data_SM1
# 
_chem_comp.id                                    SM1 
_chem_comp.name                                  N-(BENZYLSULFONYL)-D-SERYL-N-(4-{[AMINO(IMINO)METHYL]AMINO}BENZYL)-L-ALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H28 N6 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-06-15 
_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                        476.549 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SM1 
_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        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
SM1 N6   N6   N 0 1 N N N 35.215 4.523  27.334 -0.288 0.934  -11.461 N6   SM1 1  
SM1 C18  C18  C 0 1 N N N 33.874 4.562  27.521 -0.412 0.353  -10.221 C18  SM1 2  
SM1 N5   N5   N 0 1 N N N 33.228 3.391  27.579 -0.175 -0.919 -10.071 N5   SM1 3  
SM1 N4   N4   N 0 1 N N N 33.214 5.736  27.650 -0.786 1.115  -9.137  N4   SM1 4  
SM1 C14  C14  C 0 1 Y N N 31.915 6.004  27.961 -0.798 0.552  -7.857  C14  SM1 5  
SM1 C13  C13  C 0 1 Y N N 31.287 7.054  27.266 0.131  -0.420 -7.516  C13  SM1 6  
SM1 C12  C12  C 0 1 Y N N 30.005 7.492  27.657 0.115  -0.974 -6.251  C12  SM1 7  
SM1 C17  C17  C 0 1 Y N N 29.346 6.860  28.729 -0.823 -0.561 -5.324  C17  SM1 8  
SM1 C16  C16  C 0 1 Y N N 29.945 5.741  29.351 -1.754 0.403  -5.663  C16  SM1 9  
SM1 C15  C15  C 0 1 Y N N 31.204 5.277  28.945 -1.741 0.966  -6.924  C15  SM1 10 
SM1 C11  C11  C 0 1 N N N 28.034 7.336  29.224 -0.837 -1.167 -3.945  C11  SM1 11 
SM1 N3   N3   N 0 1 N N N 28.166 8.219  30.315 0.024  -0.382 -3.057  N3   SM1 12 
SM1 C10  C10  C 0 1 N N N 28.445 9.501  30.197 0.166  -0.741 -1.766  C10  SM1 13 
SM1 O5   O5   O 0 1 N N N 28.546 10.070 29.100 -0.418 -1.713 -1.339  O5   SM1 14 
SM1 C8   C8   C 0 1 N N S 28.659 10.316 31.394 1.052  0.066  -0.853  C8   SM1 15 
SM1 C22  C22  C 0 1 N N N 27.434 11.224 31.664 2.482  0.063  -1.397  C22  SM1 16 
SM1 N2   N2   N 0 1 N N N 29.759 11.182 31.247 1.039  -0.523 0.487   N2   SM1 17 
SM1 C7   C7   C 0 1 N N N 31.008 10.890 30.989 1.212  0.260  1.569   C7   SM1 18 
SM1 C5   C5   C 0 1 N N R 32.008 11.949 30.856 1.198  -0.346 2.949   C5   SM1 19 
SM1 C6   C6   C 0 1 N N N 32.722 12.272 32.199 2.317  -1.383 3.061   C6   SM1 20 
SM1 O3   O3   O 0 1 N N N 31.750 12.583 33.210 3.578  -0.751 2.831   O3   SM1 21 
SM1 N1   N1   N 0 1 N N N 33.103 11.594 29.916 1.406  0.705  3.947   N1   SM1 22 
SM1 O4   O4   O 0 1 N N N 31.352 9.715  30.848 1.379  1.454  1.434   O4   SM1 23 
SM1 O2   O2   O 0 1 N N N 32.388 13.391 28.076 0.857  1.993  5.908   O2   SM1 24 
SM1 S1   S1   S 0 1 N N N 32.866 11.936 28.283 0.254  0.991  5.101   S1   SM1 25 
SM1 O1   O1   O 0 1 N N N 34.243 11.655 27.612 -0.910 1.244  4.328   O1   SM1 26 
SM1 C1   C1   C 0 1 N N N 31.648 10.876 27.604 0.143  -0.594 5.976   C1   SM1 27 
SM1 C4   C4   C 0 1 Y N N 31.470 11.088 26.149 -0.882 -0.491 7.075   C4   SM1 28 
SM1 C19  C19  C 0 1 Y N N 32.210 10.316 25.216 -2.204 -0.804 6.818   C19  SM1 29 
SM1 C20  C20  C 0 1 Y N N 32.093 10.536 23.826 -3.145 -0.709 7.826   C20  SM1 30 
SM1 C21  C21  C 0 1 Y N N 31.190 11.514 23.359 -2.765 -0.302 9.091   C21  SM1 31 
SM1 C2   C2   C 0 1 Y N N 30.404 12.247 24.278 -1.443 0.009  9.348   C2   SM1 32 
SM1 C3   C3   C 0 1 Y N N 30.565 12.062 25.673 -0.501 -0.089 8.341   C3   SM1 33 
SM1 H6N1 1H6N H 0 0 N N N 35.707 5.415  27.290 -0.024 0.397  -12.224 H6N1 SM1 34 
SM1 H6N2 2H6N H 0 0 N N N 35.713 3.638  27.237 -0.465 1.881  -11.572 H6N2 SM1 35 
SM1 H51  H51  H 0 1 N N N 32.209 3.371  27.535 0.088  -1.457 -10.834 H51  SM1 36 
SM1 H4   H4   H 0 1 N N N 33.788 6.563  27.486 -1.041 2.043  -9.262  H4   SM1 37 
SM1 H13  H13  H 0 1 N N N 31.798 7.535  26.415 0.865  -0.743 -8.238  H13  SM1 38 
SM1 H12  H12  H 0 1 N N N 29.520 8.327  27.125 0.838  -1.731 -5.984  H12  SM1 39 
SM1 H16  H16  H 0 1 N N N 29.414 5.225  30.168 -2.487 0.724  -4.937  H16  SM1 40 
SM1 H15  H15  H 0 1 N N N 31.633 4.361  29.385 -2.465 1.723  -7.186  H15  SM1 41 
SM1 H111 1H11 H 0 0 N N N 27.363 6.482  29.475 -1.856 -1.165 -3.557  H111 SM1 42 
SM1 H112 2H11 H 0 0 N N N 27.435 7.795  28.403 -0.469 -2.192 -3.995  H112 SM1 43 
SM1 H3   H3   H 0 1 N N N 28.038 7.842  31.254 0.492  0.395  -3.399  H3   SM1 44 
SM1 H8   H8   H 0 1 N N N 28.827 9.649  32.272 0.685  1.091  -0.803  H8   SM1 45 
SM1 H221 1H22 H 0 0 N N N 27.597 11.845 32.576 2.850  -0.961 -1.448  H221 SM1 46 
SM1 H222 2H22 H 0 0 N N N 26.489 10.635 31.728 2.492  0.502  -2.395  H222 SM1 47 
SM1 H223 3H22 H 0 0 N N N 27.181 11.851 30.777 3.123  0.647  -0.737  H223 SM1 48 
SM1 H2   H2   H 0 1 N N N 29.554 12.175 31.357 0.906  -1.477 0.596   H2   SM1 49 
SM1 H5   H5   H 0 1 N N N 31.504 12.873 30.487 0.237  -0.828 3.124   H5   SM1 50 
SM1 H6C1 1H6C H 0 0 N N N 33.480 13.082 32.085 2.163  -2.166 2.318   H6C1 SM1 51 
SM1 H6C2 2H6C H 0 0 N N N 33.407 11.451 32.516 2.308  -1.822 4.059   H6C2 SM1 52 
SM1 HA   HA   H 0 1 N N N 32.186 12.780 34.030 4.254  -1.438 2.911   HA   SM1 53 
SM1 H1   H1   H 0 1 N N N 33.965 11.160 30.247 2.219  1.235  3.932   H1   SM1 54 
SM1 H1C1 1H1C H 0 0 N N N 30.679 10.974 28.147 1.113  -0.839 6.407   H1C1 SM1 55 
SM1 H1C2 2H1C H 0 0 N N N 31.871 9.807  27.832 -0.151 -1.375 5.276   H1C2 SM1 56 
SM1 H19  H19  H 0 1 N N N 32.890 9.529  25.584 -2.501 -1.122 5.830   H19  SM1 57 
SM1 H20  H20  H 0 1 N N N 32.700 9.951  23.115 -4.178 -0.953 7.625   H20  SM1 58 
SM1 H21  H21  H 0 1 N N N 31.097 11.707 22.277 -3.500 -0.228 9.878   H21  SM1 59 
SM1 HC   HC   H 0 1 N N N 29.659 12.969 23.905 -1.145 0.328  10.336  HC   SM1 60 
SM1 HB   HB   H 0 1 N N N 29.986 12.676 26.384 0.531  0.154  8.542   HB   SM1 61 
# 
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 
SM1 N6  C18  SING N N 1  
SM1 N6  H6N1 SING N N 2  
SM1 N6  H6N2 SING N N 3  
SM1 C18 N5   DOUB N Z 4  
SM1 C18 N4   SING N N 5  
SM1 N5  H51  SING N N 6  
SM1 N4  C14  SING N N 7  
SM1 N4  H4   SING N N 8  
SM1 C14 C13  DOUB Y N 9  
SM1 C14 C15  SING Y N 10 
SM1 C13 C12  SING Y N 11 
SM1 C13 H13  SING N N 12 
SM1 C12 C17  DOUB Y N 13 
SM1 C12 H12  SING N N 14 
SM1 C17 C16  SING Y N 15 
SM1 C17 C11  SING N N 16 
SM1 C16 C15  DOUB Y N 17 
SM1 C16 H16  SING N N 18 
SM1 C15 H15  SING N N 19 
SM1 C11 N3   SING N N 20 
SM1 C11 H111 SING N N 21 
SM1 C11 H112 SING N N 22 
SM1 N3  C10  SING N N 23 
SM1 N3  H3   SING N N 24 
SM1 C10 O5   DOUB N N 25 
SM1 C10 C8   SING N N 26 
SM1 C8  C22  SING N N 27 
SM1 C8  N2   SING N N 28 
SM1 C8  H8   SING N N 29 
SM1 C22 H221 SING N N 30 
SM1 C22 H222 SING N N 31 
SM1 C22 H223 SING N N 32 
SM1 N2  C7   SING N N 33 
SM1 N2  H2   SING N N 34 
SM1 C7  C5   SING N N 35 
SM1 C7  O4   DOUB N N 36 
SM1 C5  C6   SING N N 37 
SM1 C5  N1   SING N N 38 
SM1 C5  H5   SING N N 39 
SM1 C6  O3   SING N N 40 
SM1 C6  H6C1 SING N N 41 
SM1 C6  H6C2 SING N N 42 
SM1 O3  HA   SING N N 43 
SM1 N1  S1   SING N N 44 
SM1 N1  H1   SING N N 45 
SM1 O2  S1   DOUB N N 46 
SM1 S1  O1   DOUB N N 47 
SM1 S1  C1   SING N N 48 
SM1 C1  C4   SING N N 49 
SM1 C1  H1C1 SING N N 50 
SM1 C1  H1C2 SING N N 51 
SM1 C4  C19  DOUB Y N 52 
SM1 C4  C3   SING Y N 53 
SM1 C19 C20  SING Y N 54 
SM1 C19 H19  SING N N 55 
SM1 C20 C21  DOUB Y N 56 
SM1 C20 H20  SING N N 57 
SM1 C21 C2   SING Y N 58 
SM1 C21 H21  SING N N 59 
SM1 C2  C3   DOUB Y N 60 
SM1 C2  HC   SING N N 61 
SM1 C3  HB   SING N N 62 
# 
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 
SM1 SMILES           ACDLabs              10.04 O=S(=O)(NC(C(=O)NC(C(=O)NCc1ccc(NC(=[N@H])N)cc1)C)CO)Cc2ccccc2 
SM1 InChI            InChI                1.02b 
InChI=1/C21H28N6O5S/c1-14(19(29)24-11-15-7-9-17(10-8-15)26-21(22)23)25-20(30)18(12-28)27-33(31,32)13-16-5-3-2-4-6-16/h2-10,14,18,27-28H,11-13H2,1H3,(H,24,29)(H,25,30)(H4,22,23,26)/t14-,18+/m0/s1/f/h22,24-26H,23H2/b22-21- 
SM1 InChIKey         InChI                1.02b GIFIGLJPDYSYDF-PJBYANSIDJ 
SM1 SMILES_CANONICAL CACTVS               3.341 C[C@H](NC(=O)[C@@H](CO)N[S](=O)(=O)Cc1ccccc1)C(=O)NCc2ccc(NC(N)=N)cc2 
SM1 SMILES           CACTVS               3.341 C[CH](NC(=O)[CH](CO)N[S](=O)(=O)Cc1ccccc1)C(=O)NCc2ccc(NC(N)=N)cc2 
SM1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/N)\Nc1ccc(cc1)CNC(=O)[C@H](C)NC(=O)[C@@H](CO)NS(=O)(=O)Cc2ccccc2 
SM1 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)Nc1ccc(cc1)CNC(=O)C(C)NC(=O)C(CO)NS(=O)(=O)Cc2ccccc2 
# 
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 
SM1 "SYSTEMATIC NAME" ACDLabs              10.04 N-(benzylsulfonyl)-D-seryl-N-(4-carbamimidamidobenzyl)-L-alaninamide                                                        
SM1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-N-[(2S)-1-[(4-carbamimidamidophenyl)methylamino]-1-oxo-propan-2-yl]-3-hydroxy-2-(phenylmethylsulfonylamino)propanamide 
# 
