data_GPB
# 
_chem_comp.id                                    GPB 
_chem_comp.name                                  "N-[4-[2-(2-AMINO-4-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYL]GLUTAMIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H23 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-05-18 
_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                        425.438 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GPB 
_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        1E26 
_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 
GPB N1   N1   N 0 1 Y N N 10.254 2.758  13.195 0.607  0.013  -7.712 N1   GPB 1  
GPB C2   C2   C 0 1 Y N N 10.575 1.974  12.190 1.747  0.618  -7.424 C2   GPB 2  
GPB NA2  NA2  N 0 1 N N N 9.790  1.116  11.699 2.656  0.850  -8.443 NA2  GPB 3  
GPB N3   N3   N 0 1 Y N N 11.879 2.095  11.622 2.053  1.011  -6.193 N3   GPB 4  
GPB C4   C4   C 0 1 Y N N 12.851 2.976  12.040 1.220  0.813  -5.186 C4   GPB 5  
GPB C5   C5   C 0 1 N N N 13.964 2.993  11.464 1.576  1.263  -3.792 C5   GPB 6  
GPB C4A  C4A  C 0 1 Y N N 12.470 3.878  13.195 0.007  0.175  -5.439 C4A  GPB 7  
GPB C6   C6   C 0 1 Y N N 12.952 5.030  14.140 -1.149 -0.210 -4.629 C6   GPB 8  
GPB C7   C7   C 0 1 Y N N 11.889 5.245  14.920 -2.026 -0.796 -5.458 C7   GPB 9  
GPB N8   N8   N 0 1 Y N N 10.838 4.532  14.738 -1.523 -0.812 -6.735 N8   GPB 10 
GPB C8A  C8A  C 0 1 Y N N 11.201 3.715  13.701 -0.288 -0.225 -6.759 C8A  GPB 11 
GPB C9   C9   C 0 1 N N N 14.258 5.807  14.254 -1.320 0.005  -3.147 C9   GPB 12 
GPB C10  C10  C 0 1 N N N 15.305 6.162  13.183 -0.765 -1.201 -2.389 C10  GPB 13 
GPB C11  C11  C 0 1 Y N N 15.016 8.299  9.352  -1.249 -0.591 1.815  C11  GPB 14 
GPB C12  C12  C 0 1 Y N N 16.220 7.767  9.805  -2.254 -1.219 1.077  C12  GPB 15 
GPB C13  C13  C 0 1 Y N N 16.302 7.109  11.015 -2.091 -1.413 -0.278 C13  GPB 16 
GPB C14  C14  C 0 1 Y N N 15.128 6.939  11.871 -0.935 -0.986 -0.907 C14  GPB 17 
GPB C15  C15  C 0 1 Y N N 13.904 7.449  11.492 0.066  -0.367 -0.181 C15  GPB 18 
GPB C16  C16  C 0 1 Y N N 13.845 8.137  10.219 -0.085 -0.162 1.174  C16  GPB 19 
GPB C    C    C 0 1 N N N 14.962 8.958  8.108  -1.417 -0.379 3.268  C    GPB 20 
GPB O    O    O 0 1 N N N 15.879 9.589  7.621  -2.431 -0.753 3.824  O    GPB 21 
GPB N    N    N 0 1 N N N 13.865 8.936  7.498  -0.444 0.227  3.978  N    GPB 22 
GPB CA   CA   C 0 1 N N S 13.516 9.625  6.257  -0.610 0.436  5.418  CA   GPB 23 
GPB CB   CB   C 0 1 N N N 13.706 8.537  5.167  0.759  0.415  6.098  CB   GPB 24 
GPB CG   CG   C 0 1 N N N 14.818 8.897  4.093  1.429  -0.937 5.853  CG   GPB 25 
GPB CD   CD   C 0 1 N N N 14.759 7.670  3.177  2.779  -0.958 6.523  CD   GPB 26 
GPB OE1  OE1  O 0 1 N N N 15.983 7.129  3.291  3.166  0.010  7.133  OE1  GPB 27 
GPB OE2  OE2  O 0 1 N N N 13.644 7.369  2.459  3.552  -2.052 6.441  OE2  GPB 28 
GPB CT   CT   C 0 1 N N N 12.020 10.013 6.275  -1.270 1.770  5.659  CT   GPB 29 
GPB O1   O1   O 0 1 N N N 11.211 9.499  7.075  -1.077 2.780  4.796  O1   GPB 30 
GPB O2   O2   O 0 1 N N N 11.641 10.880 5.458  -1.973 1.929  6.628  O2   GPB 31 
GPB HA22 2HA2 H 0 0 N N N 10.039 0.507  10.919 2.450  0.570  -9.349 HA22 GPB 32 
GPB HA21 1HA2 H 0 0 N N N 8.932  1.603  11.440 3.498  1.292  -8.252 HA21 GPB 33 
GPB H53  3H5  H 0 1 N N N 14.751 3.706  11.802 1.225  2.284  -3.639 H53  GPB 34 
GPB H52  2H5  H 0 1 N N N 14.388 1.962  11.482 1.103  0.603  -3.065 H52  GPB 35 
GPB H51  1H5  H 0 1 N N N 13.795 3.143  10.372 2.658  1.228  -3.665 H51  GPB 36 
GPB H7   H7   H 0 1 N N N 11.879 6.010  15.713 -2.985 -1.196 -5.164 H7   GPB 37 
GPB H8   H8   H 0 1 N N N 9.966  4.596  15.264 -1.977 -1.184 -7.507 H8   GPB 38 
GPB H91  1H9  H 0 1 N N N 13.972 6.783  14.711 -0.780 0.903  -2.846 H91  GPB 39 
GPB H92  2H9  H 0 1 N N N 14.832 5.287  15.056 -2.378 0.124  -2.917 H92  GPB 40 
GPB H101 1H10 H 0 0 N N N 16.118 6.691  13.731 -1.305 -2.099 -2.690 H101 GPB 41 
GPB H102 2H10 H 0 0 N N N 15.767 5.190  12.889 0.293  -1.320 -2.619 H102 GPB 42 
GPB H12  H12  H 0 1 N N N 17.130 7.869  9.190  -3.157 -1.552 1.567  H12  GPB 43 
GPB H13  H13  H 0 1 N N N 17.296 6.722  11.295 -2.868 -1.898 -0.850 H13  GPB 44 
GPB H15  H15  H 0 1 N N N 13.035 7.316  12.158 0.966  -0.036 -0.678 H15  GPB 45 
GPB H16  H16  H 0 1 N N N 12.874 8.552  9.898  0.695  0.323  1.739  H16  GPB 46 
GPB H    H    H 0 1 N N N 13.234 8.336  8.030  0.364  0.525  3.534  H    GPB 47 
GPB HA1  1HA  H 0 1 N N N 14.122 10.546 6.098  -1.233 -0.356 5.831  HA1  GPB 48 
GPB HB2  2HB  H 0 1 N N N 13.915 7.545  5.632  1.382  1.209  5.684  HB2  GPB 49 
GPB HB1  1HB  H 0 1 N N N 12.736 8.307  4.667  0.636  0.571  7.169  HB1  GPB 50 
GPB HG2  2HG  H 0 1 N N N 14.688 9.879  3.582  0.807  -1.731 6.266  HG2  GPB 51 
GPB HG1  1HG  H 0 1 N N N 15.824 9.133  4.509  1.553  -1.093 4.781  HG1  GPB 52 
GPB HE2O OHE2 H 0 0 N N N 13.607 6.608  1.891  4.418  -2.065 6.871  HE2O GPB 53 
GPB H1O  OH1  H 0 1 N N N 10.291 9.737  7.086  -1.500 3.635  4.951  H1O  GPB 54 
# 
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 
GPB N1  C2   DOUB Y N 1  
GPB N1  C8A  SING Y N 2  
GPB C2  NA2  SING N N 3  
GPB C2  N3   SING Y N 4  
GPB NA2 HA22 SING N N 5  
GPB NA2 HA21 SING N N 6  
GPB N3  C4   DOUB Y N 7  
GPB C4  C5   SING N N 8  
GPB C4  C4A  SING Y N 9  
GPB C5  H53  SING N N 10 
GPB C5  H52  SING N N 11 
GPB C5  H51  SING N N 12 
GPB C4A C6   SING Y N 13 
GPB C4A C8A  DOUB Y N 14 
GPB C6  C7   DOUB Y N 15 
GPB C6  C9   SING N N 16 
GPB C7  N8   SING Y N 17 
GPB C7  H7   SING N N 18 
GPB N8  C8A  SING Y N 19 
GPB N8  H8   SING N N 20 
GPB C9  C10  SING N N 21 
GPB C9  H91  SING N N 22 
GPB C9  H92  SING N N 23 
GPB C10 C14  SING N N 24 
GPB C10 H101 SING N N 25 
GPB C10 H102 SING N N 26 
GPB C11 C12  DOUB Y N 27 
GPB C11 C16  SING Y N 28 
GPB C11 C    SING N N 29 
GPB C12 C13  SING Y N 30 
GPB C12 H12  SING N N 31 
GPB C13 C14  DOUB Y N 32 
GPB C13 H13  SING N N 33 
GPB C14 C15  SING Y N 34 
GPB C15 C16  DOUB Y N 35 
GPB C15 H15  SING N N 36 
GPB C16 H16  SING N N 37 
GPB C   O    DOUB N N 38 
GPB C   N    SING N N 39 
GPB N   CA   SING N N 40 
GPB N   H    SING N N 41 
GPB CA  CB   SING N N 42 
GPB CA  CT   SING N N 43 
GPB CA  HA1  SING N N 44 
GPB CB  CG   SING N N 45 
GPB CB  HB2  SING N N 46 
GPB CB  HB1  SING N N 47 
GPB CG  CD   SING N N 48 
GPB CG  HG2  SING N N 49 
GPB CG  HG1  SING N N 50 
GPB CD  OE1  DOUB N N 51 
GPB CD  OE2  SING N N 52 
GPB OE2 HE2O SING N N 53 
GPB CT  O1   SING N N 54 
GPB CT  O2   DOUB N N 55 
GPB O1  H1O  SING N N 56 
# 
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 
GPB SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)CCc3c2c(nc(nc2nc3)N)C)CCC(=O)O 
GPB InChI            InChI                1.02b 
InChI=1/C21H23N5O5/c1-11-17-14(10-23-18(17)26-21(22)24-11)7-4-12-2-5-13(6-3-12)19(29)25-15(20(30)31)8-9-16(27)28/h2-3,5-6,10,15H,4,7-9H2,1H3,(H,25,29)(H,27,28)(H,30,31)(H3,22,23,24,26)/t15-/m0/s1/f/h23,25,27,30H,22H2 
GPB InChIKey         InChI                1.02b FICRNCFTTZHHPO-SVUMLQEHDP 
GPB SMILES_CANONICAL CACTVS               3.341 Cc1nc(N)nc2[nH]cc(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c12 
GPB SMILES           CACTVS               3.341 Cc1nc(N)nc2[nH]cc(CCc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)c12 
GPB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c2c(c[nH]c2nc(n1)N)CCc3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
GPB SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c2c(c[nH]c2nc(n1)N)CCc3ccc(cc3)C(=O)NC(CCC(=O)O)C(=O)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 
GPB "SYSTEMATIC NAME" ACDLabs              10.04 "N-({4-[2-(2-amino-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl}carbonyl)-L-glutamic acid"            
GPB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[2-(2-amino-4-methyl-7H-pyrrolo[4,5-e]pyrimidin-5-yl)ethyl]phenyl]carbonylamino]pentanedioic acid" 
# 
