data_03R
# 
_chem_comp.id                                    03R 
_chem_comp.name                                  "2-({6-{3-[AMINO(IMINO)METHYL]PHENOXY}-3,5-DIFLUORO-4-[(1-METHYL-3-PHENYLPROPYL)AMINO]-2-PYRIDINYL}OXY)BENZOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H26 F2 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-08-01 
_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                        532.538 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     03R 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2AEI 
_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 
03R C1   C1   C 0 1 Y N N 31.103 7.354  7.198  -1.366 -0.825 -0.321 C1   03R 1  
03R N2   N2   N 0 1 Y N N 30.615 7.415  8.491  -1.411 0.136  0.588  N2   03R 2  
03R C3   C3   C 0 1 Y N N 32.318 8.017  6.903  -0.152 -1.293 -0.801 C3   03R 3  
03R O4   O4   O 0 1 N N N 30.537 6.682  6.153  -2.523 -1.356 -0.794 O4   03R 4  
03R C5   C5   C 0 1 Y N N 31.294 8.112  9.469  -0.309 0.684  1.079  C5   03R 5  
03R C6   C6   C 0 1 Y N N 33.017 8.722  7.892  1.030  -0.744 -0.305 C6   03R 6  
03R F7   F7   F 0 1 N N N 32.769 7.962  5.687  -0.115 -2.274 -1.729 F7   03R 7  
03R C8   C8   C 0 1 Y N N 29.338 6.033  6.102  -3.216 -1.806 0.282  C8   03R 8  
03R C9   C9   C 0 1 Y N N 32.494 8.745  9.158  0.942  0.266  0.652  C9   03R 9  
03R O10  O10  O 0 1 N N N 30.966 8.345  10.746 -0.406 1.667  2.010  O10  03R 10 
03R N11  N11  N 0 1 N N N 34.174 9.364  7.572  2.271  -1.191 -0.760 N11  03R 11 
03R C12  C12  C 0 1 Y N N 28.033 6.532  6.503  -4.533 -2.263 0.131  C12  03R 12 
03R C13  C13  C 0 1 Y N N 29.468 4.702  5.642  -2.627 -1.812 1.538  C13  03R 13 
03R F14  F14  F 0 1 N N N 33.091 9.393  10.110 2.061  0.831  1.156  F14  03R 14 
03R C15  C15  C 0 1 Y N N 29.997 7.958  11.572 -1.089 2.690  1.432  C15  03R 15 
03R C16  C16  C 0 1 N N S 34.555 10.741 7.844  2.991  -1.704 0.413  C16  03R 16 
03R C17  C17  C 0 1 Y N N 26.931 5.640  6.453  -5.235 -2.729 1.246  C17  03R 17 
03R C18  C18  C 0 1 N N N 27.773 7.859  6.862  -5.170 -2.261 -1.199 C18  03R 18 
03R C19  C19  C 0 1 Y N N 28.353 3.851  5.590  -3.333 -2.270 2.632  C19  03R 19 
03R C20  C20  C 0 1 Y N N 30.306 7.402  12.836 -1.647 2.527  0.175  C20  03R 20 
03R C21  C21  C 0 1 Y N N 28.657 8.198  11.240 -1.222 3.901  2.099  C21  03R 21 
03R C22  C22  C 0 1 N N N 35.797 10.826 8.739  4.498  -1.629 0.160  C22  03R 22 
03R C23  C23  C 0 1 N N N 33.421 11.616 8.450  2.588  -3.159 0.663  C23  03R 23 
03R C24  C24  C 0 1 Y N N 27.087 4.316  6.011  -4.633 -2.727 2.485  C24  03R 24 
03R O25  O25  O 0 1 N N N 26.842 8.147  7.638  -6.433 -2.710 -1.341 O25  03R 25 
03R O26  O26  O 0 1 N N N 28.507 8.881  6.385  -4.557 -1.855 -2.166 O26  03R 26 
03R C27  C27  C 0 1 Y N N 29.282 7.079  13.762 -2.351 3.577  -0.413 C27  03R 27 
03R C28  C28  C 0 1 Y N N 27.650 7.891  12.119 -1.915 4.944  1.515  C28  03R 28 
03R C29  C29  C 0 1 N N N 36.745 9.604  8.815  4.921  -0.164 0.033  C29  03R 29 
03R C30  C30  C 0 1 Y N N 27.959 7.342  13.369 -2.479 4.789  0.265  C30  03R 30 
03R C31  C31  C 0 1 N N N 29.546 6.541  15.041 -2.956 3.408  -1.754 C31  03R 31 
03R C32  C32  C 0 1 Y N N 36.619 8.782  10.036 6.406  -0.090 -0.216 C32  03R 32 
03R N33  N33  N 0 1 N N N 29.137 7.167  16.161 -3.647 4.449  -2.334 N33  03R 33 
03R N34  N34  N 0 1 N N N 30.212 5.385  15.249 -2.835 2.275  -2.384 N34  03R 34 
03R C35  C35  C 0 1 Y N N 35.629 7.772  10.126 6.890  -0.100 -1.511 C35  03R 35 
03R C36  C36  C 0 1 Y N N 37.485 8.991  11.143 7.282  -0.005 0.850  C36  03R 36 
03R C37  C37  C 0 1 Y N N 35.503 6.990  11.286 8.252  -0.032 -1.739 C37  03R 37 
03R C38  C38  C 0 1 Y N N 37.360 8.207  12.308 8.644  0.059  0.621  C38  03R 38 
03R C39  C39  C 0 1 Y N N 36.369 7.207  12.381 9.129  0.047  -0.674 C39  03R 39 
03R H11  H11  H 0 1 N N N 34.876 8.830  8.044  2.775  -0.376 -1.076 H11  03R 40 
03R H13  H13  H 0 1 N N N 30.435 4.337  5.328  -1.614 -1.457 1.660  H13  03R 41 
03R H16  H16  H 0 1 N N N 34.784 11.156 6.851  2.739  -1.102 1.286  H16  03R 42 
03R H17  H17  H 0 1 N N N 25.955 5.985  6.760  -6.248 -3.087 1.137  H17  03R 43 
03R H19  H19  H 0 1 N N N 28.463 2.840  5.228  -2.870 -2.272 3.607  H19  03R 44 
03R H20  H20  H 0 1 N N N 31.338 7.221  13.099 -1.544 1.586  -0.345 H20  03R 45 
03R H21  H21  H 0 1 N N N 28.414 8.630  10.280 -0.782 4.027  3.077  H21  03R 46 
03R H221 1H22 H 0 0 N N N 35.393 10.921 9.758  5.030  -2.090 0.992  H221 03R 47 
03R H222 2H22 H 0 0 N N N 36.399 11.665 8.359  4.738  -2.157 -0.763 H222 03R 48 
03R H231 1H23 H 0 0 N N N 32.464 11.079 8.374  2.840  -3.761 -0.210 H231 03R 49 
03R H232 2H23 H 0 0 N N N 33.355 12.565 7.897  3.122  -3.539 1.533  H232 03R 50 
03R H233 3H23 H 0 0 N N N 33.642 11.823 9.508  1.514  -3.213 0.843  H233 03R 51 
03R H24  H24  H 0 1 N N N 26.236 3.651  5.993  -5.177 -3.085 3.347  H24  03R 52 
03R H26  H26  H 0 1 N N N 28.177 9.700  6.737  ?      ?      ?      H26  03R 53 
03R H28  H28  H 0 1 N N N 26.621 8.072  11.847 -2.015 5.884  2.038  H28  03R 54 
03R H291 1H29 H 0 0 N N N 37.768 10.008 8.821  4.390  0.298  -0.799 H291 03R 55 
03R H292 2H29 H 0 0 N N N 36.522 8.956  7.954  4.681  0.364  0.956  H292 03R 56 
03R H30  H30  H 0 1 N N N 27.155 7.113  14.053 -3.021 5.607  -0.188 H30  03R 57 
03R H33  H33  H 0 1 N N N 29.415 6.636  16.962 -4.043 4.338  -3.212 H33  03R 58 
03R H341 1H34 H 0 0 N N N 30.410 4.986  16.145 ?      ?      ?      H341 03R 59 
03R H342 2H34 H 0 0 N N N 30.477 4.989  14.370 -3.231 2.164  -3.263 H342 03R 60 
03R H35  H35  H 0 1 N N N 34.963 7.602  9.293  6.205  -0.162 -2.343 H35  03R 61 
03R H36  H36  H 0 1 N N N 38.245 9.757  11.091 6.903  0.004  1.861  H36  03R 62 
03R H37  H37  H 0 1 N N N 34.744 6.223  11.341 8.631  -0.042 -2.751 H37  03R 63 
03R H38  H38  H 0 1 N N N 38.023 8.372  13.144 9.329  0.121  1.454  H38  03R 64 
03R H39  H39  H 0 1 N N N 36.272 6.607  13.274 10.193 0.100  -0.852 H39  03R 65 
# 
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 
03R C1  N2   DOUB Y N 1  
03R C1  C3   SING Y N 2  
03R C1  O4   SING N N 3  
03R N2  C5   SING Y N 4  
03R C3  C6   DOUB Y N 5  
03R C3  F7   SING N N 6  
03R O4  C8   SING N N 7  
03R C5  C9   DOUB Y N 8  
03R C5  O10  SING N N 9  
03R C6  C9   SING Y N 10 
03R C6  N11  SING N N 11 
03R C8  C12  SING Y N 12 
03R C8  C13  DOUB Y N 13 
03R C9  F14  SING N N 14 
03R O10 C15  SING N N 15 
03R N11 C16  SING N N 16 
03R N11 H11  SING N N 17 
03R C12 C17  DOUB Y N 18 
03R C12 C18  SING N N 19 
03R C13 C19  SING Y N 20 
03R C13 H13  SING N N 21 
03R C15 C20  SING Y N 22 
03R C15 C21  DOUB Y N 23 
03R C16 C22  SING N N 24 
03R C16 C23  SING N N 25 
03R C16 H16  SING N N 26 
03R C17 C24  SING Y N 27 
03R C17 H17  SING N N 28 
03R C18 O25  DOUB N N 29 
03R C18 O26  SING N N 30 
03R C19 C24  DOUB Y N 31 
03R C19 H19  SING N N 32 
03R C20 C27  DOUB Y N 33 
03R C20 H20  SING N N 34 
03R C21 C28  SING Y N 35 
03R C21 H21  SING N N 36 
03R C22 C29  SING N N 37 
03R C22 H221 SING N N 38 
03R C22 H222 SING N N 39 
03R C23 H231 SING N N 40 
03R C23 H232 SING N N 41 
03R C23 H233 SING N N 42 
03R C24 H24  SING N N 43 
03R O26 H26  SING N N 44 
03R C27 C30  SING Y N 45 
03R C27 C31  SING N N 46 
03R C28 C30  DOUB Y N 47 
03R C28 H28  SING N N 48 
03R C29 C32  SING N N 49 
03R C29 H291 SING N N 50 
03R C29 H292 SING N N 51 
03R C30 H30  SING N N 52 
03R C31 N33  DOUB N Z 53 
03R C31 N34  SING N N 54 
03R C32 C35  SING Y N 55 
03R C32 C36  DOUB Y N 56 
03R N33 H33  SING N N 57 
03R N34 H341 SING N N 58 
03R N34 H342 SING N N 59 
03R C35 C37  DOUB Y N 60 
03R C35 H35  SING N N 61 
03R C36 C38  SING Y N 62 
03R C36 H36  SING N N 63 
03R C37 C39  SING Y N 64 
03R C37 H37  SING N N 65 
03R C38 C39  DOUB Y N 66 
03R C38 H38  SING N N 67 
03R C39 H39  SING N N 68 
# 
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 
03R SMILES           ACDLabs              10.04 O=C(O)c4c(Oc2nc(Oc1cc(C(=[N@H])N)ccc1)c(F)c(c2F)NC(C)CCc3ccccc3)cccc4 
03R InChI            InChI                1.02b 
InChI=1/C29H26F2N4O4/c1-17(14-15-18-8-3-2-4-9-18)34-25-23(30)27(38-20-11-7-10-19(16-20)26(32)33)35-28(24(25)31)39-22-13-6-5-12-21(22)29(36)37/h2-13,16-17H,14-15H2,1H3,(H3,32,33)(H,34,35)(H,36,37)/t17-/m0/s1/f/h32,34,36H,33H2/b32-26- 
03R InChIKey         InChI                1.02b BUZNVJZUYOBGFM-VTNUSDJBDI 
03R SMILES_CANONICAL CACTVS               3.341 C[C@@H](CCc1ccccc1)Nc2c(F)c(Oc3cccc(c3)C(N)=N)nc(Oc4ccccc4C(O)=O)c2F 
03R SMILES           CACTVS               3.341 C[CH](CCc1ccccc1)Nc2c(F)c(Oc3cccc(c3)C(N)=N)nc(Oc4ccccc4C(O)=O)c2F 
03R SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/c1cccc(c1)Oc2c(c(c(c(n2)Oc3ccccc3C(=O)O)F)N[C@@H](C)CCc4ccccc4)F)\N 
03R SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1cccc(c1)Oc2c(c(c(c(n2)Oc3ccccc3C(=O)O)F)NC(C)CCc4ccccc4)F)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 
03R "SYSTEMATIC NAME" ACDLabs              10.04 "2-{[6-(3-carbamimidoylphenoxy)-3,5-difluoro-4-{[(1S)-1-methyl-3-phenylpropyl]amino}pyridin-2-yl]oxy}benzoic acid" 
03R "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[6-(3-carbamimidoylphenoxy)-3,5-difluoro-4-[[(2S)-4-phenylbutan-2-yl]amino]pyridin-2-yl]oxybenzoic acid"        
# 
