data_AZ4
# 
_chem_comp.id                                    AZ4 
_chem_comp.name                                  "N-[(2S)-4-(5-fluoropyrimidin-2-yl)-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)butan-2-yl]-N-hydroxyformamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H23 F4 N7 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-12-20 
_chem_comp.pdbx_modified_date                    2014-02-28 
_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                        537.488 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AZ4 
_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        4JP4 
_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 
AZ4 C1  C1  C 0 1 N N N 28.391 11.529 19.722 4.121   2.250  1.212  C1  AZ4 1  
AZ4 C2  C2  C 0 1 N N S 28.912 13.492 21.154 4.089   0.657  -0.632 C2  AZ4 2  
AZ4 C3  C3  C 0 1 N N N 30.338 13.749 21.571 5.323   -0.100 -0.134 C3  AZ4 3  
AZ4 O4  O4  O 0 1 N N N 25.816 15.953 21.299 1.301   0.534  -2.248 O4  AZ4 4  
AZ4 O5  O5  O 0 1 N N N 22.459 13.090 12.172 -7.981  -0.839 -0.037 O5  AZ4 5  
AZ4 N6  N6  N 0 1 Y N N 24.564 14.502 14.832 -4.568  -1.897 -0.339 N6  AZ4 6  
AZ4 C7  C7  C 0 1 Y N N 33.239 10.490 19.037 9.953   -1.538 0.631  C7  AZ4 7  
AZ4 C8  C8  C 0 1 Y N N 32.372 9.805  19.853 9.454   -0.450 1.334  C8  AZ4 8  
AZ4 C9  C9  C 0 1 N N N 28.154 14.800 21.069 2.825   -0.047 -0.137 C9  AZ4 9  
AZ4 C10 C10 C 0 1 N N N 25.879 15.283 18.588 -0.551  0.304  1.031  C10 AZ4 10 
AZ4 C11 C11 C 0 1 N N N 25.896 14.812 17.163 -2.062  0.415  0.807  C11 AZ4 11 
AZ4 C12 C12 C 0 1 N N N 24.885 12.642 17.923 -1.970  -1.087 -1.095 C12 AZ4 12 
AZ4 C13 C13 C 0 1 N N N 25.023 13.118 19.346 -0.454  -1.260 -0.948 C13 AZ4 13 
AZ4 C14 C14 C 0 1 Y N N 24.304 13.588 15.775 -3.946  -0.839 0.160  C14 AZ4 14 
AZ4 C15 C15 C 0 1 Y N N 23.970 14.349 13.644 -5.888  -1.931 -0.419 C15 AZ4 15 
AZ4 C16 C16 C 0 1 Y N N 23.119 13.311 13.369 -6.622  -0.839 0.029  C16 AZ4 16 
AZ4 C19 C19 C 0 1 Y N N 22.909 12.410 14.385 -5.935  0.253  0.546  C19 AZ4 17 
AZ4 O1  O1  O 0 1 N N N 29.417 13.378 18.771 4.142   3.122  -1.017 O1  AZ4 18 
AZ4 N1  N1  N 0 1 N N N 28.938 12.735 19.916 4.118   2.029  -0.117 N1  AZ4 19 
AZ4 O2  O2  O 0 1 N N N 28.450 10.919 18.669 4.105   1.314  1.983  O2  AZ4 20 
AZ4 C4  C4  C 0 1 N N N 31.028 12.445 21.953 6.583   0.530  -0.730 C4  AZ4 21 
AZ4 C5  C5  C 0 1 Y N N 31.810 11.754 20.880 7.797   -0.215 -0.240 C5  AZ4 22 
AZ4 N2  N2  N 0 1 Y N N 32.610 12.523 20.118 8.242   -1.243 -0.934 N2  AZ4 23 
AZ4 C6  C6  C 0 1 Y N N 33.322 11.848 19.205 9.305   -1.922 -0.536 C6  AZ4 24 
AZ4 F1  F1  F 0 1 N N N 33.974 9.847  18.102 11.045  -2.203 1.067  F1  AZ4 25 
AZ4 N3  N3  N 0 1 Y N N 31.645 10.424 20.793 8.385   0.179  0.872  N3  AZ4 26 
AZ4 S1  S1  S 0 1 N N N 26.382 14.635 21.044 1.365   0.762  -0.847 S1  AZ4 27 
AZ4 O3  O3  O 0 1 N N N 25.996 13.564 21.941 1.207   2.067  -0.309 O3  AZ4 28 
AZ4 N4  N4  N 0 1 N N N 26.075 14.135 19.480 0.082   -0.090 -0.237 N4  AZ4 29 
AZ4 N5  N5  N 0 1 N N N 24.911 13.768 17.011 -2.561  -0.839 0.227  N5  AZ4 30 
AZ4 C17 C17 C 0 1 N N N 22.651 14.163 11.275 -8.653  0.326  0.446  C17 AZ4 31 
AZ4 C18 C18 C 0 1 N N N 21.705 13.908 10.122 -10.165 0.142  0.291  C18 AZ4 32 
AZ4 F2  F2  F 0 1 N N N 20.413 13.925 10.533 -10.577 -0.974 1.026  F2  AZ4 33 
AZ4 F3  F3  F 0 1 N N N 21.904 14.821 9.136  -10.823 1.282  0.764  F3  AZ4 34 
AZ4 F4  F4  F 0 1 N N N 21.888 12.684 9.564  -10.475 -0.049 -1.060 F4  AZ4 35 
AZ4 N7  N7  N 0 1 Y N N 23.491 12.535 15.578 -4.613  0.219  0.595  N7  AZ4 36 
AZ4 H1  H1  H 0 1 N N N 27.867 11.070 20.547 4.141   3.261  1.591  H1  AZ4 37 
AZ4 H2  H2  H 0 1 N N N 28.437 12.877 21.933 4.091   0.677  -1.721 H2  AZ4 38 
AZ4 H3  H3  H 0 1 N N N 30.881 14.214 20.735 5.368   -0.044 0.954  H3  AZ4 39 
AZ4 H4  H4  H 0 1 N N N 30.345 14.429 22.436 5.257   -1.143 -0.442 H4  AZ4 40 
AZ4 H5  H5  H 0 1 N N N 32.273 8.736  19.733 9.931   -0.122 2.246  H5  AZ4 41 
AZ4 H6  H6  H 0 1 N N N 28.463 15.315 20.148 2.847   -1.093 -0.444 H6  AZ4 42 
AZ4 H7  H7  H 0 1 N N N 28.428 15.412 21.941 2.779   0.010  0.951  H7  AZ4 43 
AZ4 H8  H8  H 0 1 N N N 26.688 16.012 18.744 -0.157  1.268  1.353  H8  AZ4 44 
AZ4 H9  H9  H 0 1 N N N 24.911 15.757 18.807 -0.345  -0.448 1.793  H9  AZ4 45 
AZ4 H10 H10 H 0 1 N N N 26.893 14.420 16.914 -2.559  0.598  1.760  H10 AZ4 46 
AZ4 H11 H11 H 0 1 N N N 25.654 15.650 16.493 -2.270  1.239  0.124  H11 AZ4 47 
AZ4 H12 H12 H 0 1 N N N 23.931 12.106 17.811 -2.178  -0.243 -1.751 H12 AZ4 48 
AZ4 H13 H13 H 0 1 N N N 25.717 11.963 17.685 -2.400  -1.994 -1.521 H13 AZ4 49 
AZ4 H14 H14 H 0 1 N N N 24.065 13.551 19.671 -0.242  -2.164 -0.378 H14 AZ4 50 
AZ4 H15 H15 H 0 1 N N N 25.274 12.259 19.986 0.003   -1.330 -1.935 H15 AZ4 51 
AZ4 H16 H16 H 0 1 N N N 24.169 15.074 12.869 -6.389  -2.797 -0.827 H16 AZ4 52 
AZ4 H17 H17 H 0 1 N N N 22.250 11.572 14.211 -6.473  1.119  0.903  H17 AZ4 53 
AZ4 H18 H18 H 0 1 N N N 29.329 12.800 18.022 4.137   2.864  -1.949 H18 AZ4 54 
AZ4 H19 H19 H 0 1 N N N 30.252 11.747 22.300 6.537   0.475  -1.818 H19 AZ4 55 
AZ4 H20 H20 H 0 1 N N N 31.720 12.665 22.780 6.648   1.574  -0.422 H20 AZ4 56 
AZ4 H21 H21 H 0 1 N N N 33.996 12.403 18.569 9.664   -2.764 -1.110 H21 AZ4 57 
AZ4 H22 H22 H 0 1 N N N 23.692 14.184 10.920 -8.412  0.475  1.498  H22 AZ4 58 
AZ4 H23 H23 H 0 1 N N N 22.411 15.119 11.764 -8.332  1.195  -0.127 H23 AZ4 59 
# 
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 
AZ4 F3  C18 SING N N 1  
AZ4 F4  C18 SING N N 2  
AZ4 C18 F2  SING N N 3  
AZ4 C18 C17 SING N N 4  
AZ4 C17 O5  SING N N 5  
AZ4 O5  C16 SING N N 6  
AZ4 C16 C15 DOUB Y N 7  
AZ4 C16 C19 SING Y N 8  
AZ4 C15 N6  SING Y N 9  
AZ4 C19 N7  DOUB Y N 10 
AZ4 N6  C14 DOUB Y N 11 
AZ4 N7  C14 SING Y N 12 
AZ4 C14 N5  SING N N 13 
AZ4 N5  C11 SING N N 14 
AZ4 N5  C12 SING N N 15 
AZ4 C11 C10 SING N N 16 
AZ4 C12 C13 SING N N 17 
AZ4 F1  C7  SING N N 18 
AZ4 C10 N4  SING N N 19 
AZ4 O2  C1  DOUB N N 20 
AZ4 O1  N1  SING N N 21 
AZ4 C7  C6  DOUB Y N 22 
AZ4 C7  C8  SING Y N 23 
AZ4 C6  N2  SING Y N 24 
AZ4 C13 N4  SING N N 25 
AZ4 N4  S1  SING N N 26 
AZ4 C1  N1  SING N N 27 
AZ4 C8  N3  DOUB Y N 28 
AZ4 N1  C2  SING N N 29 
AZ4 N2  C5  DOUB Y N 30 
AZ4 N3  C5  SING Y N 31 
AZ4 C5  C4  SING N N 32 
AZ4 S1  C9  SING N N 33 
AZ4 S1  O4  DOUB N N 34 
AZ4 S1  O3  DOUB N N 35 
AZ4 C9  C2  SING N N 36 
AZ4 C2  C3  SING N N 37 
AZ4 C3  C4  SING N N 38 
AZ4 C1  H1  SING N N 39 
AZ4 C2  H2  SING N N 40 
AZ4 C3  H3  SING N N 41 
AZ4 C3  H4  SING N N 42 
AZ4 C8  H5  SING N N 43 
AZ4 C9  H6  SING N N 44 
AZ4 C9  H7  SING N N 45 
AZ4 C10 H8  SING N N 46 
AZ4 C10 H9  SING N N 47 
AZ4 C11 H10 SING N N 48 
AZ4 C11 H11 SING N N 49 
AZ4 C12 H12 SING N N 50 
AZ4 C12 H13 SING N N 51 
AZ4 C13 H14 SING N N 52 
AZ4 C13 H15 SING N N 53 
AZ4 C15 H16 SING N N 54 
AZ4 C19 H17 SING N N 55 
AZ4 O1  H18 SING N N 56 
AZ4 C4  H19 SING N N 57 
AZ4 C4  H20 SING N N 58 
AZ4 C6  H21 SING N N 59 
AZ4 C17 H22 SING N N 60 
AZ4 C17 H23 SING N N 61 
# 
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 
AZ4 SMILES           ACDLabs              12.01 "O=S(=O)(N2CCN(c1ncc(OCC(F)(F)F)cn1)CC2)CC(N(O)C=O)CCc3ncc(F)cn3"                                                                                                            
AZ4 InChI            InChI                1.03  "InChI=1S/C19H23F4N7O5S/c20-14-7-24-17(25-8-14)2-1-15(30(32)13-31)11-36(33,34)29-5-3-28(4-6-29)18-26-9-16(10-27-18)35-12-19(21,22)23/h7-10,13,15,32H,1-6,11-12H2/t15-/m0/s1" 
AZ4 InChIKey         InChI                1.03  BEMGDWJRAZUSRP-HNNXBMFYSA-N                                                                                                                                                  
AZ4 SMILES_CANONICAL CACTVS               3.385 "ON(C=O)[C@@H](CCc1ncc(F)cn1)C[S](=O)(=O)N2CCN(CC2)c3ncc(OCC(F)(F)F)cn3"                                                                                                     
AZ4 SMILES           CACTVS               3.385 "ON(C=O)[CH](CCc1ncc(F)cn1)C[S](=O)(=O)N2CCN(CC2)c3ncc(OCC(F)(F)F)cn3"                                                                                                       
AZ4 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1c(cnc(n1)N2CCN(CC2)S(=O)(=O)C[C@H](CCc3ncc(cn3)F)N(C=O)O)OCC(F)(F)F"                                                                                                      
AZ4 SMILES           "OpenEye OEToolkits" 1.7.6 "c1c(cnc(n1)N2CCN(CC2)S(=O)(=O)CC(CCc3ncc(cn3)F)N(C=O)O)OCC(F)(F)F"                                                                                                          
# 
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 
AZ4 "SYSTEMATIC NAME" ACDLabs              12.01 "N-[(2S)-4-(5-fluoropyrimidin-2-yl)-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)butan-2-yl]-N-hydroxyformamide"             
AZ4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[(2S)-4-(5-fluoranylpyrimidin-2-yl)-1-[4-[5-[2,2,2-tris(fluoranyl)ethoxy]pyrimidin-2-yl]piperazin-1-yl]sulfonyl-butan-2-yl]-N-oxidanyl-methanamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
AZ4 "Create component" 2013-12-20 PDBJ 
AZ4 "Initial release"  2014-03-05 RCSB 
# 
