data_GDN
# 
_chem_comp.id                                    GDN 
_chem_comp.name                                  "GLUTATHIONE S-(2,4 DINITROBENZENE)" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H19 N5 O10 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                         GDB 
_chem_comp.formula_weight                        473.415 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GDN 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1HNA 
_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 
GDN N1    N1    N 0  1 N N N 2.162  19.979 23.252 -0.961 -4.175 3.575  N1    GDN 1  
GDN CA1   CA1   C 0  1 N N S 2.163  19.966 24.711 -2.137 -3.563 3.011  CA1   GDN 2  
GDN C1    C1    C 0  1 N N N 1.109  19.018 25.251 -3.284 -3.890 3.946  C1    GDN 3  
GDN O11   O11   O 0  1 N N N 0.210  18.661 24.475 -3.420 -4.942 4.557  O11   GDN 4  
GDN O12   O12   O 0  1 N N N 1.199  18.607 26.422 -4.197 -2.884 3.999  O12   GDN 5  
GDN CB1   CB1   C 0  1 N N N 1.925  21.373 25.237 -2.442 -4.074 1.600  CB1   GDN 6  
GDN CG1   CG1   C 0  1 N N N 2.342  21.591 26.673 -1.339 -3.760 0.588  CG1   GDN 7  
GDN CD1   CD1   C 0  1 N N N 2.233  23.039 27.071 -1.044 -2.276 0.450  CD1   GDN 8  
GDN OE1   OE1   O 0  1 N N N 2.247  23.935 26.225 -1.895 -1.403 0.601  OE1   GDN 9  
GDN N2    N2    N 0  1 N N N 2.024  23.268 28.356 0.281  -2.047 0.109  N2    GDN 10 
GDN CA2   CA2   C 0  1 N N S 1.893  24.618 28.865 0.813  -0.722 -0.109 CA2   GDN 11 
GDN C2    C2    C 0  1 N N N 2.907  24.883 29.985 1.866  -0.787 -1.213 C2    GDN 12 
GDN O2    O2    O 0  1 N N N 2.686  25.730 30.840 2.247  -1.843 -1.713 O2    GDN 13 
GDN CB2   CB2   C 0  1 N N N 0.461  24.843 29.371 1.326  -0.081 1.183  CB2   GDN 14 
GDN SG2   SG2   S 0  1 N N N -0.845 24.763 28.096 2.723  -0.973 1.941  SG2   GDN 15 
GDN N3    N3    N 0  1 N N N 4.036  24.193 29.956 2.346  0.469  -1.555 N3    GDN 16 
GDN CA3   CA3   C 0  1 N N N 5.088  24.338 30.952 3.366  0.667  -2.558 CA3   GDN 17 
GDN C3    C3    C 0  1 N N N 6.279  25.061 30.362 4.707  0.622  -1.892 C3    GDN 18 
GDN O31   O31   O 0  1 N N N 6.134  25.689 29.298 4.956  0.937  -0.738 O31   GDN 19 
GDN O32   O32   O 0  1 N N N 7.361  25.010 30.970 5.643  0.169  -2.766 O32   GDN 20 
GDN "C1'" "C1'" C 0  1 Y N N ?      ?      ?      3.000  0.054  3.349  "C1'" GDN 21 
GDN "C2'" "C2'" C 0  1 Y N N ?      ?      ?      2.908  -0.415 4.675  "C2'" GDN 22 
GDN "C3'" "C3'" C 0  1 Y N N ?      ?      ?      3.136  0.439  5.754  "C3'" GDN 23 
GDN "C4'" "C4'" C 0  1 Y N N ?      ?      ?      3.461  1.776  5.529  "C4'" GDN 24 
GDN "C5'" "C5'" C 0  1 Y N N ?      ?      ?      3.557  2.260  4.224  "C5'" GDN 25 
GDN "C6'" "C6'" C 0  1 Y N N ?      ?      ?      3.329  1.407  3.145  "C6'" GDN 26 
GDN "N2'" "N2'" N 1  1 N N N ?      ?      ?      2.579  -1.773 4.952  "N2'" GDN 27 
GDN O2A   O2A   O -1 1 N N N ?      ?      ?      2.509  -2.145 6.146  O2A   GDN 28 
GDN O2B   O2B   O 0  1 N N N ?      ?      ?      2.371  -2.551 3.993  O2B   GDN 29 
GDN "N4'" "N4'" N 1  1 N N N ?      ?      ?      3.693  2.646  6.627  "N4'" GDN 30 
GDN O4A   O4A   O -1 1 N N N ?      ?      ?      3.984  3.846  6.402  O4A   GDN 31 
GDN O4B   O4B   O 0  1 N N N ?      ?      ?      3.601  2.191  7.793  O4B   GDN 32 
GDN HN1   1HN   H 0  1 N N N 2.162  20.925 22.927 -0.111 -3.639 3.631  HN1   GDN 33 
GDN HN2A  2HN   H 0  0 N N N 2.978  19.511 22.914 -0.947 -5.172 3.713  HN2A  GDN 34 
GDN HA1   HA1   H 0  1 N N N 3.145  19.610 25.055 -1.954 -2.484 3.029  HA1   GDN 35 
GDN H12   H12   H 0  1 N N N 0.489  18.002 26.601 -4.979 -3.058 4.565  H12   GDN 36 
GDN HB11  1HB1  H 0  0 N N N 2.504  22.067 24.611 -2.584 -5.163 1.631  HB11  GDN 37 
GDN HB12  2HB1  H 0  0 N N N 0.839  21.542 25.197 -3.393 -3.653 1.250  HB12  GDN 38 
GDN HG11  1HG1  H 0  0 N N N 1.687  20.995 27.325 -0.415 -4.292 0.845  HG11  GDN 39 
GDN HG12  2HG1  H 0  0 N N N 3.393  21.284 26.776 -1.656 -4.115 -0.400 HG12  GDN 40 
GDN HN2   HN2   H 0  1 N N N 1.955  22.496 28.988 0.903  -2.844 0.009  HN2   GDN 41 
GDN HA2   HA2   H 0  1 N N N 2.102  25.324 28.048 -0.027 -0.126 -0.487 HA2   GDN 42 
GDN HB21  1HB2  H 0  0 N N N 0.246  24.061 30.115 1.657  0.947  0.997  HB21  GDN 43 
GDN HB22  2HB2  H 0  0 N N N 0.436  25.867 29.771 0.522  -0.040 1.925  HB22  GDN 44 
GDN HN3   HN3   H 0  1 N N N 4.173  23.539 29.212 1.942  1.294  -1.121 HN3   GDN 45 
GDN HA31  1HA3  H 0  0 N N N 4.701  24.916 31.804 3.221  1.645  -3.025 HA31  GDN 46 
GDN HA32  2HA3  H 0  0 N N N 5.406  23.338 31.283 3.294  -0.129 -3.303 HA32  GDN 47 
GDN H32   H32   H 0  1 N N N 8.015  25.511 30.496 6.535  0.127  -2.358 H32   GDN 48 
GDN "H3'" "H3'" H 0  1 N N N ?      ?      ?      3.062  0.063  6.773  "H3'" GDN 49 
GDN "H5'" "H5'" H 0  1 N N N ?      ?      ?      3.810  3.301  4.034  "H5'" GDN 50 
GDN "H6'" "H6'" H 0  1 N N N ?      ?      ?      3.410  1.806  2.136  "H6'" GDN 51 
# 
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 
GDN N1    CA1   SING N N 1  
GDN N1    HN1   SING N N 2  
GDN N1    HN2A  SING N N 3  
GDN CA1   C1    SING N N 4  
GDN CA1   CB1   SING N N 5  
GDN CA1   HA1   SING N N 6  
GDN C1    O11   DOUB N N 7  
GDN C1    O12   SING N N 8  
GDN O12   H12   SING N N 9  
GDN CB1   CG1   SING N N 10 
GDN CB1   HB11  SING N N 11 
GDN CB1   HB12  SING N N 12 
GDN CG1   CD1   SING N N 13 
GDN CG1   HG11  SING N N 14 
GDN CG1   HG12  SING N N 15 
GDN CD1   OE1   DOUB N N 16 
GDN CD1   N2    SING N N 17 
GDN N2    CA2   SING N N 18 
GDN N2    HN2   SING N N 19 
GDN CA2   C2    SING N N 20 
GDN CA2   CB2   SING N N 21 
GDN CA2   HA2   SING N N 22 
GDN C2    O2    DOUB N N 23 
GDN C2    N3    SING N N 24 
GDN CB2   SG2   SING N N 25 
GDN CB2   HB21  SING N N 26 
GDN CB2   HB22  SING N N 27 
GDN SG2   "C1'" SING N N 28 
GDN N3    CA3   SING N N 29 
GDN N3    HN3   SING N N 30 
GDN CA3   C3    SING N N 31 
GDN CA3   HA31  SING N N 32 
GDN CA3   HA32  SING N N 33 
GDN C3    O31   DOUB N N 34 
GDN C3    O32   SING N N 35 
GDN O32   H32   SING N N 36 
GDN "C1'" "C2'" DOUB Y N 37 
GDN "C1'" "C6'" SING Y N 38 
GDN "C2'" "C3'" SING Y N 39 
GDN "C2'" "N2'" SING N N 40 
GDN "C3'" "C4'" DOUB Y N 41 
GDN "C3'" "H3'" SING N N 42 
GDN "C4'" "C5'" SING Y N 43 
GDN "C4'" "N4'" SING N N 44 
GDN "C5'" "C6'" DOUB Y N 45 
GDN "C5'" "H5'" SING N N 46 
GDN "C6'" "H6'" SING N N 47 
GDN "N2'" O2A   SING N N 48 
GDN "N2'" O2B   DOUB N N 49 
GDN "N4'" O4A   SING N N 50 
GDN "N4'" O4B   DOUB N N 51 
# 
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 
GDN SMILES           ACDLabs              10.04 O=C(O)C(N)CCC(=O)NC(C(=O)NCC(=O)O)CSc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O                                                                                                                                       
GDN InChI            InChI                1.02b InChI=1/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/t9-,10-/m0/s1/f/h18-19,23,26H 
GDN InChIKey         InChI                1.02b FXEUKVKGTKDDIQ-ZMIYAPQADI                                                                                                                                                                                    
GDN SMILES_CANONICAL CACTVS               3.341 N[C@@H](CCC(=O)N[C@@H](CSc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O)C(=O)NCC(O)=O)C(O)=O                                                                                                                             
GDN SMILES           CACTVS               3.341 N[CH](CCC(=O)N[CH](CSc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O)C(=O)NCC(O)=O)C(O)=O                                                                                                                                 
GDN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N                                                                                                                           
GDN SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c(cc1[N+](=O)[O-])[N+](=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 
GDN "SYSTEMATIC NAME" ACDLabs              10.04 L-gamma-glutamyl-S-(2,4-dinitrophenyl)-L-cysteinylglycine                                                                  
GDN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-(2,4-dinitrophenyl)sulfanyl-1-oxo-propan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
