data_GMK
# 
_chem_comp.id                                    GMK 
_chem_comp.name                                  "(3-Deoxy-3-(3-methoxy-benzamido)-b-D-galactopyranosyl)-(3-deoxy-3-(3-methoxy-benzamido)-2-O-sulfo-b-D-galactopyranosyl)-sulfide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H36 N2 O15 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-05-03 
_chem_comp.pdbx_modified_date                    2014-09-05 
_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                        704.720 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GMK 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4bli 
_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 
GMK O1  O1G O 0 1 N N N -26.795 7.398  0.554  5.862   -0.210 -1.503 O1  GMK 1  
GMK C1  C1F C 0 1 N N N -26.845 8.500  1.235  6.287   -0.088 -0.371 C1  GMK 2  
GMK C2  C4F C 0 1 Y N N -27.461 8.485  2.638  7.572   0.605  -0.134 C2  GMK 3  
GMK C3  C5F C 0 1 Y N N -28.176 7.340  3.103  8.062   0.747  1.164  C3  GMK 4  
GMK C4  C6F C 0 1 Y N N -28.799 7.352  4.364  9.262   1.394  1.381  C4  GMK 5  
GMK O2  O1H O 0 1 N N N -27.890 10.917 5.402  10.210  2.269  -2.024 O2  GMK 6  
GMK C5  C1H C 0 1 N N N -27.020 12.000 5.046  11.442  2.925  -1.715 C5  GMK 7  
GMK C6  C1G C 0 1 Y N N -28.785 8.503  5.174  9.981   1.903  0.315  C6  GMK 8  
GMK C7  C2F C 0 1 Y N N -28.118 9.668  4.725  9.500   1.766  -0.980 C7  GMK 9  
GMK C8  C3F C 0 1 Y N N -27.503 9.656  3.471  8.301   1.114  -1.210 C8  GMK 10 
GMK N1  N1E N 0 1 N N N -25.869 9.454  1.019  5.585   -0.578 0.670  N1  GMK 11 
GMK C9  C4D C 0 1 N N S -24.991 9.380  -0.128 4.309   -1.259 0.436  C9  GMK 12 
GMK C10 C5D C 0 1 N N R -25.653 9.973  -1.366 4.021   -2.220 1.594  C10 GMK 13 
GMK O3  O2D O 0 1 N N N -25.875 11.382 -1.146 4.021   -1.497 2.826  O3  GMK 14 
GMK C11 C1D C 0 1 N N R -24.669 9.757  -2.534 2.651   -2.868 1.381  C11 GMK 15 
GMK C12 C1E C 0 1 N N N -25.276 10.453 -3.755 2.330   -3.784 2.563  C12 GMK 16 
GMK O4  O1F O 0 1 N N N -24.239 10.621 -4.726 1.106   -4.477 2.311  O4  GMK 17 
GMK O5  O1D O 0 1 N N N -23.380 10.290 -2.285 1.654   -1.849 1.283  O5  GMK 18 
GMK C13 C3D C 0 1 N N R -23.611 9.978  0.095  3.183   -0.224 0.355  C13 GMK 19 
GMK O6  O1E O 0 1 N N N -23.092 9.292  1.225  3.403   0.634  -0.767 O6  GMK 20 
GMK C14 C2D C 0 1 N N S -22.757 9.695  -1.109 1.844   -0.949 0.190  C14 GMK 21 
GMK S1  S1C S 0 1 N N N -21.139 10.314 -0.978 0.498   0.266  0.164  S1  GMK 22 
GMK C15 C1C C 0 1 N N S -20.152 8.954  -1.568 -0.963  -0.752 -0.186 C15 GMK 23 
GMK C16 C2C C 0 1 N N R -18.676 9.280  -1.526 -2.220  0.119  -0.118 C16 GMK 24 
GMK O7  O4K O 0 1 N N N -18.451 10.247 -2.578 -2.369  0.641  1.204  O7  GMK 25 
GMK S2  S2K S 0 1 N N N -17.751 11.661 -2.196 -2.273  2.158  1.285  S2  GMK 26 
GMK O8  O2K O 0 1 N N N -18.494 12.326 -1.061 -3.563  2.722  0.707  O8  GMK 27 
GMK O9  O1K O 0 1 N N N -18.087 12.409 -3.341 -2.274  2.486  2.668  O9  GMK 28 
GMK O10 O3K O 0 1 N N N -16.328 11.454 -1.795 -1.233  2.542  0.396  O10 GMK 29 
GMK O11 O5C O 0 1 N N N -20.452 7.794  -0.744 -0.847  -1.318 -1.493 O11 GMK 30 
GMK C17 C5C C 0 1 N N R -19.727 6.586  -1.169 -1.939  -2.163 -1.862 C17 GMK 31 
GMK C18 C6C C 0 1 N N N -20.239 5.461  -0.301 -1.695  -2.732 -3.261 C18 GMK 32 
GMK O12 O6C O 0 1 N N N -21.621 5.279  -0.480 -0.549  -3.586 -3.234 O12 GMK 33 
GMK C19 C4C C 0 1 N N R -18.273 6.839  -0.957 -3.236  -1.349 -1.861 C19 GMK 34 
GMK O13 O4C O 0 1 N N N -17.949 7.119  0.378  -3.147  -0.308 -2.836 O13 GMK 35 
GMK C20 C3C C 0 1 N N S -17.869 8.050  -1.803 -3.442  -0.734 -0.474 C20 GMK 36 
GMK N2  NA  N 0 1 N N N -16.451 8.369  -1.676 -4.641  0.109  -0.484 N2  GMK 37 
GMK C21 C1A C 0 1 N N N -15.643 8.043  -2.741 -5.840  -0.422 -0.176 C21 GMK 38 
GMK O14 OA  O 0 1 N N N -15.939 7.214  -3.701 -5.928  -1.600 0.112  O14 GMK 39 
GMK C22 C2A C 0 1 Y N N -14.238 8.477  -2.595 -7.050  0.428  -0.187 C22 GMK 40 
GMK C23 C3A C 0 1 Y N N -13.173 7.793  -3.142 -6.953  1.779  -0.522 C23 GMK 41 
GMK C24 C4A C 0 1 Y N N -11.882 8.208  -3.022 -8.084  2.570  -0.531 C24 GMK 42 
GMK C25 C5A C 0 1 Y N N -11.576 9.348  -2.317 -9.315  2.027  -0.209 C25 GMK 43 
GMK C26 C6A C 0 1 Y N N -12.626 10.020 -1.752 -9.421  0.684  0.126  C26 GMK 44 
GMK C27 C7A C 0 1 Y N N -13.905 9.649  -1.943 -8.293  -0.119 0.132  C27 GMK 45 
GMK O15 O1A O 0 1 N N N -12.430 11.255 -1.095 -10.633 0.157  0.443  O15 GMK 46 
GMK C28 C1B C 0 1 N N N -13.556 11.898 -0.430 -11.754 1.042  0.410  C28 GMK 47 
GMK H1  H1  H 0 1 N N N -28.239 6.459  2.482  7.503   0.352  1.999  H1  GMK 48 
GMK H2  H2  H 0 1 N N N -29.297 6.461  4.717  9.640   1.503  2.387  H2  GMK 49 
GMK H3  H3  H 0 1 N N N -27.101 12.799 5.798  12.111  2.225  -1.216 H3  GMK 50 
GMK H4  H4  H 0 1 N N N -25.982 11.638 5.006  11.906  3.278  -2.636 H4  GMK 51 
GMK H5  H5  H 0 1 N N N -27.309 12.394 4.060  11.247  3.773  -1.058 H5  GMK 52 
GMK H6  H6  H 0 1 N N N -29.281 8.497  6.133  10.919  2.408  0.491  H6  GMK 53 
GMK H7  H7  H 0 1 N N N -27.040 10.564 3.112  7.928   1.003  -2.217 H7  GMK 54 
GMK H8  H8  H 0 1 N N N -25.768 10.209 1.667  5.924   -0.481 1.573  H8  GMK 55 
GMK H9  H9  H 0 1 N N N -24.833 8.313  -0.346 4.359   -1.817 -0.499 H9  GMK 56 
GMK H10 H10 H 0 1 N N N -26.598 9.450  -1.574 4.790   -2.993 1.625  H10 GMK 57 
GMK H11 H11 H 0 1 N N N -26.482 11.499 -0.425 3.845   -2.045 3.603  H11 GMK 58 
GMK H12 H12 H 0 1 N N N -24.602 8.679  -2.740 2.664   -3.453 0.461  H12 GMK 59 
GMK H13 H13 H 0 1 N N N -25.678 11.435 -3.464 3.136   -4.507 2.692  H13 GMK 60 
GMK H14 H14 H 0 1 N N N -26.084 9.835  -4.174 2.230   -3.187 3.469  H14 GMK 61 
GMK H15 H15 H 0 1 N N N -24.592 11.052 -5.495 0.840   -5.077 3.021  H15 GMK 62 
GMK H16 H16 H 0 1 N N N -23.686 11.061 0.271  3.166   0.369  1.269  H16 GMK 63 
GMK H17 H17 H 0 1 N N N -23.635 9.474  1.983  2.726   1.315  -0.879 H17 GMK 64 
GMK H18 H18 H 0 1 N N N -22.667 8.607  -1.243 1.847   -1.509 -0.746 H18 GMK 65 
GMK H19 H19 H 0 1 N N N -20.459 8.774  -2.609 -1.034  -1.551 0.551  H19 GMK 66 
GMK H20 H20 H 0 1 N N N -18.410 9.697  -0.544 -2.132  0.942  -0.827 H20 GMK 67 
GMK H21 H21 H 0 1 N N N -19.927 6.367  -2.228 -2.023  -2.981 -1.146 H21 GMK 68 
GMK H22 H22 H 0 1 N N N -19.715 4.532  -0.570 -2.567  -3.303 -3.578 H22 GMK 69 
GMK H23 H23 H 0 1 N N N -20.041 5.701  0.754  -1.522  -1.914 -3.960 H23 GMK 70 
GMK H24 H24 H 0 1 N N N -21.922 4.568  0.074  -0.335  -3.983 -4.090 H24 GMK 71 
GMK H25 H25 H 0 1 N N N -17.705 5.965  -1.309 -4.076  -2.001 -2.100 H25 GMK 72 
GMK H26 H26 H 0 1 N N N -18.191 6.381  0.925  -3.010  -0.626 -3.739 H26 GMK 73 
GMK H27 H27 H 0 1 N N N -18.052 7.775  -2.852 -3.561  -1.527 0.265  H27 GMK 74 
GMK H28 H28 H 0 1 N N N -16.084 8.804  -0.854 -4.571  1.048  -0.714 H28 GMK 75 
GMK H29 H29 H 0 1 N N N -13.372 6.885  -3.692 -5.994  2.206  -0.774 H29 GMK 76 
GMK H30 H30 H 0 1 N N N -11.091 7.637  -3.485 -8.008  3.615  -0.791 H30 GMK 77 
GMK H31 H31 H 0 1 N N N -10.559 9.696  -2.214 -10.197 2.651  -0.217 H31 GMK 78 
GMK H32 H32 H 0 1 N N N -14.696 10.287 -1.576 -8.375  -1.166 0.389  H32 GMK 79 
GMK H33 H33 H 0 1 N N N -13.223 12.843 0.025  -11.595 1.856  1.118  H33 GMK 80 
GMK H34 H34 H 0 1 N N N -14.347 12.104 -1.166 -11.866 1.450  -0.594 H34 GMK 81 
GMK H35 H35 H 0 1 N N N -13.948 11.232 0.353  -12.657 0.495  0.683  H35 GMK 82 
GMK H36 H36 H 0 1 N N N -18.990 13.064 -1.396 -3.606  3.688  0.711  H36 GMK 83 
# 
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 
GMK O4  C12 SING N N 1  
GMK C12 C11 SING N N 2  
GMK O14 C21 DOUB N N 3  
GMK O9  S2  DOUB N N 4  
GMK C23 C24 DOUB Y N 5  
GMK C23 C22 SING Y N 6  
GMK C24 C25 SING Y N 7  
GMK C21 C22 SING N N 8  
GMK C21 N2  SING N N 9  
GMK C22 C27 DOUB Y N 10 
GMK O7  S2  SING N N 11 
GMK O7  C16 SING N N 12 
GMK C11 O5  SING N N 13 
GMK C11 C10 SING N N 14 
GMK C25 C26 DOUB Y N 15 
GMK O5  C14 SING N N 16 
GMK S2  O10 DOUB N N 17 
GMK S2  O8  SING N N 18 
GMK C27 C26 SING Y N 19 
GMK C20 N2  SING N N 20 
GMK C20 C16 SING N N 21 
GMK C20 C19 SING N N 22 
GMK C26 O15 SING N N 23 
GMK C15 C16 SING N N 24 
GMK C15 S1  SING N N 25 
GMK C15 O11 SING N N 26 
GMK C10 O3  SING N N 27 
GMK C10 C9  SING N N 28 
GMK C17 C19 SING N N 29 
GMK C17 O11 SING N N 30 
GMK C17 C18 SING N N 31 
GMK C14 S1  SING N N 32 
GMK C14 C13 SING N N 33 
GMK O15 C28 SING N N 34 
GMK C19 O13 SING N N 35 
GMK O12 C18 SING N N 36 
GMK C9  C13 SING N N 37 
GMK C9  N1  SING N N 38 
GMK C13 O6  SING N N 39 
GMK O1  C1  DOUB N N 40 
GMK N1  C1  SING N N 41 
GMK C1  C2  SING N N 42 
GMK C2  C3  DOUB Y N 43 
GMK C2  C8  SING Y N 44 
GMK C3  C4  SING Y N 45 
GMK C8  C7  DOUB Y N 46 
GMK C4  C6  DOUB Y N 47 
GMK C7  C6  SING Y N 48 
GMK C7  O2  SING N N 49 
GMK C5  O2  SING N N 50 
GMK C3  H1  SING N N 51 
GMK C4  H2  SING N N 52 
GMK C5  H3  SING N N 53 
GMK C5  H4  SING N N 54 
GMK C5  H5  SING N N 55 
GMK C6  H6  SING N N 56 
GMK C8  H7  SING N N 57 
GMK N1  H8  SING N N 58 
GMK C9  H9  SING N N 59 
GMK C10 H10 SING N N 60 
GMK O3  H11 SING N N 61 
GMK C11 H12 SING N N 62 
GMK C12 H13 SING N N 63 
GMK C12 H14 SING N N 64 
GMK O4  H15 SING N N 65 
GMK C13 H16 SING N N 66 
GMK O6  H17 SING N N 67 
GMK C14 H18 SING N N 68 
GMK C15 H19 SING N N 69 
GMK C16 H20 SING N N 70 
GMK C17 H21 SING N N 71 
GMK C18 H22 SING N N 72 
GMK C18 H23 SING N N 73 
GMK O12 H24 SING N N 74 
GMK C19 H25 SING N N 75 
GMK O13 H26 SING N N 76 
GMK C20 H27 SING N N 77 
GMK N2  H28 SING N N 78 
GMK C23 H29 SING N N 79 
GMK C24 H30 SING N N 80 
GMK C25 H31 SING N N 81 
GMK C27 H32 SING N N 82 
GMK C28 H33 SING N N 83 
GMK C28 H34 SING N N 84 
GMK C28 H35 SING N N 85 
GMK O8  H36 SING N N 86 
# 
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 
GMK SMILES           ACDLabs              12.01 "O=S(=O)(O)OC4C(NC(=O)c1cccc(OC)c1)C(O)C(OC4SC3OC(CO)C(O)C(NC(=O)c2cccc(OC)c2)C3O)CO" 
GMK InChI            InChI                1.03  
;InChI=1S/C28H36N2O15S2/c1-41-15-7-3-5-13(9-15)25(36)29-19-21(33)17(11-31)43-27(23(19)35)46-28-24(45-47(38,39)40)20(22(34)18(12-32)44-28)30-26(37)14-6-4-8-16(10-14)42-2/h3-10,17-24,27-28,31-35H,11-12H2,1-2H3,(H,29,36)(H,30,37)(H,38,39,40)/t17-,18-,19+,20+,21+,22+,23-,24-,27+,28+/m1/s1
;
GMK InChIKey         InChI                1.03  CNUFQRWWCPUUQG-CWKIZLMASA-N 
GMK SMILES_CANONICAL CACTVS               3.385 "COc1cccc(c1)C(=O)N[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](S[C@@H]3O[C@H](CO)[C@H](O)[C@H](NC(=O)c4cccc(OC)c4)[C@H]3O[S](O)(=O)=O)[C@@H]2O" 
GMK SMILES           CACTVS               3.385 "COc1cccc(c1)C(=O)N[CH]2[CH](O)[CH](CO)O[CH](S[CH]3O[CH](CO)[CH](O)[CH](NC(=O)c4cccc(OC)c4)[CH]3O[S](O)(=O)=O)[CH]2O" 
GMK SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "COc1cccc(c1)C(=O)N[C@H]2[C@H]([C@H](O[C@H]([C@@H]2O)S[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)NC(=O)c4cccc(c4)OC)OS(=O)(=O)O)CO)O" 
GMK SMILES           "OpenEye OEToolkits" 1.9.2 "COc1cccc(c1)C(=O)NC2C(C(OC(C2O)SC3C(C(C(C(O3)CO)O)NC(=O)c4cccc(c4)OC)OS(=O)(=O)O)CO)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 
GMK "SYSTEMATIC NAME" ACDLabs              12.01 "3-deoxy-3-[(3-methoxybenzoyl)amino]-beta-D-galactopyranosyl 3-deoxy-3-[(3-methoxybenzoyl)amino]-2-O-sulfo-1-thio-beta-D-galactopyranoside" 
GMK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 
"[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-4-[(3-methoxyphenyl)carbonylamino]-3,5-bis(oxidanyl)oxan-2-yl]sulfanyl-4-[(3-methoxyphenyl)carbonylamino]-5-oxidanyl-oxan-3-yl] hydrogen sulfate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
GMK "Create component"  2013-05-03 EBI  
GMK "Initial release"   2014-05-21 RCSB 
GMK "Modify descriptor" 2014-09-05 RCSB 
# 
