data_D05
# 
_chem_comp.id                                    D05 
_chem_comp.name                                  6-(3,4-DIHYDROXYBENZYL)-3-ETHYL-1-(2,4,6-TRICHLOROPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H15 Cl3 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DIN-232305 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-28 
_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                        465.717 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     D05 
_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        2B54 
_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 
D05 N8   N8   N  0 1 Y N N 120.488 -84.937 91.864 2.484  -3.018 -0.412 N8   D05 1  
D05 C7   C7   C  0 1 Y N N 119.817 -83.751 91.759 1.176  -2.655 -0.430 C7   D05 2  
D05 N6   N6   N  0 1 Y N N 119.025 -83.237 92.723 0.780  -1.424 -0.283 N6   D05 3  
D05 C5   C5   C  0 1 Y N N 118.910 -83.947 93.872 1.647  -0.417 -0.101 C5   D05 4  
D05 C4   C4   C  0 1 Y N N 119.595 -85.178 94.053 3.023  -0.695 -0.074 C4   D05 5  
D05 C9   C9   C  0 1 Y N N 120.391 -85.652 93.022 3.449  -2.085 -0.236 C9   D05 6  
D05 N1   N1   N  0 1 Y N N 118.128 -83.685 94.994 1.519  0.926  0.075  N1   D05 7  
D05 N2   N2   N  0 1 Y N N 118.315 -84.686 95.924 2.800  1.475  0.215  N2   D05 8  
D05 C3   C3   C  0 1 Y N N 119.180 -85.581 95.397 3.692  0.526  0.131  C3   D05 9  
D05 O9   O9   O  0 1 N N N 120.950 -86.744 93.157 4.628  -2.391 -0.217 O9   D05 10 
D05 C11  C11  C  0 1 Y N N 117.159 -82.629 95.103 0.313  1.639  0.110  C11  D05 11 
D05 C16  C16  C  0 1 Y N N 115.817 -82.978 95.073 0.219  2.880  -0.507 C16  D05 12 
D05 C12  C12  C  0 1 Y N N 117.439 -81.268 95.324 -0.794 1.102  0.757  C12  D05 13 
D05 C15  C15  C  0 1 Y N N 114.787 -82.025 95.271 -0.973 3.580  -0.471 C15  D05 14 
D05 C13  C13  C  0 1 Y N N 116.430 -80.310 95.516 -1.981 1.809  0.794  C13  D05 15 
D05 C14  C14  C  0 1 Y N N 115.085 -80.667 95.503 -2.071 3.045  0.179  C14  D05 16 
D05 CL14 4CL1 CL 0 0 N N N 113.835 -79.427 95.839 -3.566 3.927  0.222  CL14 D05 17 
D05 C1   C1   C  0 1 N N N 119.483 -86.803 96.213 5.185  0.708  0.232  C1   D05 18 
D05 C2   C2   C  0 1 N N N 118.547 -87.952 95.844 5.618  0.575  1.693  C2   D05 19 
D05 C20  C20  C  0 1 N N N 119.896 -82.956 90.460 0.136  -3.726 -0.629 C20  D05 20 
D05 CL16 6CL1 CL 0 0 N N N 115.442 -84.638 94.682 1.596  3.551  -1.322 CL16 D05 21 
D05 CL12 2CL1 CL 0 0 N N N 119.039 -80.650 95.362 -0.681 -0.449 1.529  CL12 D05 22 
D05 C21  C21  C  0 1 Y N N 121.178 -82.159 90.277 -1.236 -3.103 -0.615 C21  D05 23 
D05 C22  C22  C  0 1 Y N N 121.251 -80.789 90.632 -1.928 -2.984 0.576  C22  D05 24 
D05 C23  C23  C  0 1 Y N N 122.497 -80.109 90.502 -3.187 -2.407 0.591  C23  D05 25 
D05 C24  C24  C  0 1 Y N N 123.628 -80.794 90.026 -3.758 -1.957 -0.595 C24  D05 26 
D05 C25  C25  C  0 1 Y N N 123.538 -82.150 89.639 -3.061 -2.084 -1.787 C25  D05 27 
D05 C26  C26  C  0 1 Y N N 122.309 -82.819 89.767 -1.803 -2.656 -1.794 C26  D05 28 
D05 O23  O23  O  0 1 N N N 122.655 -78.776 90.872 -3.867 -2.284 1.763  O23  D05 29 
D05 O24  O24  O  0 1 N N N 124.855 -80.144 89.995 -4.996 -1.394 -0.586 O24  D05 30 
D05 HN8  HN8  H  0 1 N N N 121.053 -85.283 91.089 2.728  -3.950 -0.526 HN8  D05 31 
D05 H15  H15  H  0 1 N N N 113.732 -82.346 95.244 -1.046 4.545  -0.949 H15  D05 32 
D05 H13  H13  H  0 1 N N N 116.700 -79.253 95.680 -2.840 1.394  1.301  H13  D05 33 
D05 H11  1H1  H  0 1 N N N 120.554 -87.100 96.126 5.457  1.696  -0.139 H11  D05 34 
D05 H12  2H1  H  0 1 N N N 119.456 -86.585 97.306 5.685  -0.055 -0.366 H12  D05 35 
D05 H21  1H2  H  0 1 N N N 118.772 -88.860 96.450 5.118  1.338  2.291  H21  D05 36 
D05 H22A 2H2  H  0 0 N N N 117.476 -87.654 95.930 5.346  -0.413 2.064  H22A D05 37 
D05 H23A 3H2  H  0 0 N N N 118.574 -88.170 94.750 6.697  0.707  1.766  H23A D05 38 
D05 H201 1H20 H  0 0 N N N 119.730 -83.627 89.585 0.301  -4.219 -1.587 H201 D05 39 
D05 H202 2H20 H  0 0 N N N 119.008 -82.288 90.361 0.210  -4.459 0.174  H202 D05 40 
D05 H22  H22  H  0 1 N N N 120.355 -80.262 91.002 -1.483 -3.334 1.496  H22  D05 41 
D05 H25  H25  H  0 1 N N N 124.418 -82.681 89.240 -3.502 -1.735 -2.709 H25  D05 42 
D05 H26  H26  H  0 1 N N N 122.231 -83.876 89.463 -1.262 -2.754 -2.724 H26  D05 43 
D05 H23  H23  H  0 1 N N N 123.485 -78.322 90.785 -4.386 -3.093 1.871  H23  D05 44 
D05 H24  H24  H  0 1 N N N 125.619 -80.607 89.673 -5.630 -2.112 -0.718 H24  D05 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 
D05 N8  C7   SING Y N 1  
D05 N8  C9   SING Y N 2  
D05 N8  HN8  SING N N 3  
D05 C7  N6   DOUB Y N 4  
D05 C7  C20  SING N N 5  
D05 N6  C5   SING Y N 6  
D05 C5  C4   DOUB Y N 7  
D05 C5  N1   SING Y N 8  
D05 C4  C9   SING Y N 9  
D05 C4  C3   SING Y N 10 
D05 C9  O9   DOUB N N 11 
D05 N1  N2   SING Y N 12 
D05 N1  C11  SING N N 13 
D05 N2  C3   DOUB Y N 14 
D05 C3  C1   SING N N 15 
D05 C11 C16  SING Y N 16 
D05 C11 C12  DOUB Y N 17 
D05 C16 C15  DOUB Y N 18 
D05 C16 CL16 SING N N 19 
D05 C12 C13  SING Y N 20 
D05 C12 CL12 SING N N 21 
D05 C15 C14  SING Y N 22 
D05 C15 H15  SING N N 23 
D05 C13 C14  DOUB Y N 24 
D05 C13 H13  SING N N 25 
D05 C14 CL14 SING N N 26 
D05 C1  C2   SING N N 27 
D05 C1  H11  SING N N 28 
D05 C1  H12  SING N N 29 
D05 C2  H21  SING N N 30 
D05 C2  H22A SING N N 31 
D05 C2  H23A SING N N 32 
D05 C20 C21  SING N N 33 
D05 C20 H201 SING N N 34 
D05 C20 H202 SING N N 35 
D05 C21 C22  DOUB Y N 36 
D05 C21 C26  SING Y N 37 
D05 C22 C23  SING Y N 38 
D05 C22 H22  SING N N 39 
D05 C23 C24  DOUB Y N 40 
D05 C23 O23  SING N N 41 
D05 C24 C25  SING Y N 42 
D05 C24 O24  SING N N 43 
D05 C25 C26  DOUB Y N 44 
D05 C25 H25  SING N N 45 
D05 C26 H26  SING N N 46 
D05 O23 H23  SING N N 47 
D05 O24 H24  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 
D05 SMILES           ACDLabs              10.04 Clc1cc(Cl)cc(Cl)c1n4nc(c2c4N=C(NC2=O)Cc3ccc(O)c(O)c3)CC                                                                                                          
D05 InChI            InChI                1.02b InChI=1/C20H15Cl3N4O3/c1-2-13-17-19(27(26-13)18-11(22)7-10(21)8-12(18)23)24-16(25-20(17)30)6-9-3-4-14(28)15(29)5-9/h3-5,7-8,28-29H,2,6H2,1H3,(H,24,25,30)/f/h25H 
D05 InChIKey         InChI                1.02b OPRAIFVPXXVXDL-LNNLXFCOCE                                                                                                                                        
D05 SMILES_CANONICAL CACTVS               3.341 CCc1nn(c2N=C(Cc3ccc(O)c(O)c3)NC(=O)c12)c4c(Cl)cc(Cl)cc4Cl                                                                                                        
D05 SMILES           CACTVS               3.341 CCc1nn(c2N=C(Cc3ccc(O)c(O)c3)NC(=O)c12)c4c(Cl)cc(Cl)cc4Cl                                                                                                        
D05 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1c2c(n(n1)c3c(cc(cc3Cl)Cl)Cl)N=C(NC2=O)Cc4ccc(c(c4)O)O                                                                                                        
D05 SMILES           "OpenEye OEToolkits" 1.5.0 CCc1c2c(n(n1)c3c(cc(cc3Cl)Cl)Cl)N=C(NC2=O)Cc4ccc(c(c4)O)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 
D05 "SYSTEMATIC NAME" ACDLabs              10.04 6-(3,4-dihydroxybenzyl)-3-ethyl-1-(2,4,6-trichlorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
D05 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-[(3,4-dihydroxyphenyl)methyl]-3-ethyl-1-(2,4,6-trichlorophenyl)-5H-pyrazolo[4,5-e]pyrimidin-4-one     
# 
