data_DBD
# 
_chem_comp.id                                    DBD 
_chem_comp.name                                  "7-(1,1-DIOXO-1H-BENZO[D]ISOTHIAZOL-3-YLOXYMETHYL)-2-(OXALYL-AMINO)-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRAN-3-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H14 N2 O9 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-03-26 
_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                        466.442 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DBD 
_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        1L8G 
_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 
DBD O1   O1   O 0 1 N N N 13.892 44.198 17.349 -2.981 -0.050 -0.439 O1   DBD 1  
DBD C2   C2   C 0 1 N N S 13.816 45.044 18.486 -1.759 -0.760 -0.201 C2   DBD 2  
DBD C3   C3   C 0 1 Y N N 12.387 45.372 18.768 -1.304 -0.469 1.192  C3   DBD 3  
DBD C4   C4   C 0 1 Y N N 11.353 45.039 17.981 -2.077 0.029  2.187  C4   DBD 4  
DBD C5   C5   C 0 1 N N N 11.543 44.211 16.758 -3.545 0.322  1.896  C5   DBD 5  
DBD C6   C6   C 0 1 N N N 12.784 43.377 17.076 -3.901 -0.403 0.592  C6   DBD 6  
DBD S7   S7   S 0 1 Y N N 11.937 46.075 20.258 0.291  -0.670 1.923  S7   DBD 7  
DBD C8   C8   C 0 1 Y N N 10.288 45.912 19.771 -0.058 -0.100 3.522  C8   DBD 8  
DBD C9   C9   C 0 1 Y N N 10.047 45.402 18.557 -1.410 0.227  3.455  C9   DBD 9  
DBD C10  C10  C 0 1 N N N 8.663  45.297 17.953 -2.125 0.756  4.618  C10  DBD 10 
DBD O11  O11  O 0 1 N N N 8.537  45.250 16.765 -2.678 -0.004 5.390  O11  DBD 11 
DBD O12  O12  O 0 1 N N N 7.552  45.243 18.690 -2.170 2.087  4.834  O12  DBD 12 
DBD N13  N13  N 0 1 N N N 9.206  46.366 20.611 0.796  -0.000 4.605  N13  DBD 13 
DBD C14  C14  C 0 1 N N N 9.318  47.070 21.737 2.085  -0.374 4.483  C14  DBD 14 
DBD C15  C15  C 0 1 N N N 7.975  47.489 22.364 3.007  -0.267 5.652  C15  DBD 15 
DBD O16  O16  O 0 1 N N N 7.777  48.528 22.914 2.597  0.156  6.711  O16  DBD 16 
DBD O17  O17  O 0 1 N N N 7.008  46.559 22.413 4.294  -0.640 5.530  O17  DBD 17 
DBD O18  O18  O 0 1 N N N 10.375 47.351 22.323 2.495  -0.799 3.423  O18  DBD 18 
DBD C19  C19  C 0 1 N N N 14.638 46.212 18.060 -0.691 -0.300 -1.197 C19  DBD 19 
DBD O20  O20  O 0 1 N N N 15.877 45.679 17.667 -1.129 -0.579 -2.528 O20  DBD 20 
DBD C21  C21  C 0 1 N N N 16.713 45.231 18.698 -0.151 -0.154 -3.359 C21  DBD 21 
DBD C22  C22  C 0 1 Y N N 17.949 44.543 18.423 -0.295 -0.305 -4.814 C22  DBD 22 
DBD C23  C23  C 0 1 Y N N 18.635 44.315 19.609 0.813  0.196  -5.509 C23  DBD 23 
DBD S24  S24  S 0 1 N N N 17.780 44.784 21.023 1.869  0.769  -4.206 S24  DBD 24 
DBD N25  N25  N 0 1 N N N 16.601 45.291 20.050 0.922  0.384  -2.881 N25  DBD 25 
DBD C26  C26  C 0 1 Y N N 18.462 44.268 17.177 -1.346 -0.840 -5.575 C26  DBD 26 
DBD C27  C27  C 0 1 Y N N 19.670 43.576 17.086 -1.262 -0.871 -6.949 C27  DBD 27 
DBD C28  C28  C 0 1 Y N N 20.396 43.313 18.253 -0.152 -0.374 -7.607 C28  DBD 28 
DBD C29  C29  C 0 1 Y N N 19.871 43.620 19.501 0.893  0.164  -6.871 C29  DBD 29 
DBD O30  O30  O 0 1 N N N 18.420 45.879 21.625 1.897  2.187  -4.293 O30  DBD 30 
DBD O31  O31  O 0 1 N N N 17.376 43.603 21.782 2.993  -0.099 -4.175 O31  DBD 31 
DBD H2   H2   H 0 1 N N N 14.191 44.610 19.442 -1.929 -1.830 -0.315 H2   DBD 32 
DBD H51  1H5  H 0 1 N N N 11.611 44.796 15.811 -3.693 1.396  1.776  H51  DBD 33 
DBD H52  2H5  H 0 1 N N N 10.649 43.613 16.463 -4.167 -0.050 2.710  H52  DBD 34 
DBD H61  1H6  H 0 1 N N N 12.593 42.657 17.906 -4.909 -0.123 0.288  H61  DBD 35 
DBD H62  2H6  H 0 1 N N N 13.006 42.646 16.264 -3.862 -1.479 0.757  H62  DBD 36 
DBD H12  H12  H 0 1 N N N 6.683  45.177 18.311 -2.643 2.436  5.603  H12  DBD 37 
DBD H13  H13  H 0 1 N N N 8.234  46.163 20.378 0.467  0.338  5.453  H13  DBD 38 
DBD H17  H17  H 0 1 N N N 6.180  46.817 22.800 4.892  -0.571 6.287  H17  DBD 39 
DBD H191 1H19 H 0 0 N N N 14.719 47.009 18.836 -0.528 0.771  -1.085 H191 DBD 40 
DBD H192 2H19 H 0 0 N N N 14.152 46.839 17.277 0.239  -0.832 -1.002 H192 DBD 41 
DBD H26  H26  H 0 1 N N N 17.919 44.594 16.274 -2.222 -1.233 -5.081 H26  DBD 42 
DBD H27  H27  H 0 1 N N N 20.046 43.241 16.105 -2.076 -1.291 -7.522 H27  DBD 43 
DBD H28  H28  H 0 1 N N N 21.398 42.857 18.188 -0.099 -0.404 -8.685 H28  DBD 44 
DBD H29  H29  H 0 1 N N N 20.432 43.314 20.400 1.765  0.556  -7.373 H29  DBD 45 
# 
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 
DBD O1  C2   SING N N 1  
DBD O1  C6   SING N N 2  
DBD C2  C3   SING N N 3  
DBD C2  C19  SING N N 4  
DBD C2  H2   SING N N 5  
DBD C3  C4   DOUB Y N 6  
DBD C3  S7   SING Y N 7  
DBD C4  C5   SING N N 8  
DBD C4  C9   SING Y N 9  
DBD C5  C6   SING N N 10 
DBD C5  H51  SING N N 11 
DBD C5  H52  SING N N 12 
DBD C6  H61  SING N N 13 
DBD C6  H62  SING N N 14 
DBD S7  C8   SING Y N 15 
DBD C8  C9   DOUB Y N 16 
DBD C8  N13  SING N N 17 
DBD C9  C10  SING N N 18 
DBD C10 O11  DOUB N N 19 
DBD C10 O12  SING N N 20 
DBD O12 H12  SING N N 21 
DBD N13 C14  SING N N 22 
DBD N13 H13  SING N N 23 
DBD C14 C15  SING N N 24 
DBD C14 O18  DOUB N N 25 
DBD C15 O16  DOUB N N 26 
DBD C15 O17  SING N N 27 
DBD O17 H17  SING N N 28 
DBD C19 O20  SING N N 29 
DBD C19 H191 SING N N 30 
DBD C19 H192 SING N N 31 
DBD O20 C21  SING N N 32 
DBD C21 C22  SING N N 33 
DBD C21 N25  DOUB N N 34 
DBD C22 C23  DOUB Y N 35 
DBD C22 C26  SING Y N 36 
DBD C23 S24  SING N N 37 
DBD C23 C29  SING Y N 38 
DBD S24 N25  SING N N 39 
DBD S24 O30  DOUB N N 40 
DBD S24 O31  DOUB N N 41 
DBD C26 C27  DOUB Y N 42 
DBD C26 H26  SING N N 43 
DBD C27 C28  SING Y N 44 
DBD C27 H27  SING N N 45 
DBD C28 C29  DOUB Y N 46 
DBD C28 H28  SING N N 47 
DBD C29 H29  SING N N 48 
# 
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 
DBD SMILES           ACDLabs              10.04 O=C(O)C(=O)Nc1sc2c(c1C(=O)O)CCOC2COC4=NS(=O)(=O)c3ccccc34                                                                                                                              
DBD InChI            InChI                1.02b InChI=1/C18H14N2O9S2/c21-14(18(24)25)19-16-12(17(22)23)9-5-6-28-10(13(9)30-16)7-29-15-8-3-1-2-4-11(8)31(26,27)20-15/h1-4,10H,5-7H2,(H,19,21)(H,22,23)(H,24,25)/t10-/m0/s1/f/h19,22,24H 
DBD InChIKey         InChI                1.02b MDYIGSPVMWSFEZ-FXATUZQIDJ                                                                                                                                                              
DBD SMILES_CANONICAL CACTVS               3.341 OC(=O)C(=O)Nc1sc2[C@H](COC3=N[S](=O)(=O)c4ccccc34)OCCc2c1C(O)=O                                                                                                                        
DBD SMILES           CACTVS               3.341 OC(=O)C(=O)Nc1sc2[CH](COC3=N[S](=O)(=O)c4ccccc34)OCCc2c1C(O)=O                                                                                                                         
DBD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)C(=NS2(=O)=O)OC[C@H]3c4c(c(c(s4)NC(=O)C(=O)O)C(=O)O)CCO3                                                                                                                    
DBD SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)C(=NS2(=O)=O)OCC3c4c(c(c(s4)NC(=O)C(=O)O)C(=O)O)CCO3                                                                                                                        
# 
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 
DBD "SYSTEMATIC NAME" ACDLabs              10.04 "(7S)-2-[(carboxycarbonyl)amino]-7-{[(1,1-dioxido-1,2-benzisothiazol-3-yl)oxy]methyl}-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid" 
DBD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(7S)-2-(carboxycarbonylamino)-7-[(1,1-dioxo-1,2-benzothiazol-3-yl)oxymethyl]-5,7-dihydro-4H-thieno[5,4-c]pyran-3-carboxylic acid"         
# 
