data_S1S
# 
_chem_comp.id                                    S1S 
_chem_comp.name                                  "2-(4-((9S,10S,14S,Z)-18-(2-AMINO-2-OXOETHYL)-9-(CARBOXYMETHYL)-14-(NAPHTHALEN-1-YLMETHYL)-8,17,20-TRIOXO-7,16,19-TRIAZASPIRO[5.14]ICOS-11-EN-10-YL)PHENYL)MALONIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C41 H46 N4 O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-02 
_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                        754.825 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     S1S 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2AOA 
_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 
S1S O9   O9   O 0 1 N N N 43.009 22.961 5.294  6.776  3.559  0.051  O9   S1S 1   
S1S C40  C40  C 0 1 N N N 42.430 22.259 4.453  5.645  3.001  0.512  C40  S1S 2   
S1S O8   O8   O 0 1 N N N 41.912 22.738 3.331  5.698  2.132  1.350  O8   S1S 3   
S1S C39  C39  C 0 1 N N N 42.617 20.770 4.910  4.310  3.460  -0.014 C39  S1S 4   
S1S C38  C38  C 0 1 N N S 44.110 20.277 4.972  3.193  2.670  0.671  C38  S1S 5   
S1S C15  C15  C 0 1 N N S 44.574 19.051 5.839  1.835  3.220  0.230  C15  S1S 6   
S1S C16  C16  C 0 1 Y N N 44.220 19.124 7.287  1.258  2.333  -0.843 C16  S1S 7   
S1S C17  C17  C 0 1 Y N N 42.979 18.679 7.721  1.353  2.703  -2.171 C17  S1S 8   
S1S C18  C18  C 0 1 Y N N 42.619 18.882 9.069  0.823  1.889  -3.155 C18  S1S 9   
S1S C19  C19  C 0 1 Y N N 43.474 19.513 9.991  0.199  0.705  -2.811 C19  S1S 10  
S1S C22  C22  C 0 1 N N N 42.964 19.597 11.407 -0.380 -0.182 -3.883 C22  S1S 11  
S1S C24  C24  C 0 1 N N N 43.215 18.365 12.187 0.289  -1.531 -3.834 C24  S1S 12  
S1S O3   O3   O 0 1 N N N 44.076 17.593 11.737 -0.069 -2.490 -4.703 O3   S1S 13  
S1S O2   O2   O 0 1 N N N 42.529 18.028 13.175 1.147  -1.750 -3.012 O2   S1S 14  
S1S C23  C23  C 0 1 N N N 43.411 20.844 12.055 -1.860 -0.346 -3.655 C23  S1S 15  
S1S O1   O1   O 0 1 N N N 43.985 20.781 13.173 -2.589 -1.100 -4.493 O1   S1S 16  
S1S O    O    O 0 1 N N N 43.062 21.889 11.416 -2.391 0.201  -2.717 O    S1S 17  
S1S C20  C20  C 0 1 Y N N 44.747 20.047 9.520  0.104  0.335  -1.482 C20  S1S 18  
S1S C21  C21  C 0 1 Y N N 45.015 19.881 8.166  0.638  1.146  -0.499 C21  S1S 19  
S1S C14  C14  C 0 1 N N N 43.973 17.775 5.164  0.900  3.254  1.411  C14  S1S 20  
S1S C13  C13  C 0 1 N N N 44.717 16.695 4.867  -0.349 2.887  1.268  C13  S1S 21  
S1S C12  C12  C 0 1 N N N 44.228 15.418 4.175  -1.284 2.920  2.449  C12  S1S 22  
S1S C37  C37  C 0 1 N N N 44.877 20.461 3.742  3.296  1.217  0.286  C37  S1S 23  
S1S O7   O7   O 0 1 N N N 44.451 19.709 2.844  3.226  0.876  -0.876 O7   S1S 24  
S1S N3   N3   N 0 1 N N N 45.988 21.163 3.447  3.471  0.289  1.281  N3   S1S 25  
S1S C31  C31  C 0 1 N N N 46.580 21.408 2.092  3.577  -1.109 0.797  C31  S1S 26  
S1S C32  C32  C 0 1 N N N 47.816 22.215 2.634  4.922  -1.685 1.241  C32  S1S 27  
S1S C33  C33  C 0 1 N N N 47.601 23.715 2.854  5.059  -3.118 0.722  C33  S1S 28  
S1S C34  C34  C 0 1 N N N 46.777 24.392 1.700  4.979  -3.117 -0.806 C34  S1S 29  
S1S C35  C35  C 0 1 N N N 45.472 23.731 1.516  3.629  -2.546 -1.245 C35  S1S 30  
S1S C36  C36  C 0 1 N N N 45.604 22.132 1.300  3.490  -1.112 -0.729 C36  S1S 31  
S1S C30  C30  C 0 1 N N N 46.958 20.072 1.565  2.453  -1.920 1.378  C30  S1S 32  
S1S O6   O6   O 0 1 N N N 46.828 19.867 0.404  2.660  -3.039 1.797  O6   S1S 33  
S1S N2   N2   N 0 1 N N N 47.554 19.294 2.380  1.200  -1.386 1.431  N2   S1S 34  
S1S C27  C27  C 0 1 N N R 47.951 17.864 2.460  0.149  -2.262 1.993  C27  S1S 35  
S1S C28  C28  C 0 1 N N N 49.298 17.600 2.841  -0.533 -3.035 0.863  C28  S1S 36  
S1S C29  C29  C 0 1 N N N 49.070 17.422 4.158  -1.491 -4.040 1.449  C29  S1S 37  
S1S N1   N1   N 0 1 N N N 49.798 16.568 4.808  -2.303 -4.749 0.640  N1   S1S 38  
S1S O5   O5   O 0 1 N N N 48.202 18.061 4.718  -1.530 -4.212 2.649  O5   S1S 39  
S1S C26  C26  C 0 1 N N N 47.126 16.597 1.996  -0.868 -1.410 2.707  C26  S1S 40  
S1S O4   O4   O 0 1 N N N 47.569 15.541 1.514  -1.467 -1.840 3.670  O4   S1S 41  
S1S N    N    N 0 1 N N N 45.816 16.896 2.151  -1.103 -0.143 2.253  N    S1S 42  
S1S C25  C25  C 0 1 N N N 44.719 15.854 1.730  -2.119 0.630  2.999  C25  S1S 43  
S1S C11  C11  C 0 1 N N S 44.874 14.869 2.908  -2.419 1.918  2.230  C11  S1S 44  
S1S C10  C10  C 0 1 N N N 44.056 13.621 2.515  -2.541 1.604  0.738  C10  S1S 45  
S1S C    C    C 0 1 Y N N 44.263 12.444 3.451  -3.735 0.715  0.507  C    S1S 46  
S1S C1   C1   C 0 1 Y N N 43.231 12.064 4.322  -3.580 -0.637 0.446  C1   S1S 47  
S1S C2   C2   C 0 1 Y N N 43.353 10.836 5.086  -4.672 -1.475 0.234  C2   S1S 48  
S1S C3   C3   C 0 1 Y N N 44.544 10.093 5.105  -5.926 -0.968 0.082  C3   S1S 49  
S1S C9   C9   C 0 1 Y N N 45.604 10.432 4.215  -6.126 0.422  0.140  C9   S1S 50  
S1S C8   C8   C 0 1 Y N N 45.526 11.618 3.407  -5.015 1.275  0.361  C8   S1S 51  
S1S C7   C7   C 0 1 Y N N 46.633 11.963 2.492  -5.214 2.665  0.413  C7   S1S 52  
S1S C6   C6   C 0 1 Y N N 47.744 11.069 2.437  -6.468 3.172  0.261  C6   S1S 53  
S1S C5   C5   C 0 1 Y N N 47.825 9.973  3.292  -7.561 2.333  0.049  C5   S1S 54  
S1S C4   C4   C 0 1 Y N N 46.837 9.621  4.189  -7.406 0.982  -0.012 C4   S1S 55  
S1S HO9  HO9  H 0 1 N N N 43.015 23.866 5.002  7.633  3.265  0.389  HO9  S1S 56  
S1S H391 1H39 H 0 0 N N N 42.192 20.675 5.921  4.266  3.291  -1.090 H391 S1S 57  
S1S H392 2H39 H 0 0 N N N 42.113 20.146 4.156  4.183  4.522  0.192  H392 S1S 58  
S1S H38  H38  H 0 1 N N N 44.397 21.041 5.708  3.290  2.767  1.752  H38  S1S 59  
S1S H15  H15  H 0 1 N N N 45.673 19.035 5.855  1.962  4.229  -0.162 H15  S1S 60  
S1S H17  H17  H 0 1 N N N 42.301 18.186 7.039  1.840  3.628  -2.440 H17  S1S 61  
S1S H18  H18  H 0 1 N N N 41.651 18.542 9.405  0.897  2.179  -4.193 H18  S1S 62  
S1S H22  H22  H 0 1 N N N 41.866 19.654 11.371 -0.211 0.272  -4.860 H22  S1S 63  
S1S HO2  HO2  H 0 1 N N N 42.790 17.160 13.459 ?      ?      ?      HO2  S1S 64  
S1S HO1  HO1  H 0 1 N N N 44.135 21.659 13.504 -3.539 -1.205 -4.346 HO1  S1S 65  
S1S H20  H20  H 0 1 N N N 45.440 20.541 10.185 -0.384 -0.591 -1.213 H20  S1S 66  
S1S H21  H21  H 0 1 N N N 45.892 20.366 7.763  0.564  0.857  0.539  H21  S1S 67  
S1S H14  H14  H 0 1 N N N 42.920 17.761 4.926  1.260  3.582  2.375  H14  S1S 68  
S1S H13  H13  H 0 1 N N N 45.761 16.731 5.142  -0.709 2.558  0.304  H13  S1S 69  
S1S H121 1H12 H 0 0 N N N 43.181 15.620 3.902  -0.736 2.656  3.354  H121 S1S 70  
S1S H122 2H12 H 0 0 N N N 44.473 14.644 4.916  -1.699 3.922  2.556  H122 S1S 71  
S1S HN3  HN3  H 0 1 N N N 46.474 21.569 4.221  3.521  0.526  2.220  HN3  S1S 72  
S1S H321 1H32 H 0 0 N N N 48.090 21.780 3.606  5.729  -1.073 0.838  H321 S1S 73  
S1S H322 2H32 H 0 0 N N N 48.588 22.136 1.856  4.975  -1.686 2.330  H322 S1S 74  
S1S H331 1H33 H 0 0 N N N 48.586 24.202 2.905  6.020  -3.527 1.035  H331 S1S 75  
S1S H332 2H33 H 0 0 N N N 47.027 23.835 3.785  4.254  -3.730 1.128  H332 S1S 76  
S1S H341 1H34 H 0 0 N N N 47.348 24.317 0.764  5.783  -2.504 -1.212 H341 S1S 77  
S1S H342 2H34 H 0 0 N N N 46.599 25.443 1.970  5.079  -4.138 -1.175 H342 S1S 78  
S1S H351 1H35 H 0 0 N N N 44.988 24.162 0.628  3.571  -2.547 -2.334 H351 S1S 79  
S1S H352 2H35 H 0 0 N N N 44.884 23.895 2.431  2.825  -3.158 -0.838 H352 S1S 80  
S1S H361 1H36 H 0 0 N N N 44.621 21.701 1.541  2.527  -0.706 -1.038 H361 S1S 81  
S1S H362 2H36 H 0 0 N N N 45.952 22.022 0.263  4.292  -0.498 -1.140 H362 S1S 82  
S1S HN2  HN2  H 0 1 N N N 47.756 19.957 3.127  1.009  -0.488 1.118  HN2  S1S 83  
S1S H27  H27  H 0 1 N N N 46.966 18.016 2.960  0.597  -2.963 2.697  H27  S1S 84  
S1S H281 1H28 H 0 0 N N N 49.736 16.723 2.343  0.221  -3.554 0.271  H281 S1S 85  
S1S H282 2H28 H 0 0 N N N 50.038 18.370 2.575  -1.080 -2.340 0.226  H282 S1S 86  
S1S HN11 1HN1 H 0 0 N N N 50.472 16.121 4.218  -2.919 -5.396 1.017  HN11 S1S 87  
S1S HN12 2HN1 H 0 0 N N N 49.698 16.377 5.784  -2.274 -4.608 -0.320 HN12 S1S 88  
S1S HN   HN   H 0 1 N N N 45.546 17.781 2.532  -0.634 0.226  1.488  HN   S1S 89  
S1S H251 1H25 H 0 0 N N N 43.711 16.290 1.658  -1.736 0.876  3.989  H251 S1S 90  
S1S H252 2H25 H 0 0 N N N 44.840 15.417 0.728  -3.031 0.040  3.094  H252 S1S 91  
S1S H11  H11  H 0 1 N N N 45.940 14.676 3.098  -3.355 2.346  2.589  H11  S1S 92  
S1S H101 1H10 H 0 0 N N N 42.990 13.889 2.531  -2.667 2.533  0.180  H101 S1S 93  
S1S H102 2H10 H 0 0 N N N 44.399 13.308 1.517  -1.638 1.096  0.398  H102 S1S 94  
S1S HC1  HC1  H 0 1 N N N 42.352 12.683 4.423  -2.596 -1.065 0.563  HC1  S1S 95  
S1S HC2  HC2  H 0 1 N N N 42.504 10.484 5.655  -4.522 -2.544 0.189  HC2  S1S 96  
S1S HC3  HC3  H 0 1 N N N 44.658 9.269  5.793  -6.764 -1.630 -0.082 HC3  S1S 97  
S1S HC7  HC7  H 0 1 N N N 46.604 12.859 1.888  -4.377 3.327  0.575  HC7  S1S 98  
S1S HC6  HC6  H 0 1 N N N 48.534 11.243 1.721  -6.618 4.241  0.305  HC6  S1S 99  
S1S HC5  HC5  H 0 1 N N N 48.714 9.362  3.253  -8.545 2.761  -0.068 HC5  S1S 100 
S1S HC4  HC4  H 0 1 N N N 46.961 8.778  4.851  -8.262 0.345  -0.178 HC4  S1S 101 
# 
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 
S1S O9  C40  SING N N 1   
S1S O9  HO9  SING N N 2   
S1S C40 O8   DOUB N N 3   
S1S C40 C39  SING N N 4   
S1S C39 C38  SING N N 5   
S1S C39 H391 SING N N 6   
S1S C39 H392 SING N N 7   
S1S C38 C15  SING N N 8   
S1S C38 C37  SING N N 9   
S1S C38 H38  SING N N 10  
S1S C15 C16  SING N N 11  
S1S C15 C14  SING N N 12  
S1S C15 H15  SING N N 13  
S1S C16 C17  SING Y N 14  
S1S C16 C21  DOUB Y N 15  
S1S C17 C18  DOUB Y N 16  
S1S C17 H17  SING N N 17  
S1S C18 C19  SING Y N 18  
S1S C18 H18  SING N N 19  
S1S C19 C22  SING N N 20  
S1S C19 C20  DOUB Y N 21  
S1S C22 C24  SING N N 22  
S1S C22 C23  SING N N 23  
S1S C22 H22  SING N N 24  
S1S C24 O3   DOUB N N 25  
S1S C24 O2   SING N N 26  
S1S O2  HO2  SING N N 27  
S1S C23 O1   SING N N 28  
S1S C23 O    DOUB N N 29  
S1S O1  HO1  SING N N 30  
S1S C20 C21  SING Y N 31  
S1S C20 H20  SING N N 32  
S1S C21 H21  SING N N 33  
S1S C14 C13  DOUB N E 34  
S1S C14 H14  SING N N 35  
S1S C13 C12  SING N N 36  
S1S C13 H13  SING N N 37  
S1S C12 C11  SING N N 38  
S1S C12 H121 SING N N 39  
S1S C12 H122 SING N N 40  
S1S C37 O7   DOUB N N 41  
S1S C37 N3   SING N N 42  
S1S N3  C31  SING N N 43  
S1S N3  HN3  SING N N 44  
S1S C31 C32  SING N N 45  
S1S C31 C36  SING N N 46  
S1S C31 C30  SING N N 47  
S1S C32 C33  SING N N 48  
S1S C32 H321 SING N N 49  
S1S C32 H322 SING N N 50  
S1S C33 C34  SING N N 51  
S1S C33 H331 SING N N 52  
S1S C33 H332 SING N N 53  
S1S C34 C35  SING N N 54  
S1S C34 H341 SING N N 55  
S1S C34 H342 SING N N 56  
S1S C35 C36  SING N N 57  
S1S C35 H351 SING N N 58  
S1S C35 H352 SING N N 59  
S1S C36 H361 SING N N 60  
S1S C36 H362 SING N N 61  
S1S C30 O6   DOUB N N 62  
S1S C30 N2   SING N N 63  
S1S N2  C27  SING N N 64  
S1S N2  HN2  SING N N 65  
S1S C27 C28  SING N N 66  
S1S C27 C26  SING N N 67  
S1S C27 H27  SING N N 68  
S1S C28 C29  SING N N 69  
S1S C28 H281 SING N N 70  
S1S C28 H282 SING N N 71  
S1S C29 N1   SING N N 72  
S1S C29 O5   DOUB N N 73  
S1S N1  HN11 SING N N 74  
S1S N1  HN12 SING N N 75  
S1S C26 O4   DOUB N N 76  
S1S C26 N    SING N N 77  
S1S N   C25  SING N N 78  
S1S N   HN   SING N N 79  
S1S C25 C11  SING N N 80  
S1S C25 H251 SING N N 81  
S1S C25 H252 SING N N 82  
S1S C11 C10  SING N N 83  
S1S C11 H11  SING N N 84  
S1S C10 C    SING N N 85  
S1S C10 H101 SING N N 86  
S1S C10 H102 SING N N 87  
S1S C   C1   SING Y N 88  
S1S C   C8   DOUB Y N 89  
S1S C1  C2   DOUB Y N 90  
S1S C1  HC1  SING N N 91  
S1S C2  C3   SING Y N 92  
S1S C2  HC2  SING N N 93  
S1S C3  C9   DOUB Y N 94  
S1S C3  HC3  SING N N 95  
S1S C9  C8   SING Y N 96  
S1S C9  C4   SING Y N 97  
S1S C8  C7   SING Y N 98  
S1S C7  C6   DOUB Y N 99  
S1S C7  HC7  SING N N 100 
S1S C6  C5   SING Y N 101 
S1S C6  HC6  SING N N 102 
S1S C5  C4   DOUB Y N 103 
S1S C5  HC5  SING N N 104 
S1S C4  HC4  SING N N 105 
# 
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 
S1S SMILES           ACDLabs              10.04 O=C(O)C(C(=O)O)c1ccc(cc1)C2C=CCC(CNC(=O)C(NC(=O)C3(NC(=O)C2CC(=O)O)CCCCC3)CC(=O)N)Cc5c4ccccc4ccc5 
S1S InChI            InChI                1.02b 
;InChI=1/C41H46N4O10/c42-33(46)22-32-37(50)43-23-24(20-28-11-7-10-25-9-2-3-12-29(25)28)8-6-13-30(26-14-16-27(17-15-26)35(38(51)52)39(53)54)31(21-34(47)48)36(49)45-41(40(55)44-32)18-4-1-5-19-41/h2-3,6-7,9-17,24,30-32,35H,1,4-5,8,18-23H2,(H2,42,46)(H,43,50)(H,44,55)(H,45,49)(H,47,48)(H,51,52)(H,53,54)/b13-6+/t24-,30+,31-,32+/m0/s1/f/h43-45,47,51,53H,42H2
;
S1S InChIKey         InChI                1.02b FYIJOFSDJMOTGX-IYCAWKLMDW 
S1S SMILES_CANONICAL CACTVS               3.341 NC(=O)C[C@H]1NC(=O)C2(CCCCC2)NC(=O)[C@@H](CC(O)=O)[C@H](\C=C\C[C@H](CNC1=O)Cc3cccc4ccccc34)c5ccc(cc5)C(C(O)=O)C(O)=O 
S1S SMILES           CACTVS               3.341 NC(=O)C[CH]1NC(=O)C2(CCCCC2)NC(=O)[CH](CC(O)=O)[CH](C=CC[CH](CNC1=O)Cc3cccc4ccccc34)c5ccc(cc5)C(C(O)=O)C(O)=O 
S1S SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)cccc2C[C@@H]3C\C=C\[C@@H]([C@@H](C(=O)NC4(CCCCC4)C(=O)NC(C(=O)NC3)CC(=O)N)CC(=O)O)c5ccc(cc5)C(C(=O)O)C(=O)O 
S1S SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)cccc2CC3CC=CC(C(C(=O)NC4(CCCCC4)C(=O)NC(C(=O)NC3)CC(=O)N)CC(=O)O)c5ccc(cc5)C(C(=O)O)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 
S1S "SYSTEMATIC NAME" ACDLabs              10.04 "{4-[(9S,10S,11E,14S,18R)-18-(2-amino-2-oxoethyl)-9-(carboxymethyl)-14-(naphthalen-1-ylmethyl)-8,17,20-trioxo-7,16,19-triazaspiro[5.14]icos-11-en-10-yl]phenyl}propanedioic acid" 
S1S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[4-[(9S,10S,11E,14S)-18-(2-amino-2-oxo-ethyl)-9-(carboxymethyl)-14-(naphthalen-1-ylmethyl)-8,17,20-trioxo-7,16,19-triazaspiro[5.14]icos-11-en-10-yl]phenyl]propanedioic acid"  
# 
