data_4IG
# 
_chem_comp.id                                    4IG 
_chem_comp.name                                  (2S)-6-(2,4-DIAMINO-6-ETHYLPYRIMIDIN-5-YL)-2-(3,5-DIFLUOROPHENYL)-4-(3-METHOXYPROPYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H25 F2 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-21 
_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                        469.484 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4IG 
_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        2G1S 
_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 
4IG C1   C1   C 0 1 Y N N 78.834 24.884 71.457 -3.968 -0.077 -0.946 C1   4IG 1  
4IG N1   N1   N 0 1 Y N N 78.234 25.895 72.134 -5.177 -0.077 -0.399 N1   4IG 2  
4IG C2   C2   C 0 1 Y N N 78.536 26.004 73.432 -5.445 0.684  0.653  C2   4IG 3  
4IG N2   N2   N 0 1 Y N N 79.364 25.178 74.092 -4.529 1.470  1.200  N2   4IG 4  
4IG C3   C3   C 0 1 Y N N 79.978 24.160 73.438 -3.300 1.527  0.714  C3   4IG 5  
4IG C4   C4   C 0 1 Y N N 79.766 23.980 72.039 -2.972 0.750  -0.394 C4   4IG 6  
4IG N3   N3   N 0 1 N N N 78.504 24.784 70.157 -3.692 -0.873 -2.044 N3   4IG 7  
4IG N4   N4   N 0 1 N N N 77.999 26.998 74.130 -6.718 0.656  1.194  N4   4IG 8  
4IG C5   C5   C 0 1 N N N 80.889 23.267 74.269 -2.270 2.426  1.348  C5   4IG 9  
4IG C6   C6   C 0 1 N N N 82.247 23.907 74.560 -1.524 1.657  2.440  C6   4IG 10 
4IG C7   C7   C 0 1 Y N N 80.230 21.688 70.988 -1.124 1.953  -1.559 C7   4IG 11 
4IG C8   C8   C 0 1 Y N N 81.068 20.870 70.172 0.144  1.987  -2.100 C8   4IG 12 
4IG C9   C9   C 0 1 Y N N 82.235 21.411 69.580 0.953  0.858  -2.061 C9   4IG 13 
4IG C10  C10  C 0 1 Y N N 82.581 22.805 69.810 0.474  -0.308 -1.466 C10  4IG 14 
4IG C11  C11  C 0 1 Y N N 81.721 23.561 70.623 -0.795 -0.349 -0.921 C11  4IG 15 
4IG C12  C12  C 0 1 Y N N 80.560 23.041 71.215 -1.606 0.785  -0.971 C12  4IG 16 
4IG O3   O3   O 0 1 N N N 83.062 20.580 68.756 2.192  0.902  -2.608 O3   4IG 17 
4IG C14  C14  C 0 1 N N S 83.683 21.436 67.777 3.102  0.194  -1.777 C14  4IG 18 
4IG C15  C15  C 0 1 N N N 84.563 22.556 68.365 2.635  -1.225 -1.573 C15  4IG 19 
4IG N5   N5   N 0 1 N N N 83.760 23.345 69.198 1.304  -1.442 -1.419 N5   4IG 20 
4IG C16  C16  C 0 1 N N N 84.189 24.766 69.375 0.761  -2.787 -1.217 C16  4IG 21 
4IG C17  C17  C 0 1 N N N 85.072 25.004 70.600 0.710  -3.096 0.281  C17  4IG 22 
4IG C18  C18  C 0 1 N N N 84.993 26.460 71.073 0.143  -4.501 0.493  C18  4IG 23 
4IG O1   O1   O 0 1 N N N 86.093 26.708 71.921 0.096  -4.790 1.892  O1   4IG 24 
4IG C19  C19  C 0 1 N N N 86.167 28.009 72.451 -0.440 -6.108 2.024  C19  4IG 25 
4IG O4   O4   O 0 1 N N N 85.725 22.732 68.063 3.425  -2.145 -1.546 O4   4IG 26 
4IG C20  C20  C 0 1 Y N N 83.919 21.136 63.960 3.783  0.833  1.883  C20  4IG 27 
4IG C21  C21  C 0 1 Y N N 84.329 21.023 65.308 3.698  0.202  0.654  C21  4IG 28 
4IG C22  C22  C 0 1 Y N N 83.381 21.305 66.322 3.193  0.882  -0.439 C22  4IG 29 
4IG C23  C23  C 0 1 Y N N 82.062 21.659 65.965 2.777  2.193  -0.307 C23  4IG 30 
4IG C24  C24  C 0 1 Y N N 81.688 21.763 64.627 2.856  2.824  0.923  C24  4IG 31 
4IG C25  C25  C 0 1 Y N N 82.599 21.508 63.591 3.361  2.145  2.018  C25  4IG 32 
4IG F2   F2   F 0 1 N N N 84.799 20.891 62.989 4.276  0.169  2.951  F2   4IG 33 
4IG F1   F1   F 0 1 N N N 80.427 22.118 64.377 2.445  4.105  1.053  F1   4IG 34 
4IG HN31 1HN3 H 0 0 N N N 77.508 24.759 70.066 -4.386 -1.436 -2.421 HN31 4IG 35 
4IG HN32 2HN3 H 0 0 N N N 78.864 25.574 69.660 -2.806 -0.866 -2.438 HN32 4IG 36 
4IG HN41 1HN4 H 0 0 N N N 77.864 26.706 75.077 -6.929 1.208  1.964  HN41 4IG 37 
4IG HN42 2HN4 H 0 0 N N N 78.611 27.789 74.109 -7.399 0.086  0.805  HN42 4IG 38 
4IG H51  1H5  H 0 1 N N N 80.391 23.061 75.228 -2.764 3.292  1.787  H51  4IG 39 
4IG H52  2H5  H 0 1 N N N 81.072 22.350 73.690 -1.561 2.758  0.589  H52  4IG 40 
4IG H61  1H6  H 0 1 N N N 82.790 24.061 73.616 -0.779 2.307  2.899  H61  4IG 41 
4IG H62  2H6  H 0 1 N N N 82.096 24.876 75.058 -2.233 1.324  3.199  H62  4IG 42 
4IG H63  3H6  H 0 1 N N N 82.831 23.244 75.215 -1.029 0.790  2.001  H63  4IG 43 
4IG H7   H7   H 0 1 N N N 79.340 21.270 71.434 -1.746 2.835  -1.593 H7   4IG 44 
4IG H8   H8   H 0 1 N N N 80.811 19.834 70.005 0.511  2.895  -2.557 H8   4IG 45 
4IG H11  H11  H 0 1 N N N 81.966 24.597 70.802 -1.160 -1.256 -0.462 H11  4IG 46 
4IG H14  H14  H 0 1 N N N 84.279 21.005 66.959 4.086  0.186  -2.245 H14  4IG 47 
4IG H161 1H16 H 0 0 N N N 84.760 25.061 68.483 -0.245 -2.839 -1.633 H161 4IG 48 
4IG H162 2H16 H 0 0 N N N 83.275 25.360 69.520 1.399  -3.516 -1.717 H162 4IG 49 
4IG H171 1H17 H 0 0 N N N 84.733 24.347 71.415 1.716  -3.044 0.697  H171 4IG 50 
4IG H172 2H17 H 0 0 N N N 86.114 24.785 70.324 0.072  -2.368 0.781  H172 4IG 51 
4IG H181 1H18 H 0 0 N N N 85.028 27.137 70.207 -0.863 -4.553 0.077  H181 4IG 52 
4IG H182 2H18 H 0 0 N N N 84.051 26.633 71.613 0.781  -5.230 -0.007 H182 4IG 53 
4IG H191 1H19 H 0 0 N N N 86.186 27.957 73.550 0.205  -6.816 1.504  H191 4IG 54 
4IG H192 2H19 H 0 0 N N N 87.083 28.500 72.091 -0.496 -6.374 3.079  H192 4IG 55 
4IG H193 3H19 H 0 0 N N N 85.289 28.587 72.127 -1.439 -6.140 1.588  H193 4IG 56 
4IG H21  H21  H 0 1 N N N 85.338 20.730 65.558 4.026  -0.821 0.548  H21  4IG 57 
4IG H23  H23  H 0 1 N N N 81.334 21.852 66.739 2.383  2.723  -1.162 H23  4IG 58 
4IG H25  H25  H 0 1 N N N 82.308 21.591 62.554 3.427  2.638  2.977  H25  4IG 59 
# 
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 
4IG C1  N1   SING Y N 1  
4IG C1  C4   DOUB Y N 2  
4IG C1  N3   SING N N 3  
4IG N1  C2   DOUB Y N 4  
4IG C2  N2   SING Y N 5  
4IG C2  N4   SING N N 6  
4IG N2  C3   DOUB Y N 7  
4IG C3  C4   SING Y N 8  
4IG C3  C5   SING N N 9  
4IG C4  C12  SING N N 10 
4IG N3  HN31 SING N N 11 
4IG N3  HN32 SING N N 12 
4IG N4  HN41 SING N N 13 
4IG N4  HN42 SING N N 14 
4IG C5  C6   SING N N 15 
4IG C5  H51  SING N N 16 
4IG C5  H52  SING N N 17 
4IG C6  H61  SING N N 18 
4IG C6  H62  SING N N 19 
4IG C6  H63  SING N N 20 
4IG C7  C8   DOUB Y N 21 
4IG C7  C12  SING Y N 22 
4IG C7  H7   SING N N 23 
4IG C8  C9   SING Y N 24 
4IG C8  H8   SING N N 25 
4IG C9  C10  DOUB Y N 26 
4IG C9  O3   SING N N 27 
4IG C10 C11  SING Y N 28 
4IG C10 N5   SING N N 29 
4IG C11 C12  DOUB Y N 30 
4IG C11 H11  SING N N 31 
4IG O3  C14  SING N N 32 
4IG C14 C15  SING N N 33 
4IG C14 C22  SING N N 34 
4IG C14 H14  SING N N 35 
4IG C15 N5   SING N N 36 
4IG C15 O4   DOUB N N 37 
4IG N5  C16  SING N N 38 
4IG C16 C17  SING N N 39 
4IG C16 H161 SING N N 40 
4IG C16 H162 SING N N 41 
4IG C17 C18  SING N N 42 
4IG C17 H171 SING N N 43 
4IG C17 H172 SING N N 44 
4IG C18 O1   SING N N 45 
4IG C18 H181 SING N N 46 
4IG C18 H182 SING N N 47 
4IG O1  C19  SING N N 48 
4IG C19 H191 SING N N 49 
4IG C19 H192 SING N N 50 
4IG C19 H193 SING N N 51 
4IG C20 C21  DOUB Y N 52 
4IG C20 C25  SING Y N 53 
4IG C20 F2   SING N N 54 
4IG C21 C22  SING Y N 55 
4IG C21 H21  SING N N 56 
4IG C22 C23  DOUB Y N 57 
4IG C23 C24  SING Y N 58 
4IG C23 H23  SING N N 59 
4IG C24 C25  DOUB Y N 60 
4IG C24 F1   SING N N 61 
4IG C25 H25  SING N N 62 
# 
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 
4IG SMILES           ACDLabs              10.04 Fc1cc(cc(F)c1)C4Oc3ccc(c2c(nc(nc2N)N)CC)cc3N(C4=O)CCCOC                                                                                                                                             
4IG InChI            InChI                1.02b InChI=1/C24H25F2N5O3/c1-3-17-20(22(27)30-24(28)29-17)13-5-6-19-18(11-13)31(7-4-8-33-2)23(32)21(34-19)14-9-15(25)12-16(26)10-14/h5-6,9-12,21H,3-4,7-8H2,1-2H3,(H4,27,28,29,30)/t21-/m0/s1/f/h27-28H2 
4IG InChIKey         InChI                1.02b KHZQOXQOUCGGGA-QQURLOOJDM                                                                                                                                                                           
4IG SMILES_CANONICAL CACTVS               3.341 CCc1nc(N)nc(N)c1c2ccc3O[C@H](C(=O)N(CCCOC)c3c2)c4cc(F)cc(F)c4                                                                                                                                       
4IG SMILES           CACTVS               3.341 CCc1nc(N)nc(N)c1c2ccc3O[CH](C(=O)N(CCCOC)c3c2)c4cc(F)cc(F)c4                                                                                                                                        
4IG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)c2ccc3c(c2)N(C(=O)C(O3)c4cc(cc(c4)F)F)CCCOC                                                                                                                                       
4IG SMILES           "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)c2ccc3c(c2)N(C(=O)C(O3)c4cc(cc(c4)F)F)CCCOC                                                                                                                                       
# 
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 
4IG "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-6-(2,4-diamino-6-ethylpyrimidin-5-yl)-2-(3,5-difluorophenyl)-4-(3-methoxypropyl)-2H-1,4-benzoxazin-3(4H)-one 
4IG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-(3,5-difluorophenyl)-4-(3-methoxypropyl)-1,4-benzoxazin-3-one            
# 
