data_NH8
# 
_chem_comp.id                                    NH8 
_chem_comp.name                                  3-{2-[(S)-(4-cyanophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl]-5-nitro-1-benzofuran-7-yl}benzonitrile 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H17 N5 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-02-26 
_chem_comp.pdbx_modified_date                    2009-02-20 
_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                        475.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     NH8 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2ZIS 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
NH8 C2  C2  C 0  1 Y N N 72.325 80.627 3.180  -1.659 3.399  2.392  C2  NH8 1  
NH8 C7  C7  C 0  1 N N S 70.040 80.209 0.336  -2.339 -0.035 1.342  C7  NH8 2  
NH8 C10 C10 C 0  1 Y N N 68.590 79.856 0.594  -0.988 -0.614 1.008  C10 NH8 3  
NH8 C11 C11 C 0  1 Y N N 67.566 80.517 1.218  -0.595 -1.862 1.299  C11 NH8 4  
NH8 C12 C12 C 0  1 Y N N 66.488 79.606 1.336  0.778  -1.986 0.793  C12 NH8 5  
NH8 C13 C13 C 0  1 Y N N 65.231 79.610 1.990  1.723  -3.012 0.783  C13 NH8 6  
NH8 C14 C14 C 0  1 Y N N 64.441 78.462 1.855  2.959  -2.801 0.211  C14 NH8 7  
NH8 C15 C15 C 0  1 Y N N 64.819 77.335 1.055  3.270  -1.576 -0.355 C15 NH8 8  
NH8 C16 C16 C 0  1 Y N N 66.031 77.330 0.356  2.341  -0.541 -0.354 C16 NH8 9  
NH8 C21 C21 C 0  1 Y N N 70.534 79.110 -0.560 -3.291 -0.292 0.202  C21 NH8 10 
NH8 C22 C22 C 0  1 Y N N 71.023 77.917 -0.021 -2.916 0.021  -1.092 C22 NH8 11 
NH8 C24 C24 C 0  1 Y N N 71.326 77.065 -2.271 -5.041 -0.765 -1.892 C24 NH8 12 
NH8 C27 C27 C 0  1 N N N 71.718 75.986 -3.116 -5.946 -1.008 -2.975 C27 NH8 13 
NH8 C31 C31 C 0  1 Y N N 66.452 76.252 -0.570 2.684  0.768  -0.961 C31 NH8 14 
NH8 C32 C32 C 0  1 Y N N 65.616 75.833 -1.623 1.815  1.362  -1.877 C32 NH8 15 
NH8 C33 C33 C 0  1 Y N N 66.002 74.833 -2.509 2.131  2.581  -2.444 C33 NH8 16 
NH8 C34 C34 C 0  1 Y N N 67.250 74.228 -2.355 3.308  3.220  -2.110 C34 NH8 17 
NH8 C35 C35 C 0  1 Y N N 68.116 74.618 -1.315 4.187  2.636  -1.194 C35 NH8 18 
NH8 N1  N1  N 0  1 Y N N 72.067 80.700 1.842  -1.516 2.068  2.568  N1  NH8 19 
NH8 N3  N3  N 0  1 Y N N 71.298 80.202 3.861  -2.399 3.605  1.337  N3  NH8 20 
NH8 C4  C4  C 0  1 Y N N 70.375 80.003 2.939  -2.751 2.424  0.807  C4  NH8 21 
NH8 C5  C5  C 0  1 Y N N 70.767 80.287 1.664  -2.208 1.450  1.562  C5  NH8 22 
NH8 C6  C6  C 0  1 N N N 73.049 81.113 0.810  -0.760 1.408  3.635  C6  NH8 23 
NH8 O8  O8  O 0  1 N N N 70.139 81.477 -0.300 -2.841 -0.651 2.530  O8  NH8 24 
NH8 O9  O9  O 0  1 Y N N 68.140 78.640 0.151  -0.004 0.044  0.370  O9  NH8 25 
NH8 C17 C17 C 0  1 Y N N 66.867 78.470 0.594  1.082  -0.740 0.223  C17 NH8 26 
NH8 C23 C23 C 0  1 Y N N 71.424 76.895 -0.884 -3.783 -0.211 -2.140 C23 NH8 27 
NH8 C25 C25 C 0  1 Y N N 70.835 78.271 -2.803 -5.410 -1.084 -0.584 C25 NH8 28 
NH8 C26 C26 C 0  1 Y N N 70.432 79.297 -1.942 -4.534 -0.846 0.454  C26 NH8 29 
NH8 N28 N28 N 0  1 N N N 71.985 75.090 -3.778 -6.664 -1.201 -3.833 N28 NH8 30 
NH8 C36 C36 C 0  1 Y N N 67.710 75.628 -0.429 3.869  1.408  -0.615 C36 NH8 31 
NH8 C37 C37 C 0  1 N N N 69.404 73.985 -1.181 5.408  3.299  -0.848 C37 NH8 32 
NH8 N38 N38 N 0  1 N N N 70.440 73.491 -1.108 6.377  3.824  -0.573 N38 NH8 33 
NH8 N41 N41 N 1  1 N N N 63.159 78.412 2.580  3.961  -3.890 0.201  N41 NH8 34 
NH8 O42 O42 O -1 1 N N N 62.566 79.488 2.793  3.692  -4.969 0.698  O42 NH8 35 
NH8 O43 O43 O 0  1 N N N 62.703 77.308 2.955  5.055  -3.708 -0.303 O43 NH8 36 
NH8 H2  H2  H 0  1 N N N 73.273 80.891 3.625  -1.236 4.166  3.023  H2  NH8 37 
NH8 H11 H11 H 0  1 N N N 67.578 81.542 1.557  -1.171 -2.622 1.804  H11 NH8 38 
NH8 H13 H13 H 0  1 N N N 64.897 80.460 2.567  1.487  -3.970 1.223  H13 NH8 39 
NH8 H15 H15 H 0  1 N N N 64.162 76.481 0.991  4.242  -1.422 -0.800 H15 NH8 40 
NH8 H22 H22 H 0  1 N N N 71.090 77.787 1.049  -1.943 0.449  -1.283 H22 NH8 41 
NH8 H32 H32 H 0  1 N N N 64.650 76.300 -1.746 0.892  0.867  -2.143 H32 NH8 42 
NH8 H33 H33 H 0  1 N N N 65.343 74.528 -3.308 1.455  3.036  -3.152 H33 NH8 43 
NH8 H34 H34 H 0  1 N N N 67.555 73.452 -3.041 3.550  4.173  -2.557 H34 NH8 44 
NH8 H4  H4  H 0  1 N N N 69.385 79.643 3.176  -3.362 2.280  -0.072 H4  NH8 45 
NH8 H6  H6  H 0  1 N N N 72.541 81.215 -0.160 -1.415 1.231  4.488  H6  NH8 46 
NH8 H6A H6A H 0  1 N N N 73.495 82.078 1.094  -0.371 0.457  3.271  H6A NH8 47 
NH8 H6B H6B H 0  1 N N N 73.840 80.352 0.731  0.070  2.046  3.941  H6B NH8 48 
NH8 HO8 HO8 H 0  1 N N N 70.161 82.161 0.359  -2.950 -1.609 2.460  HO8 NH8 49 
NH8 H23 H23 H 0  1 N N N 71.811 75.971 -0.481 -3.490 0.035  -3.150 H23 NH8 50 
NH8 H25 H25 H 0  1 N N N 70.769 78.404 -3.873 -6.379 -1.517 -0.385 H25 NH8 51 
NH8 H26 H26 H 0  1 N N N 70.046 80.224 -2.340 -4.818 -1.092 1.467  H26 NH8 52 
NH8 H36 H36 H 0  1 N N N 68.369 75.932 0.371  4.543  0.954  0.097  H36 NH8 53 
# 
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 
NH8 C2  N1  SING Y N 1  
NH8 C2  N3  DOUB Y N 2  
NH8 C7  C10 SING N N 3  
NH8 C7  C21 SING N N 4  
NH8 C7  C5  SING N N 5  
NH8 C7  O8  SING N N 6  
NH8 C10 C11 DOUB N N 7  
NH8 C10 O9  SING Y N 8  
NH8 C11 C12 SING Y N 9  
NH8 C12 C13 DOUB Y N 10 
NH8 C12 C17 SING N N 11 
NH8 C13 C14 SING Y N 12 
NH8 C14 C15 DOUB Y N 13 
NH8 C14 N41 SING Y N 14 
NH8 C15 C16 SING N N 15 
NH8 C16 C31 SING Y N 16 
NH8 C16 C17 DOUB N N 17 
NH8 C21 C22 DOUB Y N 18 
NH8 C21 C26 SING N N 19 
NH8 C22 C23 SING N N 20 
NH8 C24 C27 SING Y N 21 
NH8 C24 C23 DOUB Y N 22 
NH8 C24 C25 SING Y N 23 
NH8 C27 N28 TRIP Y N 24 
NH8 C31 C32 DOUB N N 25 
NH8 C31 C36 SING N N 26 
NH8 C32 C33 SING Y N 27 
NH8 C33 C34 DOUB Y N 28 
NH8 C34 C35 SING N N 29 
NH8 C35 C36 DOUB Y N 30 
NH8 C35 C37 SING Y N 31 
NH8 N1  C5  SING Y N 32 
NH8 N1  C6  SING N N 33 
NH8 N3  C4  SING Y N 34 
NH8 C4  C5  DOUB N N 35 
NH8 O9  C17 SING Y N 36 
NH8 C25 C26 DOUB N N 37 
NH8 C37 N38 TRIP Y N 38 
NH8 N41 O42 SING N N 39 
NH8 N41 O43 DOUB Y N 40 
NH8 C2  H2  SING N N 41 
NH8 C11 H11 SING Y N 42 
NH8 C13 H13 SING Y N 43 
NH8 C15 H15 SING N N 44 
NH8 C22 H22 SING N N 45 
NH8 C32 H32 SING N N 46 
NH8 C33 H33 SING N N 47 
NH8 C34 H34 SING N N 48 
NH8 C4  H4  SING Y N 49 
NH8 C6  H6  SING N N 50 
NH8 C6  H6A SING Y N 51 
NH8 C6  H6B SING N N 52 
NH8 O8  HO8 SING N N 53 
NH8 C23 H23 SING N N 54 
NH8 C25 H25 SING N N 55 
NH8 C26 H26 SING N N 56 
NH8 C36 H36 SING N N 57 
# 
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 
NH8 SMILES           ACDLabs              10.04 N#Cc1ccc(cc1)C(O)(c2cncn2C)c4oc3c(cc(cc3c4)[N+]([O-])=O)c5cccc(C#N)c5                                                                                                
NH8 InChI            InChI                1.02b InChI=1/C27H17N5O4/c1-31-16-30-15-24(31)27(33,21-7-5-17(13-28)6-8-21)25-11-20-10-22(32(34)35)12-23(26(20)36-25)19-4-2-3-18(9-19)14-29/h2-12,15-16,33H,1H3/t27-/m0/s1 
NH8 InChIKey         InChI                1.02b NYEPLLLECMESPU-MHZLTWQEBO                                                                                                                                            
NH8 SMILES_CANONICAL CACTVS               3.341 Cn1cncc1[C@](O)(c2oc3c(c2)cc(cc3c4cccc(c4)C#N)[N+]([O-])=O)c5ccc(cc5)C#N                                                                                             
NH8 SMILES           CACTVS               3.341 Cn1cncc1[C](O)(c2oc3c(c2)cc(cc3c4cccc(c4)C#N)[N+]([O-])=O)c5ccc(cc5)C#N                                                                                              
NH8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1cncc1[C@@](c2ccc(cc2)C#N)(c3cc4cc(cc(c4o3)c5cccc(c5)C#N)[N+](=O)[O-])O                                                                                            
NH8 SMILES           "OpenEye OEToolkits" 1.5.0 Cn1cncc1C(c2ccc(cc2)C#N)(c3cc4cc(cc(c4o3)c5cccc(c5)C#N)[N+](=O)[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 
NH8 "SYSTEMATIC NAME" ACDLabs              10.04 3-{2-[(S)-(4-cyanophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl]-5-nitro-1-benzofuran-7-yl}benzonitrile 
NH8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(S)-[7-(3-cyanophenyl)-5-nitro-1-benzofuran-2-yl]-hydroxy-(3-methylimidazol-4-yl)methyl]benzonitrile     
# 
