data_FRG
# 
_chem_comp.id                                    FRG 
_chem_comp.name                                  "2-[3-METHYL-4-(N-METHYL-GUANIDINO)-BUTYRYLAMINO]-3-(4-PHENYLETHYNYL-PHENYL)-PROPIONIC ACID METHYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H30 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(R)-N-[2-[1-(AMINOIMINOMETHYL)-3-PIPERIDINYL]-1-OXOETHYL]-4-(PHENYLETHYNYL)-L-PHENYLALANINE METHYL ESTER" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-07-03 
_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                        446.541 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRG 
_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        1M48 
_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 
FRG N33  N33  N 0 1 N N N 3.080  -17.462 27.275 2.853  -3.063 -2.597 N33  FRG 1  
FRG C31  C31  C 0 1 N N N 3.312  -16.734 28.356 3.249  -3.931 -1.709 C31  FRG 2  
FRG N32  N32  N 0 1 N N N 4.448  -16.008 28.438 3.895  -5.077 -2.107 N32  FRG 3  
FRG N29  N29  N 0 1 N N N 2.320  -16.638 29.382 3.021  -3.699 -0.373 N29  FRG 4  
FRG C30  C30  C 0 1 N N N 2.641  -15.638 30.414 2.438  -2.428 0.077  C30  FRG 5  
FRG C28  C28  C 0 1 N N N 1.521  -17.836 29.783 3.355  -4.719 0.631  C28  FRG 6  
FRG C27  C27  C 0 1 N N N 1.773  -18.336 31.211 4.256  -4.085 1.696  C27  FRG 7  
FRG C26  C26  C 0 1 N N N 1.713  -17.187 32.220 3.568  -2.842 2.266  C26  FRG 8  
FRG C24  C24  C 0 1 N N R 2.739  -16.095 31.874 3.348  -1.820 1.149  C24  FRG 9  
FRG C23  C23  C 0 1 N N N 2.596  -14.873 32.792 2.690  -0.565 1.726  C23  FRG 10 
FRG C22  C22  C 0 1 N N N 2.929  -15.210 34.229 2.585  0.486  0.652  C22  FRG 11 
FRG O25  O25  O 0 1 N N N 4.056  -15.600 34.510 2.995  0.255  -0.466 O25  FRG 12 
FRG N21  N21  N 0 1 N N N 1.914  -15.065 35.097 2.034  1.684  0.933  N21  FRG 13 
FRG C16  C16  C 0 1 N N S 2.041  -15.341 36.517 1.931  2.706  -0.111 C16  FRG 14 
FRG C17  C17  C 0 1 N N N 1.986  -16.808 36.809 3.222  3.479  -0.186 C17  FRG 15 
FRG O19  O19  O 0 1 N N N 1.415  -17.621 36.080 4.135  3.205  0.557  O19  FRG 16 
FRG O18  O18  O 0 1 N N N 2.715  -17.266 37.968 3.359  4.473  -1.078 O18  FRG 17 
FRG C20  C20  C 0 1 N N N 2.726  -18.645 38.356 4.603  5.218  -1.150 C20  FRG 18 
FRG C15  C15  C 0 1 N N N 1.122  -14.475 37.375 0.783  3.661  0.221  C15  FRG 19 
FRG C12  C12  C 0 1 Y N N 1.265  -13.011 37.283 -0.523 2.912  0.175  C12  FRG 20 
FRG C13  C13  C 0 1 Y N N 0.193  -12.233 36.862 -1.007 2.300  1.318  C13  FRG 21 
FRG C14  C14  C 0 1 Y N N 0.324  -10.857 36.782 -2.202 1.612  1.284  C14  FRG 22 
FRG C11  C11  C 0 1 Y N N 2.494  -12.417 37.580 -1.236 2.843  -1.009 C11  FRG 23 
FRG C10  C10  C 0 1 Y N N 2.645  -11.042 37.491 -2.430 2.154  -1.060 C10  FRG 24 
FRG C9   C9   C 0 1 Y N N 1.549  -10.294 37.090 -2.924 1.533  0.091  C9   FRG 25 
FRG C8   C8   C 0 1 N N N 1.670  -8.856  36.998 -4.165 0.820  0.047  C8   FRG 26 
FRG C7   C7   C 0 1 N N N 1.743  -7.566  36.930 -5.183 0.236  0.011  C7   FRG 27 
FRG C4   C4   C 0 1 Y N N 1.788  -6.125  36.877 -6.424 -0.477 -0.033 C4   FRG 28 
FRG C5   C5   C 0 1 Y N N 0.834  -5.430  37.598 -7.147 -0.556 -1.227 C5   FRG 29 
FRG C6   C6   C 0 1 Y N N 0.859  -4.055  37.558 -8.341 -1.244 -1.261 C6   FRG 30 
FRG C3   C3   C 0 1 Y N N 2.746  -5.510  36.107 -6.915 -1.103 1.116  C3   FRG 31 
FRG C2   C2   C 0 1 Y N N 2.777  -4.129  36.078 -8.114 -1.783 1.067  C2   FRG 32 
FRG C1   C1   C 0 1 Y N N 1.833  -3.412  36.802 -8.824 -1.857 -0.118 C1   FRG 33 
FRG H33  H33  H 0 1 N N N 2.505  -17.588 28.108 3.014  -3.227 -3.540 H33  FRG 34 
FRG H321 1H32 H 0 0 N N N 4.507  -15.403 27.619 4.119  -5.759 -1.455 H321 FRG 35 
FRG H322 2H32 H 0 0 N N N 4.627  -15.447 29.271 4.127  -5.203 -3.041 H322 FRG 36 
FRG H301 1H30 H 0 0 N N N 1.908  -14.800 30.346 1.449  -2.608 0.499  H301 FRG 37 
FRG H302 2H30 H 0 0 N N N 3.588  -15.120 30.133 2.358  -1.743 -0.767 H302 FRG 38 
FRG H281 1H28 H 0 0 N N N 1.676  -18.664 29.053 3.881  -5.544 0.152  H281 FRG 39 
FRG H282 2H28 H 0 0 N N N 0.434  -17.642 29.630 2.441  -5.086 1.097  H282 FRG 40 
FRG H271 1H27 H 0 0 N N N 2.734  -18.896 31.285 5.207  -3.799 1.245  H271 FRG 41 
FRG H272 2H27 H 0 0 N N N 1.073  -19.159 31.486 4.433  -4.802 2.497  H272 FRG 42 
FRG H261 1H26 H 0 0 N N N 1.838  -17.552 33.266 4.196  -2.403 3.042  H261 FRG 43 
FRG H262 2H26 H 0 0 N N N 0.683  -16.770 32.307 2.606  -3.124 2.695  H262 FRG 44 
FRG H24  H24  H 0 1 N N N 3.740  -16.561 32.031 4.308  -1.556 0.704  H24  FRG 45 
FRG H231 1H23 H 0 0 N N N 1.582  -14.416 32.706 3.295  -0.184 2.549  H231 FRG 46 
FRG H232 2H23 H 0 0 N N N 3.205  -14.015 32.424 1.694  -0.813 2.091  H232 FRG 47 
FRG H21  H21  H 0 1 N N N 1.042  -14.744 34.676 1.706  1.869  1.827  H21  FRG 48 
FRG H16  H16  H 0 1 N N N 3.065  -15.027 36.828 1.739  2.227  -1.071 H16  FRG 49 
FRG H201 1H20 H 0 0 N N N 3.068  -19.243 37.480 4.796  5.698  -0.190 H201 FRG 50 
FRG H202 2H20 H 0 0 N N N 3.289  -18.999 39.251 5.421  4.538  -1.387 H202 FRG 51 
FRG H203 3H20 H 0 0 N N N 1.667  -18.977 38.466 4.527  5.979  -1.927 H203 FRG 52 
FRG H151 1H15 H 0 0 N N N 1.219  -14.785 38.442 0.931  4.073  1.219  H151 FRG 53 
FRG H152 2H15 H 0 0 N N N 0.062  -14.752 37.169 0.763  4.472  -0.507 H152 FRG 54 
FRG H13  H13  H 0 1 N N N -0.764 -12.709 36.591 -0.447 2.362  2.240  H13  FRG 55 
FRG H14  H14  H 0 1 N N N -0.527 -10.224 36.480 -2.577 1.135  2.177  H14  FRG 56 
FRG H11  H11  H 0 1 N N N 3.352  -13.038 37.887 -0.853 3.323  -1.897 H11  FRG 57 
FRG H10  H10  H 0 1 N N N 3.607  -10.558 37.732 -2.983 2.097  -1.986 H10  FRG 58 
FRG H5   H5   H 0 1 N N N 0.070  -5.960  38.192 -6.771 -0.078 -2.119 H5   FRG 59 
FRG H6   H6   H 0 1 N N N 0.109  -3.477  38.124 -8.901 -1.305 -2.183 H6   FRG 60 
FRG H3   H3   H 0 1 N N N 3.470  -6.108  35.528 -6.362 -1.046 2.041  H3   FRG 61 
FRG H2   H2   H 0 1 N N N 3.545  -3.606  35.485 -8.498 -2.263 1.956  H2   FRG 62 
FRG H1   H1   H 0 1 N N N 1.857  -2.310  36.776 -9.760 -2.394 -0.151 H1   FRG 63 
# 
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 
FRG N33 C31  DOUB N N 1  
FRG N33 H33  SING N N 2  
FRG C31 N32  SING N N 3  
FRG C31 N29  SING N N 4  
FRG N32 H321 SING N N 5  
FRG N32 H322 SING N N 6  
FRG N29 C30  SING N N 7  
FRG N29 C28  SING N N 8  
FRG C30 C24  SING N N 9  
FRG C30 H301 SING N N 10 
FRG C30 H302 SING N N 11 
FRG C28 C27  SING N N 12 
FRG C28 H281 SING N N 13 
FRG C28 H282 SING N N 14 
FRG C27 C26  SING N N 15 
FRG C27 H271 SING N N 16 
FRG C27 H272 SING N N 17 
FRG C26 C24  SING N N 18 
FRG C26 H261 SING N N 19 
FRG C26 H262 SING N N 20 
FRG C24 C23  SING N N 21 
FRG C24 H24  SING N N 22 
FRG C23 C22  SING N N 23 
FRG C23 H231 SING N N 24 
FRG C23 H232 SING N N 25 
FRG C22 O25  DOUB N N 26 
FRG C22 N21  SING N N 27 
FRG N21 C16  SING N N 28 
FRG N21 H21  SING N N 29 
FRG C16 C17  SING N N 30 
FRG C16 C15  SING N N 31 
FRG C16 H16  SING N N 32 
FRG C17 O19  DOUB N N 33 
FRG C17 O18  SING N N 34 
FRG O18 C20  SING N N 35 
FRG C20 H201 SING N N 36 
FRG C20 H202 SING N N 37 
FRG C20 H203 SING N N 38 
FRG C15 C12  SING N N 39 
FRG C15 H151 SING N N 40 
FRG C15 H152 SING N N 41 
FRG C12 C13  DOUB Y N 42 
FRG C12 C11  SING Y N 43 
FRG C13 C14  SING Y N 44 
FRG C13 H13  SING N N 45 
FRG C14 C9   DOUB Y N 46 
FRG C14 H14  SING N N 47 
FRG C11 C10  DOUB Y N 48 
FRG C11 H11  SING N N 49 
FRG C10 C9   SING Y N 50 
FRG C10 H10  SING N N 51 
FRG C9  C8   SING N N 52 
FRG C8  C7   TRIP N N 53 
FRG C7  C4   SING N N 54 
FRG C4  C5   DOUB Y N 55 
FRG C4  C3   SING Y N 56 
FRG C5  C6   SING Y N 57 
FRG C5  H5   SING N N 58 
FRG C6  C1   DOUB Y N 59 
FRG C6  H6   SING N N 60 
FRG C3  C2   DOUB Y N 61 
FRG C3  H3   SING N N 62 
FRG C2  C1   SING Y N 63 
FRG C2  H2   SING N N 64 
FRG C1  H1   SING N N 65 
# 
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 
FRG SMILES           ACDLabs              10.04 O=C(OC)C(NC(=O)CC1CCCN(C(=[N@H])N)C1)Cc3ccc(C#Cc2ccccc2)cc3 
FRG InChI            InChI                1.02b 
InChI=1/C26H30N4O3/c1-33-25(32)23(29-24(31)17-22-8-5-15-30(18-22)26(27)28)16-21-13-11-20(12-14-21)10-9-19-6-3-2-4-7-19/h2-4,6-7,11-14,22-23H,5,8,15-18H2,1H3,(H3,27,28)(H,29,31)/t22-,23+/m1/s1/f/h27,29H,28H2/b27-26- 
FRG InChIKey         InChI                1.02b MRNGXYMKYHNMLV-PJQSNNSDDK 
FRG SMILES_CANONICAL CACTVS               3.341 COC(=O)[C@H](Cc1ccc(cc1)C#Cc2ccccc2)NC(=O)C[C@H]3CCCN(C3)C(N)=N 
FRG SMILES           CACTVS               3.341 COC(=O)[CH](Cc1ccc(cc1)C#Cc2ccccc2)NC(=O)C[CH]3CCCN(C3)C(N)=N 
FRG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/N)\N1CCC[C@@H](C1)CC(=O)N[C@@H](Cc2ccc(cc2)C#Cc3ccccc3)C(=O)OC 
FRG SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)N1CCCC(C1)CC(=O)NC(Cc2ccc(cc2)C#Cc3ccccc3)C(=O)OC 
# 
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 
FRG "SYSTEMATIC NAME" ACDLabs              10.04 "methyl N-{[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl}-4-(phenylethynyl)-L-phenylalaninate"                   
FRG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (2S)-2-[2-[(3R)-1-carbamimidoylpiperidin-3-yl]ethanoylamino]-3-[4-(2-phenylethynyl)phenyl]propanoate" 
# 
