data_5PI
# 
_chem_comp.id                                    5PI 
_chem_comp.name                                  N-(ETHYLSULFONYL)-5-PROPOXY-L-TRYPTOPHYL-N~1~-{4-[AMINO(IMINO)METHYL]BENZYL}-L-GLUTAMAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H39 N7 O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2-[2-ETHANESULFONYLAMINO-3-(5-PROPOXY-1H-INDOL-3-YL)-PROPIONYLAMINO]-PENTANEDIOIC ACID 5-AMIDE 1-(4-CARBAMIMIDOYL-BENZYLAMIDE)" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-17 
_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                        613.728 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5PI 
_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        1WV7 
_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 
5PI C14  C14  C 0 1 N N N 35.774 6.979  10.145 -0.048 0.072  0.145   C14  5PI 1  
5PI O1   O1   O 0 1 N N N 34.901 7.202  10.975 0.581  1.106  0.069   O1   5PI 2  
5PI N5   N5   N 0 1 N N N 35.694 7.398  8.829  -0.317 -0.636 -0.968  N5   5PI 3  
5PI C15  C15  C 0 1 N N S 34.566 8.296  8.403  0.150  -0.158 -2.271  C15  5PI 4  
5PI C18  C18  C 0 1 N N N 34.574 8.643  6.945  1.541  -0.727 -2.554  C18  5PI 5  
5PI C19  C19  C 0 1 N N N 35.895 9.232  6.512  2.511  -0.267 -1.464  C19  5PI 6  
5PI C20  C20  C 0 1 N N N 33.182 7.668  8.659  -0.805 -0.611 -3.345  C20  5PI 7  
5PI O5   O5   O 0 1 N N N 32.949 6.499  8.418  -1.781 -1.269 -3.050  O5   5PI 8  
5PI N6   N6   N 0 1 N N N 32.292 8.482  9.154  -0.575 -0.286 -4.632  N6   5PI 9  
5PI C21  C21  C 0 1 N N N 30.979 7.941  9.381  -1.504 -0.727 -5.676  C21  5PI 10 
5PI C16  C16  C 0 1 Y N N 31.500 6.526  11.432 -0.167 -1.018 -7.771  C16  5PI 11 
5PI C17  C17  C 0 1 Y N N 31.259 6.210  12.769 0.276  -0.573 -8.999  C17  5PI 12 
5PI C22  C22  C 0 1 Y N N 30.253 6.884  13.499 -0.139 0.667  -9.481  C22  5PI 13 
5PI C23  C23  C 0 1 Y N N 29.420 7.784  12.820 -1.002 1.452  -8.716  C23  5PI 14 
5PI C24  C24  C 0 1 Y N N 29.632 8.075  11.482 -1.444 0.994  -7.491  C24  5PI 15 
5PI C25  C25  C 0 1 Y N N 30.696 7.490  10.787 -1.023 -0.235 -7.017  C25  5PI 16 
5PI C26  C26  C 0 1 N N N 30.139 6.711  14.968 0.333  1.150  -10.798 C26  5PI 17 
5PI N1   N1   N 0 1 N N N 30.891 5.826  15.613 -0.079 2.377  -11.271 N1   5PI 18 
5PI C2   C2   C 0 1 N N N 35.857 9.684  5.094  3.882  -0.828 -1.742  C2   5PI 19 
5PI O2   O2   O 0 1 N N N 35.856 8.905  4.183  4.065  -1.527 -2.716  O2   5PI 20 
5PI N3   N3   N 0 1 N N N 35.852 10.984 4.939  4.905  -0.553 -0.908  N3   5PI 21 
5PI C1   C1   C 0 1 N N N 38.105 7.027  11.358 0.536  -1.320 2.111   C1   5PI 22 
5PI N4   N4   N 0 1 N N N 36.414 5.167  11.451 -0.777 0.726  2.366   N4   5PI 23 
5PI C5   C5   C 0 1 N N R 37.017 6.176  10.608 -0.529 -0.418 1.486   C5   5PI 24 
5PI S1   S1   S 0 1 N N N 36.506 3.567  10.948 -2.291 0.981  2.986   S1   5PI 25 
5PI O4   O4   O 0 1 N N N 36.290 3.722  9.553  -2.098 2.102  3.837   O4   5PI 26 
5PI O3   O3   O 0 1 N N N 35.600 2.928  11.839 -3.102 1.048  1.821   O3   5PI 27 
5PI C9   C9   C 0 1 N N N 38.146 2.961  11.124 -2.609 -0.531 3.936   C9   5PI 28 
5PI C8   C8   C 0 1 N N N 38.422 2.536  12.524 -3.994 -0.446 4.581   C8   5PI 29 
5PI N2   N2   N 0 1 N N N 29.348 7.500  15.708 1.140  0.416  -11.510 N2   5PI 30 
5PI C13  C13  C 0 1 Y N N 43.109 4.800  10.856 0.314  -0.458 7.428   C13  5PI 31 
5PI C12  C12  C 0 1 Y N N 42.507 4.664  12.152 -0.325 -1.615 7.044   C12  5PI 32 
5PI C3   C3   C 0 1 Y N N 41.231 5.169  12.443 -0.358 -1.979 5.703   C3   5PI 33 
5PI C4   C4   C 0 1 Y N N 40.482 5.825  11.402 0.266  -1.159 4.746   C4   5PI 34 
5PI C27  C27  C 0 1 Y N N 41.074 5.980  10.136 0.908  0.014  5.146   C27  5PI 35 
5PI C6   C6   C 0 1 Y N N 42.397 5.486  9.822  0.934  0.356  6.484   C6   5PI 36 
5PI N7   N7   N 0 1 Y N N 40.481 5.252  13.602 -0.904 -3.049 5.025   N7   5PI 37 
5PI C29  C29  C 0 1 Y N N 39.317 5.894  13.350 -0.647 -2.931 3.687   C29  5PI 38 
5PI C28  C28  C 0 1 Y N N 39.248 6.262  11.999 0.055  -1.812 3.452   C28  5PI 39 
5PI O6   O6   O 0 1 N N N 43.058 5.644  8.593  1.562  1.495  6.880   O6   5PI 40 
5PI C7   C7   C 0 1 N N N 42.279 5.363  7.442  1.413  1.577  8.299   C7   5PI 41 
5PI C10  C10  C 0 1 N N N 43.182 5.534  6.222  2.101  2.844  8.811   C10  5PI 42 
5PI C11  C11  C 0 1 N N N 42.465 5.175  4.923  1.942  2.931  10.331  C11  5PI 43 
5PI HN5  HN5  H 0 1 N N N 36.428 7.062  8.206  -0.821 -1.463 -0.906  HN5  5PI 44 
5PI H15  H15  H 0 1 N N N 34.734 9.209  9.021  0.197  0.930  -2.263  H15  5PI 45 
5PI H181 1H18 H 0 0 N N N 33.725 9.318  6.685  1.494  -1.816 -2.562  H181 5PI 46 
5PI H182 2H18 H 0 0 N N N 34.298 7.763  6.318  1.889  -0.372 -3.524  H182 5PI 47 
5PI H191 1H19 H 0 0 N N N 36.735 8.521  6.690  2.559  0.821  -1.456  H191 5PI 48 
5PI H192 2H19 H 0 0 N N N 36.216 10.055 7.193  2.163  -0.623 -0.494  H192 5PI 49 
5PI HN6  HN6  H 0 1 N N N 32.591 9.439  9.343  0.204  0.239  -4.868  HN6  5PI 50 
5PI H211 1H21 H 0 0 N N N 30.782 7.108  8.667  -1.552 -1.816 -5.684  H211 5PI 51 
5PI H212 2H21 H 0 0 N N N 30.204 8.672  9.052  -2.496 -0.321 -5.475  H212 5PI 52 
5PI H16  H16  H 0 1 N N N 32.317 6.019  10.891 0.154  -1.978 -7.397  H16  5PI 53 
5PI H17  H17  H 0 1 N N N 31.866 5.425  13.251 0.945  -1.185 -9.587  H17  5PI 54 
5PI H23  H23  H 0 1 N N N 28.583 8.272  13.348 -1.328 2.413  -9.083  H23  5PI 55 
5PI H24  H24  H 0 1 N N N 28.951 8.775  10.968 -2.112 1.600  -6.899  H24  5PI 56 
5PI HN11 1HN1 H 0 0 N N N 31.868 6.019  15.392 0.230  2.694  -12.134 HN11 5PI 57 
5PI HN12 2HN1 H 0 0 N N N 30.813 5.707  16.623 -0.679 2.924  -10.741 HN12 5PI 58 
5PI HN31 1HN3 H 0 0 N N N 35.826 11.294 3.968  5.787  -0.914 -1.087  HN31 5PI 59 
5PI HN32 2HN3 H 0 0 N N N 35.853 11.647 5.714  4.758  0.005  -0.129  HN32 5PI 60 
5PI H11  1H1  H 0 1 N N N 37.613 7.673  12.122 1.459  -0.756 2.241   H11  5PI 61 
5PI H12A 2H1  H 0 0 N N N 38.514 7.802  10.668 0.720  -2.172 1.457   H12A 5PI 62 
5PI HN4  HN4  H 0 1 N N N 35.438 5.410  11.619 -0.054 1.334  2.585   HN4  5PI 63 
5PI H5   H5   H 0 1 N N N 37.608 5.770  9.754  -1.452 -0.983 1.356   H5   5PI 64 
5PI H91  1H9  H 0 1 N N N 38.897 3.705  10.768 -2.571 -1.393 3.270   H91  5PI 65 
5PI H92  2H9  H 0 1 N N N 38.358 2.141  10.399 -1.852 -0.638 4.713   H92  5PI 66 
5PI H81  1H8  H 0 1 N N N 37.672 1.792  12.880 -4.185 -1.355 5.151   H81  5PI 67 
5PI H82  2H8  H 0 1 N N N 39.463 2.152  12.636 -4.032 0.415  5.247   H82  5PI 68 
5PI H83  3H8  H 0 1 N N N 38.210 3.356  13.249 -4.751 -0.339 3.804   H83  5PI 69 
5PI HN2  HN2  H 0 1 N N N 29.567 8.322  15.145 1.450  0.733  -12.373 HN2  5PI 70 
5PI H13  H13  H 0 1 N N N 44.110 4.381  10.657 0.337  -0.180 8.471   H13  5PI 71 
5PI H12  H12  H 0 1 N N N 43.050 4.148  12.962 -0.802 -2.239 7.785   H12  5PI 72 
5PI H27  H27  H 0 1 N N N 40.483 6.505  9.366  1.384  0.649  4.414   H27  5PI 73 
5PI HN7  HN7  H 0 1 N N N 40.749 4.890  14.517 -1.398 -3.776 5.436   HN7  5PI 74 
5PI H29  H29  H 0 1 N N N 38.550 6.086  14.120 -0.964 -3.634 2.931   H29  5PI 75 
5PI H71  1H7  H 0 1 N N N 41.351 5.978  7.385  1.870  0.702  8.763   H71  5PI 76 
5PI H72  2H7  H 0 1 N N N 41.789 4.362  7.483  0.354  1.611  8.552   H72  5PI 77 
5PI H101 1H10 H 0 0 N N N 44.128 4.955  6.335  1.645  3.718  8.347   H101 5PI 78 
5PI H102 2H10 H 0 0 N N N 43.610 6.563  6.177  3.161  2.809  8.558   H102 5PI 79 
5PI H111 1H11 H 0 0 N N N 41.519 5.754  4.810  2.432  3.834  10.696  H111 5PI 80 
5PI H112 2H11 H 0 0 N N N 43.124 5.300  4.032  0.883  2.965  10.584  H112 5PI 81 
5PI H113 3H11 H 0 0 N N N 42.037 4.146  4.968  2.399  2.057  10.794  H113 5PI 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 
5PI C14 O1   DOUB N N 1  
5PI C14 N5   SING N N 2  
5PI C14 C5   SING N N 3  
5PI N5  C15  SING N N 4  
5PI N5  HN5  SING N N 5  
5PI C15 C18  SING N N 6  
5PI C15 C20  SING N N 7  
5PI C15 H15  SING N N 8  
5PI C18 C19  SING N N 9  
5PI C18 H181 SING N N 10 
5PI C18 H182 SING N N 11 
5PI C19 C2   SING N N 12 
5PI C19 H191 SING N N 13 
5PI C19 H192 SING N N 14 
5PI C20 O5   DOUB N N 15 
5PI C20 N6   SING N N 16 
5PI N6  C21  SING N N 17 
5PI N6  HN6  SING N N 18 
5PI C21 C25  SING N N 19 
5PI C21 H211 SING N N 20 
5PI C21 H212 SING N N 21 
5PI C16 C17  DOUB Y N 22 
5PI C16 C25  SING Y N 23 
5PI C16 H16  SING N N 24 
5PI C17 C22  SING Y N 25 
5PI C17 H17  SING N N 26 
5PI C22 C23  DOUB Y N 27 
5PI C22 C26  SING N N 28 
5PI C23 C24  SING Y N 29 
5PI C23 H23  SING N N 30 
5PI C24 C25  DOUB Y N 31 
5PI C24 H24  SING N N 32 
5PI C26 N1   SING N N 33 
5PI C26 N2   DOUB N N 34 
5PI N1  HN11 SING N N 35 
5PI N1  HN12 SING N N 36 
5PI C2  O2   DOUB N N 37 
5PI C2  N3   SING N N 38 
5PI N3  HN31 SING N N 39 
5PI N3  HN32 SING N N 40 
5PI C1  C5   SING N N 41 
5PI C1  C28  SING N N 42 
5PI C1  H11  SING N N 43 
5PI C1  H12A SING N N 44 
5PI N4  C5   SING N N 45 
5PI N4  S1   SING N N 46 
5PI N4  HN4  SING N N 47 
5PI C5  H5   SING N N 48 
5PI S1  O4   DOUB N N 49 
5PI S1  O3   DOUB N N 50 
5PI S1  C9   SING N N 51 
5PI C9  C8   SING N N 52 
5PI C9  H91  SING N N 53 
5PI C9  H92  SING N N 54 
5PI C8  H81  SING N N 55 
5PI C8  H82  SING N N 56 
5PI C8  H83  SING N N 57 
5PI N2  HN2  SING N N 58 
5PI C13 C12  DOUB Y N 59 
5PI C13 C6   SING Y N 60 
5PI C13 H13  SING N N 61 
5PI C12 C3   SING Y N 62 
5PI C12 H12  SING N N 63 
5PI C3  C4   DOUB Y N 64 
5PI C3  N7   SING Y N 65 
5PI C4  C27  SING Y N 66 
5PI C4  C28  SING Y N 67 
5PI C27 C6   DOUB Y N 68 
5PI C27 H27  SING N N 69 
5PI C6  O6   SING N N 70 
5PI N7  C29  SING Y N 71 
5PI N7  HN7  SING N N 72 
5PI C29 C28  DOUB Y N 73 
5PI C29 H29  SING N N 74 
5PI O6  C7   SING N N 75 
5PI C7  C10  SING N N 76 
5PI C7  H71  SING N N 77 
5PI C7  H72  SING N N 78 
5PI C10 C11  SING N N 79 
5PI C10 H101 SING N N 80 
5PI C10 H102 SING N N 81 
5PI C11 H111 SING N N 82 
5PI C11 H112 SING N N 83 
5PI C11 H113 SING N N 84 
# 
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 
5PI SMILES           ACDLabs              10.04 O=C(NCc1ccc(C(=[N@H])N)cc1)C(NC(=O)C(NS(=O)(=O)CC)Cc3c2cc(OCCC)ccc2nc3)CCC(=O)N 
5PI InChI            InChI                1.02b 
;InChI=1/C29H39N7O6S/c1-3-13-42-21-9-10-23-22(15-21)20(17-33-23)14-25(36-43(40,41)4-2)29(39)35-24(11-12-26(30)37)28(38)34-16-18-5-7-19(8-6-18)27(31)32/h5-10,15,17,24-25,33,36H,3-4,11-14,16H2,1-2H3,(H2,30,37)(H3,31,32)(H,34,38)(H,35,39)/t24-,25+/m0/s1/f/h31,34-35H,30,32H2/b31-27+
;
5PI InChIKey         InChI                1.02b UHMORXPPNXDKHY-LBEQDIHNDK 
5PI SMILES_CANONICAL CACTVS               3.341 CCCOc1ccc2[nH]cc(C[C@@H](N[S](=O)(=O)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)NCc3ccc(cc3)C(N)=N)c2c1 
5PI SMILES           CACTVS               3.341 CCCOc1ccc2[nH]cc(C[CH](N[S](=O)(=O)CC)C(=O)N[CH](CCC(N)=O)C(=O)NCc3ccc(cc3)C(N)=N)c2c1 
5PI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCOc1ccc2c(c1)c(c[nH]2)C[C@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NCc3ccc(cc3)C(=N)N)NS(=O)(=O)CC 
5PI SMILES           "OpenEye OEToolkits" 1.5.0 CCCOc1ccc2c(c1)c(c[nH]2)CC(C(=O)NC(CCC(=O)N)C(=O)NCc3ccc(cc3)C(=N)N)NS(=O)(=O)CC 
# 
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 
5PI "SYSTEMATIC NAME" ACDLabs              10.04 N-(ethylsulfonyl)-5-propoxy-D-tryptophyl-N~1~-(4-carbamimidoylbenzyl)-L-glutamamide                                              
5PI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-[(4-carbamimidoylphenyl)methyl]-2-[[(2R)-2-(ethylsulfonylamino)-3-(5-propoxy-1H-indol-3-yl)propanoyl]amino]pentanediamide 
# 
