data_GS2
# 
_chem_comp.id                                    GS2 
_chem_comp.name                                  2-[(2-{[1-(N,N-dimethylglycyl)-5-methoxy-1H-indol-6-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H27 F N8 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-09-24 
_chem_comp.pdbx_modified_date                    2008-12-19 
_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                        530.553 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GS2 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3EKK 
_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 
GS2 C1   C1   C 0 1 N N N -12.237 23.692 -19.726 -7.011 1.927  -2.353 C1   GS2 1  
GS2 N1   N1   N 0 1 N N N -10.952 23.885 -20.352 -6.345 0.886  -1.565 N1   GS2 2  
GS2 C2   C2   C 0 1 N N N -9.811  23.982 -19.591 -6.178 1.049  -0.237 C2   GS2 3  
GS2 O1   O1   O 0 1 N N N -9.767  24.027 -18.366 -6.580 2.061  0.306  O1   GS2 4  
GS2 C3   C3   C 0 1 Y N N -8.561  24.084 -20.376 -5.510 0.003  0.555  C3   GS2 5  
GS2 C4   C4   C 0 1 Y N N -8.612  24.649 -21.634 -6.258 -1.028 1.134  C4   GS2 6  
GS2 F1   F1   F 0 1 N N N -9.786  25.079 -22.134 -7.598 -1.068 0.968  F1   GS2 7  
GS2 C5   C5   C 0 1 Y N N -7.469  24.780 -22.388 -5.622 -2.006 1.875  C5   GS2 8  
GS2 C6   C6   C 0 1 Y N N -6.275  24.333 -21.868 -4.250 -1.971 2.048  C6   GS2 9  
GS2 C7   C7   C 0 1 Y N N -6.229  23.766 -20.614 -3.499 -0.959 1.483  C7   GS2 10 
GS2 C8   C8   C 0 1 Y N N -7.367  23.631 -19.845 -4.117 0.030  0.730  C8   GS2 11 
GS2 N2   N2   N 0 1 N N N -7.335  23.064 -18.555 -3.360 1.046  0.156  N2   GS2 12 
GS2 C9   C9   C 0 1 Y N N -6.356  22.195 -18.035 -2.018 0.841  -0.116 C9   GS2 13 
GS2 N3   N3   N 0 1 Y N N -5.287  21.751 -18.714 -1.466 -0.356 0.049  N3   GS2 14 
GS2 C10  C10  C 0 1 Y N N -4.401  20.925 -18.135 -0.180 -0.557 -0.210 C10  GS2 15 
GS2 N4   N4   N 0 1 N N N -3.286  20.456 -18.854 0.348  -1.825 -0.023 N4   GS2 16 
GS2 C11  C11  C 0 1 Y N N -2.914  20.788 -20.176 1.724  -2.038 -0.165 C11  GS2 17 
GS2 C12  C12  C 0 1 Y N N -3.834  20.954 -21.200 2.606  -0.990 0.028  C12  GS2 18 
GS2 C13  C13  C 0 1 Y N N -3.369  21.276 -22.459 3.972  -1.198 -0.113 C13  GS2 19 
GS2 N5   N5   N 0 1 Y N N -4.085  21.503 -23.642 5.076  -0.371 0.012  N5   GS2 20 
GS2 C14  C14  C 0 1 Y N N -3.156  21.815 -24.717 6.223  -1.090 -0.236 C14  GS2 21 
GS2 C15  C15  C 0 1 Y N N -1.760  21.780 -24.127 5.911  -2.361 -0.520 C15  GS2 22 
GS2 C16  C16  C 0 1 Y N N -2.036  21.431 -22.712 4.450  -2.476 -0.450 C16  GS2 23 
GS2 C17  C17  C 0 1 Y N N -1.108  21.263 -21.713 3.553  -3.529 -0.643 C17  GS2 24 
GS2 C18  C18  C 0 1 Y N N -1.565  20.937 -20.449 2.199  -3.311 -0.496 C18  GS2 25 
GS2 O2   O2   O 0 1 N N N -0.683  20.746 -19.390 1.323  -4.335 -0.678 O2   GS2 26 
GS2 C19  C19  C 0 1 N N N 0.651   20.689 -19.876 1.875  -5.609 -1.015 C19  GS2 27 
GS2 C20  C20  C 0 1 N N N -5.459  21.372 -23.785 5.034  0.939  0.328  C20  GS2 28 
GS2 O3   O3   O 0 1 N N N -6.158  20.701 -23.034 3.968  1.480  0.528  O3   GS2 29 
GS2 C21  C21  C 0 1 N N N -6.036  22.031 -25.008 6.312  1.730  0.433  C21  GS2 30 
GS2 N6   N6   N 0 1 N N N -7.421  21.549 -25.277 5.999  3.122  0.786  N6   GS2 31 
GS2 C22  C22  C 0 1 N N N -8.448  22.188 -24.420 5.424  3.205  2.135  C22  GS2 32 
GS2 C23  C23  C 0 1 N N N -7.806  21.719 -26.701 7.188  3.976  0.666  C23  GS2 33 
GS2 N7   N7   N 0 1 Y N N -4.475  20.468 -16.877 0.617  0.406  -0.641 N7   GS2 34 
GS2 C24  C24  C 0 1 Y N N -5.543  20.916 -16.226 0.150  1.638  -0.835 C24  GS2 35 
GS2 N8   N8   N 0 1 Y N N -5.882  20.616 -14.936 0.706  2.813  -1.260 N8   GS2 36 
GS2 C25  C25  C 0 1 Y N N -7.035  21.261 -14.592 -0.244 3.804  -1.277 C25  GS2 37 
GS2 C26  C26  C 0 1 Y N N -7.443  21.982 -15.691 -1.424 3.309  -0.871 C26  GS2 38 
GS2 C27  C27  C 0 1 Y N N -6.499  21.764 -16.729 -1.210 1.892  -0.577 C27  GS2 39 
GS2 H1   H1   H 0 1 N N N -12.110 23.643 -18.634 -7.053 1.620  -3.398 H1   GS2 40 
GS2 H1A  H1A  H 0 1 N N N -12.899 24.533 -19.980 -8.023 2.077  -1.976 H1A  GS2 41 
GS2 H1B  H1B  H 0 1 N N N -12.682 22.753 -20.086 -6.451 2.858  -2.270 H1B  GS2 42 
GS2 HN1  HN1  H 0 1 N N N -10.890 23.949 -21.348 -6.026 0.079  -1.998 HN1  GS2 43 
GS2 H5   H5   H 0 1 N N N -7.507  25.226 -23.371 -6.200 -2.802 2.322  H5   GS2 44 
GS2 H6   H6   H 0 1 N N N -5.369  24.428 -22.447 -3.762 -2.739 2.629  H6   GS2 45 
GS2 H7   H7   H 0 1 N N N -5.283  23.420 -20.224 -2.428 -0.939 1.624  H7   GS2 46 
GS2 HN2  HN2  H 0 1 N N N -8.088  23.305 -17.943 -3.773 1.898  -0.055 HN2  GS2 47 
GS2 HN4  HN4  H 0 1 N N N -2.688  19.814 -18.374 -0.236 -2.564 0.208  HN4  GS2 48 
GS2 H12  H12  H 0 1 N N N -4.891  20.834 -21.016 2.233  -0.010 0.287  H12  GS2 49 
GS2 H14  H14  H 0 1 N N N -3.413  22.031 -25.744 7.226  -0.689 -0.207 H14  GS2 50 
GS2 H15  H15  H 0 1 N N N -0.812  21.962 -24.611 6.605  -3.154 -0.757 H15  GS2 51 
GS2 H17  H17  H 0 1 N N N -0.053  21.382 -21.909 3.919  -4.511 -0.904 H17  GS2 52 
GS2 H19  H19  H 0 1 N N N 0.641   20.674 -20.976 2.546  -5.936 -0.220 H19  GS2 53 
GS2 H19A H19A H 0 0 N N N 1.206   21.572 -19.526 1.071  -6.335 -1.131 H19A GS2 54 
GS2 H19B H19B H 0 0 N N N 1.139   19.777 -19.502 2.431  -5.529 -1.949 H19B GS2 55 
GS2 H21  H21  H 0 1 N N N -6.062  23.119 -24.848 6.947  1.294  1.203  H21  GS2 56 
GS2 H21A H21A H 0 0 N N N -5.404  21.778 -25.872 6.833  1.707  -0.524 H21A GS2 57 
GS2 H22  H22  H 0 1 N N N -8.038  22.346 -23.412 6.138  2.813  2.859  H22  GS2 58 
GS2 H22A H22A H 0 0 N N N -8.737  23.156 -24.854 5.201  4.246  2.371  H22A GS2 59 
GS2 H22B H22B H 0 0 N N N -9.331  21.535 -24.358 4.506  2.619  2.176  H22B GS2 60 
GS2 H23  H23  H 0 1 N N N -8.902  21.761 -26.783 7.552  3.950  -0.361 H23  GS2 61 
GS2 H23A H23A H 0 0 N N N -7.374  22.653 -27.089 6.928  5.000  0.933  H23A GS2 62 
GS2 H23B H23B H 0 0 N N N -7.427  20.869 -27.287 7.966  3.612  1.337  H23B GS2 63 
GS2 HN8  HN8  H 0 1 N N N -5.361  20.012 -14.332 1.636  2.930  -1.512 HN8  GS2 64 
GS2 H25  H25  H 0 1 N N N -7.534  21.214 -13.635 -0.069 4.827  -1.573 H25  GS2 65 
GS2 H26  H26  H 0 1 N N N -8.324  22.603 -15.753 -2.353 3.851  -0.782 H26  GS2 66 
# 
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 
GS2 C1  N1   SING N N 1  
GS2 N1  C2   SING N N 2  
GS2 C2  O1   DOUB N N 3  
GS2 C2  C3   SING N N 4  
GS2 C3  C4   DOUB N N 5  
GS2 C3  C8   SING N N 6  
GS2 C4  F1   SING N N 7  
GS2 C4  C5   SING N N 8  
GS2 C5  C6   DOUB Y N 9  
GS2 C6  C7   SING Y N 10 
GS2 C7  C8   DOUB N N 11 
GS2 C8  N2   SING Y N 12 
GS2 N2  C9   SING Y N 13 
GS2 C9  N3   DOUB N N 14 
GS2 C9  C27  SING Y N 15 
GS2 N3  C10  SING N N 16 
GS2 C10 N4   SING Y N 17 
GS2 C10 N7   DOUB N N 18 
GS2 N4  C11  SING N N 19 
GS2 C11 C12  DOUB N N 20 
GS2 C11 C18  SING N N 21 
GS2 C12 C13  SING Y N 22 
GS2 C13 N5   SING Y N 23 
GS2 C13 C16  DOUB Y N 24 
GS2 N5  C14  SING N N 25 
GS2 N5  C20  SING Y N 26 
GS2 C14 C15  DOUB N N 27 
GS2 C15 C16  SING N N 28 
GS2 C16 C17  SING Y N 29 
GS2 C17 C18  DOUB Y N 30 
GS2 C18 O2   SING Y N 31 
GS2 O2  C19  SING N N 32 
GS2 C20 O3   DOUB Y N 33 
GS2 C20 C21  SING Y N 34 
GS2 C21 N6   SING Y N 35 
GS2 N6  C22  SING N N 36 
GS2 N6  C23  SING Y N 37 
GS2 N7  C24  SING N N 38 
GS2 C24 N8   SING Y N 39 
GS2 C24 C27  DOUB N N 40 
GS2 N8  C25  SING Y N 41 
GS2 C25 C26  DOUB Y N 42 
GS2 C26 C27  SING N N 43 
GS2 C1  H1   SING N N 44 
GS2 C1  H1A  SING N N 45 
GS2 C1  H1B  SING N N 46 
GS2 N1  HN1  SING N N 47 
GS2 C5  H5   SING N N 48 
GS2 C6  H6   SING N N 49 
GS2 C7  H7   SING N N 50 
GS2 N2  HN2  SING N N 51 
GS2 N4  HN4  SING N N 52 
GS2 C12 H12  SING N N 53 
GS2 C14 H14  SING N N 54 
GS2 C15 H15  SING N N 55 
GS2 C17 H17  SING N N 56 
GS2 C19 H19  SING N N 57 
GS2 C19 H19A SING N N 58 
GS2 C19 H19B SING N N 59 
GS2 C21 H21  SING N N 60 
GS2 C21 H21A SING N N 61 
GS2 C22 H22  SING Y N 62 
GS2 C22 H22A SING Y N 63 
GS2 C22 H22B SING Y N 64 
GS2 C23 H23  SING Y N 65 
GS2 C23 H23A SING N N 66 
GS2 C23 H23B SING Y N 67 
GS2 N8  HN8  SING N N 68 
GS2 C25 H25  SING Y N 69 
GS2 C26 H26  SING N N 70 
# 
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 
GS2 SMILES           ACDLabs              10.04 O=C(n2c1cc(c(OC)cc1cc2)Nc3nc5c(c(n3)Nc4cccc(F)c4C(=O)NC)ccn5)CN(C)C                                                                                                                                      
GS2 InChI            InChI                1.02b InChI=1/C27H27FN8O3/c1-29-26(38)23-17(28)6-5-7-18(23)31-25-16-8-10-30-24(16)33-27(34-25)32-19-13-20-15(12-21(19)39-4)9-11-36(20)22(37)14-35(2)3/h5-13H,14H2,1-4H3,(H,29,38)(H3,30,31,32,33,34)/f/h29-32H 
GS2 InChIKey         InChI                1.02b DESOLSKAHZZIGK-MMUUCWGACQ                                                                                                                                                                                
GS2 SMILES_CANONICAL CACTVS               3.341 CNC(=O)c1c(F)cccc1Nc2nc(Nc3cc4n(ccc4cc3OC)C(=O)CN(C)C)nc5[nH]ccc25                                                                                                                                       
GS2 SMILES           CACTVS               3.341 CNC(=O)c1c(F)cccc1Nc2nc(Nc3cc4n(ccc4cc3OC)C(=O)CN(C)C)nc5[nH]ccc25                                                                                                                                       
GS2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CNC(=O)c1c(cccc1F)Nc2c3cc[nH]c3nc(n2)Nc4cc5c(ccn5C(=O)CN(C)C)cc4OC                                                                                                                                       
GS2 SMILES           "OpenEye OEToolkits" 1.5.0 CNC(=O)c1c(cccc1F)Nc2c3cc[nH]c3nc(n2)Nc4cc5c(ccn5C(=O)CN(C)C)cc4OC                                                                                                                                       
# 
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 
GS2 "SYSTEMATIC NAME" ACDLabs              10.04 2-[(2-{[1-(N,N-dimethylglycyl)-5-methoxy-1H-indol-6-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide    
GS2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[[2-[[1-(2-dimethylaminoethanoyl)-5-methoxy-indol-6-yl]amino]-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amino]-6-fluoro-N-methyl-benzamide 
# 
