data_FRI
# 
_chem_comp.id                                    FRI 
_chem_comp.name                                  "2-GUANIDINO-4-METHYL-PENTANOIC ACID [2-(4-{5-[4-(4-ACETYLAMINO-BENZYLOXY)-2,3-DICHLORO-PHENYL]-2-METHYL-2H-PYRAZOL-3-YL}-PIPERIDIN-1-YL)-2-OXO-ETHYL]-AMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H42 Cl2 N8 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         SP4160 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-09-05 
_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                        685.644 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRI 
_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   N 
_chem_comp.pdbx_model_coordinates_db_code        1QVN 
_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 
FRI O47  O47  O  0 1 N N N 15.794 12.943 85.168 -0.862 -2.551 5.634   O47  FRI 1  
FRI C30  C30  C  0 1 N N N 16.204 13.264 84.061 -1.398 -1.467 5.546   C30  FRI 2  
FRI C29  C29  C  0 1 N N N 17.629 12.941 83.668 -0.984 -0.345 6.463   C29  FRI 3  
FRI N3   N3   N  0 1 N N N 18.373 12.294 84.738 0.073  -0.813 7.361   N3   FRI 4  
FRI C27  C27  C  0 1 N N N 18.633 10.985 84.764 0.602  0.024  8.274   C27  FRI 5  
FRI O46  O46  O  0 1 N N N 18.421 10.230 83.823 0.202  1.167  8.352   O46  FRI 6  
FRI C26  C26  C  0 1 N N R 19.217 10.464 86.047 1.691  -0.457 9.198   C26  FRI 7  
FRI C41  C41  C  0 1 N N N 18.085 9.982  86.949 3.055  -0.205 8.553   C41  FRI 8  
FRI C32  C32  C  0 1 N N N 18.213 10.525 88.369 4.154  -0.801 9.436   C32  FRI 9  
FRI C37  C37  C  0 1 N N N 17.900 9.438  89.389 4.009  -2.323 9.474   C37  FRI 10 
FRI C36  C36  C  0 1 N N N 17.305 11.731 88.587 5.524  -0.433 8.863   C36  FRI 11 
FRI N7   N7   N  0 1 N N N 20.183 9.396  85.836 1.610  0.268  10.468  N7   FRI 12 
FRI C24  C24  C  0 1 N N N 21.303 9.261  86.555 1.846  1.622  10.503  C24  FRI 13 
FRI N5   N5   N  0 1 N N N 21.914 10.320 87.090 2.141  2.260  9.405   N5   FRI 14 
FRI N4   N4   N  0 1 N N N 21.829 8.050  86.737 1.770  2.303  11.695  N4   FRI 15 
FRI N2   N2   N  0 1 N N N 15.425 13.887 83.170 -2.364 -1.265 4.628   N2   FRI 16 
FRI C31  C31  C  0 1 N N N 15.261 13.359 81.803 -3.027 0.040  4.513   C31  FRI 17 
FRI C39  C39  C  0 1 N N N 15.321 14.502 80.789 -2.927 0.512  3.055   C39  FRI 18 
FRI C19  C19  C  0 1 N N N 14.317 15.585 81.176 -3.502 -0.567 2.135   C19  FRI 19 
FRI C21  C21  C  0 1 N N N 14.779 16.164 82.505 -2.686 -1.853 2.282   C21  FRI 20 
FRI C43  C43  C  0 1 N N N 14.665 15.082 83.579 -2.779 -2.350 3.728   C43  FRI 21 
FRI C23  C23  C  0 1 Y N N 14.205 16.645 80.109 -3.440 -0.093 0.705   C23  FRI 22 
FRI N8   N8   N  0 1 Y N N 13.099 17.261 79.630 -4.403 0.593  0.054   N8   FRI 23 
FRI C38  C38  C  0 1 N N N 11.699 16.975 79.920 -5.689 1.014  0.617   C38  FRI 24 
FRI N6   N6   N  0 1 Y N N 13.450 18.294 78.760 -3.956 0.842  -1.249  N6   FRI 25 
FRI C13  C13  C  0 1 Y N N 15.049 17.204 79.376 -2.414 -0.287 -0.151  C13  FRI 26 
FRI C14  C14  C  0 1 Y N N 14.824 18.197 78.621 -2.759 0.310  -1.379  C14  FRI 27 
FRI C11  C11  C  0 1 Y N N 15.753 19.021 77.786 -1.920 0.337  -2.603  C11  FRI 28 
FRI C15  C15  C  0 1 Y N N 15.241 19.644 76.646 -2.506 0.162  -3.855  C15  FRI 29 
FRI C17  C17  C  0 1 Y N N 16.086 20.384 75.823 -1.725 0.188  -4.991  C17  FRI 30 
FRI C20  C20  C  0 1 Y N N 17.421 20.557 76.194 -0.355 0.386  -4.890  C20  FRI 31 
FRI C33  C33  C  0 1 Y N N 17.920 19.938 77.324 0.233  0.561  -3.644  C33  FRI 32 
FRI C34  C34  C  0 1 Y N N 17.097 19.169 78.122 -0.544 0.542  -2.503  C34  FRI 33 
FRI CL10 CL10 CL 0 0 N N N 17.825 18.398 79.571 0.190  0.760  -0.946  CL10 FRI 34 
FRI CL9  CL9  CL 0 0 N N N 19.647 20.128 77.762 1.947  0.810  -3.522  CL9  FRI 35 
FRI O45  O45  O  0 1 N N N 18.256 21.340 75.453 0.411  0.410  -6.012  O45  FRI 36 
FRI C40  C40  C  0 1 N N N 17.774 21.905 74.238 -0.469 0.205  -7.118  C40  FRI 37 
FRI C22  C22  C  0 1 Y N N 16.584 22.785 74.537 0.322  0.221  -8.400  C22  FRI 38 
FRI C28  C28  C  0 1 Y N N 15.857 23.347 73.485 0.515  1.411  -9.078  C28  FRI 39 
FRI C25  C25  C  0 1 Y N N 14.858 24.295 73.783 1.244  1.429  -10.250 C25  FRI 40 
FRI C35  C35  C  0 1 Y N N 14.407 24.435 75.102 1.776  0.249  -10.754 C35  FRI 41 
FRI C18  C18  C  0 1 Y N N 15.136 23.863 76.149 1.576  -0.944 -10.074 C18  FRI 42 
FRI C16  C16  C  0 1 Y N N 16.219 23.035 75.861 0.850  -0.955 -8.900  C16  FRI 43 
FRI N1   N1   N  0 1 N N N 13.265 25.133 75.338 2.510  0.264  -11.945 N1   FRI 44 
FRI C12  C12  C  0 1 N N N 13.258 26.420 75.698 2.440  -0.781 -12.793 C12  FRI 45 
FRI O44  O44  O  0 1 N N N 12.379 26.877 76.412 1.664  -1.687 -12.575 O44  FRI 46 
FRI C42  C42  C  0 1 N N N 14.380 27.273 75.172 3.327  -0.824 -14.011 C42  FRI 47 
FRI H291 1H29 H  0 0 N N N 18.160 13.852 83.305 -1.843 -0.020 7.051   H291 FRI 48 
FRI H292 2H29 H  0 0 N N N 17.658 12.331 82.735 -0.613 0.490  5.869   H292 FRI 49 
FRI HN3  HN3  H  0 1 N N N 18.745 12.803 85.540 0.393  -1.727 7.298   HN3  FRI 50 
FRI H26  H26  H  0 1 N N N 19.773 11.301 86.532 1.566  -1.524 9.381   H26  FRI 51 
FRI H411 1H41 H  0 0 N N N 18.012 8.869  86.947 3.216  0.867  8.448   H411 FRI 52 
FRI H412 2H41 H  0 0 N N N 17.089 10.225 86.512 3.085  -0.675 7.570   H412 FRI 53 
FRI H32  H32  H  0 1 N N N 19.268 10.858 88.510 4.064  -0.402 10.446  H32  FRI 54 
FRI H371 1H37 H  0 0 N N N 18.530 8.531  89.234 4.792  -2.747 10.102  H371 FRI 55 
FRI H372 2H37 H  0 0 N N N 17.994 9.835  90.427 3.033  -2.585 9.882   H372 FRI 56 
FRI H373 3H37 H  0 0 N N N 16.900 8.978  89.210 4.099  -2.722 8.463   H373 FRI 57 
FRI H361 1H36 H  0 0 N N N 16.245 11.496 88.333 5.649  -0.905 7.889   H361 FRI 58 
FRI H362 2H36 H  0 0 N N N 17.399 12.128 89.625 5.594  0.649  8.754   H362 FRI 59 
FRI H363 3H36 H  0 0 N N N 17.491 12.526 87.827 6.306  -0.780 9.538   H363 FRI 60 
FRI HN7  HN7  H  0 1 N N N 20.456 9.425  84.854 1.390  -0.206 11.285  HN7  FRI 61 
FRI HN5  HN5  H  0 1 N N N 22.849 10.320 86.681 2.308  3.216  9.429   HN5  FRI 62 
FRI HN41 1HN4 H  0 0 N N N 21.976 7.620  85.824 1.936  3.258  11.719  HN41 FRI 63 
FRI HN42 2HN4 H  0 0 N N N 22.683 7.947  87.285 1.550  1.828  12.511  HN42 FRI 64 
FRI H311 1H31 H  0 0 N N N 14.329 12.756 81.697 -4.076 -0.049 4.797   H311 FRI 65 
FRI H312 2H31 H  0 0 N N N 16.001 12.558 81.573 -2.531 0.759  5.165   H312 FRI 66 
FRI H391 1H39 H  0 0 N N N 15.171 14.145 79.744 -1.883 0.690  2.798   H391 FRI 67 
FRI H392 2H39 H  0 0 N N N 16.353 14.908 80.674 -3.495 1.434  2.932   H392 FRI 68 
FRI H19  H19  H  0 1 N N N 13.294 15.154 81.277 -4.539 -0.762 2.408   H19  FRI 69 
FRI H211 1H21 H  0 0 N N N 14.230 17.095 82.778 -1.643 -1.652 2.032   H211 FRI 70 
FRI H212 2H21 H  0 0 N N N 15.803 16.600 82.447 -3.081 -2.614 1.609   H212 FRI 71 
FRI H431 1H43 H  0 0 N N N 14.978 15.454 84.583 -2.121 -3.208 3.862   H431 FRI 72 
FRI H432 2H43 H  0 0 N N N 13.603 14.841 83.819 -3.807 -2.636 3.950   H432 FRI 73 
FRI H381 1H38 H  0 0 N N N 11.609 17.022 81.030 -6.433 0.237  0.442   H381 FRI 74 
FRI H382 2H38 H  0 0 N N N 10.788 17.482 79.525 -5.580 1.177  1.689   H382 FRI 75 
FRI H383 3H38 H  0 0 N N N 11.562 15.893 79.688 -6.010 1.939  0.138   H383 FRI 76 
FRI H13  H13  H  0 1 N N N 16.071 16.789 79.397 -1.493 -0.808 0.066   H13  FRI 77 
FRI H15  H15  H  0 1 N N N 14.171 19.552 76.396 -3.572 0.007  -3.935  H15  FRI 78 
FRI H17  H17  H  0 1 N N N 15.703 20.828 74.889 -2.180 0.052  -5.961  H17  FRI 79 
FRI H401 1H40 H  0 0 N N N 17.544 21.128 73.472 -1.214 1.001  -7.142  H401 FRI 80 
FRI H402 2H40 H  0 0 N N N 18.571 22.447 73.678 -0.969 -0.757 -7.012  H402 FRI 81 
FRI H28  H28  H  0 1 N N N 16.067 23.049 72.444 0.102  2.328  -8.685  H28  FRI 82 
FRI H25  H25  H  0 1 N N N 14.430 24.926 72.986 1.398  2.360  -10.777 H25  FRI 83 
FRI H18  H18  H  0 1 N N N 14.858 24.064 77.197 1.988  -1.863 -10.464 H18  FRI 84 
FRI H16  H16  H  0 1 N N N 16.790 22.575 76.685 0.694  -1.883 -8.370  H16  FRI 85 
FRI HN1  HN1  H  0 1 N N N 12.364 24.665 75.240 3.070  1.026  -12.161 HN1  FRI 86 
FRI H421 1H42 H  0 0 N N N 14.420 27.195 74.060 3.130  -1.738 -14.571 H421 FRI 87 
FRI H422 2H42 H  0 0 N N N 14.374 28.347 75.472 3.120  0.040  -14.642 H422 FRI 88 
FRI H423 3H42 H  0 0 N N N 15.359 26.814 75.444 4.371  -0.806 -13.701 H423 FRI 89 
# 
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 
FRI O47 C30  DOUB N N 1  
FRI C30 C29  SING N N 2  
FRI C30 N2   SING N N 3  
FRI C29 N3   SING N N 4  
FRI C29 H291 SING N N 5  
FRI C29 H292 SING N N 6  
FRI N3  C27  SING N N 7  
FRI N3  HN3  SING N N 8  
FRI C27 O46  DOUB N N 9  
FRI C27 C26  SING N N 10 
FRI C26 C41  SING N N 11 
FRI C26 N7   SING N N 12 
FRI C26 H26  SING N N 13 
FRI C41 C32  SING N N 14 
FRI C41 H411 SING N N 15 
FRI C41 H412 SING N N 16 
FRI C32 C37  SING N N 17 
FRI C32 C36  SING N N 18 
FRI C32 H32  SING N N 19 
FRI C37 H371 SING N N 20 
FRI C37 H372 SING N N 21 
FRI C37 H373 SING N N 22 
FRI C36 H361 SING N N 23 
FRI C36 H362 SING N N 24 
FRI C36 H363 SING N N 25 
FRI N7  C24  SING N N 26 
FRI N7  HN7  SING N N 27 
FRI C24 N5   DOUB N N 28 
FRI C24 N4   SING N N 29 
FRI N5  HN5  SING N N 30 
FRI N4  HN41 SING N N 31 
FRI N4  HN42 SING N N 32 
FRI N2  C31  SING N N 33 
FRI N2  C43  SING N N 34 
FRI C31 C39  SING N N 35 
FRI C31 H311 SING N N 36 
FRI C31 H312 SING N N 37 
FRI C39 C19  SING N N 38 
FRI C39 H391 SING N N 39 
FRI C39 H392 SING N N 40 
FRI C19 C21  SING N N 41 
FRI C19 C23  SING N N 42 
FRI C19 H19  SING N N 43 
FRI C21 C43  SING N N 44 
FRI C21 H211 SING N N 45 
FRI C21 H212 SING N N 46 
FRI C43 H431 SING N N 47 
FRI C43 H432 SING N N 48 
FRI C23 N8   SING Y N 49 
FRI C23 C13  DOUB Y N 50 
FRI N8  C38  SING N N 51 
FRI N8  N6   SING Y N 52 
FRI C38 H381 SING N N 53 
FRI C38 H382 SING N N 54 
FRI C38 H383 SING N N 55 
FRI N6  C14  DOUB Y N 56 
FRI C13 C14  SING Y N 57 
FRI C13 H13  SING N N 58 
FRI C14 C11  SING N N 59 
FRI C11 C15  DOUB Y N 60 
FRI C11 C34  SING Y N 61 
FRI C15 C17  SING Y N 62 
FRI C15 H15  SING N N 63 
FRI C17 C20  DOUB Y N 64 
FRI C17 H17  SING N N 65 
FRI C20 C33  SING Y N 66 
FRI C20 O45  SING N N 67 
FRI C33 C34  DOUB Y N 68 
FRI C33 CL9  SING N N 69 
FRI C34 CL10 SING N N 70 
FRI O45 C40  SING N N 71 
FRI C40 C22  SING N N 72 
FRI C40 H401 SING N N 73 
FRI C40 H402 SING N N 74 
FRI C22 C28  DOUB Y N 75 
FRI C22 C16  SING Y N 76 
FRI C28 C25  SING Y N 77 
FRI C28 H28  SING N N 78 
FRI C25 C35  DOUB Y N 79 
FRI C25 H25  SING N N 80 
FRI C35 C18  SING Y N 81 
FRI C35 N1   SING N N 82 
FRI C18 C16  DOUB Y N 83 
FRI C18 H18  SING N N 84 
FRI C16 H16  SING N N 85 
FRI N1  C12  SING N N 86 
FRI N1  HN1  SING N N 87 
FRI C12 O44  DOUB N N 88 
FRI C12 C42  SING N N 89 
FRI C42 H421 SING N N 90 
FRI C42 H422 SING N N 91 
FRI C42 H423 SING N N 92 
# 
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 
FRI SMILES           ACDLabs              10.04 O=C(Nc1ccc(cc1)COc4ccc(c2nn(c(c2)C3CCN(C(=O)CNC(=O)C(NC(=[N@H])N)CC(C)C)CC3)C)c(Cl)c4Cl)C 
FRI InChI            InChI                1.02b 
;InChI=1/C33H42Cl2N8O4/c1-19(2)15-26(40-33(36)37)32(46)38-17-29(45)43-13-11-22(12-14-43)27-16-25(41-42(27)4)24-9-10-28(31(35)30(24)34)47-18-21-5-7-23(8-6-21)39-20(3)44/h5-10,16,19,22,26H,11-15,17-18H2,1-4H3,(H,38,46)(H,39,44)(H4,36,37,40)/t26-/m1/s1/f/h36,38-40H,37H2/b36-33+
;
FRI InChIKey         InChI                1.02b VCXMTWSYQSVWRK-SKPIUPNDDP 
FRI SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@@H](NC(N)=N)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(OCc4ccc(NC(C)=O)cc4)c(Cl)c3Cl 
FRI SMILES           CACTVS               3.341 CC(C)C[CH](NC(N)=N)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(OCc4ccc(NC(C)=O)cc4)c(Cl)c3Cl 
FRI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@H](C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(c(c3Cl)Cl)OCc4ccc(cc4)NC(=O)C)NC(=N)N 
FRI SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC(C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(c(c3Cl)Cl)OCc4ccc(cc4)NC(=O)C)NC(=N)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 
FRI "SYSTEMATIC NAME" ACDLabs              10.04 N-(2-{4-[3-(4-{[4-(acetylamino)benzyl]oxy}-2,3-dichlorophenyl)-1-methyl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethyl)-N~2~-carbamimidoyl-D-leucinamide           
FRI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-N-[2-[4-[5-[4-[(4-acetamidophenyl)methoxy]-2,3-dichloro-phenyl]-2-methyl-pyrazol-3-yl]piperidin-1-yl]-2-oxo-ethyl]-2-carbamimidamido-4-methyl-pentanamide 
# 
