data_AK4
# 
_chem_comp.id                                    AK4 
_chem_comp.name                                  "(7-{[2-(2-{[(3-chlorophenyl)carbamoyl]amino}-1,3-thiazol-5-yl)ethyl]amino}-1H-pyrazolo[4,3-d]pyrimidin-1-yl)acetic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H17 Cl N8 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-05-12 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        472.908 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AK4 
_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        3D2K 
_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 
AK4 C30  C30  C  0 1 N N N 22.680 15.402 25.047 6.236   -2.339 0.004  C30  AK4 1  
AK4 C28  C28  C  0 1 Y N N 25.544 17.928 22.405 8.302   1.498  -0.412 C28  AK4 2  
AK4 C24  C24  C  0 1 Y N N 16.465 5.382  19.332 -6.951  -0.113 -0.307 C24  AK4 3  
AK4 C23  C23  C  0 1 Y N N 16.018 4.307  20.108 -8.133  0.255  -0.924 C23  AK4 4  
AK4 C22  C22  C  0 1 Y N N 16.272 4.279  21.476 -9.119  0.903  -0.201 C22  AK4 5  
AK4 C17  C17  C  0 1 Y N N 24.452 16.192 19.393 5.205   3.246  0.531  C17  AK4 6  
AK4 C20  C20  C  0 1 Y N N 17.419 6.393  21.287 -7.748  0.819  1.761  C20  AK4 7  
AK4 C15  C15  C  0 1 Y N N 24.975 17.021 21.483 7.002   1.956  -0.111 C15  AK4 8  
AK4 C13  C13  C  0 1 Y N N 23.732 14.986 21.305 4.751   1.089  -0.159 C13  AK4 9  
AK4 C14  C14  C  0 1 Y N N 24.351 15.972 22.070 6.122   0.892  -0.378 C14  AK4 10 
AK4 C10  C10  C  0 1 N N N 18.244 8.619  19.523 -4.406  -0.197 0.972  C10  AK4 11 
AK4 C8   C8   C  0 1 Y N N 19.225 10.703 18.865 -2.082  -0.647 0.829  C8   AK4 12 
AK4 C4   C4   C  0 1 Y N N 20.347 12.499 19.710 0.189   -0.803 -0.108 C4   AK4 13 
AK4 C6   C6   C  0 1 Y N N 20.103 12.669 18.394 -0.744  -0.303 -0.921 C6   AK4 14 
AK4 C3   C3   C  0 1 N N N 21.087 13.491 20.587 1.645   -0.998 -0.446 C3   AK4 15 
AK4 C2   C2   C  0 1 N N N 22.417 12.883 21.057 2.427   0.264  -0.077 C2   AK4 16 
AK4 O32  O32  O  0 1 N N N 22.422 15.392 26.280 5.794   -3.600 -0.119 O32  AK4 17 
AK4 O31  O31  O  0 1 N N N 21.814 15.299 24.151 6.510   -1.899 1.096  O31  AK4 18 
AK4 C29  C29  C  0 1 N N N 24.129 15.528 24.653 6.396   -1.473 -1.219 C29  AK4 19 
AK4 N26  N26  N  0 1 Y N N 24.470 16.199 23.385 6.888   -0.152 -0.821 N26  AK4 20 
AK4 N27  N27  N  0 1 Y N N 25.209 17.372 23.599 8.226   0.265  -0.827 N27  AK4 21 
AK4 N18  N18  N  0 1 Y N N 23.813 15.149 19.954 4.345   2.271  0.292  N18  AK4 22 
AK4 N16  N16  N  0 1 Y N N 25.042 17.138 20.141 6.497   3.112  0.341  N16  AK4 23 
AK4 N1   N1   N  0 1 N N N 23.073 13.917 21.857 3.842   0.075  -0.405 N1   AK4 24 
AK4 S5   S5   S  0 1 Y N N 19.800 11.142 20.271 -0.578  -1.195 1.429  S5   AK4 25 
AK4 N7   N7   N  0 1 Y N N 19.478 11.651 17.953 -1.951  -0.232 -0.392 N7   AK4 26 
AK4 N9   N9   N  0 1 N N N 18.578 9.545  18.601 -3.274  -0.653 1.545  N9   AK4 27 
AK4 O12  O12  O  0 1 N N N 18.500 8.770  20.710 -4.384  0.220  -0.170 O12  AK4 28 
AK4 N11  N11  N  0 1 N N N 17.608 7.515  19.101 -5.561  -0.202 1.666  N11  AK4 29 
AK4 C19  C19  C  0 1 Y N N 17.170 6.438  19.914 -6.756  0.169  1.039  C19  AK4 30 
AK4 CL25 CL25 CL 0 0 N N N 15.106 2.949  19.357 -8.379  -0.096 -2.606 CL25 AK4 31 
AK4 C21  C21  C  0 1 Y N N 16.977 5.325  22.065 -8.926  1.184  1.139  C21  AK4 32 
AK4 H28  H28  H  0 1 N N N 26.102 18.832 22.211 9.210   2.076  -0.320 H28  AK4 33 
AK4 H24  H24  H  0 1 N N N 16.263 5.395  18.271 -6.183  -0.622 -0.870 H24  AK4 34 
AK4 H22  H22  H  0 1 N N N 15.925 3.451  22.077 -10.041 1.189  -0.684 H22  AK4 35 
AK4 H17  H17  H  0 1 N N N 24.491 16.270 18.317 4.830   4.191  0.897  H17  AK4 36 
AK4 H20  H20  H  0 1 N N N 17.964 7.200  21.754 -7.599  1.039  2.807  H20  AK4 37 
AK4 H6   H6   H  0 1 N N N 20.391 13.530 17.809 -0.529  0.017  -1.929 H6   AK4 38 
AK4 H3   H3   H  0 1 N N N 21.288 14.406 20.011 2.038   -1.846 0.115  H3   AK4 39 
AK4 H3A  H3A  H  0 1 N N N 20.468 13.731 21.464 1.747   -1.189 -1.514 H3A  AK4 40 
AK4 H2   H2   H  0 1 N N N 22.239 11.981 21.660 2.034   1.113  -0.638 H2   AK4 41 
AK4 H2A  H2A  H  0 1 N N N 23.042 12.578 20.205 2.324   0.456  0.991  H2A  AK4 42 
AK4 HO32 HO32 H  0 0 N N N 21.485 15.296 26.407 5.711   -4.118 0.693  HO32 AK4 43 
AK4 H29  H29  H  0 1 N N N 24.619 16.105 25.451 7.109   -1.936 -1.901 H29  AK4 44 
AK4 H29A H29A H  0 0 N N N 24.459 14.489 24.505 5.432   -1.367 -1.718 H29A AK4 45 
AK4 HN1  HN1  H  0 1 N N N 23.764 13.433 22.394 4.142   -0.761 -0.796 HN1  AK4 46 
AK4 HN9  HN9  H  0 1 N N N 18.328 9.361  17.650 -3.291  -0.985 2.456  HN9  AK4 47 
AK4 HN11 HN11 H  0 0 N N N 17.426 7.445  18.120 -5.565  -0.463 2.600  HN11 AK4 48 
AK4 H21  H21  H  0 1 N N N 17.181 5.309  23.125 -9.698  1.691  1.700  H21  AK4 49 
# 
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 
AK4 O31  C30  DOUB N N 1  
AK4 C29  C30  SING N N 2  
AK4 C30  O32  SING N N 3  
AK4 C15  C28  SING Y N 4  
AK4 C28  N27  DOUB Y N 5  
AK4 C28  H28  SING N N 6  
AK4 C24  C19  DOUB Y N 7  
AK4 C24  C23  SING Y N 8  
AK4 C24  H24  SING N N 9  
AK4 CL25 C23  SING N N 10 
AK4 C23  C22  DOUB Y N 11 
AK4 C22  C21  SING Y N 12 
AK4 C22  H22  SING N N 13 
AK4 C17  N18  DOUB Y N 14 
AK4 C17  N16  SING Y N 15 
AK4 C17  H17  SING N N 16 
AK4 C19  C20  SING Y N 17 
AK4 C20  C21  DOUB Y N 18 
AK4 C20  H20  SING N N 19 
AK4 N16  C15  DOUB Y N 20 
AK4 C15  C14  SING Y N 21 
AK4 N18  C13  SING Y N 22 
AK4 C13  N1   SING N N 23 
AK4 C13  C14  DOUB Y N 24 
AK4 C14  N26  SING Y N 25 
AK4 N9   C10  SING N N 26 
AK4 N11  C10  SING N N 27 
AK4 C10  O12  DOUB N N 28 
AK4 N7   C8   DOUB Y N 29 
AK4 N9   C8   SING N N 30 
AK4 C8   S5   SING Y N 31 
AK4 C6   C4   DOUB Y N 32 
AK4 C4   S5   SING Y N 33 
AK4 C4   C3   SING N N 34 
AK4 N7   C6   SING Y N 35 
AK4 C6   H6   SING N N 36 
AK4 C3   C2   SING N N 37 
AK4 C3   H3   SING N N 38 
AK4 C3   H3A  SING N N 39 
AK4 C2   N1   SING N N 40 
AK4 C2   H2   SING N N 41 
AK4 C2   H2A  SING N N 42 
AK4 O32  HO32 SING N N 43 
AK4 N26  C29  SING N N 44 
AK4 C29  H29  SING N N 45 
AK4 C29  H29A SING N N 46 
AK4 N26  N27  SING Y N 47 
AK4 N1   HN1  SING N N 48 
AK4 N9   HN9  SING N N 49 
AK4 N11  C19  SING N N 50 
AK4 N11  HN11 SING N N 51 
AK4 C21  H21  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 
AK4 SMILES           ACDLabs              10.04 "O=C(Nc1ncc(s1)CCNc3ncnc2c3n(nc2)CC(=O)O)Nc4cccc(Cl)c4"                                                                                                                                 
AK4 SMILES_CANONICAL CACTVS               3.341 "OC(=O)Cn1ncc2ncnc(NCCc3sc(NC(=O)Nc4cccc(Cl)c4)nc3)c12"                                                                                                                                 
AK4 SMILES           CACTVS               3.341 "OC(=O)Cn1ncc2ncnc(NCCc3sc(NC(=O)Nc4cccc(Cl)c4)nc3)c12"                                                                                                                                 
AK4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(cc(c1)Cl)NC(=O)Nc2ncc(s2)CCNc3c4c(cnn4CC(=O)O)ncn3"                                                                                                                               
AK4 SMILES           "OpenEye OEToolkits" 1.5.0 "c1cc(cc(c1)Cl)NC(=O)Nc2ncc(s2)CCNc3c4c(cnn4CC(=O)O)ncn3"                                                                                                                               
AK4 InChI            InChI                1.03  "InChI=1S/C19H17ClN8O3S/c20-11-2-1-3-12(6-11)26-18(31)27-19-22-7-13(32-19)4-5-21-17-16-14(23-10-24-17)8-25-28(16)9-15(29)30/h1-3,6-8,10H,4-5,9H2,(H,29,30)(H,21,23,24)(H2,22,26,27,31)" 
AK4 InChIKey         InChI                1.03  WRGKHKVUWQKICT-UHFFFAOYSA-N                                                                                                                                                             
# 
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 
AK4 "SYSTEMATIC NAME" ACDLabs              10.04 "(7-{[2-(2-{[(3-chlorophenyl)carbamoyl]amino}-1,3-thiazol-5-yl)ethyl]amino}-1H-pyrazolo[4,3-d]pyrimidin-1-yl)acetic acid" 
AK4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[7-[2-[2-[(3-chlorophenyl)carbamoylamino]-1,3-thiazol-5-yl]ethylamino]pyrazolo[4,5-d]pyrimidin-1-yl]ethanoic acid"     
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
AK4 "Create component"     2008-05-12 RCSB 
AK4 "Modify aromatic_flag" 2011-06-04 RCSB 
AK4 "Modify descriptor"    2011-06-04 RCSB 
# 
