data_UA4
# 
_chem_comp.id                                    UA4 
_chem_comp.name                                  (2S)-6-(2,4-DIAMINO-6-ETHYLPYRIMIDIN-5-YL)-2-(3,5-DIFLUOROPHENYL)-4-(3-METHOXYPROPYL)-2-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H27 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                     2006-08-23 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        483.510 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     UA4 
_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        ? 
_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 
UA4 C5   C5   C 0 1 Y N N -21.661 71.761 123.495 1.405  3.423  -3.043  C5   UA4 1  
UA4 C10  C10  C 0 1 N N N -19.852 75.665 122.449 -2.250 1.225  -4.146  C10  UA4 2  
UA4 C13  C13  C 0 1 Y N N -19.914 76.216 127.596 -0.564 -2.022 -0.476  C13  UA4 3  
UA4 C15  C15  C 0 1 Y N N -17.883 75.602 126.721 -0.443 -2.652 -2.822  C15  UA4 4  
UA4 C22  C22  C 0 1 N N N -15.741 74.828 125.754 -0.038 -3.444 -5.147  C22  UA4 5  
UA4 C24  C24  C 0 1 N N N -15.404 74.392 123.317 -0.538 -2.587 -7.483  C24  UA4 6  
UA4 C26  C26  C 0 1 N N N -14.468 74.015 121.173 -1.132 -1.766 -9.603  C26  UA4 7  
UA4 C28  C28  C 0 1 Y N N -17.034 75.632 130.371 -4.018 -4.606 -3.408  C28  UA4 8  
UA4 F34  F34  F 0 1 N N N -13.525 76.188 132.326 -5.793 -2.743 -0.179  F34  UA4 9  
UA4 C31  C31  C 0 1 Y N N -14.657 76.029 131.671 -5.217 -3.349 -1.226  C31  UA4 10 
UA4 C32  C32  C 0 1 Y N N -14.925 76.719 130.552 -3.902 -3.805 -1.132  C32  UA4 11 
UA4 C30  C30  C 0 1 Y N N -15.678 75.080 132.136 -5.932 -3.521 -2.411  C30  UA4 12 
UA4 C29  C29  C 0 1 Y N N -16.814 74.960 131.430 -5.333 -4.150 -3.502  C29  UA4 13 
UA4 F33  F33  F 0 1 N N N -17.716 74.109 131.863 -6.019 -4.316 -4.640  F33  UA4 14 
UA4 C27  C27  C 0 1 Y N N -16.223 76.482 129.884 -3.311 -4.431 -2.224  C27  UA4 15 
UA4 C18  C18  C 0 1 N N S -16.562 77.229 128.608 -1.860 -4.932 -2.121  C18  UA4 16 
UA4 C35  C35  C 0 1 N N N -16.060 78.677 128.658 -1.904 -6.389 -1.621  C35  UA4 17 
UA4 C19  C19  C 0 1 N N N -15.860 76.485 127.493 -1.114 -4.908 -3.471  C19  UA4 18 
UA4 O21  O21  O 0 1 N N N -14.642 76.575 127.424 -1.099 -5.893 -4.212  O21  UA4 19 
UA4 N20  N20  N 0 1 N N N -16.533 75.702 126.633 -0.558 -3.672 -3.804  N20  UA4 20 
UA4 C23  C23  C 0 1 N N N -15.735 75.453 124.360 -1.068 -2.810 -6.072  C23  UA4 21 
UA4 O25  O25  O 0 1 N N N -14.823 74.983 122.159 -1.558 -1.979 -8.264  O25  UA4 22 
UA4 C16  C16  C 0 1 Y N N -18.542 74.756 125.934 0.006  -1.357 -3.121  C16  UA4 23 
UA4 C14  C14  C 0 1 Y N N -18.638 76.332 127.555 -0.734 -2.964 -1.493  C14  UA4 24 
UA4 O17  O17  O 0 1 N N N -17.980 77.272 128.424 -1.146 -4.211 -1.111  O17  UA4 25 
UA4 C12  C12  C 0 1 Y N N -20.563 75.462 126.910 -0.125 -0.738 -0.786  C12  UA4 26 
UA4 C11  C11  C 0 1 Y N N -19.997 74.712 126.061 0.156  -0.405 -2.108  C11  UA4 27 
UA4 C2   C2   C 0 1 Y N N -20.627 73.708 125.144 0.600  0.933  -2.435  C2   UA4 28 
UA4 C1   C1   C 0 1 Y N N -21.085 74.034 123.877 -0.291 1.938  -2.753  C1   UA4 29 
UA4 C9   C9   C 0 1 N N N -21.057 75.449 123.339 -1.764 1.682  -2.775  C9   UA4 30 
UA4 C3   C3   C 0 1 Y N N -20.690 72.280 125.565 1.933  1.293  -2.451  C3   UA4 31 
UA4 N7   N7   N 0 1 N N N -20.247 71.862 126.780 2.908  0.313  -2.134  N7   UA4 32 
UA4 N4   N4   N 0 1 Y N N -21.219 71.378 124.710 2.372  2.533  -2.751  N4   UA4 33 
UA4 N6   N6   N 0 1 Y N N -21.603 73.056 123.098 0.078  3.199  -3.062  N6   UA4 34 
UA4 N8   N8   N 0 1 N N N -22.189 70.826 122.670 1.829  4.731  -3.362  N8   UA4 35 
UA4 H101 1H10 H 0 0 N N N -20.176 75.717 121.399 -2.043 1.983  -4.910  H101 UA4 36 
UA4 H102 2H10 H 0 0 N N N -19.355 76.606 122.727 -3.329 1.044  -4.132  H102 UA4 37 
UA4 H103 3H10 H 0 0 N N N -19.149 74.828 122.574 -1.754 0.297  -4.451  H103 UA4 38 
UA4 H13  H13  H 0 1 N N N -20.450 76.839 128.297 -0.778 -2.282 0.558   H13  UA4 39 
UA4 H221 1H22 H 0 0 N N N -16.190 73.825 125.716 0.271  -4.418 -5.539  H221 UA4 40 
UA4 H222 2H22 H 0 0 N N N -14.714 74.729 126.135 0.853  -2.813 -5.058  H222 UA4 41 
UA4 H241 1H24 H 0 0 N N N -16.330 73.873 123.028 0.334  -1.924 -7.479  H241 UA4 42 
UA4 H242 2H24 H 0 0 N N N -14.683 73.684 123.751 -0.262 -3.537 -7.950  H242 UA4 43 
UA4 H261 1H26 H 0 0 N N N -14.377 74.506 120.193 -1.444 -0.772 -9.932  H261 UA4 44 
UA4 H262 2H26 H 0 0 N N N -13.507 73.553 121.442 -1.570 -2.530 -10.251 H262 UA4 45 
UA4 H263 3H26 H 0 0 N N N -15.247 73.240 121.123 -0.043 -1.836 -9.645  H263 UA4 46 
UA4 H28  H28  H 0 1 N N N -17.968 75.470 129.854 -3.559 -5.095 -4.264  H28  UA4 47 
UA4 H32  H32  H 0 1 N N N -14.214 77.426 130.151 -3.353 -3.665 -0.205  H32  UA4 48 
UA4 H30  H30  H 0 1 N N N -15.518 74.491 133.027 -6.956 -3.166 -2.484  H30  UA4 49 
UA4 H351 1H35 H 0 0 N N N -15.940 78.988 129.706 -2.927 -6.674 -1.357  H351 UA4 50 
UA4 H352 2H35 H 0 0 N N N -15.091 78.747 128.142 -1.545 -7.073 -2.395  H352 UA4 51 
UA4 H353 3H35 H 0 0 N N N -16.789 79.335 128.162 -1.274 -6.511 -0.735  H353 UA4 52 
UA4 H231 1H23 H 0 0 N N N -14.978 76.250 124.322 -1.954 -3.455 -6.123  H231 UA4 53 
UA4 H232 2H23 H 0 0 N N N -16.729 75.873 124.147 -1.417 -1.854 -5.659  H232 UA4 54 
UA4 H16  H16  H 0 1 N N N -18.022 74.126 125.228 0.249  -1.064 -4.138  H16  UA4 55 
UA4 H12  H12  H 0 1 N N N -21.637 75.427 127.022 0.001  0.002  -0.002  H12  UA4 56 
UA4 H91  1H9  H 0 1 N N N -21.009 76.152 124.184 -2.029 0.921  -2.025  H91  UA4 57 
UA4 H92  2H9  H 0 1 N N N -21.968 75.618 122.746 -2.313 2.589  -2.479  H92  UA4 58 
UA4 HN71 1HN7 H 0 0 N N N -19.253 71.759 126.756 3.805  0.372  -2.563  HN71 UA4 59 
UA4 HN72 2HN7 H 0 0 N N N -20.495 72.536 127.475 2.643  -0.461 -1.566  HN72 UA4 60 
UA4 HN81 1HN8 H 0 0 N N N -22.319 71.219 121.760 1.981  4.973  -4.320  HN81 UA4 61 
UA4 HN82 2HN8 H 0 0 N N N -21.567 70.045 122.610 2.059  5.362  -2.622  HN82 UA4 62 
# 
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 
UA4 C5  N8   SING N N 1  
UA4 C5  N6   DOUB Y N 2  
UA4 C5  N4   SING Y N 3  
UA4 C10 C9   SING N N 4  
UA4 C10 H101 SING N N 5  
UA4 C10 H102 SING N N 6  
UA4 C10 H103 SING N N 7  
UA4 C13 C12  DOUB Y N 8  
UA4 C13 C14  SING Y N 9  
UA4 C13 H13  SING N N 10 
UA4 C15 C16  SING Y N 11 
UA4 C15 N20  SING N N 12 
UA4 C15 C14  DOUB Y N 13 
UA4 C22 C23  SING N N 14 
UA4 C22 N20  SING N N 15 
UA4 C22 H221 SING N N 16 
UA4 C22 H222 SING N N 17 
UA4 C24 O25  SING N N 18 
UA4 C24 C23  SING N N 19 
UA4 C24 H241 SING N N 20 
UA4 C24 H242 SING N N 21 
UA4 C26 O25  SING N N 22 
UA4 C26 H261 SING N N 23 
UA4 C26 H262 SING N N 24 
UA4 C26 H263 SING N N 25 
UA4 C28 C27  DOUB Y N 26 
UA4 C28 C29  SING Y N 27 
UA4 C28 H28  SING N N 28 
UA4 F34 C31  SING N N 29 
UA4 C31 C32  DOUB Y N 30 
UA4 C31 C30  SING Y N 31 
UA4 C32 C27  SING Y N 32 
UA4 C32 H32  SING N N 33 
UA4 C30 C29  DOUB Y N 34 
UA4 C30 H30  SING N N 35 
UA4 C29 F33  SING N N 36 
UA4 C27 C18  SING N N 37 
UA4 C18 C19  SING N N 38 
UA4 C18 O17  SING N N 39 
UA4 C18 C35  SING N N 40 
UA4 C35 H351 SING N N 41 
UA4 C35 H352 SING N N 42 
UA4 C35 H353 SING N N 43 
UA4 C19 N20  SING N N 44 
UA4 C19 O21  DOUB N N 45 
UA4 C23 H231 SING N N 46 
UA4 C23 H232 SING N N 47 
UA4 C16 C11  DOUB Y N 48 
UA4 C16 H16  SING N N 49 
UA4 C14 O17  SING N N 50 
UA4 C12 C11  SING Y N 51 
UA4 C12 H12  SING N N 52 
UA4 C11 C2   SING N N 53 
UA4 C2  C1   DOUB Y N 54 
UA4 C2  C3   SING Y N 55 
UA4 C1  N6   SING Y N 56 
UA4 C1  C9   SING N N 57 
UA4 C9  H91  SING N N 58 
UA4 C9  H92  SING N N 59 
UA4 C3  N4   DOUB Y N 60 
UA4 C3  N7   SING N N 61 
UA4 N7  HN71 SING N N 62 
UA4 N7  HN72 SING N N 63 
UA4 N8  HN81 SING N N 64 
UA4 N8  HN82 SING N N 65 
# 
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 
UA4 SMILES           ACDLabs              10.04 Fc1cc(cc(F)c1)C4(Oc3ccc(c2c(nc(nc2N)N)CC)cc3N(C4=O)CCCOC)C                                                                                                                                           
UA4 InChI            InChI                1.02b InChI=1/C25H27F2N5O3/c1-4-18-21(22(28)31-24(29)30-18)14-6-7-20-19(10-14)32(8-5-9-34-3)23(33)25(2,35-20)15-11-16(26)13-17(27)12-15/h6-7,10-13H,4-5,8-9H2,1-3H3,(H4,28,29,30,31)/t25-/m0/s1/f/h28-29H2 
UA4 InChIKey         InChI                1.02b UAXNNGUDPWZOKX-QFLHBRKQDW                                                                                                                                                                            
UA4 SMILES_CANONICAL CACTVS               3.341 CCc1nc(N)nc(N)c1c2ccc3O[C@](C)(C(=O)N(CCCOC)c3c2)c4cc(F)cc(F)c4                                                                                                                                      
UA4 SMILES           CACTVS               3.341 CCc1nc(N)nc(N)c1c2ccc3O[C](C)(C(=O)N(CCCOC)c3c2)c4cc(F)cc(F)c4                                                                                                                                       
UA4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)c2ccc3c(c2)N(C(=O)[C@](O3)(C)c4cc(cc(c4)F)F)CCCOC                                                                                                                                  
UA4 SMILES           "OpenEye OEToolkits" 1.5.0 CCc1c(c(nc(n1)N)N)c2ccc3c(c2)N(C(=O)C(O3)(C)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 
UA4 "SYSTEMATIC NAME" ACDLabs              10.04 (2S)-6-(2,4-diamino-6-ethylpyrimidin-5-yl)-2-(3,5-difluorophenyl)-4-(3-methoxypropyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one 
UA4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-6-(2,4-diamino-6-ethyl-pyrimidin-5-yl)-2-(3,5-difluorophenyl)-4-(3-methoxypropyl)-2-methyl-1,4-benzoxazin-3-one       
# 
