data_163
# 
_chem_comp.id                                    163 
_chem_comp.name                                  "(2-{2-[(5-CARBAMIMIDOYL-1-METHYL-1H-PYRROL-2-YLMETHYL)-CARBAMOYL]-PYRROL-1-YL}- 1-CYCLOHEXYLMETHYL-2-OXO-ETHYLAMINO)-ACETIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H32 N6 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-03-19 
_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                        456.538 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     163 
_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        1O0D 
_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 
163 N    N    N 0 1 N N N 10.289 23.388 24.128 0.550  0.413  -9.402  N    163 1  
163 C    C    C 0 1 N N N 10.906 22.211 24.012 0.587  0.923  -8.200  C    163 2  
163 N1   N1   N 0 1 N N N 10.781 21.290 24.961 1.245  2.116  -7.977  N1   163 3  
163 C1   C1   C 0 1 Y N N 11.738 21.918 22.808 -0.073 0.227  -7.084  C1   163 4  
163 N2   N2   N 0 1 Y N N 12.661 22.755 22.197 -0.215 0.703  -5.803  N2   163 5  
163 C2   C2   C 0 1 N N N 13.012 24.132 22.635 0.261  1.999  -5.315  C2   163 6  
163 C3   C3   C 0 1 Y N N 11.724 20.753 22.093 -0.646 -1.011 -7.135  C3   163 7  
163 C4   C4   C 0 1 Y N N 12.638 20.883 21.048 -1.154 -1.287 -5.859  C4   163 8  
163 C5   C5   C 0 1 Y N N 13.194 22.102 21.131 -0.878 -0.225 -5.067  C5   163 9  
163 C6   C6   C 0 1 N N N 14.240 22.644 20.186 -1.245 -0.096 -3.611  C6   163 10 
163 N3   N3   N 0 1 N N N 15.565 22.478 20.811 -0.160 -0.631 -2.784  N3   163 11 
163 C7   C7   C 0 1 N N N 16.481 21.591 20.338 -0.268 -0.620 -1.441  C7   163 12 
163 O    O    O 0 1 N N N 16.241 20.891 19.367 -1.303 -0.252 -0.917  O    163 13 
163 C8   C8   C 0 1 Y N N 17.817 21.476 21.054 0.861  -1.051 -0.611  C8   163 14 
163 C9   C9   C 0 1 Y N N 18.975 21.632 20.099 2.083  -1.462 -1.063  C9   163 15 
163 C10  C10  C 0 1 Y N N 19.666 20.527 20.044 2.860  -1.781 0.058   C10  163 16 
163 C11  C11  C 0 1 Y N N 19.057 19.492 20.952 2.109  -1.562 1.161   C11  163 17 
163 N4   N4   N 0 1 Y N N 17.956 20.150 21.698 0.883  -1.109 0.769   N4   163 18 
163 C12  C12  C 0 1 N N N 17.228 19.644 22.751 -0.134 -0.782 1.589   C12  163 19 
163 O1   O1   O 0 1 N N N 16.349 20.313 23.263 -1.217 -0.507 1.128   O1   163 20 
163 C13  C13  C 0 1 N N R 17.506 18.250 23.291 0.076  -0.759 3.081   C13  163 21 
163 C14  C14  C 0 1 N N N 18.189 18.334 24.674 0.652  0.596  3.494   C14  163 22 
163 C15  C15  C 0 1 N N N 19.668 18.737 24.535 0.856  0.624  5.010   C15  163 23 
163 C16  C16  C 0 1 N N N 20.141 19.430 25.833 1.931  -0.393 5.398   C16  163 24 
163 C17  C17  C 0 1 N N N 21.629 19.841 25.707 2.136  -0.366 6.914   C17  163 25 
163 C18  C18  C 0 1 N N N 22.508 18.600 25.412 2.579  1.033  7.343   C18  163 26 
163 C19  C19  C 0 1 N N N 22.022 17.888 24.126 1.504  2.050  6.955   C19  163 27 
163 C20  C20  C 0 1 N N N 20.536 17.482 24.268 1.300  2.023  5.439   C20  163 28 
163 N5   N5   N 0 1 N N N 16.241 17.512 23.418 -1.208 -0.972 3.761   N5   163 29 
163 C21  C21  C 0 1 N N N 15.764 16.657 22.324 -1.958 0.285  3.651   C21  163 30 
163 C22  C22  C 0 1 N N N 14.764 15.656 22.853 -3.184 0.217  4.524   C22  163 31 
163 O2   O2   O 0 1 N N N 14.749 15.370 24.040 -4.025 1.261  4.583   O2   163 32 
163 O3   O3   O 0 1 N N N 13.970 15.129 22.092 -3.410 -0.777 5.172   O3   163 33 
163 H    H    H 0 1 N N N 10.832 24.246 24.039 0.985  0.872  -10.138 H    163 34 
163 H11A 1H1  H 0 0 N N N 11.252 20.390 24.872 1.507  2.672  -8.726  H11A 163 35 
163 H12  2H1  H 0 1 N N N 9.786  21.117 25.110 1.445  2.397  -7.070  H12  163 36 
163 H21  1H2  H 0 1 N N N 13.753 24.804 22.144 1.313  1.919  -5.041  H21  163 37 
163 H22  2H2  H 0 1 N N N 12.054 24.701 22.684 0.146  2.748  -6.099  H22  163 38 
163 H23  3H2  H 0 1 N N N 13.315 24.054 23.705 -0.320 2.295  -4.442  H23  163 39 
163 H3   H3   H 0 1 N N N 11.094 19.875 22.316 -0.701 -1.656 -7.999  H3   163 40 
163 H4   H4   H 0 1 N N N 12.883 20.136 20.274 -1.673 -2.186 -5.561  H4   163 41 
163 H61  1H6  H 0 1 N N N 14.183 22.180 19.173 -1.402 0.954  -3.368  H61  163 42 
163 H62  2H6  H 0 1 N N N 14.038 23.698 19.883 -2.160 -0.655 -3.416  H62  163 43 
163 HN3  HN3  H 0 1 N N N 15.868 23.012 21.625 0.635  -0.993 -3.204  HN3  163 44 
163 H9   H9   H 0 1 N N N 19.293 22.491 19.485 2.394  -1.529 -2.095  H9   163 45 
163 H10  H10  H 0 1 N N N 20.551 20.479 19.388 3.879  -2.139 0.044   H10  163 46 
163 H11  H11  H 0 1 N N N 19.363 18.437 21.052 2.428  -1.716 2.181   H11  163 47 
163 H13  H13  H 0 1 N N N 18.185 17.720 22.583 0.771  -1.550 3.362   H13  163 48 
163 H141 1H14 H 0 0 N N N 17.639 19.016 25.363 1.609  0.752  2.995   H141 163 49 
163 H142 2H14 H 0 0 N N N 18.073 17.385 25.248 -0.039 1.388  3.206   H142 163 50 
163 H15  H15  H 0 1 N N N 19.774 19.442 23.678 -0.079 0.370  5.507   H15  163 51 
163 H161 1H16 H 0 0 N N N 19.491 20.294 26.104 1.615  -1.390 5.091   H161 163 52 
163 H162 2H16 H 0 0 N N N 19.957 18.798 26.733 2.867  -0.140 4.900   H162 163 53 
163 H171 1H17 H 0 0 N N N 21.775 20.643 24.947 1.200  -0.619 7.411   H171 163 54 
163 H172 2H17 H 0 0 N N N 21.983 20.397 26.605 2.902  -1.090 7.190   H172 163 55 
163 H181 1H18 H 0 0 N N N 23.590 18.861 25.358 2.725  1.053  8.423   H181 163 56 
163 H182 2H18 H 0 0 N N N 22.548 17.903 26.282 3.516  1.286  6.846   H182 163 57 
163 H191 1H19 H 0 0 N N N 22.199 18.506 23.215 0.568  1.797  7.453   H191 163 58 
163 H192 2H19 H 0 0 N N N 22.667 17.018 23.862 1.820  3.048  7.262   H192 163 59 
163 H201 1H20 H 0 0 N N N 20.389 16.698 25.047 2.236  2.276  4.942   H201 163 60 
163 H202 2H20 H 0 0 N N N 20.174 16.903 23.386 0.534  2.748  5.163   H202 163 61 
163 H5   H5   H 0 1 N N N 15.503 18.178 23.647 -1.712 -1.658 3.219   H5   163 62 
163 H211 1H21 H 0 0 N N N 15.351 17.252 21.476 -1.327 1.113  3.974   H211 163 63 
163 H212 2H21 H 0 0 N N N 16.603 16.163 21.781 -2.258 0.440  2.615   H212 163 64 
163 HO2  HO2  H 0 1 N N N 14.120 14.740 24.372 -4.812 1.218  5.144   HO2  163 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 
163 N   C    DOUB N N 1  
163 N   H    SING N N 2  
163 C   N1   SING N N 3  
163 C   C1   SING N N 4  
163 N1  H11A SING N N 5  
163 N1  H12  SING N N 6  
163 C1  N2   SING Y N 7  
163 C1  C3   DOUB Y N 8  
163 N2  C2   SING N N 9  
163 N2  C5   SING Y N 10 
163 C2  H21  SING N N 11 
163 C2  H22  SING N N 12 
163 C2  H23  SING N N 13 
163 C3  C4   SING Y N 14 
163 C3  H3   SING N N 15 
163 C4  C5   DOUB Y N 16 
163 C4  H4   SING N N 17 
163 C5  C6   SING N N 18 
163 C6  N3   SING N N 19 
163 C6  H61  SING N N 20 
163 C6  H62  SING N N 21 
163 N3  C7   SING N N 22 
163 N3  HN3  SING N N 23 
163 C7  O    DOUB N N 24 
163 C7  C8   SING N N 25 
163 C8  C9   DOUB Y N 26 
163 C8  N4   SING Y N 27 
163 C9  C10  SING Y N 28 
163 C9  H9   SING N N 29 
163 C10 C11  DOUB Y N 30 
163 C10 H10  SING N N 31 
163 C11 N4   SING Y N 32 
163 C11 H11  SING N N 33 
163 N4  C12  SING N N 34 
163 C12 O1   DOUB N N 35 
163 C12 C13  SING N N 36 
163 C13 C14  SING N N 37 
163 C13 N5   SING N N 38 
163 C13 H13  SING N N 39 
163 C14 C15  SING N N 40 
163 C14 H141 SING N N 41 
163 C14 H142 SING N N 42 
163 C15 C16  SING N N 43 
163 C15 C20  SING N N 44 
163 C15 H15  SING N N 45 
163 C16 C17  SING N N 46 
163 C16 H161 SING N N 47 
163 C16 H162 SING N N 48 
163 C17 C18  SING N N 49 
163 C17 H171 SING N N 50 
163 C17 H172 SING N N 51 
163 C18 C19  SING N N 52 
163 C18 H181 SING N N 53 
163 C18 H182 SING N N 54 
163 C19 C20  SING N N 55 
163 C19 H191 SING N N 56 
163 C19 H192 SING N N 57 
163 C20 H201 SING N N 58 
163 C20 H202 SING N N 59 
163 N5  C21  SING N N 60 
163 N5  H5   SING N N 61 
163 C21 C22  SING N N 62 
163 C21 H211 SING N N 63 
163 C21 H212 SING N N 64 
163 C22 O2   SING N N 65 
163 C22 O3   DOUB N N 66 
163 O2  HO2  SING N N 67 
# 
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 
163 SMILES           ACDLabs              10.04 O=C(c2cccn2C(=O)C(NCC(=O)O)CC1CCCCC1)NCc3ccc(C(=[N@H])N)n3C 
163 InChI            InChI                1.02b 
InChI=1/C23H32N6O4/c1-28-16(9-10-18(28)21(24)25)13-27-22(32)19-8-5-11-29(19)23(33)17(26-14-20(30)31)12-15-6-3-2-4-7-15/h5,8-11,15,17,26H,2-4,6-7,12-14H2,1H3,(H3,24,25)(H,27,32)(H,30,31)/t17-/m1/s1/f/h24,27,30H,25H2/b24-21+ 
163 InChIKey         InChI                1.02b AXMHAIYMRMPDQD-FLOBBKGTDJ 
163 SMILES_CANONICAL CACTVS               3.341 Cn1c(CNC(=O)c2cccn2C(=O)[C@@H](CC3CCCCC3)NCC(O)=O)ccc1C(N)=N 
163 SMILES           CACTVS               3.341 Cn1c(CNC(=O)c2cccn2C(=O)[CH](CC3CCCCC3)NCC(O)=O)ccc1C(N)=N 
163 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1c(ccc1C(=N)N)CNC(=O)c2cccn2C(=O)[C@@H](CC3CCCCC3)NCC(=O)O 
163 SMILES           "OpenEye OEToolkits" 1.5.0 Cn1c(ccc1C(=N)N)CNC(=O)c2cccn2C(=O)C(CC3CCCCC3)NCC(=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 
163 "SYSTEMATIC NAME" ACDLabs              10.04 N-[(1R)-2-(2-{[(5-carbamimidoyl-1-methyl-1H-pyrrol-2-yl)methyl]carbamoyl}-1H-pyrrol-1-yl)-1-(cyclohexylmethyl)-2-oxoethyl]glycine      
163 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[(2R)-1-[2-[(5-carbamimidoyl-1-methyl-pyrrol-2-yl)methylcarbamoyl]pyrrol-1-yl]-3-cyclohexyl-1-oxo-propan-2-yl]amino]ethanoic acid" 
# 
