data_GPI
# 
_chem_comp.id                                    GPI 
_chem_comp.name                                  (2S)-[3-PYRIDYL-1-PROPYL]-1-[3,3-DIMETHYL-1,2-DIOXOPENTYL]-2-PYRROLIDINECARBOXYLATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H28 N2 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         GPI-1046 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-06-16 
_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                        360.447 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GPI 
_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        1F40 
_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 
GPI C2   C2   C 0 1 N N S -3.861  1.684  -0.804 -1.504 -0.690 0.899  C2   GPI 1  
GPI N6   N6   N 0 1 N N N -4.145  3.148  -0.447 -1.294 -0.258 2.288  N6   GPI 2  
GPI C5   C5   C 0 1 N N N -2.772  3.843  -0.504 -2.540 0.351  2.787  C5   GPI 3  
GPI C3   C3   C 0 1 N N N -2.447  1.411  -0.328 -2.967 -0.361 0.533  C3   GPI 4  
GPI C4   C4   C 0 1 N N N -1.711  2.737  -0.447 -3.662 -0.270 1.917  C4   GPI 5  
GPI C1   C1   C 0 1 N N N -4.833  0.767  -0.042 -0.567 0.044  -0.024 C1   GPI 6  
GPI O1   O1   O 0 1 N N N -4.461  0.205  0.991  0.213  0.849  0.423  O1   GPI 7  
GPI O2   O2   O 0 1 N N N -6.100  0.571  -0.516 -0.601 -0.194 -1.344 O2   GPI 8  
GPI C14  C14  C 0 1 N N N -7.038  0.541  0.566  0.300  0.514  -2.234 C14  GPI 9  
GPI C15  C15  C 0 1 N N N -8.453  0.808  0.023  0.057  0.059  -3.675 C15  GPI 10 
GPI C16  C16  C 0 1 N N N -9.376  -0.361 0.402  1.009  0.805  -4.612 C16  GPI 11 
GPI N19  N19  N 0 1 Y N N -11.357 1.229  3.295  1.265  -1.110 -7.795 N19  GPI 12 
GPI C20  C20  C 0 1 Y N N -11.083 0.341  4.359  0.394  -0.509 -8.581 C20  GPI 13 
GPI C21  C21  C 0 1 Y N N -10.254 -0.775 4.139  -0.342 0.568  -8.127 C21  GPI 14 
GPI C22  C22  C 0 1 Y N N -9.704  -0.998 2.857  -0.155 1.015  -6.828 C22  GPI 15 
GPI C17  C17  C 0 1 Y N N -9.979  -0.110 1.795  0.769  0.358  -6.031 C17  GPI 16 
GPI C18  C18  C 0 1 Y N N -10.807 1.007  2.014  1.473  -0.708 -6.556 C18  GPI 17 
GPI C7   C7   C 0 1 N N N -5.305  3.695  -0.160 -0.150 -0.391 2.988  C7   GPI 18 
GPI O7   O7   O 0 1 N N N -6.326  3.011  -0.154 0.818  -0.910 2.473  O7   GPI 19 
GPI C8   C8   C 0 1 N N N -5.382  5.197  0.173  -0.074 0.099  4.393  C8   GPI 20 
GPI O8   O8   O 0 1 N N N -5.069  6.028  -0.677 -1.038 0.616  4.905  O8   GPI 21 
GPI C9   C9   C 0 1 N N N -5.850  5.665  1.565  1.205  -0.049 5.176  C9   GPI 22 
GPI C12  C12  C 0 1 N N N -5.026  6.892  1.993  2.330  0.701  4.461  C12  GPI 23 
GPI C13  C13  C 0 1 N N N -5.653  4.536  2.593  1.568  -1.531 5.282  C13  GPI 24 
GPI C10  C10  C 0 1 N N N -7.339  6.047  1.504  1.015  0.530  6.579  C10  GPI 25 
GPI C11  C11  C 0 1 N N N -7.541  7.160  0.461  2.314  0.379  7.373  C11  GPI 26 
GPI H2   H2   H 0 1 N N N -4.005  1.630  -1.886 -1.335 -1.764 0.820  H2   GPI 27 
GPI H51  1H5  H 0 1 N N N -2.665  4.477  -1.402 -2.691 0.099  3.837  H51  GPI 28 
GPI H52  2H5  H 0 1 N N N -2.659  4.513  0.369  -2.513 1.432  2.655  H52  GPI 29 
GPI H31  1H3  H 0 1 N N N -1.964  0.641  -0.958 -3.406 -1.159 -0.066 H31  GPI 30 
GPI H32  2H3  H 0 1 N N N -2.443  1.017  0.706  -3.025 0.592  0.009  H32  GPI 31 
GPI H41  1H4  H 0 1 N N N -1.139  2.739  -1.404 -3.936 -1.259 2.283  H41  GPI 32 
GPI H42  2H4  H 0 1 N N N -0.985  2.897  0.372  -4.532 0.384  1.876  H42  GPI 33 
GPI H141 1H14 H 0 0 N N N -6.780  1.308  1.296  0.120  1.586  -2.156 H141 GPI 34 
GPI H142 2H14 H 0 0 N N N -7.013  -0.439 1.042  1.331  0.297  -1.954 H142 GPI 35 
GPI H151 1H15 H 0 0 N N N -8.415  0.905  -1.061 0.238  -1.012 -3.753 H151 GPI 36 
GPI H152 2H15 H 0 0 N N N -8.840  1.731  0.456  -0.972 0.275  -3.955 H152 GPI 37 
GPI H161 1H16 H 0 0 N N N -8.803  -1.287 0.416  0.828  1.878  -4.534 H161 GPI 38 
GPI H162 2H16 H 0 0 N N N -10.179 -0.443 -0.331 2.039  0.589  -4.332 H162 GPI 39 
GPI H20  H20  H 0 1 N N N -11.508 0.518  5.336  0.254  -0.863 -9.592 H20  GPI 40 
GPI H21  H21  H 0 1 N N N -10.040 -1.458 4.947  -1.054 1.056  -8.776 H21  GPI 41 
GPI H22  H22  H 0 1 N N N -9.067  -1.854 2.690  -0.716 1.855  -6.446 H22  GPI 42 
GPI H18  H18  H 0 1 N N N -11.021 1.690  1.206  2.195  -1.225 -5.942 H18  GPI 43 
GPI H121 1H12 H 0 0 N N N -4.103  6.910  1.456  2.071  1.757  4.385  H121 GPI 44 
GPI H122 2H12 H 0 0 N N N -5.579  7.782  1.759  3.255  0.593  5.026  H122 GPI 45 
GPI H123 3H12 H 0 0 N N N -4.833  6.852  3.045  2.465  0.288  3.461  H123 GPI 46 
GPI H131 1H13 H 0 0 N N N -6.315  3.705  2.356  0.766  -2.066 5.791  H131 GPI 47 
GPI H132 2H13 H 0 0 N N N -4.619  4.188  2.546  1.703  -1.945 4.282  H132 GPI 48 
GPI H133 3H13 H 0 0 N N N -5.873  4.905  3.596  2.493  -1.639 5.847  H133 GPI 49 
GPI H101 1H10 H 0 0 N N N -7.664  6.402  2.482  0.213  -0.004 7.088  H101 GPI 50 
GPI H102 2H10 H 0 0 N N N -7.928  5.174  1.222  0.756  1.586  6.503  H102 GPI 51 
GPI H111 1H11 H 0 0 N N N -8.157  6.801  -0.334 2.179  0.792  8.372  H111 GPI 52 
GPI H112 2H11 H 0 0 N N N -8.033  7.992  0.930  2.573  -0.676 7.448  H112 GPI 53 
GPI H113 3H11 H 0 0 N N N -6.595  7.471  0.074  3.116  0.914  6.863  H113 GPI 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 
GPI C2  N6   SING N N 1  
GPI C2  C3   SING N N 2  
GPI C2  C1   SING N N 3  
GPI C2  H2   SING N N 4  
GPI N6  C5   SING N N 5  
GPI N6  C7   SING N N 6  
GPI C5  C4   SING N N 7  
GPI C5  H51  SING N N 8  
GPI C5  H52  SING N N 9  
GPI C3  C4   SING N N 10 
GPI C3  H31  SING N N 11 
GPI C3  H32  SING N N 12 
GPI C4  H41  SING N N 13 
GPI C4  H42  SING N N 14 
GPI C1  O1   DOUB N N 15 
GPI C1  O2   SING N N 16 
GPI O2  C14  SING N N 17 
GPI C14 C15  SING N N 18 
GPI C14 H141 SING N N 19 
GPI C14 H142 SING N N 20 
GPI C15 C16  SING N N 21 
GPI C15 H151 SING N N 22 
GPI C15 H152 SING N N 23 
GPI C16 C17  SING N N 24 
GPI C16 H161 SING N N 25 
GPI C16 H162 SING N N 26 
GPI N19 C20  DOUB Y N 27 
GPI N19 C18  SING Y N 28 
GPI C20 C21  SING Y N 29 
GPI C20 H20  SING N N 30 
GPI C21 C22  DOUB Y N 31 
GPI C21 H21  SING N N 32 
GPI C22 C17  SING Y N 33 
GPI C22 H22  SING N N 34 
GPI C17 C18  DOUB Y N 35 
GPI C18 H18  SING N N 36 
GPI C7  O7   DOUB N N 37 
GPI C7  C8   SING N N 38 
GPI C8  O8   DOUB N N 39 
GPI C8  C9   SING N N 40 
GPI C9  C12  SING N N 41 
GPI C9  C13  SING N N 42 
GPI C9  C10  SING N N 43 
GPI C12 H121 SING N N 44 
GPI C12 H122 SING N N 45 
GPI C12 H123 SING N N 46 
GPI C13 H131 SING N N 47 
GPI C13 H132 SING N N 48 
GPI C13 H133 SING N N 49 
GPI C10 C11  SING N N 50 
GPI C10 H101 SING N N 51 
GPI C10 H102 SING N N 52 
GPI C11 H111 SING N N 53 
GPI C11 H112 SING N N 54 
GPI C11 H113 SING N N 55 
# 
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 
GPI SMILES           ACDLabs              10.04 O=C(OCCCc1cccnc1)C2N(C(=O)C(=O)C(C)(C)CC)CCC2                                                                                                     
GPI InChI            InChI                1.02b InChI=1/C20H28N2O4/c1-4-20(2,3)17(23)18(24)22-12-6-10-16(22)19(25)26-13-7-9-15-8-5-11-21-14-15/h5,8,11,14,16H,4,6-7,9-10,12-13H2,1-3H3/t16-/m0/s1 
GPI InChIKey         InChI                1.02b OQAHHWOPVDDWHD-INIZCTEOBR                                                                                                                         
GPI SMILES_CANONICAL CACTVS               3.341 CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)OCCCc2cccnc2                                                                                                   
GPI SMILES           CACTVS               3.341 CCC(C)(C)C(=O)C(=O)N1CCC[CH]1C(=O)OCCCc2cccnc2                                                                                                    
GPI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)OCCCc2cccnc2                                                                                                   
GPI SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)OCCCc2cccnc2                                                                                                       
# 
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 
GPI "SYSTEMATIC NAME" ACDLabs              10.04 "3-pyridin-3-ylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)-L-prolinate"                    
GPI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-pyridin-3-ylpropyl (2S)-1-(3,3-dimethyl-2-oxo-pentanoyl)pyrrolidine-2-carboxylate" 
# 
