data_GPS
# 
_chem_comp.id                                    GPS 
_chem_comp.name                                  (9S,10S)-9-(S-GLUTATHIONYL)-10-HYDROXY-9,10-DIHYDROPHENANTHRENE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H27 N3 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                         ? 
_chem_comp.formula_weight                        501.552 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GPS 
_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        6GSV 
_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 
GPS N1   N1   N 0 1 N N N 17.829 14.907 13.916 -1.936 1.959  5.059  N1   GPS 1  
GPS CA1  CA1  C 0 1 N N S 18.185 14.585 12.439 -2.758 0.790  4.722  CA1  GPS 2  
GPS C1   C1   C 0 1 N N N 17.319 13.455 11.976 -3.427 0.270  5.969  C1   GPS 3  
GPS O11  O11  O 0 1 N N N 17.227 13.146 10.750 -2.890 0.403  7.043  O11  GPS 4  
GPS O12  O12  O 0 1 N N N 16.489 12.839 12.838 -4.619 -0.340 5.886  O12  GPS 5  
GPS CB1  CB1  C 0 1 N N N 19.680 14.074 12.505 -1.869 -0.303 4.127  CB1  GPS 6  
GPS CG1  CG1  C 0 1 N N N 20.209 13.844 11.117 -1.190 0.224  2.861  CG1  GPS 7  
GPS CD1  CD1  C 0 1 N N N 21.668 13.570 11.093 -0.314 -0.853 2.275  CD1  GPS 8  
GPS OE1  OE1  O 0 1 N N N 22.412 13.717 12.088 -0.240 -1.936 2.816  OE1  GPS 9  
GPS N2   N2   N 0 1 N N N 22.144 13.212 9.923  0.386  -0.612 1.149  N2   GPS 10 
GPS CA2  CA2  C 0 1 N N R 23.394 12.442 9.742  1.237  -1.660 0.579  CA2  GPS 11 
GPS C2   C2   C 0 1 N N N 24.124 13.131 8.516  2.622  -1.555 1.163  C2   GPS 12 
GPS O2   O2   O 0 1 N N N 25.102 12.491 8.143  3.305  -2.549 1.287  O2   GPS 13 
GPS CB2  CB2  C 0 1 N N N 23.207 10.966 9.488  1.310  -1.487 -0.939 CB2  GPS 14 
GPS SG2  SG2  S 0 1 N N N 22.381 10.246 10.948 -0.356 -1.613 -1.642 SG2  GPS 15 
GPS N3   N3   N 0 1 N N N 23.607 14.218 8.117  3.102  -0.356 1.549  N3   GPS 16 
GPS CA3  CA3  C 0 1 N N N 24.008 14.782 6.747  4.449  -0.254 2.117  CA3  GPS 17 
GPS C3   C3   C 0 1 N N N 25.071 15.800 6.940  4.740  1.183  2.463  C3   GPS 18 
GPS O31  O31  O 0 1 N N N 25.425 16.286 8.053  3.909  2.035  2.256  O31  GPS 19 
GPS O32  O32  O 0 1 N N N 25.610 16.476 5.903  5.924  1.517  3.001  O32  GPS 20 
GPS CA4  CA4  C 0 1 N N R 23.924 10.339 11.676 0.024  -1.378 -3.400 CA4  GPS 21 
GPS CB4  CB4  C 0 1 Y N N 24.604 9.026  11.376 0.683  -0.038 -3.589 CB4  GPS 22 
GPS CG4  CG4  C 0 1 Y N N 25.562 9.001  10.295 2.060  0.062  -3.621 CG4  GPS 23 
GPS CD4  CD4  C 0 1 Y N N 26.100 7.784  9.902  2.660  1.300  -3.763 CD4  GPS 24 
GPS CE4  CE4  C 0 1 Y N N 25.816 6.644  10.676 1.889  2.444  -3.865 CE4  GPS 25 
GPS CZ4  CZ4  C 0 1 Y N N 24.926 6.637  11.743 0.511  2.354  -3.838 CZ4  GPS 26 
GPS CH4  CH4  C 0 1 Y N N 24.295 7.844  12.098 -0.096 1.109  -3.722 CH4  GPS 27 
GPS CH5  CH5  C 0 1 Y N N 23.292 8.000  13.196 -1.573 0.980  -3.706 CH5  GPS 28 
GPS CZ5  CZ5  C 0 1 Y N N 22.602 6.849  13.698 -2.385 2.085  -3.480 CZ5  GPS 29 
GPS CE5  CE5  C 0 1 Y N N 21.668 7.062  14.701 -3.758 1.936  -3.466 CE5  GPS 30 
GPS CD5  CD5  C 0 1 Y N N 21.296 8.351  15.079 -4.322 0.691  -3.677 CD5  GPS 31 
GPS CG5  CG5  C 0 1 Y N N 22.009 9.461  14.624 -3.518 -0.409 -3.912 CG5  GPS 32 
GPS CB5  CB5  C 0 1 Y N N 22.967 9.254  13.644 -2.144 -0.271 -3.935 CB5  GPS 33 
GPS CA5  CA5  C 0 1 N N R 23.672 10.515 13.159 -1.266 -1.461 -4.210 CA5  GPS 34 
GPS O5   O5   O 0 1 N N N 25.022 10.370 13.745 -0.946 -1.498 -5.602 O5   GPS 35 
GPS HN11 1HN1 H 0 0 N N N 18.419 15.676 14.231 -1.430 2.209  4.223  HN11 GPS 36 
GPS HN12 2HN1 H 0 0 N N N 17.896 14.089 14.521 -1.250 1.649  5.731  HN12 GPS 37 
GPS HA1  HA1  H 0 1 N N N 18.047 15.455 11.755 -3.517 1.076  3.995  HA1  GPS 38 
GPS HO2  HO2  H 0 1 N N N 15.939 12.121 12.544 -5.048 -0.674 6.686  HO2  GPS 39 
GPS HB11 1HB1 H 0 0 N N N 20.331 14.763 13.090 -1.109 -0.590 4.854  HB11 GPS 40 
GPS HB12 2HB1 H 0 0 N N N 19.783 13.167 13.146 -2.479 -1.171 3.877  HB12 GPS 41 
GPS HG11 1HG1 H 0 0 N N N 19.642 13.032 10.603 -1.949 0.510  2.134  HG11 GPS 42 
GPS HG12 2HG1 H 0 0 N N N 19.952 14.696 10.446 -0.580 1.092  3.111  HG12 GPS 43 
GPS HN2  HN2  H 0 1 N N N 21.546 13.529 9.159  0.327  0.253  0.717  HN2  GPS 44 
GPS HA2  HA2  H 0 1 N N N 23.981 12.468 10.689 0.817  -2.638 0.814  HA2  GPS 45 
GPS HB21 1HB2 H 0 0 N N N 22.663 10.756 8.537  1.730  -0.509 -1.174 HB21 GPS 46 
GPS HB22 2HB2 H 0 0 N N N 24.160 10.447 9.231  1.943  -2.266 -1.363 HB22 GPS 47 
GPS HN3  HN3  H 0 1 N N N 22.954 14.589 8.807  2.556  0.439  1.450  HN3  GPS 48 
GPS HA31 1HA3 H 0 0 N N N 24.308 13.983 6.029  4.510  -0.864 3.018  HA31 GPS 49 
GPS HA32 2HA3 H 0 0 N N N 23.135 15.180 6.178  5.178  -0.607 1.388  HA32 GPS 50 
GPS HO3  HO3  H 0 1 N N N 26.290 17.127 6.026  6.111  2.439  3.223  HO3  GPS 51 
GPS HA4  HA4  H 0 1 N N N 24.564 11.175 11.309 0.705  -2.163 -3.728 HA4  GPS 52 
GPS HG4  HG4  H 0 1 N N N 25.883 9.914  9.767  2.668  -0.825 -3.535 HG4  GPS 53 
GPS HD4  HD4  H 0 1 N N N 26.734 7.724  9.001  3.737  1.374  -3.796 HD4  GPS 54 
GPS HE4  HE4  H 0 1 N N N 26.323 5.695  10.430 2.365  3.408  -3.964 HE4  GPS 55 
GPS HZ4  HZ4  H 0 1 N N N 24.726 5.701  12.291 -0.091 3.247  -3.908 HZ4  GPS 56 
GPS HZ5  HZ5  H 0 1 N N N 22.784 5.827  13.323 -1.944 3.057  -3.316 HZ5  GPS 57 
GPS HE5  HE5  H 0 1 N N N 21.214 6.192  15.205 -4.391 2.793  -3.290 HE5  GPS 58 
GPS HD5  HD5  H 0 1 N N N 20.428 8.494  15.745 -5.396 0.577  -3.658 HD5  GPS 59 
GPS HG5  HG5  H 0 1 N N N 21.821 10.470 15.026 -3.965 -1.378 -4.078 HG5  GPS 60 
GPS HA5  HA5  H 0 1 N N N 23.117 11.452 13.397 -1.800 -2.372 -3.940 HA5  GPS 61 
GPS HO5  HO5  H 0 1 N N N 24.863 10.480 14.675 -1.785 -1.550 -6.080 HO5  GPS 62 
# 
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 
GPS N1  CA1  SING N N 1  
GPS N1  HN11 SING N N 2  
GPS N1  HN12 SING N N 3  
GPS CA1 C1   SING N N 4  
GPS CA1 CB1  SING N N 5  
GPS CA1 HA1  SING N N 6  
GPS C1  O11  DOUB N N 7  
GPS C1  O12  SING N N 8  
GPS O12 HO2  SING N N 9  
GPS CB1 CG1  SING N N 10 
GPS CB1 HB11 SING N N 11 
GPS CB1 HB12 SING N N 12 
GPS CG1 CD1  SING N N 13 
GPS CG1 HG11 SING N N 14 
GPS CG1 HG12 SING N N 15 
GPS CD1 OE1  DOUB N N 16 
GPS CD1 N2   SING N N 17 
GPS N2  CA2  SING N N 18 
GPS N2  HN2  SING N N 19 
GPS CA2 C2   SING N N 20 
GPS CA2 CB2  SING N N 21 
GPS CA2 HA2  SING N N 22 
GPS C2  O2   DOUB N N 23 
GPS C2  N3   SING N N 24 
GPS CB2 SG2  SING N N 25 
GPS CB2 HB21 SING N N 26 
GPS CB2 HB22 SING N N 27 
GPS SG2 CA4  SING N N 28 
GPS N3  CA3  SING N N 29 
GPS N3  HN3  SING N N 30 
GPS CA3 C3   SING N N 31 
GPS CA3 HA31 SING N N 32 
GPS CA3 HA32 SING N N 33 
GPS C3  O31  DOUB N N 34 
GPS C3  O32  SING N N 35 
GPS O32 HO3  SING N N 36 
GPS CA4 CB4  SING N N 37 
GPS CA4 CA5  SING N N 38 
GPS CA4 HA4  SING N N 39 
GPS CB4 CG4  DOUB Y N 40 
GPS CB4 CH4  SING Y N 41 
GPS CG4 CD4  SING Y N 42 
GPS CG4 HG4  SING N N 43 
GPS CD4 CE4  DOUB Y N 44 
GPS CD4 HD4  SING N N 45 
GPS CE4 CZ4  SING Y N 46 
GPS CE4 HE4  SING N N 47 
GPS CZ4 CH4  DOUB Y N 48 
GPS CZ4 HZ4  SING N N 49 
GPS CH4 CH5  SING N N 50 
GPS CH5 CZ5  SING Y N 51 
GPS CH5 CB5  DOUB Y N 52 
GPS CZ5 CE5  DOUB Y N 53 
GPS CZ5 HZ5  SING N N 54 
GPS CE5 CD5  SING Y N 55 
GPS CE5 HE5  SING N N 56 
GPS CD5 CG5  DOUB Y N 57 
GPS CD5 HD5  SING N N 58 
GPS CG5 CB5  SING Y N 59 
GPS CG5 HG5  SING N N 60 
GPS CB5 CA5  SING N N 61 
GPS CA5 O5   SING N N 62 
GPS CA5 HA5  SING N N 63 
GPS O5  HO5  SING N N 64 
# 
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 
GPS SMILES           ACDLabs              10.04 O=C(O)C(N)CCC(=O)NC(C(=O)NCC(=O)O)CSC3c1ccccc1c2c(cccc2)C3O 
GPS InChI            InChI                1.02b 
InChI=1/C24H27N3O7S/c25-17(24(33)34)9-10-19(28)27-18(23(32)26-11-20(29)30)12-35-22-16-8-4-2-6-14(16)13-5-1-3-7-15(13)21(22)31/h1-8,17-18,21-22,31H,9-12,25H2,(H,26,32)(H,27,28)(H,29,30)(H,33,34)/t17-,18-,21+,22+/m0/s1/f/h26-27,29,33H 
GPS InChIKey         InChI                1.02b JNNIZILNBMPOAC-PPOVSMFFDN 
GPS SMILES_CANONICAL CACTVS               3.341 N[C@@H](CCC(=O)N[C@@H](CS[C@H]1[C@H](O)c2ccccc2c3ccccc13)C(=O)NCC(O)=O)C(O)=O 
GPS SMILES           CACTVS               3.341 N[CH](CCC(=O)N[CH](CS[CH]1[CH](O)c2ccccc2c3ccccc13)C(=O)NCC(O)=O)C(O)=O 
GPS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)-c3ccccc3[C@H]([C@@H]2O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N 
GPS SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)-c3ccccc3C(C2O)SCC(C(=O)NCC(=O)O)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 
GPS "SYSTEMATIC NAME" ACDLabs              10.04 L-gamma-glutamyl-S-[(9R,10R)-10-hydroxy-9,10-dihydrophenanthren-9-yl]-L-cysteinylglycine                                                                    
GPS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[[(9R,10R)-10-hydroxy-9,10-dihydrophenanthren-9-yl]sulfanyl]-1-oxo-propan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
