data_3FR
# 
_chem_comp.id                                    3FR 
_chem_comp.name                                  "3'-chloro-5'-(3-methyl-6-{[(1S)-1-phenylethyl]amino}-1H-pyrazolo[4,3-c]pyridin-1-yl)biphenyl-2-carboxamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H24 Cl N5 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;3'-chloro-5'-[3-methyl-6-(1-phenyl-ethylamino)-pyrazolo[4,3-c]pyridin-1-yl]-biphenyl-2-carboxylic acid amide
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-06-16 
_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                        481.976 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3FR 
_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        3DBD 
_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 
3FR C31  C31  C  0 1 Y N N 60.074 14.727 48.187 6.778  -0.673 -2.406 C31  3FR 1  
3FR C30  C30  C  0 1 Y N N 58.838 15.089 48.718 5.626  -0.338 -3.098 C30  3FR 2  
3FR C28  C28  C  0 1 Y N N 59.049 17.288 47.721 4.347  -0.502 -1.073 C28  3FR 3  
3FR C26  C26  C  0 1 N N N 57.164 23.386 42.151 0.091  5.704  0.125  C26  3FR 4  
3FR C24  C24  C  0 1 N N N 53.733 15.137 42.824 -3.921 -1.153 1.657  C24  3FR 5  
3FR C23  C23  C  0 1 Y N N 58.115 19.096 46.226 2.310  0.770  -0.407 C23  3FR 6  
3FR C22  C22  C  0 1 Y N N 58.474 18.648 47.503 3.049  -0.410 -0.363 C22  3FR 7  
3FR C17  C17  C  0 1 Y N N 57.123 22.272 43.161 -0.077 4.207  0.158  C17  3FR 8  
3FR C20  C20  C  0 1 Y N N 57.757 20.744 48.409 1.354  -1.420 1.012  C20  3FR 9  
3FR C12  C12  C  0 1 Y N N 56.381 21.038 42.781 -1.345 3.485  0.154  C12  3FR 10 
3FR C13  C13  C  0 1 Y N N 55.684 20.685 41.628 -2.688 3.859  0.122  C13  3FR 11 
3FR C11  C11  C  0 1 Y N N 56.486 20.172 43.861 -1.015 2.111  0.192  C11  3FR 12 
3FR C10  C10  C  0 1 Y N N 55.869 18.928 43.771 -2.052 1.183  0.197  C10  3FR 13 
3FR C9   C9   C  0 1 Y N N 55.174 18.592 42.600 -3.358 1.642  0.163  C9   3FR 14 
3FR C7   C7   C  0 1 N N S 54.513 16.307 43.420 -4.118 -0.712 0.206  C7   3FR 15 
3FR C4   C4   C  0 1 Y N N 55.999 15.272 45.126 -5.032 -2.562 -1.211 C4   3FR 16 
3FR C5   C5   C  0 1 Y N N 55.860 15.838 43.857 -5.272 -1.470 -0.398 C5   3FR 17 
3FR C6   C6   C  0 1 Y N N 56.987 15.954 43.036 -6.571 -1.075 -0.136 C6   3FR 18 
3FR C3   C3   C  0 1 Y N N 57.244 14.824 45.565 -6.091 -3.257 -1.764 C3   3FR 19 
3FR C2   C2   C  0 1 Y N N 58.363 14.944 44.743 -7.390 -2.862 -1.504 C2   3FR 20 
3FR C1   C1   C  0 1 Y N N 58.234 15.512 43.477 -7.630 -1.771 -0.689 C1   3FR 21 
3FR O36  O36  O  0 1 N N N 61.673 18.809 46.924 4.558  -0.643 1.751  O36  3FR 22 
3FR C34  C34  C  0 1 N N N 61.100 17.884 46.372 5.458  -1.111 1.081  C34  3FR 23 
3FR N35  N35  N  0 1 N N N 61.170 17.698 45.055 6.404  -1.875 1.663  N35  3FR 24 
3FR C33  C33  C  0 1 Y N N 60.289 16.924 47.195 5.516  -0.842 -0.369 C33  3FR 25 
3FR C32  C32  C  0 1 Y N N 60.797 15.645 47.427 6.730  -0.925 -1.050 C32  3FR 26 
3FR C29  C29  C  0 1 Y N N 58.330 16.366 48.487 4.415  -0.252 -2.440 C29  3FR 27 
3FR C21  C21  C  0 1 Y N N 58.292 19.479 48.603 2.564  -1.506 0.351  C21  3FR 28 
3FR CL   CL   CL 0 0 N N N 57.507 21.843 49.806 0.753  -2.785 1.900  CL   3FR 29 
3FR C19  C19  C  0 1 Y N N 57.411 21.160 47.126 0.620  -0.248 0.968  C19  3FR 30 
3FR C18  C18  C  0 1 Y N N 57.564 20.366 45.985 1.096  0.849  0.260  C18  3FR 31 
3FR N15  N15  N  0 1 Y N N 57.219 20.838 44.773 0.351  2.033  0.218  N15  3FR 32 
3FR N16  N16  N  0 1 Y N N 57.634 22.127 44.398 0.883  3.327  0.191  N16  3FR 33 
3FR N14  N14  N  0 1 Y N N 55.102 19.476 41.569 -3.632 2.942  0.128  N14  3FR 34 
3FR N8   N8   N  0 1 N N N 54.558 17.390 42.441 -4.404 0.725  0.166  N8   3FR 35 
3FR H31  H31  H  0 1 N N N 60.471 13.738 48.364 7.719  -0.742 -2.932 H31  3FR 36 
3FR H30  H30  H  0 1 N N N 58.274 14.381 49.308 5.675  -0.144 -4.159 H30  3FR 37 
3FR H26  H26  H  0 1 N N N 57.174 24.354 42.673 0.114  6.090  1.144  H26  3FR 38 
3FR H26A H26A H  0 0 N N N 58.072 23.291 41.537 1.025  5.953  -0.379 H26A 3FR 39 
3FR H26B H26B H  0 0 N N N 56.276 23.327 41.504 -0.743 6.152  -0.415 H26B 3FR 40 
3FR H24  H24  H  0 1 N N N 53.545 15.326 41.757 -3.708 -2.222 1.686  H24  3FR 41 
3FR H24A H24A H  0 0 N N N 54.318 14.212 42.935 -3.086 -0.604 2.093  H24A 3FR 42 
3FR H24B H24B H  0 0 N N N 52.774 15.030 43.351 -4.827 -0.947 2.226  H24B 3FR 43 
3FR H23  H23  H  0 1 N N N 58.269 18.434 45.387 2.684  1.622  -0.954 H23  3FR 44 
3FR H13  H13  H  0 1 N N N 55.613 21.371 40.797 -2.955 4.905  0.092  H13  3FR 45 
3FR H10  H10  H  0 1 N N N 55.925 18.230 44.593 -1.842 0.124  0.226  H10  3FR 46 
3FR H7   H7   H  0 1 N N N 54.018 16.704 44.318 -3.211 -0.917 -0.363 H7   3FR 47 
3FR H4   H4   H  0 1 N N N 55.137 15.181 45.771 -4.018 -2.868 -1.419 H4   3FR 48 
3FR H6   H6   H  0 1 N N N 56.890 16.390 42.052 -6.759 -0.223 0.500  H6   3FR 49 
3FR H3   H3   H  0 1 N N N 57.342 14.382 46.546 -5.904 -4.110 -2.401 H3   3FR 50 
3FR H2   H2   H  0 1 N N N 59.327 14.598 45.086 -8.217 -3.405 -1.936 H2   3FR 51 
3FR H1   H1   H  0 1 N N N 59.099 15.610 42.838 -8.644 -1.462 -0.485 H1   3FR 52 
3FR HN35 HN35 H  0 0 N N N 60.650 16.900 44.750 6.366  -2.052 2.616  HN35 3FR 53 
3FR HN3A HN3A H  0 0 N N N 61.687 18.292 44.438 7.122  -2.248 1.129  HN3A 3FR 54 
3FR H32  H32  H  0 1 N N N 61.755 15.365 47.015 7.632  -1.186 -0.517 H32  3FR 55 
3FR H29  H29  H  0 1 N N N 57.373 16.645 48.903 3.522  0.011  -2.987 H29  3FR 56 
3FR H21  H21  H  0 1 N N N 58.563 19.145 49.593 3.134  -2.423 0.387  H21  3FR 57 
3FR H19  H19  H  0 1 N N N 57.001 22.152 47.005 -0.325 -0.185 1.486  H19  3FR 58 
3FR HN8  HN8  H  0 1 N N N 53.598 17.624 42.289 -5.323 1.036  0.143  HN8  3FR 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 
3FR C31 C30  DOUB Y N 1  
3FR C31 C32  SING Y N 2  
3FR C30 C29  SING N N 3  
3FR C28 C22  SING Y N 4  
3FR C28 C33  SING N N 5  
3FR C28 C29  DOUB N N 6  
3FR C26 C17  SING Y N 7  
3FR C24 C7   SING Y N 8  
3FR C23 C22  DOUB N N 9  
3FR C23 C18  SING N N 10 
3FR C22 C21  SING N N 11 
3FR C17 C12  SING N N 12 
3FR C17 N16  DOUB N N 13 
3FR C20 C21  DOUB N N 14 
3FR C20 CL   SING N N 15 
3FR C20 C19  SING N N 16 
3FR C12 C13  DOUB Y N 17 
3FR C12 C11  SING Y N 18 
3FR C13 N14  SING N N 19 
3FR C11 C10  DOUB Y N 20 
3FR C11 N15  SING Y N 21 
3FR C10 C9   SING Y N 22 
3FR C9  N14  DOUB Y N 23 
3FR C9  N8   SING N N 24 
3FR C7  C5   SING Y N 25 
3FR C7  N8   SING Y N 26 
3FR C4  C5   DOUB Y N 27 
3FR C4  C3   SING Y N 28 
3FR C5  C6   SING N N 29 
3FR C6  C1   DOUB Y N 30 
3FR C3  C2   DOUB Y N 31 
3FR C2  C1   SING Y N 32 
3FR O36 C34  DOUB N N 33 
3FR C34 N35  SING Y N 34 
3FR C34 C33  SING N N 35 
3FR C33 C32  DOUB N N 36 
3FR C19 C18  DOUB N N 37 
3FR C18 N15  SING N N 38 
3FR N15 N16  SING Y N 39 
3FR C31 H31  SING Y N 40 
3FR C30 H30  SING N N 41 
3FR C26 H26  SING Y N 42 
3FR C26 H26A SING Y N 43 
3FR C26 H26B SING N N 44 
3FR C24 H24  SING Y N 45 
3FR C24 H24A SING N N 46 
3FR C24 H24B SING Y N 47 
3FR C23 H23  SING N N 48 
3FR C13 H13  SING N N 49 
3FR C10 H10  SING N N 50 
3FR C7  H7   SING N N 51 
3FR C4  H4   SING N N 52 
3FR C6  H6   SING N N 53 
3FR C3  H3   SING N N 54 
3FR C2  H2   SING Y N 55 
3FR C1  H1   SING N N 56 
3FR N35 HN35 SING N N 57 
3FR N35 HN3A SING N N 58 
3FR C32 H32  SING Y N 59 
3FR C29 H29  SING N N 60 
3FR C21 H21  SING N N 61 
3FR C19 H19  SING Y N 62 
3FR N8  HN8  SING N N 63 
# 
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 
3FR SMILES           ACDLabs              10.04 O=C(N)c1ccccc1c2cc(cc(Cl)c2)n5nc(c3c5cc(nc3)NC(c4ccccc4)C)C                                                                                                                                 
3FR InChI            InChI                1.02b InChI=1/C28H24ClN5O/c1-17(19-8-4-3-5-9-19)32-27-15-26-25(16-31-27)18(2)33-34(26)22-13-20(12-21(29)14-22)23-10-6-7-11-24(23)28(30)35/h3-17H,1-2H3,(H2,30,35)(H,31,32)/t17-/m0/s1/f/h32H,30H2 
3FR InChIKey         InChI                1.02b IFCBXJXWEYHVPY-MDCUEOSODJ                                                                                                                                                                   
3FR SMILES_CANONICAL CACTVS               3.341 C[C@H](Nc1cc2n(nc(C)c2cn1)c3cc(Cl)cc(c3)c4ccccc4C(N)=O)c5ccccc5                                                                                                                             
3FR SMILES           CACTVS               3.341 C[CH](Nc1cc2n(nc(C)c2cn1)c3cc(Cl)cc(c3)c4ccccc4C(N)=O)c5ccccc5                                                                                                                              
3FR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c2cnc(cc2n(n1)c3cc(cc(c3)Cl)c4ccccc4C(=O)N)N[C@@H](C)c5ccccc5                                                                                                                            
3FR SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c2cnc(cc2n(n1)c3cc(cc(c3)Cl)c4ccccc4C(=O)N)NC(C)c5ccccc5                                                                                                                                 
# 
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 
3FR "SYSTEMATIC NAME" ACDLabs              10.04 "3'-chloro-5'-(3-methyl-6-{[(1S)-1-phenylethyl]amino}-1H-pyrazolo[4,3-c]pyridin-1-yl)biphenyl-2-carboxamide" 
3FR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[3-chloro-5-[3-methyl-6-[[(1S)-1-phenylethyl]amino]pyrazolo[5,4-d]pyridin-1-yl]phenyl]benzamide            
# 
