data_GCG
# 
_chem_comp.id                                    GCG 
_chem_comp.name                                  BIS(GAMMA-GLUTAMYL-CYSTEINYL-GLYCINYL)SPERMIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H49 N9 O10 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         TRYPANOTHIONE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                         TS3 
_chem_comp.formula_weight                        723.862 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GCG 
_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        1BZL 
_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 
GCG C1   C1   C 0 1 N N N 58.422 11.745 6.094  1.128  -1.288 18.668  C1   GCG 1  
GCG CA1  CA1  C 0 1 N N S 58.103 10.261 5.874  1.467  -0.362 17.529  CA1  GCG 2  
GCG O11  O11  O 0 1 N N N 57.459 12.519 6.107  0.144  -0.969 19.523  O11  GCG 3  
GCG O21  O21  O 0 1 N N N 59.584 12.130 6.217  1.742  -2.319 18.811  O21  GCG 4  
GCG CB1  CB1  C 0 1 N N N 59.339 9.347  6.222  0.630  -0.732 16.304  CB1  GCG 5  
GCG N1   N1   N 0 1 N N N 57.857 10.286 4.405  2.894  -0.488 17.204  N1   GCG 6  
GCG CG1  CG1  C 0 1 N N N 59.233 7.875  5.706  0.974  0.208  15.147  CG1  GCG 7  
GCG CD1  CD1  C 0 1 N N N 60.364 6.961  6.224  0.149  -0.155 13.940  CD1  GCG 8  
GCG OD1  OD1  O 0 1 N N N 60.272 6.429  7.334  -0.636 -1.077 13.999  OD1  GCG 9  
GCG N2   N2   N 0 1 N N N 61.404 6.739  5.406  0.285  0.542  12.795  N2   GCG 10 
GCG CA2  CA2  C 0 1 N N R 62.516 5.894  5.839  -0.516 0.188  11.622  CA2  GCG 11 
GCG C2   C2   C 0 1 N N N 63.782 6.748  5.856  0.249  0.526  10.369  C2   GCG 12 
GCG O2   O2   O 0 1 N N N 64.254 7.172  4.795  1.356  1.016  10.448  O2   GCG 13 
GCG CB2  CB2  C 0 1 N N N 62.688 4.707  4.882  -1.829 0.973  11.645  CB2  GCG 14 
GCG SG2  SG2  S 0 1 N N N 62.780 3.063  5.677  -2.751 0.566  13.153  SG2  GCG 15 
GCG N3   N3   N 0 1 N N N 64.325 7.004  7.066  -0.295 0.286  9.160   N3   GCG 16 
GCG CA3  CA3  C 0 1 N N N 65.517 7.832  7.206  0.449  0.615  7.942   CA3  GCG 17 
GCG C3   C3   C 0 1 N N N 66.734 7.401  6.406  -0.376 0.250  6.735   C3   GCG 18 
GCG O3   O3   O 0 1 N N N 66.799 6.274  5.907  -1.477 -0.236 6.878   O3   GCG 19 
GCG N1S  N1S  N 0 1 N N N 67.708 8.315  6.256  0.110  0.465  5.496   N1S  GCG 20 
GCG C2S  C2S  C 0 1 N N N 68.958 8.073  5.535  -0.691 0.111  4.323   C2S  GCG 21 
GCG C3S  C3S  C 0 1 N N N 69.129 8.573  4.092  0.085  0.455  3.051   C3S  GCG 22 
GCG C4S  C4S  C 0 1 N N N 68.343 8.057  2.874  -0.751 0.085  1.825   C4S  GCG 23 
GCG C5S  C5S  C 0 1 N N N 68.391 6.556  2.520  0.026  0.429  0.553   C5S  GCG 24 
GCG C7S  C7S  C 0 1 N N N 66.951 4.607  2.607  0.021  0.427  -1.803  C7S  GCG 25 
GCG N6S  N6S  N 0 1 N N N 67.477 5.756  3.334  -0.778 0.073  -0.623  N6S  GCG 26 
GCG C8S  C8S  C 0 1 N N N 67.869 3.384  2.481  -0.760 0.081  -3.072  C8S  GCG 27 
GCG C9S  C9S  C 0 1 N N N 67.285 2.284  1.540  0.072  0.449  -4.301  C9S  GCG 28 
GCG N11  N10S N 0 1 N N N 66.170 1.430  1.957  -0.677 0.118  -5.516  N11  GCG 29 
GCG C5   C5   C 0 1 N N N 64.900 1.858  2.103  -0.136 0.357  -6.727  C5   GCG 30 
GCG N5   N5   N 0 1 N N N 62.757 1.651  3.016  -0.109 0.370  -9.153  N5   GCG 31 
GCG CA5  CA5  C 0 1 N N N 63.858 0.843  2.538  -0.907 0.017  -7.976  CA5  GCG 32 
GCG O5   O5   O 0 1 N N N 64.562 3.034  1.926  0.970  0.847  -6.811  O5   GCG 33 
GCG C6   C6   C 0 1 N N N 61.489 1.288  2.921  -0.600 0.153  -10.390 C6   GCG 34 
GCG N6   N6   N 0 1 N N N 59.504 2.727  2.519  -0.529 0.184  -12.815 N6   GCG 35 
GCG CA6  CA6  C 0 1 N N R 60.536 2.332  3.470  0.220  0.515  -11.601 CA6  GCG 36 
GCG O6   O6   O 0 1 N N N 61.109 0.218  2.436  -1.702 -0.334 -10.528 O6   GCG 37 
GCG CB6  CB6  C 0 1 N N N 59.966 1.872  4.771  0.522  2.015  -11.581 CB6  GCG 38 
GCG SG6  SG6  S 0 1 N N N 60.878 2.568  6.195  1.510  2.452  -13.038 SG6  GCG 39 
GCG CD7  CD7  C 0 1 N N N 58.966 3.953  2.670  0.128  -0.162 -13.939 CD7  GCG 40 
GCG C7   C7   C 0 1 N N N 54.967 1.969  1.126  0.517  -1.555 -18.683 C7   GCG 41 
GCG CA7  CA7  C 0 1 N N S 56.440 2.351  1.264  -0.446 -1.204 -17.579 CA7  GCG 42 
GCG O17  O17  O 0 1 N N N 54.147 2.450  1.902  0.979  -0.596 -19.500 O17  GCG 43 
GCG O27  O27  O 0 1 N N N 54.653 1.190  0.218  0.873  -2.700 -18.833 O27  GCG 44 
GCG CB7  CB7  C 0 1 N N N 56.565 3.758  1.845  0.336  -0.859 -16.310 CB7  GCG 45 
GCG N7   N7   N 0 1 N N N 56.929 2.327  -0.145 -1.326 -2.350 -17.314 N7   GCG 46 
GCG CG7  CG7  C 0 1 N N N 57.920 4.392  1.650  -0.641 -0.502 -15.189 CG7  GCG 47 
GCG OD7  OD7  O 0 1 N N N 59.269 4.697  3.602  1.341  -0.200 -13.945 OD7  GCG 48 
GCG HA1  HA1  H 0 1 N N N 57.273 9.855  6.498  1.251  0.665  17.820  HA1  GCG 49 
GCG HO11 HO11 H 0 0 N N N 57.656 13.438 6.243  -0.073 -1.563 20.254  HO11 GCG 50 
GCG HB11 1HB1 H 0 0 N N N 60.281 9.817  5.856  0.846  -1.759 16.012  HB11 GCG 51 
GCG HB12 2HB1 H 0 0 N N N 59.530 9.358  7.320  -0.428 -0.638 16.545  HB12 GCG 52 
GCG HN11 1HN1 H 0 0 N N N 57.644 9.299  4.258  3.047  -1.450 16.941  HN11 GCG 53 
GCG HN12 2HN1 H 0 0 N N N 58.604 10.675 3.830  3.053  0.066  16.376  HN12 GCG 54 
GCG HG11 1HG1 H 0 0 N N N 58.233 7.442  5.946  0.758  1.236  15.439  HG11 GCG 55 
GCG HG12 2HG1 H 0 0 N N N 59.182 7.849  4.592  2.033  0.115  14.906  HG12 GCG 56 
GCG H2   H2   H 0 1 N N N 61.351 7.193  4.494  0.914  1.279  12.748  H2   GCG 57 
GCG HA2  HA2  H 0 1 N N N 62.313 5.486  6.857  -0.732 -0.880 11.638  HA2  GCG 58 
GCG HB21 1HB2 H 0 0 N N N 61.879 4.715  4.114  -1.613 2.042  11.629  HB21 GCG 59 
GCG HB22 2HB2 H 0 0 N N N 63.579 4.867  4.231  -2.426 0.710  10.772  HB22 GCG 60 
GCG HG2  HG2  H 0 1 N N N 62.886 2.328  5.084  -3.837 1.340  12.979  HG2  GCG 61 
GCG H3   H3   H 0 1 N N N 63.843 6.580  7.859  -1.181 -0.105 9.096   H3   GCG 62 
GCG HA31 1HA3 H 0 0 N N N 65.268 8.893  6.970  0.664  1.683  7.926   HA31 GCG 63 
GCG HA32 2HA3 H 0 0 N N N 65.787 7.922  8.283  1.384  0.055  7.925   HA32 GCG 64 
GCG HNS1 1HNS H 0 0 N N N 67.494 9.209  6.697  0.991  0.855  5.382   HNS1 GCG 65 
GCG H2S1 1H2S H 0 0 N N N 69.799 8.473  6.147  -0.907 -0.957 4.339   H2S1 GCG 66 
GCG H2S2 2H2S H 0 0 N N N 69.167 6.978  5.554  -1.627 0.671  4.339   H2S2 GCG 67 
GCG H3S1 1H3S H 0 0 N N N 68.987 9.678  4.118  0.301  1.523  3.034   H3S1 GCG 68 
GCG H3S2 2H3S H 0 0 N N N 70.210 8.465  3.842  1.021  -0.104 3.034   H3S2 GCG 69 
GCG H4S1 1H4S H 0 0 N N N 67.276 8.363  2.982  -0.967 -0.983 1.841   H4S1 GCG 70 
GCG H4S2 2H4S H 0 0 N N N 68.650 8.644  1.977  -1.686 0.644  1.842   H4S2 GCG 71 
GCG H5S1 1H5S H 0 0 N N N 68.204 6.395  1.432  0.241  1.497  0.537   H5S1 GCG 72 
GCG H5S2 2H5S H 0 0 N N N 69.432 6.162  2.583  0.961  -0.130 0.537   H5S2 GCG 73 
GCG H7S1 1H7S H 0 0 N N N 65.977 4.297  3.054  0.237  1.495  -1.789  H7S1 GCG 74 
GCG H7S2 2H7S H 0 0 N N N 66.618 4.928  1.592  0.956  -0.132 -1.789  H7S2 GCG 75 
GCG HNS6 6HNS H 0 0 N N N 66.723 6.329  3.712  -0.864 -0.931 -0.622  HNS6 GCG 76 
GCG H8S1 1H8S H 0 0 N N N 68.892 3.684  2.156  -0.976 -0.986 -3.086  H8S1 GCG 77 
GCG H8S2 2H8S H 0 0 N N N 68.113 2.962  3.484  -1.696 0.641  -3.086  H8S2 GCG 78 
GCG H9S1 1H9S H 0 0 N N N 67.001 2.771  0.578  0.287  1.518  -4.287  H9S1 GCG 79 
GCG H9S2 2H9S H 0 0 N N N 68.124 1.621  1.225  1.007  -0.109 -4.287  H9S2 GCG 80 
GCG H10S H10S H 0 0 N N N 66.289 0.439  2.166  -1.562 -0.272 -5.448  H10S GCG 81 
GCG H5   H5   H 0 1 N N N 62.886 2.559  3.460  0.771  0.759  -9.043  H5   GCG 82 
GCG HA51 1HA5 H 0 0 N N N 63.577 0.107  1.748  -1.122 -1.051 -7.990  HA51 GCG 83 
GCG HA52 2HA5 H 0 0 N N N 64.229 0.093  3.274  -1.842 0.577  -7.990  HA52 GCG 84 
GCG H6   H6   H 0 1 N N N 59.160 2.148  1.752  -1.498 0.215  -12.811 H6   GCG 85 
GCG HA6  HA6  H 0 1 N N N 61.126 3.260  3.652  1.155  -0.043 -11.587 HA6  GCG 86 
GCG HB61 1HB6 H 0 0 N N N 58.875 2.095  4.838  -0.412 2.575  -11.595 HB61 GCG 87 
GCG HB62 2HB6 H 0 0 N N N 59.919 0.759  4.823  1.080  2.261  -10.677 HB62 GCG 88 
GCG HG6  HG6  H 0 1 N N N 60.515 2.275  7.022  1.660  3.772  -12.832 HG6  GCG 89 
GCG HA7  HA7  H 0 1 N N N 57.012 1.674  1.940  -1.047 -0.346 -17.880 HA7  GCG 90 
GCG HO17 HO17 H 0 0 N N N 53.231 2.212  1.816  1.598  -0.821 -20.208 HO17 GCG 91 
GCG HB71 1HB7 H 0 0 N N N 55.763 4.419  1.440  0.989  -0.008 -16.506 HB71 GCG 92 
GCG HB72 2HB7 H 0 0 N N N 56.285 3.759  2.924  0.937  -1.716 -16.009 HB72 GCG 93 
GCG HN71 1HN7 H 0 0 N N N 57.912 2.582  -0.052 -0.729 -3.117 -17.040 HN71 GCG 94 
GCG HN72 2HN7 H 0 0 N N N 56.396 2.911  -0.789 -1.879 -2.110 -16.505 HN72 GCG 95 
GCG HG71 1HG7 H 0 0 N N N 57.832 5.503  1.633  -1.294 -1.353 -14.992 HG71 GCG 96 
GCG HG72 2HG7 H 0 0 N N N 58.288 4.215  0.612  -1.243 0.355  -15.490 HG72 GCG 97 
# 
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 
GCG C1  CA1  SING N N 1  
GCG C1  O11  SING N N 2  
GCG C1  O21  DOUB N N 3  
GCG CA1 CB1  SING N N 4  
GCG CA1 N1   SING N N 5  
GCG CA1 HA1  SING N N 6  
GCG O11 HO11 SING N N 7  
GCG CB1 CG1  SING N N 8  
GCG CB1 HB11 SING N N 9  
GCG CB1 HB12 SING N N 10 
GCG N1  HN11 SING N N 11 
GCG N1  HN12 SING N N 12 
GCG CG1 CD1  SING N N 13 
GCG CG1 HG11 SING N N 14 
GCG CG1 HG12 SING N N 15 
GCG CD1 OD1  DOUB N N 16 
GCG CD1 N2   SING N N 17 
GCG N2  CA2  SING N N 18 
GCG N2  H2   SING N N 19 
GCG CA2 C2   SING N N 20 
GCG CA2 CB2  SING N N 21 
GCG CA2 HA2  SING N N 22 
GCG C2  O2   DOUB N N 23 
GCG C2  N3   SING N N 24 
GCG CB2 SG2  SING N N 25 
GCG CB2 HB21 SING N N 26 
GCG CB2 HB22 SING N N 27 
GCG SG2 HG2  SING N N 28 
GCG N3  CA3  SING N N 29 
GCG N3  H3   SING N N 30 
GCG CA3 C3   SING N N 31 
GCG CA3 HA31 SING N N 32 
GCG CA3 HA32 SING N N 33 
GCG C3  O3   DOUB N N 34 
GCG C3  N1S  SING N N 35 
GCG N1S C2S  SING N N 36 
GCG N1S HNS1 SING N N 37 
GCG C2S C3S  SING N N 38 
GCG C2S H2S1 SING N N 39 
GCG C2S H2S2 SING N N 40 
GCG C3S C4S  SING N N 41 
GCG C3S H3S1 SING N N 42 
GCG C3S H3S2 SING N N 43 
GCG C4S C5S  SING N N 44 
GCG C4S H4S1 SING N N 45 
GCG C4S H4S2 SING N N 46 
GCG C5S N6S  SING N N 47 
GCG C5S H5S1 SING N N 48 
GCG C5S H5S2 SING N N 49 
GCG C7S N6S  SING N N 50 
GCG C7S C8S  SING N N 51 
GCG C7S H7S1 SING N N 52 
GCG C7S H7S2 SING N N 53 
GCG N6S HNS6 SING N N 54 
GCG C8S C9S  SING N N 55 
GCG C8S H8S1 SING N N 56 
GCG C8S H8S2 SING N N 57 
GCG C9S N11  SING N N 58 
GCG C9S H9S1 SING N N 59 
GCG C9S H9S2 SING N N 60 
GCG N11 C5   SING N N 61 
GCG N11 H10S SING N N 62 
GCG C5  CA5  SING N N 63 
GCG C5  O5   DOUB N N 64 
GCG N5  CA5  SING N N 65 
GCG N5  C6   SING N N 66 
GCG N5  H5   SING N N 67 
GCG CA5 HA51 SING N N 68 
GCG CA5 HA52 SING N N 69 
GCG C6  CA6  SING N N 70 
GCG C6  O6   DOUB N N 71 
GCG N6  CA6  SING N N 72 
GCG N6  CD7  SING N N 73 
GCG N6  H6   SING N N 74 
GCG CA6 CB6  SING N N 75 
GCG CA6 HA6  SING N N 76 
GCG CB6 SG6  SING N N 77 
GCG CB6 HB61 SING N N 78 
GCG CB6 HB62 SING N N 79 
GCG SG6 HG6  SING N N 80 
GCG CD7 CG7  SING N N 81 
GCG CD7 OD7  DOUB N N 82 
GCG C7  CA7  SING N N 83 
GCG C7  O17  SING N N 84 
GCG C7  O27  DOUB N N 85 
GCG CA7 CB7  SING N N 86 
GCG CA7 N7   SING N N 87 
GCG CA7 HA7  SING N N 88 
GCG O17 HO17 SING N N 89 
GCG CB7 CG7  SING N N 90 
GCG CB7 HB71 SING N N 91 
GCG CB7 HB72 SING N N 92 
GCG N7  HN71 SING N N 93 
GCG N7  HN72 SING N N 94 
GCG CG7 HG71 SING N N 95 
GCG CG7 HG72 SING N N 96 
# 
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 
GCG SMILES           ACDLabs              10.04 O=C(NCC(=O)NCCCNCCCCNC(=O)CNC(=O)C(NC(=O)CCC(C(=O)O)N)CS)C(NC(=O)CCC(C(=O)O)N)CS 
GCG InChI            InChI                1.02b 
;InChI=1/C27H49N9O10S2/c28-16(26(43)44)4-6-20(37)35-18(14-47)24(41)33-12-22(39)31-10-2-1-8-30-9-3-11-32-23(40)13-34-25(42)19(15-48)36-21(38)7-5-17(29)27(45)46/h16-19,30,47-48H,1-15,28-29H2,(H,31,39)(H,32,40)(H,33,41)(H,34,42)(H,35,37)(H,36,38)(H,43,44)(H,45,46)/t16-,17-,18-,19-/m0/s1/f/h31-36,43,45H
;
GCG InChIKey         InChI                1.02b PHDOXVGRXXAYEB-LPGGKDDXDI 
GCG SMILES_CANONICAL CACTVS               3.341 N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)NCCCCNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(O)=O)C(O)=O 
GCG SMILES           CACTVS               3.341 N[CH](CCC(=O)N[CH](CS)C(=O)NCC(=O)NCCCCNCCCNC(=O)CNC(=O)[CH](CS)NC(=O)CC[CH](N)C(O)=O)C(O)=O 
GCG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C(CCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@@H](C(=O)O)N)CNCCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@@H](C(=O)O)N 
GCG SMILES           "OpenEye OEToolkits" 1.5.0 C(CCNC(=O)CNC(=O)C(CS)NC(=O)CCC(C(=O)O)N)CNCCCNC(=O)CNC(=O)C(CS)NC(=O)CCC(C(=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 
GCG "SYSTEMATIC NAME" ACDLabs              10.04 "(2S,7R,26R,31S)-2,31-diamino-5,8,11,22,25,28-hexaoxo-7,26-bis(sulfanylmethyl)-6,9,12,16,21,24,27-heptaazadotriacontane-1,32-dioic acid (non-preferred name)" 
GCG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"(2S)-2-amino-5-[[(2R)-1-[[2-[4-[3-[2-[[(2R)-2-[[(4S)-4-amino-5-hydroxy-5-oxo-pentanoyl]amino]-3-sulfanyl-propanoyl]amino]ethanoylamino]propylamino]butylamino]-2-oxo-ethyl]amino]-1-oxo-3-sulfanyl-propan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
