data_MCK
# 
_chem_comp.id                                    MCK 
_chem_comp.name                                  "N-[(2,3-dihydroxyphenyl)carbonyl]-O-[(2S)-2-{[(2,3-dihydroxyphenyl)carbonyl]amino}-3-(L-seryloxy)propanoyl]-L-serine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H25 N3 O13" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-10-20 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        551.457 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MCK 
_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        3K3L 
_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 
MCK C1   C1   C 0 1 Y N N 52.173 40.548 43.345 4.987  1.234  0.168  C1   MCK 1  
MCK C2   C2   C 0 1 Y N N 50.869 40.169 43.647 5.605  1.577  1.376  C2   MCK 2  
MCK C3   C3   C 0 1 Y N N 50.316 40.496 44.873 6.958  1.903  1.389  C3   MCK 3  
MCK C4   C4   C 0 1 Y N N 51.048 41.207 45.816 7.685  1.886  0.211  C4   MCK 4  
MCK C5   C5   C 0 1 Y N N 52.347 41.593 45.521 7.073  1.547  -0.984 C5   MCK 5  
MCK C6   C6   C 0 1 Y N N 52.909 41.267 44.290 5.735  1.222  -1.013 C6   MCK 6  
MCK C7   C7   C 0 1 N N N 52.798 40.216 42.016 3.554  0.881  0.141  C7   MCK 7  
MCK O8   O8   O 0 1 N N N 54.011 40.295 41.904 2.908  0.888  1.171  O8   MCK 8  
MCK N9   N9   N 0 1 N N N 52.017 39.904 40.976 2.963  0.551  -1.024 N9   MCK 9  
MCK O10  O10  O 0 1 N N N 50.112 39.472 42.754 4.888  1.593  2.528  O10  MCK 10 
MCK O11  O11  O 0 1 N N N 49.045 40.116 45.150 7.565  2.238  2.559  O11  MCK 11 
MCK C12  C12  C 0 1 N N S 52.524 39.782 39.617 1.540  0.201  -1.049 C12  MCK 12 
MCK C13  C13  C 0 1 N N N 51.412 39.849 38.598 0.727  1.365  -0.544 C13  MCK 13 
MCK C14  C14  C 0 1 N N N 53.338 38.504 39.436 1.299  -1.016 -0.155 C14  MCK 14 
MCK O15  O15  O 0 1 N N N 52.471 37.374 39.383 1.988  -2.168 -0.708 O15  MCK 15 
MCK O16  O16  O 0 1 N N N 51.580 39.404 37.473 1.251  2.222  0.126  O16  MCK 16 
MCK O17  O17  O 0 1 N N N 50.129 40.455 38.951 -0.580 1.449  -0.840 O17  MCK 17 
MCK C18  C18  C 0 1 N N N 49.078 40.662 37.997 -1.301 2.597  -0.320 C18  MCK 18 
MCK C19  C19  C 0 1 N N S 47.842 39.819 38.340 -2.765 2.520  -0.757 C19  MCK 19 
MCK N20  N20  N 0 1 N N N 48.023 39.152 39.621 -3.398 1.353  -0.140 N20  MCK 20 
MCK C21  C21  C 0 1 N N N 47.539 38.842 37.237 -2.836 2.395  -2.257 C21  MCK 21 
MCK O22  O22  O 0 1 N N N 47.169 39.239 36.143 -3.361 1.430  -2.759 O22  MCK 22 
MCK O23  O23  O 0 1 N N N 47.675 37.410 37.455 -2.315 3.356  -3.036 O23  MCK 23 
MCK C24  C24  C 0 1 N N N 52.678 36.220 40.245 1.877  -3.326 -0.037 C24  MCK 24 
MCK O25  O25  O 0 1 N N N 51.735 35.833 40.919 1.224  -3.375 0.979  O25  MCK 25 
MCK C26  C26  C 0 1 N N S 54.003 35.505 40.306 2.565  -4.564 -0.551 C26  MCK 26 
MCK N27  N27  N 0 1 N N N 54.921 36.005 39.297 2.706  -5.535 0.542  N27  MCK 27 
MCK C28  C28  C 0 1 N N N 54.638 35.680 41.680 1.732  -5.180 -1.677 C28  MCK 28 
MCK C29  C29  C 0 1 N N N 47.006 38.766 40.393 -4.732 1.333  0.054  C29  MCK 29 
MCK O30  O30  O 0 1 N N N 45.836 38.899 40.064 -5.409 2.285  -0.284 O30  MCK 30 
MCK C31  C31  C 0 1 Y N N 47.332 38.165 41.732 -5.370 0.157  0.676  C31  MCK 31 
MCK C32  C32  C 0 1 Y N N 48.041 36.972 41.826 -6.755 0.134  0.879  C32  MCK 32 
MCK C33  C33  C 0 1 Y N N 48.338 36.431 43.074 -7.346 -0.981 1.467  C33  MCK 33 
MCK C34  C34  C 0 1 Y N N 47.927 37.085 44.233 -6.565 -2.059 1.847  C34  MCK 34 
MCK C35  C35  C 0 1 Y N N 47.217 38.275 44.138 -5.194 -2.035 1.646  C35  MCK 35 
MCK C36  C36  C 0 1 Y N N 46.926 38.821 42.891 -4.595 -0.941 1.061  C36  MCK 36 
MCK O37  O37  O 0 1 N N N 48.447 36.327 40.696 -7.517 1.193  0.505  O37  MCK 37 
MCK O38  O38  O 0 1 N N N 49.029 35.261 43.174 -8.691 -1.012 1.667  O38  MCK 38 
MCK O45  O45  O 0 1 N N N 55.628 34.662 41.864 2.440  -6.286 -2.242 O45  MCK 39 
MCK H4   H4   H 0 1 N N N 50.609 41.457 46.771 8.735  2.140  0.224  H4   MCK 40 
MCK H5   H5   H 0 1 N N N 52.923 42.147 46.247 7.648  1.537  -1.899 H5   MCK 41 
MCK H6   H6   H 0 1 N N N 53.920 41.572 44.064 5.263  0.958  -1.949 H6   MCK 42 
MCK HN9  HN9  H 0 1 N N N 51.043 39.748 41.139 3.478  0.546  -1.845 HN9  MCK 43 
MCK HO10 HO10 H 0 0 N N N 49.256 39.302 43.129 4.883  0.748  3.000  HO10 MCK 44 
MCK HO11 HO11 H 0 0 N N N 48.809 40.411 46.022 7.944  1.486  3.034  HO11 MCK 45 
MCK H12  H12  H 0 1 N N N 53.191 40.640 39.448 1.243  -0.034 -2.071 H12  MCK 46 
MCK H14  H14  H 0 1 N N N 53.909 38.567 38.498 1.678  -0.812 0.847  H14  MCK 47 
MCK H14A H14A H 0 0 N N N 54.030 38.391 40.284 0.230  -1.223 -0.103 H14A MCK 48 
MCK H18  H18  H 0 1 N N N 48.796 41.725 38.002 -1.246 2.598  0.768  H18  MCK 49 
MCK H18A H18A H 0 0 N N N 49.441 40.373 36.999 -0.853 3.513  -0.707 H18A MCK 50 
MCK H19  H19  H 0 1 N N N 46.972 40.486 38.432 -3.286 3.425  -0.443 H19  MCK 51 
MCK HN20 HN20 H 0 0 N N N 48.955 38.975 39.938 -2.858 0.594  0.130  HN20 MCK 52 
MCK HO23 HO23 H 0 0 N N N 47.441 36.945 36.661 -2.384 3.232  -3.993 HO23 MCK 53 
MCK H26  H26  H 0 1 N N N 53.810 34.439 40.116 3.552  -4.300 -0.932 H26  MCK 54 
MCK HN27 HN27 H 0 0 N N N 55.789 35.513 39.362 3.305  -5.176 1.270  HN27 MCK 55 
MCK HN2A HN2A H 0 0 N N N 54.526 35.865 38.389 1.804  -5.796 0.912  HN2A MCK 56 
MCK H28  H28  H 0 1 N N N 55.109 36.672 41.747 0.779  -5.525 -1.277 H28  MCK 57 
MCK H28A H28A H 0 0 N N N 53.866 35.592 42.459 1.553  -4.431 -2.448 H28A MCK 58 
MCK H34  H34  H 0 1 N N N 48.159 36.668 45.202 -7.026 -2.922 2.302  H34  MCK 59 
MCK H35  H35  H 0 1 N N N 46.889 38.779 45.035 -4.592 -2.880 1.947  H35  MCK 60 
MCK H36  H36  H 0 1 N N N 46.385 39.753 42.823 -3.527 -0.930 0.903  H36  MCK 61 
MCK HO37 HO37 H 0 0 N N N 48.914 35.535 40.934 -7.849 1.138  -0.401 HO37 MCK 62 
MCK HO38 HO38 H 0 0 N N N 49.144 35.038 44.090 -9.191 -1.382 0.927  HO38 MCK 63 
MCK HO45 HO45 H 0 0 N N N 56.031 34.762 42.719 1.970  -6.726 -2.964 HO45 MCK 64 
# 
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 
MCK C7  C1   SING N N 1  
MCK C1  C2   DOUB Y N 2  
MCK C1  C6   SING Y N 3  
MCK O10 C2   SING N N 4  
MCK C2  C3   SING Y N 5  
MCK C3  O11  SING N N 6  
MCK C3  C4   DOUB Y N 7  
MCK C5  C4   SING Y N 8  
MCK C4  H4   SING N N 9  
MCK C6  C5   DOUB Y N 10 
MCK C5  H5   SING N N 11 
MCK C6  H6   SING N N 12 
MCK N9  C7   SING N N 13 
MCK O8  C7   DOUB N N 14 
MCK C12 N9   SING N N 15 
MCK N9  HN9  SING N N 16 
MCK O10 HO10 SING N N 17 
MCK O11 HO11 SING N N 18 
MCK C13 C12  SING N N 19 
MCK C14 C12  SING N N 20 
MCK C12 H12  SING N N 21 
MCK O16 C13  DOUB N N 22 
MCK C13 O17  SING N N 23 
MCK O15 C14  SING N N 24 
MCK C14 H14  SING N N 25 
MCK C14 H14A SING N N 26 
MCK O15 C24  SING N N 27 
MCK C18 O17  SING N N 28 
MCK C18 C19  SING N N 29 
MCK C18 H18  SING N N 30 
MCK C18 H18A SING N N 31 
MCK C21 C19  SING N N 32 
MCK C19 N20  SING N N 33 
MCK C19 H19  SING N N 34 
MCK N20 C29  SING N N 35 
MCK N20 HN20 SING N N 36 
MCK O22 C21  DOUB N N 37 
MCK C21 O23  SING N N 38 
MCK O23 HO23 SING N N 39 
MCK C24 C26  SING N N 40 
MCK C24 O25  DOUB N N 41 
MCK N27 C26  SING N N 42 
MCK C26 C28  SING N N 43 
MCK C26 H26  SING N N 44 
MCK N27 HN27 SING N N 45 
MCK N27 HN2A SING N N 46 
MCK C28 O45  SING N N 47 
MCK C28 H28  SING N N 48 
MCK C28 H28A SING N N 49 
MCK O30 C29  DOUB N N 50 
MCK C29 C31  SING N N 51 
MCK C31 C32  DOUB Y N 52 
MCK C31 C36  SING Y N 53 
MCK O37 C32  SING N N 54 
MCK C32 C33  SING Y N 55 
MCK C33 O38  SING N N 56 
MCK C33 C34  DOUB Y N 57 
MCK C35 C34  SING Y N 58 
MCK C34 H34  SING N N 59 
MCK C36 C35  DOUB Y N 60 
MCK C35 H35  SING N N 61 
MCK C36 H36  SING N N 62 
MCK O37 HO37 SING N N 63 
MCK O38 HO38 SING N N 64 
MCK O45 HO45 SING N N 65 
# 
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 
MCK SMILES           ACDLabs              11.02 "O=C(O)C(NC(=O)c1cccc(O)c1O)COC(=O)C(NC(=O)c2cccc(O)c2O)COC(=O)C(N)CO" 
MCK SMILES_CANONICAL CACTVS               3.352 "N[C@@H](CO)C(=O)OC[C@H](NC(=O)c1cccc(O)c1O)C(=O)OC[C@H](NC(=O)c2cccc(O)c2O)C(O)=O" 
MCK SMILES           CACTVS               3.352 "N[CH](CO)C(=O)OC[CH](NC(=O)c1cccc(O)c1O)C(=O)OC[CH](NC(=O)c2cccc(O)c2O)C(O)=O" 
MCK SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1cc(c(c(c1)O)O)C(=O)N[C@@H](COC(=O)[C@H](CO)N)C(=O)OC[C@@H](C(=O)O)NC(=O)c2cccc(c2O)O" 
MCK SMILES           "OpenEye OEToolkits" 1.7.0 "c1cc(c(c(c1)O)O)C(=O)NC(COC(=O)C(CO)N)C(=O)OCC(C(=O)O)NC(=O)c2cccc(c2O)O" 
MCK InChI            InChI                1.03  
"InChI=1S/C23H25N3O13/c24-12(7-27)22(36)38-9-14(26-20(33)11-4-2-6-16(29)18(11)31)23(37)39-8-13(21(34)35)25-19(32)10-3-1-5-15(28)17(10)30/h1-6,12-14,27-31H,7-9,24H2,(H,25,32)(H,26,33)(H,34,35)/t12-,13-,14-/m0/s1" 
MCK InChIKey         InChI                1.03  AVZOYWMPRGKOPV-IHRRRGAJSA-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 
MCK "SYSTEMATIC NAME" ACDLabs              11.02 "N-[(2,3-dihydroxyphenyl)carbonyl]-O-[(2S)-2-{[(2,3-dihydroxyphenyl)carbonyl]amino}-3-(L-seryloxy)propanoyl]-L-serine"                                           
MCK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "(2S)-3-[(2S)-3-[(2S)-2-azanyl-3-hydroxy-propanoyl]oxy-2-[(2,3-dihydroxyphenyl)carbonylamino]propanoyl]oxy-2-[(2,3-dihydroxyphenyl)carbonylamino]propanoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
MCK "Create component"     2009-10-20 RCSB 
MCK "Modify aromatic_flag" 2011-06-04 RCSB 
MCK "Modify descriptor"    2011-06-04 RCSB 
# 
