C14  C14  C 0 1 N N N -10.112 2.267  8.247  -1.162 -0.139 7.474  C14  DSA 23 
DSA C28  C28  C 0 1 N N N 3.545   -0.258 2.271  2.173  -0.276 -7.934 C28  DSA 24 
DSA C15  C15  C 0 1 N N N -10.331 3.530  10.273 -1.048 -0.210 9.897  C15  DSA 25 
DSA N17  N17  N 0 1 Y N N -2.471  0.568  0.520  -0.195 0.074  -2.423 N17  DSA 26 
DSA N12  N12  N 0 1 N N N -4.856  0.900  3.441  0.605  0.109  0.412  N12  DSA 27 
DSA N1   N1   N 0 1 Y N N -9.694  1.258  5.989  0.846  -0.053 5.933  N1   DSA 28 
DSA O24  O24  O 0 1 N N N 3.031   0.051  0.987  0.747  -0.250 -7.833 O24  DSA 29 
DSA O16  O16  O 0 1 N N N -5.113  0.478  1.242  2.708  0.264  -0.288 O16  DSA 30 
DSA O6   O6   O 0 1 N N N -9.722  -0.029 3.293  3.449  0.042  4.397  O6   DSA 31 
DSA O22  O22  O 0 1 N N N -0.794  0.292  -1.946 -2.508 -0.005 -4.364 O22  DSA 32 
DSA O23  O23  O 0 1 N N N 2.025   0.176  -1.523 -1.879 -0.168 -7.027 O23  DSA 33 
DSA O15  O15  O 0 1 N N N -9.504  3.015  9.245  -0.410 -0.158 8.594  O15  DSA 34 
DSA O14  O14  O 0 1 N N N -11.305 1.970  8.322  -2.374 -0.166 7.556  O14  DSA 35 
DSA H25  H25  H 0 1 N N N 1.166   0.495  2.962  2.494  -0.162 -5.901 H25  DSA 36 
DSA H19  H19  H 0 1 N N N -1.712  0.847  3.709  3.029  0.003  -3.005 H19  DSA 37 
DSA H7   H7   H 0 1 N N N -7.295  -0.040 2.209  3.041  0.113  1.832  H7   DSA 38 
DSA H111 1H11 H 0 0 N N N -3.461  2.280  4.279  -1.165 0.992  -0.315 H111 DSA 39 
DSA H112 2H11 H 0 0 N N N -3.371  0.590  4.893  -1.130 -0.796 -0.369 H112 DSA 40 
DSA H10  H10  H 0 1 N N N -4.866  2.781  6.073  -2.037 -0.878 1.738  H10  DSA 41 
DSA H131 1H13 H 0 0 N N N -4.657  -0.257 6.551  -3.145 1.282  1.147  H131 DSA 42 
DSA H132 2H13 H 0 0 N N N -5.665  0.817  7.531  -2.726 1.223  2.876  H132 DSA 43 
DSA H133 3H13 H 0 0 N N N -3.689  0.673  7.258  -1.722 2.165  1.749  H133 DSA 44 
DSA H261 1H26 H 0 0 N N N -1.262  -0.883 -3.551 -3.953 -1.379 -3.821 H261 DSA 45 
DSA H262 2H26 H 0 0 N N N 0.329   -1.198 -2.848 -2.685 -1.989 -4.913 H262 DSA 46 
DSA H263 3H26 H 0 0 N N N -1.143  -1.740 -2.004 -2.317 -1.698 -3.196 H263 DSA 47 
DSA H271 1H27 H 0 0 N N N 3.087   1.252  -2.902 -2.813 1.182  -8.281 H271 DSA 48 
DSA H272 2H27 H 0 0 N N N 1.516   1.945  -2.456 -2.456 1.778  -6.643 H272 DSA 49 
DSA H273 3H27 H 0 0 N N N 2.888   2.039  -1.324 -1.140 1.588  -7.826 H273 DSA 50 
DSA H3   H3   H 0 1 N N N -7.270  2.527  7.821  -2.233 -0.091 4.816  H3   DSA 51 
DSA H281 1H28 H 0 0 N N N 3.428   0.586  2.947  2.461  -0.341 -8.983 H281 DSA 52 
DSA H282 2H28 H 0 0 N N N 3.044   -1.135 2.679  2.584  0.634  -7.500 H282 DSA 53 
DSA H283 3H28 H 0 0 N N N 4.608   -0.475 2.178  2.559  -1.142 -7.397 H283 DSA 54 
DSA H151 1H15 H 0 0 N N N -9.717  4.112  10.961 -0.285 -0.218 10.675 H151 DSA 55 
DSA H152 2H15 H 0 0 N N N -11.098 4.182  9.852  -1.687 0.663  10.023 H152 DSA 56 
DSA H153 3H15 H 0 0 N N N -10.802 2.716  10.826 -1.652 -1.114 9.970  H153 DSA 57 
DSA H17  H17  H 0 1 N N N -3.135  0.519  -0.239 -0.985 0.117  -1.863 H17  DSA 58 
DSA H1   H1   H 0 1 N N N -10.663 1.024  5.836  1.532  -0.061 6.619  H1   DSA 59 
DSA H6   H6   H 0 1 N N N -9.583  -0.379 2.411  3.718  -0.881 4.492  H6   DSA 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 
DSA C20 C21  DOUB Y N 1  
DSA C20 C25  SING Y N 2  
DSA C20 C19  SING Y N 3  
DSA C21 C22  SING Y N 4  
DSA C21 N17  SING Y N 5  
DSA C22 C23  DOUB Y N 6  
DSA C22 O22  SING N N 7  
DSA C23 C24  SING Y N 8  
DSA C23 O23  SING N N 9  
DSA C24 C25  DOUB Y N 10 
DSA C24 O24  SING N N 11 
DSA C25 H25  SING N N 12 
DSA C18 C19  DOUB Y N 13 
DSA C18 C16  SING N N 14 
DSA C18 N17  SING Y N 15 
DSA C19 H19  SING N N 16 
DSA C16 N12  SING N N 17 
DSA C16 O16  DOUB N N 18 
DSA C6  C7   SING Y N 19 
DSA C6  C5   DOUB Y N 20 
DSA C6  O6   SING N N 21 
DSA C7  C8   DOUB Y N 22 
DSA C7  H7   SING N N 23 
DSA C8  C9   SING Y N 24 
DSA C8  N12  SING N N 25 
DSA C11 C10  SING N N 26 
DSA C11 N12  SING N N 27 
DSA C11 H111 SING N N 28 
DSA C11 H112 SING N N 29 
DSA C10 C13  SING N N 30 
DSA C10 C9   SING N N 31 
DSA C10 H10  SING N N 32 
DSA C13 H131 SING N N 33 
DSA C13 H132 SING N N 34 
DSA C13 H133 SING N N 35 
DSA C9  C4   DOUB Y N 36 
DSA C26 O22  SING N N 37 
DSA C26 H261 SING N N 38 
DSA C26 H262 SING N N 39 
DSA C26 H263 SING N N 40 
DSA C27 O23  SING N N 41 
DSA C27 H271 SING N N 42 
DSA C27 H272 SING N N 43 
DSA C27 H273 SING N N 44 
DSA C5  C4   SING Y N 45 
DSA C5  N1   SING Y N 46 
DSA C4  C3   SING Y N 47 
DSA C3  C2   DOUB Y N 48 
DSA C3  H3   SING N N 49 
DSA C2  C14  SING N N 50 
DSA C2  N1   SING Y N 51 
DSA C14 O15  SING N N 52 
DSA C14 O14  DOUB N N 53 
DSA C28 O24  SING N N 54 
DSA C28 H281 SING N N 55 
DSA C28 H282 SING N N 56 
DSA C28 H283 SING N N 57 
DSA C15 O15  SING N N 58 
DSA C15 H151 SING N N 59 
DSA C15 H152 SING N N 60 
DSA C15 H153 SING N N 61 
DSA N17 H17  SING N N 62 
DSA N1  H1   SING N N 63 
DSA O6  H6   SING N N 64 
# 
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 
DSA SMILES           ACDLabs              10.04 O=C(N3c2cc(O)c1c(cc(C(=O)OC)n1)c2C(C)C3)c5cc4cc(OC)c(OC)c(OC)c4n5                                                                                                          
DSA InChI            InChI                1.02b InChI=1/C25H25N3O7/c1-11-10-28(16-9-17(29)21-13(19(11)16)8-15(27-21)25(31)35-5)24(30)14-6-12-7-18(32-2)22(33-3)23(34-4)20(12)26-14/h6-9,11,26-27,29H,10H2,1-5H3/t11-/m0/s1 
DSA InChIKey         InChI                1.02b JMVYAMWFXLCMJM-NSHDSACABH                                                                                                                                                  
DSA SMILES_CANONICAL CACTVS               3.341 COC(=O)c1[nH]c2c(O)cc3N(C[C@H](C)c3c2c1)C(=O)c4[nH]c5c(c4)cc(OC)c(OC)c5OC                                                                                                  
DSA SMILES           CACTVS               3.341 COC(=O)c1[nH]c2c(O)cc3N(C[CH](C)c3c2c1)C(=O)c4[nH]c5c(c4)cc(OC)c(OC)c5OC                                                                                                   
DSA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1CN(c2c1c3cc([nH]c3c(c2)O)C(=O)OC)C(=O)c4cc5cc(c(c(c5[nH]4)OC)OC)OC                                                                                                  
DSA SMILES           "OpenEye OEToolkits" 1.5.0 CC1CN(c2c1c3cc([nH]c3c(c2)O)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 
DSA "SYSTEMATIC NAME" ACDLabs              10.04 "methyl (8R)-4-hydroxy-8-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate" 
DSA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (8R)-4-hydroxy-8-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate"    
# 
