data_GBX
# 
_chem_comp.id                                    GBX 
_chem_comp.name                                  "2-AMINO-4-[1-(CARBOXYMETHYL-CARBAMOYL)-2-(9-HYDROXY-7,8-DIOXO-7,8,9,10-TETRAHYDRO-BENZO[DEF]CHRYSEN-10-YLSULFANYL)-ETHYLCARBAMOYL]-BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H27 N3 O9 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "GLUTATHIONE CONJUGATE OF (+)-ANTI-BPDE" 
_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                        605.615 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GBX 
_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        1F3B 
_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 
GBX O2    O2    O 0 1 N N N 18.103 13.633 12.367 -2.382 3.051  3.138  O2    GBX 1  
GBX C1    C1    C 0 1 N N N 21.809 7.492  14.934 5.147  -0.340 5.785  C1    GBX 2  
GBX C2    C2    C 0 1 N N N 17.891 12.987 11.342 -1.992 1.902  3.137  C2    GBX 3  
GBX C3    C3    C 0 1 N N N 19.057 15.290 8.798  -3.760 0.327  5.977  C3    GBX 4  
GBX N1    N1    N 0 1 N N N 23.319 6.807  13.037 3.155  -1.690 6.120  N1    GBX 5  
GBX C7    C7    C 0 1 N N N 15.908 10.517 7.977  -1.045 -3.027 -2.114 C7    GBX 6  
GBX N2    N2    N 0 1 N N N 18.769 10.944 12.265 -0.169 0.374  2.659  N2    GBX 7  
GBX N3    N3    N 0 1 N N N 17.820 13.535 10.129 -2.448 1.035  4.062  N3    GBX 8  
GBX CA1   CA1   C 0 1 N N S 22.431 7.882  13.589 3.931  -0.938 5.126  CA1   GBX 9  
GBX O11   O11   O 0 1 N N N 21.579 8.349  15.784 5.112  -0.034 6.953  O11   GBX 10 
GBX O12   O12   O 0 1 N N N 21.552 6.288  15.105 6.269  -0.147 5.074  O12   GBX 11 
GBX CB1   CB1   C 0 1 N N N 21.330 8.242  12.594 3.065  0.180  4.543  CB1   GBX 12 
GBX CG1   CG1   C 0 1 N N N 20.639 9.566  12.914 1.830  -0.426 3.874  CG1   GBX 13 
GBX CD1   CD1   C 0 1 N N N 19.592 9.966  11.890 0.977  0.675  3.300  CD1   GBX 14 
GBX OE1   OE1   O 0 1 N N N 19.528 9.403  10.788 1.323  1.831  3.415  OE1   GBX 15 
GBX CA2   CA2   C 0 1 N N R 17.702 11.480 11.419 -0.998 1.445  2.101  CA2   GBX 16 
GBX CB2   CB2   C 0 1 N N N 16.316 11.169 12.000 -1.746 0.924  0.872  CB2   GBX 17 
GBX SG2   SG2   S 0 1 N N N 15.908 9.406  12.153 -0.549 0.373  -0.374 SG2   GBX 18 
GBX CA3   CA3   C 0 1 N N N 17.976 14.968 9.844  -3.415 1.479  5.070  CA3   GBX 19 
GBX O31   O31   O 0 1 N N N 19.239 16.456 8.438  -3.251 -0.754 5.801  O31   GBX 20 
GBX O32   O32   O 0 1 N N N 19.729 14.345 8.319  -4.633 0.502  6.982  O32   GBX 21 
GBX O7    O7    O 0 1 N N N 16.877 11.247 8.274  -0.876 -4.213 -2.313 O7    GBX 22 
GBX C8    C8    C 0 1 N N N 16.185 9.260  8.014  -1.760 -2.516 -0.894 C8    GBX 23 
GBX O8    O8    O 0 1 N N N 15.293 8.607  7.440  -1.679 -3.059 0.181  O8    GBX 24 
GBX C9    C9    C 0 1 N N S 16.437 8.688  9.481  -2.592 -1.265 -1.117 C9    GBX 25 
GBX O9    O9    O 0 1 N N N 16.700 7.273  9.432  -3.643 -1.540 -2.045 O9    GBX 26 
GBX C10   C10   C 0 1 N N S 15.235 8.941  10.478 -1.684 -0.175 -1.679 C10   GBX 27 
GBX "C1'" "C1'" C 0 1 Y N N 13.816 11.940 8.348  0.212  -2.398 -4.156 "C1'" GBX 28 
GBX "C2'" "C2'" C 0 1 Y N N 14.644 10.833 8.766  -0.560 -1.993 -3.062 "C2'" GBX 29 
GBX "C3'" "C3'" C 0 1 Y N N 14.299 10.059 9.956  -0.879 -0.653 -2.855 "C3'" GBX 30 
GBX "C4'" "C4'" C 0 1 Y N N 12.573 9.475  11.713 -0.746 1.719  -3.599 "C4'" GBX 31 
GBX "C5'" "C5'" C 0 1 Y N N 11.307 9.716  12.340 -0.290 2.630  -4.487 "C5'" GBX 32 
GBX "C6'" "C6'" C 0 1 Y N N 9.249  11.087 12.548 0.971  3.182  -6.510 "C6'" GBX 33 
GBX "C7'" "C7'" C 0 1 Y N N 8.461  12.211 12.125 1.738  2.786  -7.587 "C7'" GBX 34 
GBX "C8'" "C8'" C 0 1 Y N N 8.902  13.064 11.071 2.058  1.457  -7.790 "C8'" GBX 35 
GBX "C9'" "C9'" C 0 1 Y N N 10.583 13.649 9.341  1.931  -0.927 -7.095 "C9'" GBX 36 
GBX C9A   C9A   C 0 1 Y N N 11.813 13.370 8.655  1.487  -1.858 -6.221 C9A   GBX 37 
GBX C11   C11   C 0 1 Y N N 12.625 12.247 9.051  0.678  -1.459 -5.072 C11   GBX 38 
GBX C12   C12   C 0 1 Y N N 12.212 11.418 10.181 0.357  -0.094 -4.880 C12   GBX 39 
GBX C13   C13   C 0 1 Y N N 13.049 10.333 10.643 -0.427 0.304  -3.774 C13   GBX 40 
GBX C16   C16   C 0 1 Y N N 10.503 10.818 11.916 0.498  2.236  -5.595 C16   GBX 41 
GBX C17   C17   C 0 1 Y N N 10.957 11.676 10.828 0.819  0.873  -5.789 C17   GBX 42 
GBX C18   C18   C 0 1 Y N N 10.142 12.804 10.405 1.605  0.482  -6.899 C18   GBX 43 
GBX HN11  1HN1  H 0 0 N N N 23.733 7.066  12.141 2.888  -1.033 6.838  HN11  GBX 44 
GBX HN12  2HN1  H 0 0 N N N 22.822 5.918  12.968 2.304  -1.983 5.664  HN12  GBX 45 
GBX HN2   HN2   H 0 1 N N N 18.957 11.285 13.207 -0.445 -0.550 2.567  HN2   GBX 46 
GBX HN3   HN3   H 0 1 N N N 17.642 12.841 9.402  -2.137 0.116  4.061  HN3   GBX 47 
GBX HA1   HA1   H 0 1 N N N 23.078 8.773  13.760 4.244  -1.609 4.326  HA1   GBX 48 
GBX H12   H12   H 0 1 N N N 21.166 6.046  15.938 7.050  0.236  5.497  H12   GBX 49 
GBX HB11  1HB1  H 0 0 N N N 21.722 8.241  11.550 2.752  0.851  5.343  HB11  GBX 50 
GBX HB12  2HB1  H 0 0 N N N 20.585 7.416  12.510 3.641  0.738  3.805  HB12  GBX 51 
GBX HG11  1HG1  H 0 0 N N N 20.200 9.544  13.939 2.144  -1.097 3.074  HG11  GBX 52 
GBX HG12  2HG1  H 0 0 N N N 21.389 10.379 13.050 1.255  -0.985 4.612  HG12  GBX 53 
GBX HA2   HA2   H 0 1 N N N 17.757 11.009 10.409 -0.364 2.283  1.812  HA2   GBX 54 
GBX HB21  1HB2  H 0 0 N N N 16.193 11.675 12.985 -2.380 0.086  1.161  HB21  GBX 55 
GBX HB22  2HB2  H 0 0 N N N 15.528 11.692 11.409 -2.363 1.721  0.457  HB22  GBX 56 
GBX HA31  1HA3  H 0 0 N N N 18.163 15.534 10.785 -2.981 2.288  5.658  HA31  GBX 57 
GBX HA32  2HA3  H 0 0 N N N 16.999 15.414 9.545  -4.318 1.835  4.574  HA32  GBX 58 
GBX H32   H32   H 0 1 N N N 20.396 14.543 7.673  -4.855 -0.237 7.564  H32   GBX 59 
GBX H9    H9    H 0 1 N N N 17.320 9.245  9.870  -3.017 -0.934 -0.169 H9    GBX 60 
GBX HO9   HO9   H 0 1 N N N 16.850 6.932  10.306 -4.190 -2.233 -1.649 HO9   GBX 61 
GBX H10   H10   H 0 1 N N N 14.637 8.002  10.557 -2.298 0.668  -1.991 H10   GBX 62 
GBX "H1'" "H1'" H 0 1 N N N 14.097 12.559 7.479  0.449  -3.443 -4.289 "H1'" GBX 63 
GBX "H4'" "H4'" H 0 1 N N N 13.184 8.623  12.056 -1.345 2.037  -2.758 "H4'" GBX 64 
GBX "H5'" "H5'" H 0 1 N N N 10.951 9.054  13.147 -0.532 3.674  -4.350 "H5'" GBX 65 
GBX "H6'" "H6'" H 0 1 N N N 8.891  10.430 13.358 0.734  4.227  -6.374 "H6'" GBX 66 
GBX "H7'" "H7'" H 0 1 N N N 7.498  12.423 12.619 2.096  3.529  -8.284 "H7'" GBX 67 
GBX "H8'" "H8'" H 0 1 N N N 8.283  13.926 10.770 2.660  1.172  -8.640 "H8'" GBX 68 
GBX "H9'" "H9'" H 0 1 N N N 9.972  14.519 9.048  2.529  -1.227 -7.943 "H9'" GBX 69 
GBX H9A   H9A   H 0 1 N N N 12.134 14.019 7.823  1.732  -2.899 -6.372 H9A   GBX 70 
# 
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 
GBX O2    C2    DOUB N N 1  
GBX C1    CA1   SING N N 2  
GBX C1    O11   DOUB N N 3  
GBX C1    O12   SING N N 4  
GBX C2    N3    SING N N 5  
GBX C2    CA2   SING N N 6  
GBX C3    CA3   SING N N 7  
GBX C3    O31   DOUB N N 8  
GBX C3    O32   SING N N 9  
GBX N1    CA1   SING N N 10 
GBX N1    HN11  SING N N 11 
GBX N1    HN12  SING N N 12 
GBX C7    O7    DOUB N N 13 
GBX C7    C8    SING N N 14 
GBX C7    "C2'" SING N N 15 
GBX N2    CD1   SING N N 16 
GBX N2    CA2   SING N N 17 
GBX N2    HN2   SING N N 18 
GBX N3    CA3   SING N N 19 
GBX N3    HN3   SING N N 20 
GBX CA1   CB1   SING N N 21 
GBX CA1   HA1   SING N N 22 
GBX O12   H12   SING N N 23 
GBX CB1   CG1   SING N N 24 
GBX CB1   HB11  SING N N 25 
GBX CB1   HB12  SING N N 26 
GBX CG1   CD1   SING N N 27 
GBX CG1   HG11  SING N N 28 
GBX CG1   HG12  SING N N 29 
GBX CD1   OE1   DOUB N N 30 
GBX CA2   CB2   SING N N 31 
GBX CA2   HA2   SING N N 32 
GBX CB2   SG2   SING N N 33 
GBX CB2   HB21  SING N N 34 
GBX CB2   HB22  SING N N 35 
GBX SG2   C10   SING N N 36 
GBX CA3   HA31  SING N N 37 
GBX CA3   HA32  SING N N 38 
GBX O32   H32   SING N N 39 
GBX C8    O8    DOUB N N 40 
GBX C8    C9    SING N N 41 
GBX C9    O9    SING N N 42 
GBX C9    C10   SING N N 43 
GBX C9    H9    SING N N 44 
GBX O9    HO9   SING N N 45 
GBX C10   "C3'" SING N N 46 
GBX C10   H10   SING N N 47 
GBX "C1'" "C2'" SING Y N 48 
GBX "C1'" C11   DOUB Y N 49 
GBX "C1'" "H1'" SING N N 50 
GBX "C2'" "C3'" DOUB Y N 51 
GBX "C3'" C13   SING Y N 52 
GBX "C4'" "C5'" DOUB Y N 53 
GBX "C4'" C13   SING Y N 54 
GBX "C4'" "H4'" SING N N 55 
GBX "C5'" C16   SING Y N 56 
GBX "C5'" "H5'" SING N N 57 
GBX "C6'" "C7'" DOUB Y N 58 
GBX "C6'" C16   SING Y N 59 
GBX "C6'" "H6'" SING N N 60 
GBX "C7'" "C8'" SING Y N 61 
GBX "C7'" "H7'" SING N N 62 
GBX "C8'" C18   DOUB Y N 63 
GBX "C8'" "H8'" SING N N 64 
GBX "C9'" C9A   DOUB Y N 65 
GBX "C9'" C18   SING Y N 66 
GBX "C9'" "H9'" SING N N 67 
GBX C9A   C11   SING Y N 68 
GBX C9A   H9A   SING N N 69 
GBX C11   C12   SING Y N 70 
GBX C12   C13   DOUB Y N 71 
GBX C12   C17   SING Y N 72 
GBX C16   C17   DOUB Y N 73 
GBX C17   C18   SING Y N 74 
# 
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 
GBX SMILES           ACDLabs              10.04 O=C(O)C(N)CCC(=O)NC(C(=O)NCC(=O)O)CSC3c2c1ccc5c4c1c(cc2C(=O)C(=O)C3O)ccc4ccc5 
GBX InChI            InChI                1.02b 
;InChI=1/C30H27N3O9S/c31-18(30(41)42)8-9-20(34)33-19(29(40)32-11-21(35)36)12-43-28-24-16-7-6-14-3-1-2-13-4-5-15(23(16)22(13)14)10-17(24)25(37)26(38)27(28)39/h1-7,10,18-19,27-28,39H,8-9,11-12,31H2,(H,32,40)(H,33,34)(H,35,36)(H,41,42)/t18-,19-,27-,28-/m0/s1/f/h32-33,35,41H
;
GBX InChIKey         InChI                1.02b DUWOHLGCRJLRRU-QIQVIVIHDR 
GBX SMILES_CANONICAL CACTVS               3.341 N[C@@H](CCC(=O)N[C@@H](CS[C@@H]1[C@@H](O)C(=O)C(=O)c2cc3ccc4cccc5ccc(c12)c3c45)C(=O)NCC(O)=O)C(O)=O 
GBX SMILES           CACTVS               3.341 N[CH](CCC(=O)N[CH](CS[CH]1[CH](O)C(=O)C(=O)c2cc3ccc4cccc5ccc(c12)c3c45)C(=O)NCC(O)=O)C(O)=O 
GBX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2ccc3cc4c(c5c3c2c(c1)cc5)[C@@H]([C@H](C(=O)C4=O)O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N 
GBX SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2ccc3cc4c(c5c3c2c(c1)cc5)C(C(C(=O)C4=O)O)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 
GBX "SYSTEMATIC NAME" ACDLabs              10.04 L-gamma-glutamyl-S-[(9S,10S)-9-hydroxy-7,8-dioxo-7,8,9,10-tetrahydrobenzo[pqr]tetraphen-10-yl]-L-cysteinylglycine                                                       
GBX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[[(9S,10S)-9-hydroxy-7,8-dioxo-9,10-dihydrobenzo[a]pyren-10-yl]sulfanyl]-1-oxo-propan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
