data_AMK
# 
_chem_comp.id                                    AMK 
_chem_comp.name                                  "(S)-4-AMINO-4-{(S)-1-[(S)-2-CARBAMOYL-1-((S)-1-{(S)-[(1R,2R)-2-((S)-1-CARBOXY-ETHYLCARBAMOYL)-CYCLOPENTYL]-HYDROXY-METHYL}-3-METHYL-BUTYLCARBAMOYL)-ETHYLCARBAMOYL]-2-METHYL-PROPYLCARBAMOYL}-BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H50 N6 O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-01-26 
_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                        642.741 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AMK 
_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        1YM4 
_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 
AMK N1   N1   N 0 1 N N N 29.606 5.986  9.635  -1.403  -0.994 0.990  N1   AMK 1  
AMK C3   C3   C 0 1 N N S 30.869 5.275  9.509  -2.576  -1.837 0.744  C3   AMK 2  
AMK C5   C5   C 0 1 N N S 31.095 4.690  8.095  -3.841  -1.088 1.170  C5   AMK 3  
AMK O7   O7   O 0 1 N N N 30.088 3.735  7.743  -3.762  -0.776 2.563  O7   AMK 4  
AMK C9   C9   C 0 1 N N R 31.139 5.759  7.024  -3.964  0.206  0.364  C9   AMK 5  
AMK C11  C11  C 0 1 N N R 31.675 5.019  5.756  -5.208  1.003  0.808  C11  AMK 6  
AMK C13  C13  C 0 1 N N N 30.820 5.483  4.582  -4.810  2.491  0.771  C13  AMK 7  
AMK C16  C16  C 0 1 N N N 29.450 5.841  5.184  -3.342  2.544  0.301  C16  AMK 8  
AMK C19  C19  C 0 1 N N N 29.689 6.185  6.682  -2.775  1.151  0.669  C19  AMK 9  
AMK C22  C22  C 0 1 N N N 33.146 5.288  5.536  -6.354  0.751  -0.137 C22  AMK 10 
AMK O23  O23  O 0 1 N N N 33.608 6.391  5.778  -6.215  -0.012 -1.068 O23  AMK 11 
AMK N24  N24  N 0 1 N N N 33.892 4.276  5.078  -7.534  1.375  0.054  N24  AMK 12 
AMK C26  C26  C 0 1 N N S 35.301 4.549  4.789  -8.648  1.130  -0.865 C26  AMK 13 
AMK C28  C28  C 0 1 N N N 36.064 3.239  4.636  -9.407  -0.124 -0.424 C28  AMK 14 
AMK C32  C32  C 0 1 N N N 35.384 5.347  3.512  -9.582  2.313  -0.849 C32  AMK 15 
AMK O33  O33  O 0 1 N N N 34.411 5.939  3.053  -10.681 2.311  -1.619 O33  AMK 16 
AMK O34  O34  O 0 1 N N N 36.568 5.360  2.906  -9.340  3.263  -0.143 O34  AMK 17 
AMK C36  C36  C 0 1 N N N 30.951 4.170  10.595 -2.453  -3.131 1.550  C36  AMK 18 
AMK C39  C39  C 0 1 N N N 30.928 4.845  11.980 -3.604  -4.071 1.185  C39  AMK 19 
AMK C41  C41  C 0 1 N N N 32.286 5.539  12.234 -3.461  -4.508 -0.274 C41  AMK 20 
AMK C45  C45  C 0 1 N N N 30.667 3.800  13.091 -3.564  -5.302 2.093  C45  AMK 21 
AMK C49  C49  C 0 1 N N N 29.631 7.324  9.540  -0.293  -1.149 0.241  C49  AMK 22 
AMK O50  O50  O 0 1 N N N 30.623 7.946  9.211  -0.297  -1.917 -0.697 O50  AMK 23 
AMK C51  C51  C 0 1 N N S 28.366 8.030  9.864  0.953   -0.369 0.571  C51  AMK 24 
AMK N53  N53  N 0 1 N N N 28.280 8.024  11.310 2.011   -0.712 -0.382 N53  AMK 25 
AMK C55  C55  C 0 1 N N N 27.080 7.927  11.859 3.305   -0.603 -0.021 C55  AMK 26 
AMK O56  O56  O 0 1 N N N 26.042 7.922  11.203 3.593   -0.308 1.119  O56  AMK 27 
AMK C57  C57  C 0 1 N N S 27.025 7.831  13.352 4.393   -0.846 -1.035 C57  AMK 28 
AMK N59  N59  N 0 1 N N N 25.780 8.478  13.792 5.701   -0.666 -0.400 N59  AMK 29 
AMK C61  C61  C 0 1 N N N 25.888 9.451  14.714 6.772   -0.332 -1.146 C61  AMK 30 
AMK O62  O62  O 0 1 N N N 26.880 9.585  15.398 6.654   -0.180 -2.344 O62  AMK 31 
AMK C63  C63  C 0 1 N N S 24.751 10.396 14.891 8.118   -0.147 -0.493 C63  AMK 32 
AMK N65  N65  N 0 1 N N N 23.796 10.299 13.781 9.175   -0.266 -1.507 N65  AMK 33 
AMK C68  C68  C 0 1 N N N 24.061 10.228 16.264 8.185   1.238  0.154  C68  AMK 34 
AMK C71  C71  C 0 1 N N N 23.878 11.636 16.901 9.500   1.379  0.922  C71  AMK 35 
AMK C74  C74  C 0 1 N N N 22.428 11.915 17.299 9.566   2.743  1.559  C74  AMK 36 
AMK O75  O75  O 0 1 N N N 21.599 11.028 17.428 8.654   3.522  1.413  O75  AMK 37 
AMK O76  O76  O 0 1 N N N 22.117 13.205 17.509 10.638  3.092  2.288  O76  AMK 38 
AMK C78  C78  C 0 1 N N N 27.155 6.351  13.781 4.279   -2.273 -1.573 C78  AMK 39 
AMK C80  C80  C 0 1 N N N 27.354 6.206  15.327 5.384   -2.520 -2.602 C80  AMK 40 
AMK C84  C84  C 0 1 N N N 25.930 5.550  13.340 4.427   -3.267 -0.419 C84  AMK 41 
AMK C88  C88  C 0 1 N N N 28.353 9.515  9.332  0.654   1.129  0.483  C88  AMK 42 
AMK C91  C91  C 0 1 N N N 26.942 10.121 9.351  0.282   1.485  -0.933 C91  AMK 43 
AMK O92  O92  O 0 1 N N N 26.112 9.768  8.527  0.184   0.614  -1.771 O92  AMK 44 
AMK N93  N93  N 0 1 N N N 26.663 11.038 10.310 0.057   2.771  -1.268 N93  AMK 45 
AMK HN1  HN1  H 0 1 N N N 28.700 5.545  9.791  -1.426  -0.325 1.691  HN1  AMK 46 
AMK H3   H3   H 0 1 N N N 31.690 6.013  9.666  -2.636  -2.075 -0.318 H3   AMK 47 
AMK H5   H5   H 0 1 N N N 32.088 4.185  8.142  -4.713  -1.715 0.987  H5   AMK 48 
AMK HO7  HO7  H 0 1 N N N 30.227 3.376  6.875  -2.978  -0.222 2.681  HO7  AMK 49 
AMK H9   H9   H 0 1 N N N 31.745 6.640  7.340  -4.012  -0.013 -0.703 H9   AMK 50 
AMK H11  H11  H 0 1 N N N 31.595 3.914  5.877  -5.490  0.718  1.822  H11  AMK 51 
AMK H131 1H13 H 0 0 N N N 30.764 4.743  3.750  -4.900  2.929  1.765  H131 AMK 52 
AMK H132 2H13 H 0 0 N N N 31.280 6.310  3.993  -5.447  3.029  0.068  H132 AMK 53 
AMK H161 1H16 H 0 0 N N N 28.684 5.045  5.034  -2.800  3.328  0.830  H161 AMK 54 
AMK H162 2H16 H 0 0 N N N 28.924 6.651  4.627  -3.291  2.704  -0.776 H162 AMK 55 
AMK H191 1H19 H 0 0 N N N 29.479 7.253  6.924  -2.509  1.108  1.726  H191 AMK 56 
AMK H192 2H19 H 0 0 N N N 28.929 5.732  7.361  -1.916  0.905  0.044  H192 AMK 57 
AMK H24  H24  H 0 1 N N N 33.428 3.376  4.960  -7.645  1.986  0.799  H24  AMK 58 
AMK H26  H26  H 0 1 N N N 35.756 5.127  5.627  -8.263  0.985  -1.874 H26  AMK 59 
AMK H281 1H28 H 0 0 N N N 35.602 2.573  3.871  -9.793  0.021  0.585  H281 AMK 60 
AMK H282 2H28 H 0 0 N N N 37.137 3.447  4.416  -10.236 -0.306 -1.107 H282 AMK 61 
AMK H283 3H28 H 0 0 N N N 35.940 2.577  5.524  -8.732  -0.979 -0.435 H283 AMK 62 
AMK H33  H33  H 0 1 N N N 34.463 6.442  2.249  -11.280 3.070  -1.609 H33  AMK 63 
AMK H361 1H36 H 0 0 N N N 31.832 3.501  10.459 -2.496  -2.901 2.615  H361 AMK 64 
AMK H362 2H36 H 0 0 N N N 30.155 3.398  10.482 -1.503  -3.613 1.320  H362 AMK 65 
AMK H39  H39  H 0 1 N N N 30.106 5.599  11.999 -4.553  -3.552 1.318  H39  AMK 66 
AMK H411 1H41 H 0 0 N N N 32.554 6.253  11.421 -2.471  -4.936 -0.430 H411 AMK 67 
AMK H412 2H41 H 0 0 N N N 32.269 6.027  13.236 -4.220  -5.256 -0.505 H412 AMK 68 
AMK H413 3H41 H 0 0 N N N 33.146 4.839  12.120 -3.591  -3.645 -0.927 H413 AMK 69 
AMK H451 1H45 H 0 0 N N N 31.401 2.962  13.051 -2.615  -5.821 1.960  H451 AMK 70 
AMK H452 2H45 H 0 0 N N N 30.650 4.288  14.093 -3.666  -4.990 3.132  H452 AMK 71 
AMK H453 3H45 H 0 0 N N N 29.737 3.216  12.900 -4.384  -5.972 1.832  H453 AMK 72 
AMK H51  H51  H 0 1 N N N 27.502 7.522  9.376  1.280   -0.615 1.581  H51  AMK 73 
AMK H53  H53  H 0 1 N N N 29.073 8.089  11.948 1.780   -1.019 -1.273 H53  AMK 74 
AMK H57  H57  H 0 1 N N N 27.874 8.361  13.844 4.288   -0.138 -1.857 H57  AMK 75 
AMK H59  H59  H 0 1 N N N 24.843 8.252  13.458 5.796   -0.787 0.558  H59  AMK 76 
AMK H63  H63  H 0 1 N N N 25.176 11.427 14.875 8.259   -0.912 0.270  H63  AMK 77 
AMK H651 1H65 H 0 0 N N N 23.469 9.341  13.652 9.005   0.457  -2.189 H651 AMK 78 
AMK H652 2H65 H 0 0 N N N 23.017 10.946 13.902 10.043  -0.034 -1.048 H652 AMK 79 
AMK H681 1H68 H 0 0 N N N 24.607 9.523  16.934 8.132   2.003  -0.621 H681 AMK 80 
AMK H682 2H68 H 0 0 N N N 23.103 9.662  16.195 7.348   1.359  0.841  H682 AMK 81 
AMK H711 1H71 H 0 0 N N N 24.270 12.435 16.229 9.552   0.613  1.696  H711 AMK 82 
AMK H712 2H71 H 0 0 N N N 24.566 11.777 17.767 10.337  1.258  0.235  H712 AMK 83 
AMK H76  H76  H 0 1 N N N 21.216 13.378 17.756 10.680  3.967  2.697  H76  AMK 84 
AMK H78  H78  H 0 1 N N N 28.062 5.944  13.277 3.306   -2.407 -2.046 H78  AMK 85 
AMK H801 1H80 H 0 0 N N N 26.541 6.721  15.890 5.303   -3.537 -2.986 H801 AMK 86 
AMK H802 2H80 H 0 0 N N N 27.448 5.139  15.636 5.279   -1.812 -3.425 H802 AMK 87 
AMK H803 3H80 H 0 0 N N N 28.223 6.809  15.682 6.357   -2.386 -2.130 H803 AMK 88 
AMK H841 1H84 H 0 0 N N N 25.745 5.648  12.245 3.639   -3.091 0.315  H841 AMK 89 
AMK H842 2H84 H 0 0 N N N 26.024 4.483  13.649 4.345   -4.284 -0.802 H842 AMK 90 
AMK H843 3H84 H 0 0 N N N 24.983 6.006  13.712 5.400   -3.133 0.054  H843 AMK 91 
AMK H881 1H88 H 0 0 N N N 28.810 9.585  8.317  -0.173  1.375  1.149  H881 AMK 92 
AMK H882 2H88 H 0 0 N N N 29.075 10.152 9.894  1.539   1.694  0.779  H882 AMK 93 
AMK H931 1H93 H 0 0 N N N 25.726 11.441 10.323 0.135   3.468  -0.597 H931 AMK 94 
AMK H932 2H93 H 0 0 N N N 27.356 11.333 10.998 -0.183  3.000  -2.179 H932 AMK 95 
# 
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 
AMK N1  C3   SING N N 1  
AMK N1  C49  SING N N 2  
AMK N1  HN1  SING N N 3  
AMK C3  C5   SING N N 4  
AMK C3  C36  SING N N 5  
AMK C3  H3   SING N N 6  
AMK C5  O7   SING N N 7  
AMK C5  C9   SING N N 8  
AMK C5  H5   SING N N 9  
AMK O7  HO7  SING N N 10 
AMK C9  C11  SING N N 11 
AMK C9  C19  SING N N 12 
AMK C9  H9   SING N N 13 
AMK C11 C13  SING N N 14 
AMK C11 C22  SING N N 15 
AMK C11 H11  SING N N 16 
AMK C13 C16  SING N N 17 
AMK C13 H131 SING N N 18 
AMK C13 H132 SING N N 19 
AMK C16 C19  SING N N 20 
AMK C16 H161 SING N N 21 
AMK C16 H162 SING N N 22 
AMK C19 H191 SING N N 23 
AMK C19 H192 SING N N 24 
AMK C22 O23  DOUB N N 25 
AMK C22 N24  SING N N 26 
AMK N24 C26  SING N N 27 
AMK N24 H24  SING N N 28 
AMK C26 C28  SING N N 29 
AMK C26 C32  SING N N 30 
AMK C26 H26  SING N N 31 
AMK C28 H281 SING N N 32 
AMK C28 H282 SING N N 33 
AMK C28 H283 SING N N 34 
AMK C32 O33  SING N N 35 
AMK C32 O34  DOUB N N 36 
AMK O33 H33  SING N N 37 
AMK C36 C39  SING N N 38 
AMK C36 H361 SING N N 39 
AMK C36 H362 SING N N 40 
AMK C39 C41  SING N N 41 
AMK C39 C45  SING N N 42 
AMK C39 H39  SING N N 43 
AMK C41 H411 SING N N 44 
AMK C41 H412 SING N N 45 
AMK C41 H413 SING N N 46 
AMK C45 H451 SING N N 47 
AMK C45 H452 SING N N 48 
AMK C45 H453 SING N N 49 
AMK C49 O50  DOUB N N 50 
AMK C49 C51  SING N N 51 
AMK C51 N53  SING N N 52 
AMK C51 C88  SING N N 53 
AMK C51 H51  SING N N 54 
AMK N53 C55  SING N N 55 
AMK N53 H53  SING N N 56 
AMK C55 O56  DOUB N N 57 
AMK C55 C57  SING N N 58 
AMK C57 N59  SING N N 59 
AMK C57 C78  SING N N 60 
AMK C57 H57  SING N N 61 
AMK N59 C61  SING N N 62 
AMK N59 H59  SING N N 63 
AMK C61 O62  DOUB N N 64 
AMK C61 C63  SING N N 65 
AMK C63 N65  SING N N 66 
AMK C63 C68  SING N N 67 
AMK C63 H63  SING N N 68 
AMK N65 H651 SING N N 69 
AMK N65 H652 SING N N 70 
AMK C68 C71  SING N N 71 
AMK C68 H681 SING N N 72 
AMK C68 H682 SING N N 73 
AMK C71 C74  SING N N 74 
AMK C71 H711 SING N N 75 
AMK C71 H712 SING N N 76 
AMK C74 O75  DOUB N N 77 
AMK C74 O76  SING N N 78 
AMK O76 H76  SING N N 79 
AMK C78 C80  SING N N 80 
AMK C78 C84  SING N N 81 
AMK C78 H78  SING N N 82 
AMK C80 H801 SING N N 83 
AMK C80 H802 SING N N 84 
AMK C80 H803 SING N N 85 
AMK C84 H841 SING N N 86 
AMK C84 H842 SING N N 87 
AMK C84 H843 SING N N 88 
AMK C88 C91  SING N N 89 
AMK C88 H881 SING N N 90 
AMK C88 H882 SING N N 91 
AMK C91 O92  DOUB N N 92 
AMK C91 N93  SING N N 93 
AMK N93 H931 SING N N 94 
AMK N93 H932 SING N N 95 
# 
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 
AMK SMILES           ACDLabs              10.04 O=C(NC(C(=O)O)C)C1CCCC1C(O)C(NC(=O)C(NC(=O)C(NC(=O)C(N)CCC(=O)O)C(C)C)CC(=O)N)CC(C)C 
AMK InChI            InChI                1.02b 
;InChI=1/C29H50N6O10/c1-13(2)11-19(24(39)16-7-6-8-17(16)25(40)32-15(5)29(44)45)33-27(42)20(12-21(31)36)34-28(43)23(14(3)4)35-26(41)18(30)9-10-22(37)38/h13-20,23-24,39H,6-12,30H2,1-5H3,(H2,31,36)(H,32,40)(H,33,42)(H,34,43)(H,35,41)(H,37,38)(H,44,45)/t15-,16+,17+,18-,19-,20-,23-,24-/m0/s1/f/h32-35,37,44H,31H2
;
AMK InChIKey         InChI                1.02b WQVHGVDOXBCVGL-UMJRVETNDF 
AMK SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)C(C)C)[C@@H](O)[C@@H]1CCC[C@H]1C(=O)N[C@@H](C)C(O)=O 
AMK SMILES           CACTVS               3.341 CC(C)C[CH](NC(=O)[CH](CC(N)=O)NC(=O)[CH](NC(=O)[CH](N)CCC(O)=O)C(C)C)[CH](O)[CH]1CCC[CH]1C(=O)N[CH](C)C(O)=O 
AMK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@@H]([C@H]([C@@H]1CCC[C@H]1C(=O)N[C@@H](C)C(=O)O)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)N 
AMK SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC(C(C1CCCC1C(=O)NC(C)C(=O)O)O)NC(=O)C(CC(=O)N)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)N 
# 
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 
AMK "SYSTEMATIC NAME" ACDLabs              10.04 L-alpha-glutamyl-L-valyl-N~1~-{(1S)-1-[(S)-[(1R,2R)-2-{[(1S)-1-carboxyethyl]carbamoyl}cyclopentyl](hydroxy)methyl]-3-methylbutyl}-L-aspartamide 
AMK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"(4S)-4-amino-5-[[(2S)-1-[[(2S)-4-amino-1-[[(1S,2S)-1-hydroxy-1-[(1R,2R)-2-[[(2S)-1-hydroxy-1-oxo-propan-2-yl]carbamoyl]cyclopentyl]-4-methyl-pentan-2-yl]amino]-1,4-dioxo-butan-2-yl]amino]-3-methyl-1-oxo-butan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
