data_FRH
# 
_chem_comp.id                                    FRH 
_chem_comp.name                                  "5-[2,3-DICHLORO-4-(5-{1-[2-(2-GUANIDINO-4-METHYL-PENTANOYLAMINO)-ACETYL]-PIPERIDIN-4-YL}-1-METHYL-1H-PYRAZOL-3-YL)-PHENOXYMETHYL]-FURAN-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H37 Cl2 N7 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-08-05 
_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                        662.564 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRH 
_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        1PY2 
_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 
FRH O45  O45  O  0 1 N N N 32.968 9.661  -1.913 0.181  1.375  7.790   O45  FRH 1  
FRH C26  C26  C  0 1 N N N 31.885 9.975  -1.440 0.445  0.192  7.791   C26  FRH 2  
FRH C25  C25  C  0 1 N N R 30.621 9.741  -2.219 1.439  -0.358 8.781   C25  FRH 3  
FRH C32  C32  C  0 1 N N N 30.559 10.621 -3.465 2.843  -0.307 8.176   C32  FRH 4  
FRH C36  C36  C  0 1 N N N 29.883 11.967 -3.219 3.836  -0.967 9.135   C36  FRH 5  
FRH C38  C38  C  0 1 N N N 28.368 11.841 -3.105 3.519  -2.460 9.248   C38  FRH 6  
FRH C37  C37  C  0 1 N N N 30.246 12.952 -4.323 5.258  -0.787 8.600   C37  FRH 7  
FRH N5   N5   N  0 1 N N N 30.514 8.350  -2.609 1.405  0.446  10.005  N5   FRH 8  
FRH C17  C17  C  0 1 N N N 29.382 7.664  -2.507 1.804  1.762  9.974   C17  FRH 9  
FRH N4   N4   N  0 1 N N N 28.653 7.726  -1.393 1.772  2.517  11.122  N4   FRH 10 
FRH N1   N1   N  0 1 N N N 28.984 6.908  -3.528 2.212  2.293  8.856   N1   FRH 11 
FRH N2   N2   N  0 1 N N N 31.732 10.524 -0.233 -0.150 -0.631 6.906   N2   FRH 12 
FRH C28  C28  C  0 1 N N N 32.747 10.486 0.808  -1.117 -0.097 5.943   C28  FRH 13 
FRH C14  C14  C  0 1 N N N 32.695 11.726 1.675  -1.633 -1.215 5.075   C14  FRH 14 
FRH O44  O44  O  0 1 N N N 31.650 12.356 1.740  -1.233 -2.348 5.244   O44  FRH 15 
FRH N6   N6   N  0 1 N N N 33.802 12.099 2.336  -2.539 -0.957 4.111   N6   FRH 16 
FRH C22  C22  C  0 1 N N N 33.844 13.352 3.099  -3.037 0.407  3.899   C22  FRH 17 
FRH C15  C15  C  0 1 N N N 34.167 12.997 4.552  -2.836 0.776  2.421   C15  FRH 18 
FRH C19  C19  C  0 1 N N N 35.497 12.248 4.622  -3.506 -0.280 1.541   C19  FRH 19 
FRH C27  C27  C  0 1 N N N 35.377 10.976 3.783  -2.854 -1.642 1.790   C27  FRH 20 
FRH C29  C29  C  0 1 N N N 35.041 11.314 2.330  -3.051 -2.038 3.257   C29  FRH 21 
FRH C23  C23  C  0 1 Y N N 35.903 11.919 6.040  -3.343 0.095  0.091   C23  FRH 22 
FRH C11  C11  C  0 1 Y N N 35.261 11.804 7.129  -2.321 -0.267 -0.713  C11  FRH 23 
FRH C13  C13  C  0 1 Y N N 36.020 11.488 8.102  -2.553 0.292  -1.985  C13  FRH 24 
FRH N7   N7   N  0 1 Y N N 37.234 11.232 7.619  -3.682 0.967  -1.930  N7   FRH 25 
FRH N3   N3   N  0 1 Y N N 37.157 11.668 6.395  -4.197 0.851  -0.633  N3   FRH 26 
FRH C34  C34  C  0 1 N N N 38.383 11.828 5.623  -5.440 1.452  -0.144  C34  FRH 27 
FRH C24  C24  C  0 1 Y N N 35.784 11.379 9.585  -1.679 0.147  -3.175  C24  FRH 28 
FRH C10  C10  C  0 1 Y N N 36.753 11.885 10.452 -2.243 -0.031 -4.437  C10  FRH 29 
FRH C21  C21  C  0 1 Y N N 34.640 10.781 10.110 -0.293 0.195  -3.034  C21  FRH 30 
FRH CL8  CL8  CL 0 0 N N N 33.363 10.110 9.043  0.413  0.418  -1.465  CL8  FRH 31 
FRH C16  C16  C  0 1 Y N N 34.469 10.699 11.485 0.516  0.054  -4.144  C16  FRH 32 
FRH CL9  CL9  CL 0 0 N N N 32.991 9.931  12.157 2.243  0.108  -3.971  CL9  FRH 33 
FRH C30  C30  C  0 1 Y N N 35.432 11.201 12.349 -0.049 -0.123 -5.400  C30  FRH 34 
FRH C33  C33  C  0 1 Y N N 36.580 11.801 11.831 -1.429 -0.166 -5.542  C33  FRH 35 
FRH O43  O43  O  0 1 N N N 35.231 11.105 13.704 0.749  -0.257 -6.491  O43  FRH 36 
FRH C35  C35  C  0 1 N N N 36.290 10.801 14.613 -0.113 -0.422 -7.618  C35  FRH 37 
FRH C18  C18  C  0 1 Y N N 36.356 11.900 15.646 0.714  -0.576 -8.867  C18  FRH 38 
FRH C39  C39  C  0 1 Y N N 36.762 11.796 16.838 1.169  -1.745 -9.371  C39  FRH 39 
FRH O42  O42  O  0 1 Y N N 35.950 13.272 15.455 1.125  0.422  -9.658  O42  FRH 40 
FRH C31  C31  C  0 1 Y N N 35.868 13.758 16.807 1.843  -0.083 -10.682 C31  FRH 41 
FRH C12  C12  C  0 1 Y N N 36.386 12.772 17.561 1.889  -1.441 -10.536 C12  FRH 42 
FRH C20  C20  C  0 1 N N N 35.322 15.040 17.249 2.465  0.687  -11.761 C20  FRH 43 
FRH O40  O40  O  0 1 N N N 34.610 15.692 16.454 2.342  2.030  -11.788 O40  FRH 44 
FRH O41  O41  O  0 1 N N N 35.577 15.455 18.402 3.091  0.116  -12.634 O41  FRH 45 
FRH H25  H25  H  0 1 N N N 29.768 10.009 -1.553 1.182  -1.390 9.018   H25  FRH 46 
FRH H321 1H32 H  0 0 N N N 30.070 10.080 -4.308 3.131  0.731  8.013   H321 FRH 47 
FRH H322 2H32 H  0 0 N N N 31.575 10.762 -3.902 2.848  -0.839 7.224   H322 FRH 48 
FRH H36  H36  H  0 1 N N N 30.260 12.350 -2.242 3.755  -0.503 10.117  H36  FRH 49 
FRH H381 1H38 H  0 0 N N N 28.083 11.099 -2.323 4.226  -2.930 9.931   H381 FRH 50 
FRH H382 2H38 H  0 0 N N N 27.874 12.824 -2.925 2.506  -2.588 9.629   H382 FRH 51 
FRH H383 3H38 H  0 0 N N N 27.938 11.332 -3.999 3.600  -2.924 8.265   H383 FRH 52 
FRH H371 1H37 H  0 0 N N N 30.010 12.547 -5.335 5.364  -1.326 7.659   H371 FRH 53 
FRH H372 2H37 H  0 0 N N N 29.752 13.935 -4.143 5.453  0.272  8.436   H372 FRH 54 
FRH H373 3H37 H  0 0 N N N 31.350 13.057 -4.440 5.971  -1.179 9.325   H373 FRH 55 
FRH HN5  HN5  H  0 1 N N N 31.234 7.833  -2.104 1.101  0.051  10.837  HN5  FRH 56 
FRH HN41 1HN4 H  0 0 N N N 28.452 8.706  -1.196 2.053  3.445  11.100  HN41 FRH 57 
FRH HN42 2HN4 H  0 0 N N N 27.783 7.199  -1.315 1.468  2.121  11.954  HN42 FRH 58 
FRH HN1  HN1  H  0 1 N N N 28.330 6.883  -2.746 2.493  3.221  8.834   HN1  FRH 59 
FRH HN2  HN2  H  0 1 N N N 30.828 10.978 -0.104 0.059  -1.578 6.907   HN2  FRH 60 
FRH H281 1H28 H  0 0 N N N 33.765 10.328 0.381  -1.948 0.360  6.479   H281 FRH 61 
FRH H282 2H28 H  0 0 N N N 32.671 9.557  1.419  -0.630 0.652  5.319   H282 FRH 62 
FRH H221 1H22 H  0 0 N N N 32.912 13.955 2.996  -4.097 0.458  4.147   H221 FRH 63 
FRH H222 2H22 H  0 0 N N N 34.550 14.100 2.668  -2.479 1.101  4.528   H222 FRH 64 
FRH H151 1H15 H  0 0 N N N 33.340 12.428 5.037  -1.770 0.815  2.195   H151 FRH 65 
FRH H152 2H15 H  0 0 N N N 34.157 13.894 5.214  -3.285 1.750  2.226   H152 FRH 66 
FRH H19  H19  H  0 1 N N N 36.299 12.908 4.217  -4.567 -0.336 1.785   H19  FRH 67 
FRH H271 1H27 H  0 0 N N N 34.642 10.261 4.221  -1.788 -1.581 1.571   H271 FRH 68 
FRH H272 2H27 H  0 0 N N N 36.292 10.344 3.859  -3.316 -2.390 1.147   H272 FRH 69 
FRH H291 1H29 H  0 0 N N N 35.877 11.825 1.798  -2.504 -2.958 3.464   H291 FRH 70 
FRH H292 2H29 H  0 0 N N N 34.982 10.413 1.676  -4.112 -2.188 3.456   H292 FRH 71 
FRH H11  H11  H  0 1 N N N 34.173 11.960 7.219  -1.476 -0.878 -0.432  H11  FRH 72 
FRH H341 1H34 H  0 0 N N N 38.380 12.890 5.282  -6.266 0.759  -0.304  H341 FRH 73 
FRH H342 2H34 H  0 0 N N N 39.437 11.617 5.921  -5.346 1.665  0.920   H342 FRH 74 
FRH H343 3H34 H  0 0 N N N 38.220 11.245 4.686  -5.633 2.378  -0.685  H343 FRH 75 
FRH H10  H10  H  0 1 N N N 37.663 12.355 10.044 -3.316 -0.065 -4.550  H10  FRH 76 
FRH H33  H33  H  0 1 N N N 37.349 12.208 12.510 -1.866 -0.304 -6.520  H33  FRH 77 
FRH H351 1H35 H  0 0 N N N 37.265 10.637 14.098 -0.727 -1.312 -7.477  H351 FRH 78 
FRH H352 2H35 H  0 0 N N N 36.188 9.789  15.069 -0.757 0.451  -7.714  H352 FRH 79 
FRH H39  H39  H  0 1 N N N 37.372 10.953 17.204 1.004  -2.729 -8.957  H39  FRH 80 
FRH H12  H12  H  0 1 N N N 36.492 12.765 18.659 2.387  -2.143 -11.188 H12  FRH 81 
FRH H40  H40  H  0 1 N N N 34.255 16.525 16.741 2.753  2.539  -12.501 H40  FRH 82 
# 
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 
FRH O45 C26  DOUB N N 1  
FRH C26 C25  SING N N 2  
FRH C26 N2   SING N N 3  
FRH C25 C32  SING N N 4  
FRH C25 N5   SING N N 5  
FRH C25 H25  SING N N 6  
FRH C32 C36  SING N N 7  
FRH C32 H321 SING N N 8  
FRH C32 H322 SING N N 9  
FRH C36 C38  SING N N 10 
FRH C36 C37  SING N N 11 
FRH C36 H36  SING N N 12 
FRH C38 H381 SING N N 13 
FRH C38 H382 SING N N 14 
FRH C38 H383 SING N N 15 
FRH C37 H371 SING N N 16 
FRH C37 H372 SING N N 17 
FRH C37 H373 SING N N 18 
FRH N5  C17  SING N N 19 
FRH N5  HN5  SING N N 20 
FRH C17 N4   SING N N 21 
FRH C17 N1   DOUB N N 22 
FRH N4  HN41 SING N N 23 
FRH N4  HN42 SING N N 24 
FRH N1  HN1  SING N N 25 
FRH N2  C28  SING N N 26 
FRH N2  HN2  SING N N 27 
FRH C28 C14  SING N N 28 
FRH C28 H281 SING N N 29 
FRH C28 H282 SING N N 30 
FRH C14 O44  DOUB N N 31 
FRH C14 N6   SING N N 32 
FRH N6  C22  SING N N 33 
FRH N6  C29  SING N N 34 
FRH C22 C15  SING N N 35 
FRH C22 H221 SING N N 36 
FRH C22 H222 SING N N 37 
FRH C15 C19  SING N N 38 
FRH C15 H151 SING N N 39 
FRH C15 H152 SING N N 40 
FRH C19 C27  SING N N 41 
FRH C19 C23  SING N N 42 
FRH C19 H19  SING N N 43 
FRH C27 C29  SING N N 44 
FRH C27 H271 SING N N 45 
FRH C27 H272 SING N N 46 
FRH C29 H291 SING N N 47 
FRH C29 H292 SING N N 48 
FRH C23 C11  DOUB Y N 49 
FRH C23 N3   SING Y N 50 
FRH C11 C13  SING Y N 51 
FRH C11 H11  SING N N 52 
FRH C13 N7   DOUB Y N 53 
FRH C13 C24  SING N N 54 
FRH N7  N3   SING Y N 55 
FRH N3  C34  SING N N 56 
FRH C34 H341 SING N N 57 
FRH C34 H342 SING N N 58 
FRH C34 H343 SING N N 59 
FRH C24 C10  DOUB Y N 60 
FRH C24 C21  SING Y N 61 
FRH C10 C33  SING Y N 62 
FRH C10 H10  SING N N 63 
FRH C21 CL8  SING N N 64 
FRH C21 C16  DOUB Y N 65 
FRH C16 CL9  SING N N 66 
FRH C16 C30  SING Y N 67 
FRH C30 C33  DOUB Y N 68 
FRH C30 O43  SING N N 69 
FRH C33 H33  SING N N 70 
FRH O43 C35  SING N N 71 
FRH C35 C18  SING N N 72 
FRH C35 H351 SING N N 73 
FRH C35 H352 SING N N 74 
FRH C18 C39  DOUB Y N 75 
FRH C18 O42  SING Y N 76 
FRH C39 C12  SING Y N 77 
FRH C39 H39  SING N N 78 
FRH O42 C31  SING Y N 79 
FRH C31 C12  DOUB Y N 80 
FRH C31 C20  SING N N 81 
FRH C12 H12  SING N N 82 
FRH C20 O40  SING N N 83 
FRH C20 O41  DOUB N N 84 
FRH O40 H40  SING N N 85 
# 
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 
FRH SMILES           ACDLabs              10.04 O=C(NCC(=O)N4CCC(c1cc(nn1C)c3ccc(OCc2oc(cc2)C(=O)O)c(Cl)c3Cl)CC4)C(NC(=[N@H])N)CC(C)C 
FRH InChI            InChI                1.02b 
;InChI=1/C30H37Cl2N7O6/c1-16(2)12-21(36-30(33)34)28(41)35-14-25(40)39-10-8-17(9-11-39)22-13-20(37-38(22)3)19-5-7-23(27(32)26(19)31)44-15-18-4-6-24(45-18)29(42)43/h4-7,13,16-17,21H,8-12,14-15H2,1-3H3,(H,35,41)(H,42,43)(H4,33,34,36)/t21-/m1/s1/f/h33,35-36,42H,34H2/b33-30+
;
FRH InChIKey         InChI                1.02b VNZHOIDQBPFEJU-UNXJNEFWDA 
FRH SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@@H](NC(N)=N)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(OCc4oc(cc4)C(O)=O)c(Cl)c3Cl 
FRH SMILES           CACTVS               3.341 CC(C)C[CH](NC(N)=N)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(OCc4oc(cc4)C(O)=O)c(Cl)c3Cl 
FRH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\N)/N[C@H](CC(C)C)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(c(c3Cl)Cl)OCc4ccc(o4)C(=O)O 
FRH SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)NC(CC(C)C)C(=O)NCC(=O)N1CCC(CC1)c2cc(nn2C)c3ccc(c(c3Cl)Cl)OCc4ccc(o4)C(=O)O 
# 
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 
FRH "SYSTEMATIC NAME" ACDLabs              10.04 N~2~-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide                 
FRH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[[4-[5-[1-[2-[[(2R)-2-carbamimidamido-4-methyl-pentanoyl]amino]ethanoyl]piperidin-4-yl]-1-methyl-pyrazol-3-yl]-2,3-dichloro-phenoxy]methyl]furan-2-carboxylic acid" 
# 
