data_DSI
# 
_chem_comp.id                                    DSI 
_chem_comp.name                                  "4-HYDROXY-6-(1H-INDOLE-2-CARBONYL)-8-METHYL-3,6,7,8-TETRAHYDRO-3,6-DIAZA-AS-INDACENE-2-CARBOXYLIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C22 H19 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(+)DUOCARMYCIN SA-INDOLE" 
_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                        389.404 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DSI 
_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        1DSI 
_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 
DSI C20  C20  C 0 1 Y N N -0.433  0.204  3.012  0.468  -0.071 -5.755 C20  DSI 1  
DSI C21  C21  C 0 1 Y N N -0.709  0.284  1.616  -0.833 0.088  -5.239 C21  DSI 2  
DSI C22  C22  C 0 1 Y N N 0.266   0.004  0.647  -1.914 0.133  -6.114 C22  DSI 3  
DSI C23  C23  C 0 1 Y N N 1.552   -0.382 1.058  -1.703 0.022  -7.471 C23  DSI 4  
DSI C25  C25  C 0 1 Y N N 0.878   -0.158 3.392  0.656  -0.182 -7.139 C25  DSI 5  
DSI C24  C24  C 0 1 Y N N 1.854   -0.468 2.427  -0.419 -0.135 -7.976 C24  DSI 6  
DSI C18  C18  C 0 1 Y N N -2.618  0.822  2.771  0.607  0.065  -3.522 C18  DSI 7  
DSI C19  C19  C 0 1 Y N N -1.650  0.526  3.737  1.352  -0.076 -4.650 C19  DSI 8  
DSI N17  N17  N 0 1 Y N N -2.042  0.647  1.522  -0.725 0.169  -3.871 N17  DSI 9  
DSI C16  C16  C 0 1 N N N -4.038  1.198  2.911  1.135  0.106  -2.151 C16  DSI 10 
DSI O16  O16  O 0 1 N N N -4.752  1.188  1.909  2.336  0.110  -1.962 O16  DSI 11 
DSI C6   C6   C 0 1 Y N N -8.381  1.581  4.410  2.151  -0.066 2.150  C6   DSI 12 
DSI C7   C7   C 0 1 Y N N -7.142  1.341  3.797  1.960  -0.020 0.787  C7   DSI 13 
DSI O6   O6   O 0 1 N N N -9.557  1.244  3.806  3.409  -0.166 2.656  O6   DSI 14 
DSI C8   C8   C 0 1 Y N N -5.958  1.749  4.456  0.671  0.081  0.241  C8   DSI 15 
DSI N12  N12  N 0 1 N N N -4.621  1.590  4.120  0.287  0.140  -1.103 N12  DSI 16 
DSI C11  C11  C 0 1 N N N -3.806  1.993  5.303  -1.170 0.243  -1.205 C11  DSI 17 
DSI C10  C10  C 0 1 N N S -4.687  2.834  6.225  -1.673 0.244  0.247  C10  DSI 18 
DSI C13  C13  C 0 1 N N N -4.603  4.342  5.926  -2.587 -0.957 0.496  C13  DSI 19 
DSI C9   C9   C 0 1 Y N N -5.992  2.408  5.663  -0.417 0.137  1.083  C9   DSI 20 
DSI C5   C5   C 0 1 Y N N -8.415  2.233  5.660  1.054  -0.011 3.013  C5   DSI 21 
DSI C4   C4   C 0 1 Y N N -7.202  2.644  6.283  -0.240 0.091  2.474  C4   DSI 22 
DSI C3   C3   C 0 1 Y N N -7.558  3.289  7.542  -1.141 0.122  3.566  C3   DSI 23 
DSI C2   C2   C 0 1 Y N N -8.949  3.241  7.627  -0.408 0.049  4.710  C2   DSI 24 
DSI N1   N1   N 0 1 Y N N -9.450  2.609  6.502  0.930  -0.035 4.384  N1   DSI 25 
DSI C14  C14  C 0 1 N N N -9.778  3.757  8.714  -0.955 0.053  6.073  C14  DSI 26 
DSI O15  O15  O 0 1 N N N -11.128 3.464  8.580  -0.125 -0.029 7.132  O15  DSI 27 
DSI O14  O14  O 0 1 N N N -9.368  4.402  9.681  -2.156 0.132  6.246  O14  DSI 28 
DSI C15  C15  C 0 1 N N N -11.959 3.677  9.708  -0.666 -0.025 8.480  C15  DSI 29 
DSI H22  H22  H 0 1 N N N 0.025   0.072  -0.403 -2.916 0.255  -5.731 H22  DSI 30 
DSI H23  H23  H 0 1 N N N 2.308   -0.611 0.321  -2.544 0.058  -8.147 H23  DSI 31 
DSI H25  H25  H 0 1 N N N 1.130   -0.211 4.439  1.651  -0.305 -7.541 H25  DSI 32 
DSI H24  H24  H 0 1 N N N 2.844   -0.764 2.742  -0.271 -0.221 -9.043 H24  DSI 33 
DSI H19  H19  H 0 1 N N N -1.800  0.521  4.799  2.427  -0.176 -4.694 H19  DSI 34 
DSI H17  H17  H 0 1 N N N -2.572  0.789  0.674  -1.464 0.282  -3.252 H17  DSI 35 
DSI H7   H7   H 0 1 N N N -7.104  0.825  2.850  2.815  -0.063 0.128  H7   DSI 36 
DSI H6   H6   H 0 1 N N N -10.332 1.564  4.269  3.603  -1.110 2.738  H6   DSI 37 
DSI H111 1H11 H 0 0 N N N -2.922  2.564  5.021  -1.450 1.172  -1.703 H111 DSI 38 
DSI H112 2H11 H 0 0 N N N -3.537  1.098  5.863  -1.574 -0.612 -1.745 H112 DSI 39 
DSI H10  H10  H 0 1 N N N -4.565  2.583  7.273  -2.198 1.173  0.467  H10  DSI 40 
DSI H131 1H13 H 0 0 N N N -4.495  4.431  4.855  -3.456 -0.893 -0.157 H131 DSI 41 
DSI H132 2H13 H 0 0 N N N -5.544  4.809  6.200  -2.042 -1.878 0.287  H132 DSI 42 
DSI H133 3H13 H 0 0 N N N -4.835  4.549  4.855  -2.913 -0.956 1.536  H133 DSI 43 
DSI H3   H3   H 0 1 N N N -6.929  3.727  8.302  -2.217 0.192  3.502  H3   DSI 44 
DSI H1   H1   H 0 1 N N N -10.442 2.480  6.374  1.663  -0.102 5.017  H1   DSI 45 
DSI H151 1H15 H 0 0 N N N -12.979 3.391  9.450  0.150  -0.099 9.199  H151 DSI 46 
DSI H152 2H15 H 0 0 N N N -11.956 4.728  10.003 -1.215 0.900  8.648  H152 DSI 47 
DSI H153 3H15 H 0 0 N N N -11.623 3.063  10.544 -1.338 -0.874 8.605  H153 DSI 48 
# 
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 
DSI C20 C21  DOUB Y N 1  
DSI C20 C25  SING Y N 2  
DSI C20 C19  SING Y N 3  
DSI C21 C22  SING Y N 4  
DSI C21 N17  SING Y N 5  
DSI C22 C23  DOUB Y N 6  
DSI C22 H22  SING N N 7  
DSI C23 C24  SING Y N 8  
DSI C23 H23  SING N N 9  
DSI C25 C24  DOUB Y N 10 
DSI C25 H25  SING N N 11 
DSI C24 H24  SING N N 12 
DSI C18 C19  DOUB Y N 13 
DSI C18 N17  SING Y N 14 
DSI C18 C16  SING N N 15 
DSI C19 H19  SING N N 16 
DSI N17 H17  SING N N 17 
DSI C16 O16  DOUB N N 18 
DSI C16 N12  SING N N 19 
DSI C6  C7   DOUB Y N 20 
DSI C6  O6   SING N N 21 
DSI C6  C5   SING Y N 22 
DSI C7  C8   SING Y N 23 
DSI C7  H7   SING N N 24 
DSI O6  H6   SING N N 25 
DSI C8  N12  SING N N 26 
DSI C8  C9   DOUB Y N 27 
DSI N12 C11  SING N N 28 
DSI C11 C10  SING N N 29 
DSI C11 H111 SING N N 30 
DSI C11 H112 SING N N 31 
DSI C10 C13  SING N N 32 
DSI C10 C9   SING N N 33 
DSI C10 H10  SING N N 34 
DSI C13 H131 SING N N 35 
DSI C13 H132 SING N N 36 
DSI C13 H133 SING N N 37 
DSI C9  C4   SING Y N 38 
DSI C5  C4   DOUB Y N 39 
DSI C5  N1   SING Y N 40 
DSI C4  C3   SING Y N 41 
DSI C3  C2   DOUB Y N 42 
DSI C3  H3   SING N N 43 
DSI C2  N1   SING Y N 44 
DSI C2  C14  SING N N 45 
DSI N1  H1   SING N N 46 
DSI C14 O15  SING N N 47 
DSI C14 O14  DOUB N N 48 
DSI O15 C15  SING N N 49 
DSI C15 H151 SING N N 50 
DSI C15 H152 SING N N 51 
DSI C15 H153 SING N N 52 
# 
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 
DSI SMILES           ACDLabs              10.04 O=C(OC)c2nc1c(O)cc3c(c1c2)C(CN3C(=O)c5cc4ccccc4n5)C                                                                                                      
DSI InChI            InChI                1.02b InChI=1/C22H19N3O4/c1-11-10-25(21(27)15-7-12-5-3-4-6-14(12)23-15)17-9-18(26)20-13(19(11)17)8-16(24-20)22(28)29-2/h3-9,11,23-24,26H,10H2,1-2H3/t11-/m1/s1 
DSI InChIKey         InChI                1.02b SVXVQSGKGYZESS-LLVKDONJBM                                                                                                                                
DSI SMILES_CANONICAL CACTVS               3.341 COC(=O)c1[nH]c2c(O)cc3N(C[C@@H](C)c3c2c1)C(=O)c4[nH]c5ccccc5c4                                                                                           
DSI SMILES           CACTVS               3.341 COC(=O)c1[nH]c2c(O)cc3N(C[CH](C)c3c2c1)C(=O)c4[nH]c5ccccc5c4                                                                                             
DSI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]1CN(c2c1c3cc([nH]c3c(c2)O)C(=O)OC)C(=O)c4cc5ccccc5[nH]4                                                                                           
DSI SMILES           "OpenEye OEToolkits" 1.5.0 CC1CN(c2c1c3cc([nH]c3c(c2)O)C(=O)OC)C(=O)c4cc5ccccc5[nH]4                                                                                                
# 
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 
DSI "SYSTEMATIC NAME" ACDLabs              10.04 "methyl (8S)-4-hydroxy-6-(1H-indol-2-ylcarbonyl)-8-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate" 
DSI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (8S)-4-hydroxy-6-(1H-indol-2-ylcarbonyl)-8-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate"    
# 
