data_MKR
# 
_chem_comp.id                                    MKR 
_chem_comp.name                                  1-{(3R,3AR)-3-[3-(4-ACETYLPIPERAZIN-1-YL)PROPYL]-8-FLUORO-3-PHENYL-3A,4-DIHYDRO-3H-PYRAZOLO[5,1-C][1,4]BENZOXAZIN-2-YL}ETHANONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H31 F N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-05-31 
_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                        478.558 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MKR 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "Corina V3.40" 
_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 
MKR C1   C1   C 0 1 Y N N 36.656 16.838 53.495 2.800  4.436  0.714  C1   MKR 1  
MKR C2   C2   C 0 1 Y N N 37.893 17.043 52.825 2.287  3.187  1.026  C2   MKR 2  
MKR C3   C3   C 0 1 Y N N 38.378 15.891 52.133 2.262  2.198  0.062  C3   MKR 3  
MKR C4   C4   C 0 1 Y N N 37.609 14.713 52.122 2.747  2.442  -1.227 C4   MKR 4  
MKR C5   C5   C 0 1 Y N N 36.379 14.516 52.800 3.262  3.695  -1.525 C5   MKR 5  
MKR C6   C6   C 0 1 Y N N 35.903 15.621 53.516 3.286  4.683  -0.559 C6   MKR 6  
MKR N2   N2   N 0 1 N N N 39.578 15.862 51.369 1.764  0.918  0.328  N2   MKR 7  
MKR N12  N12  N 0 1 N N N 40.054 16.859 50.807 1.623  0.310  1.433  N12  MKR 8  
MKR C8   C8   C 0 1 N N N 40.935 16.663 49.842 1.430  -0.977 1.354  C8   MKR 9  
MKR C14  C14  C 0 1 N N R 41.135 15.030 49.749 1.343  -1.354 -0.115 C14  MKR 10 
MKR C15  C15  C 0 1 N N R 40.134 14.683 50.877 1.388  0.024  -0.797 C15  MKR 11 
MKR C18  C18  C 0 1 Y N N 40.874 14.457 48.278 2.523  -2.197 -0.526 C18  MKR 12 
MKR C20  C20  C 0 1 N N N 41.649 17.764 49.051 1.322  -1.864 2.442  C20  MKR 13 
MKR C9   C9   C 0 1 N N N 41.299 19.288 49.176 1.545  -1.365 3.846  C9   MKR 14 
MKR O25  O25  O 0 1 N N N 42.627 17.357 48.431 1.048  -3.032 2.248  O25  MKR 15 
MKR C26  C26  C 0 1 Y N N 39.807 15.101 47.520 3.569  -2.398 0.355  C26  MKR 16 
MKR C27  C27  C 0 1 Y N N 39.385 14.713 46.157 4.651  -3.171 -0.022 C27  MKR 17 
MKR C28  C28  C 0 1 Y N N 40.173 13.635 45.601 4.686  -3.745 -1.280 C28  MKR 18 
MKR C29  C29  C 0 1 Y N N 41.266 13.041 46.323 3.639  -3.545 -2.160 C29  MKR 19 
MKR C30  C30  C 0 1 Y N N 41.584 13.468 47.649 2.555  -2.774 -1.781 C30  MKR 20 
MKR O1   O1   O 0 1 N N N 38.041 13.653 51.381 2.713  1.479  -2.182 O1   MKR 21 
MKR F1   F1   F 0 1 N N N 36.089 17.799 54.164 2.820  5.412  1.647  F1   MKR 22 
MKR C7   C7   C 0 1 N N N 38.855 14.069 50.331 2.540  0.110  -1.804 C7   MKR 23 
MKR C10  C10  C 0 1 N N N 42.543 14.639 50.317 0.027  -2.073 -0.419 C10  MKR 24 
MKR C11  C11  C 0 1 N N N 42.981 15.381 51.570 -1.146 -1.207 0.044  C11  MKR 25 
MKR C12  C12  C 0 1 N N N 44.482 15.562 51.893 -2.463 -1.905 -0.301 C12  MKR 26 
MKR N3   N3   N 0 1 N N N 44.695 15.493 53.386 -3.589 -1.074 0.143  N3   MKR 27 
MKR C16  C16  C 0 1 N N N 44.782 16.892 53.929 -4.857 -1.809 0.046  C16  MKR 28 
MKR C17  C17  C 0 1 N N N 45.534 14.515 54.086 -3.644 0.185  -0.613 C17  MKR 29 
MKR C19  C19  C 0 1 N N N 46.074 17.445 53.269 -5.976 -0.979 0.684  C19  MKR 30 
MKR C21  C21  C 0 1 N N N 46.989 14.987 53.744 -4.713 1.097  -0.002 C21  MKR 31 
MKR N1   N1   N 0 1 N N N 47.193 16.513 53.824 -5.981 0.354  0.062  N1   MKR 32 
MKR C22  C22  C 0 1 N N N 48.337 17.099 54.396 -7.117 0.880  -0.436 C22  MKR 33 
MKR C24  C24  C 0 1 N N N 49.133 16.001 55.187 -7.080 2.195  -1.172 C24  MKR 34 
MKR O2   O2   O 0 1 N N N 48.596 18.319 54.308 -8.170 0.296  -0.292 O2   MKR 35 
MKR H2   H2   H 0 1 N N N 38.419 17.986 52.838 1.908  2.989  2.018  H2   MKR 36 
MKR H5   H5   H 0 1 N N N 35.846 13.577 52.766 3.645  3.899  -2.514 H5   MKR 37 
MKR H6   H6   H 0 1 N N N 34.982 15.556 54.076 3.688  5.657  -0.799 H6   MKR 38 
MKR H15  H15  H 0 1 N N N 40.699 14.049 51.576 0.428  0.295  -1.238 H15  MKR 39 
MKR H91  1H9  H 0 1 N N N 41.217 19.560 50.239 1.778  -0.300 3.820  H91  MKR 40 
MKR H92  2H9  H 0 1 N N N 42.093 19.886 48.705 0.643  -1.525 4.436  H92  MKR 41 
MKR H93  3H9  H 0 1 N N N 40.342 19.487 48.672 2.376  -1.908 4.297  H93  MKR 42 
MKR H26  H26  H 0 1 N N N 39.286 15.923 47.989 3.541  -1.950 1.337  H26  MKR 43 
MKR H27  H27  H 0 1 N N N 38.570 15.187 45.630 5.469  -3.328 0.666  H27  MKR 44 
MKR H28  H28  H 0 1 N N N 39.934 13.265 44.615 5.532  -4.348 -1.574 H28  MKR 45 
MKR H29  H29  H 0 1 N N N 41.853 12.263 45.858 3.667  -3.992 -3.142 H29  MKR 46 
MKR H30  H30  H 0 1 N N N 42.406 12.999 48.169 1.736  -2.621 -2.468 H30  MKR 47 
MKR H71  1H7  H 0 1 N N N 38.319 14.819 49.731 3.456  -0.261 -1.343 H71  MKR 48 
MKR H72  2H7  H 0 1 N N N 39.109 13.201 49.705 2.302  -0.486 -2.684 H72  MKR 49 
MKR H101 1H10 H 0 0 N N N 42.513 13.567 50.563 -0.052 -2.249 -1.492 H101 MKR 50 
MKR H102 2H10 H 0 0 N N N 43.269 14.909 49.536 0.005  -3.027 0.108  H102 MKR 51 
MKR H111 1H11 H 0 0 N N N 42.567 16.396 51.480 -1.085 -1.058 1.122  H111 MKR 52 
MKR H112 2H11 H 0 0 N N N 42.622 14.735 52.385 -1.105 -0.241 -0.459 H112 MKR 53 
MKR H121 1H12 H 0 0 N N N 45.059 14.763 51.405 -2.524 -2.054 -1.379 H121 MKR 54 
MKR H122 2H12 H 0 0 N N N 44.818 16.542 51.523 -2.504 -2.872 0.202  H122 MKR 55 
MKR H161 1H16 H 0 0 N N N 43.899 17.489 53.656 -5.092 -1.992 -1.002 H161 MKR 56 
MKR H162 2H16 H 0 0 N N N 44.812 16.926 55.028 -4.766 -2.761 0.570  H162 MKR 57 
MKR H171 1H17 H 0 0 N N N 45.349 14.523 55.170 -2.674 0.680  -0.567 H171 MKR 58 
MKR H172 2H17 H 0 0 N N N 45.334 13.478 53.778 -3.897 -0.026 -1.652 H172 MKR 59 
MKR H191 1H19 H 0 0 N N N 46.018 17.399 52.171 -6.936 -1.466 0.514  H191 MKR 60 
MKR H192 2H19 H 0 0 N N N 46.250 18.506 53.500 -5.795 -0.882 1.755  H192 MKR 61 
MKR H211 1H21 H 0 0 N N N 47.676 14.515 54.462 -4.411 1.393  1.003  H211 MKR 62 
MKR H212 2H21 H 0 0 N N N 47.183 14.693 52.702 -4.839 1.982  -0.625 H212 MKR 63 
MKR H241 1H24 H 0 0 N N N 49.319 15.138 54.531 -6.045 2.517  -1.287 H241 MKR 64 
MKR H242 2H24 H 0 0 N N N 50.093 16.417 55.526 -7.534 2.073  -2.156 H242 MKR 65 
MKR H243 3H24 H 0 0 N N N 48.544 15.678 56.058 -7.633 2.944  -0.607 H243 MKR 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 
MKR C1  C2   DOUB Y N 1  
MKR C1  C6   SING Y N 2  
MKR C1  F1   SING N N 3  
MKR C2  C3   SING Y N 4  
MKR C2  H2   SING N N 5  
MKR C3  N2   SING N N 6  
MKR C3  C4   DOUB Y N 7  
MKR C4  O1   SING N N 8  
MKR C4  C5   SING Y N 9  
MKR C5  C6   DOUB Y N 10 
MKR C5  H5   SING N N 11 
MKR C6  H6   SING N N 12 
MKR N2  N12  SING N N 13 
MKR N2  C15  SING N N 14 
MKR N12 C8   DOUB N N 15 
MKR C8  C20  SING N N 16 
MKR C8  C14  SING N N 17 
MKR C14 C18  SING N N 18 
MKR C14 C10  SING N N 19 
MKR C14 C15  SING N N 20 
MKR C15 C7   SING N N 21 
MKR C15 H15  SING N N 22 
MKR C18 C26  DOUB Y N 23 
MKR C18 C30  SING Y N 24 
MKR C20 O25  DOUB N N 25 
MKR C20 C9   SING N N 26 
MKR C9  H91  SING N N 27 
MKR C9  H92  SING N N 28 
MKR C9  H93  SING N N 29 
MKR C26 C27  SING Y N 30 
MKR C26 H26  SING N N 31 
MKR C27 C28  DOUB Y N 32 
MKR C27 H27  SING N N 33 
MKR C28 C29  SING Y N 34 
MKR C28 H28  SING N N 35 
MKR C29 C30  DOUB Y N 36 
MKR C29 H29  SING N N 37 
MKR C30 H30  SING N N 38 
MKR O1  C7   SING N N 39 
MKR C7  H71  SING N N 40 
MKR C7  H72  SING N N 41 
MKR C10 C11  SING N N 42 
MKR C10 H101 SING N N 43 
MKR C10 H102 SING N N 44 
MKR C11 C12  SING N N 45 
MKR C11 H111 SING N N 46 
MKR C11 H112 SING N N 47 
MKR C12 N3   SING N N 48 
MKR C12 H121 SING N N 49 
MKR C12 H122 SING N N 50 
MKR N3  C16  SING N N 51 
MKR N3  C17  SING N N 52 
MKR C16 C19  SING N N 53 
MKR C16 H161 SING N N 54 
MKR C16 H162 SING N N 55 
MKR C17 C21  SING N N 56 
MKR C17 H171 SING N N 57 
MKR C17 H172 SING N N 58 
MKR C19 N1   SING N N 59 
MKR C19 H191 SING N N 60 
MKR C19 H192 SING N N 61 
MKR C21 N1   SING N N 62 
MKR C21 H211 SING N N 63 
MKR C21 H212 SING N N 64 
MKR N1  C22  SING N N 65 
MKR C22 O2   DOUB N N 66 
MKR C22 C24  SING N N 67 
MKR C24 H241 SING N N 68 
MKR C24 H242 SING N N 69 
MKR C24 H243 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 
MKR SMILES           ACDLabs              10.04 O=C(N1CCN(CC1)CCCC3(C(=NN2c4c(OCC23)ccc(F)c4)C(=O)C)c5ccccc5)C                                                                                                                         
MKR InChI            InChI                1.02b InChI=1/C27H31FN4O3/c1-19(33)26-27(21-7-4-3-5-8-21,11-6-12-30-13-15-31(16-14-30)20(2)34)25-18-35-24-10-9-22(28)17-23(24)32(25)29-26/h3-5,7-10,17,25H,6,11-16,18H2,1-2H3/t25-,27+/m0/s1 
MKR InChIKey         InChI                1.02b BWKAHABETZLDBG-AHKZPQOWBZ                                                                                                                                                              
MKR SMILES_CANONICAL CACTVS               3.341 CC(=O)N1CCN(CCC[C@]2([C@@H]3COc4ccc(F)cc4N3N=C2C(C)=O)c5ccccc5)CC1                                                                                                                     
MKR SMILES           CACTVS               3.341 CC(=O)N1CCN(CCC[C]2([CH]3COc4ccc(F)cc4N3N=C2C(C)=O)c5ccccc5)CC1                                                                                                                        
MKR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)C1=NN2c3cc(ccc3OC[C@H]2[C@@]1(CCCN4CCN(CC4)C(=O)C)c5ccccc5)F                                                                                                                     
MKR SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)C1=NN2c3cc(ccc3OCC2C1(CCCN4CCN(CC4)C(=O)C)c5ccccc5)F                                                                                                                             
# 
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 
MKR "SYSTEMATIC NAME" ACDLabs              10.04 1-{(3R,3aR)-3-[3-(4-acetylpiperazin-1-yl)propyl]-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl}ethanone 
MKR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(3R,3aR)-3-[3-(4-ethanoylpiperazin-1-yl)propyl]-8-fluoro-3-phenyl-3a,4-dihydropyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone   
# 
