data_DOO
# 
_chem_comp.id                                    DOO 
_chem_comp.name                                  "6-fluoro-4-[(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]-N-methyl-2-[(2-methylpyrimidin-5-yl)oxy]-9H-pyrimido[4,5-b]indol-8-amine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H23 F N8 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-04-23 
_chem_comp.pdbx_modified_date                    2014-01-10 
_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                        434.469 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DOO 
_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        4K4O 
_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 
DOO F30 F30 F 0 1 N N N 10.150 -1.281  10.287 -5.044 -2.871 -0.119 F30 DOO 1  
DOO C6  C6  C 0 1 Y N N 10.894 -2.154  10.987 -3.695 -2.835 -0.065 C6  DOO 2  
DOO C1  C1  C 0 1 Y N N 12.235 -2.299  10.610 -2.974 -4.019 -0.011 C1  DOO 3  
DOO C5  C5  C 0 1 Y N N 10.277 -2.885  12.008 -3.039 -1.620 -0.069 C5  DOO 4  
DOO C4  C4  C 0 1 Y N N 11.074 -3.803  12.680 -1.645 -1.582 -0.014 C4  DOO 5  
DOO C7  C7  C 0 1 Y N N 10.841 -4.738  13.779 -0.659 -0.491 -0.002 C7  DOO 6  
DOO C13 C13 C 0 1 Y N N 9.705  -5.171  14.622 -0.740 0.907  -0.040 C13 DOO 7  
DOO N22 N22 N 0 1 N N N 8.454  -4.602  14.716 -1.967 1.542  -0.106 N22 DOO 8  
DOO C26 C26 C 0 1 N N N 7.374  -5.194  15.500 -2.217 2.346  1.118  C26 DOO 9  
DOO C25 C25 C 0 1 N N R 7.049  -4.005  16.418 -3.295 3.366  0.699  C25 DOO 10 
DOO C27 C27 C 0 1 N N N 7.709  -4.047  17.805 -2.924 4.752  1.269  C27 DOO 11 
DOO C28 C28 C 0 1 N N N 8.260  -2.650  18.063 -3.153 5.697  0.062  C28 DOO 12 
DOO N29 N29 N 0 1 N N N 8.515  -2.167  16.722 -2.685 4.892  -1.093 N29 DOO 13 
DOO C24 C24 C 0 1 N N R 7.602  -2.759  15.747 -3.136 3.507  -0.836 C24 DOO 14 
DOO C23 C23 C 0 1 N N N 8.243  -3.196  14.424 -1.993 2.538  -1.207 C23 DOO 15 
DOO N12 N12 N 0 1 Y N N 9.967  -6.137  15.520 0.388  1.611  -0.012 N12 DOO 16 
DOO C11 C11 C 0 1 Y N N 11.185 -6.699  15.635 1.565  1.006  0.051  C11 DOO 17 
DOO N10 N10 N 0 1 Y N N 12.249 -6.376  14.900 1.685  -0.309 0.089  N10 DOO 18 
DOO C8  C8  C 0 1 Y N N 12.118 -5.433  13.972 0.607  -1.093 0.065  C8  DOO 19 
DOO N9  N9  N 0 1 Y N N 13.025 -4.938  13.126 0.438  -2.455 0.093  N9  DOO 20 
DOO C3  C3  C 0 1 Y N N 12.481 -4.004  12.322 -0.912 -2.775 0.046  C3  DOO 21 
DOO C2  C2  C 0 1 Y N N 13.068 -3.214  11.247 -1.590 -3.996 0.044  C2  DOO 22 
DOO N31 N31 N 0 1 N N N 14.364 -3.451  10.963 -0.872 -5.195 0.099  N31 DOO 23 
DOO C32 C32 C 0 1 N N N 15.022 -2.867  9.812  -1.583 -6.475 0.099  C32 DOO 24 
DOO O14 O14 O 0 1 N N N 11.395 -7.709  16.500 2.688  1.764  0.077  O14 DOO 25 
DOO C15 C15 C 0 1 Y N N 10.419 -8.301  17.253 3.888  1.128  0.030  C15 DOO 26 
DOO C20 C20 C 0 1 Y N N 10.215 -9.673  17.195 4.368  0.598  -1.163 C20 DOO 27 
DOO N19 N19 N 0 1 Y N N 9.284  -10.212 17.994 5.541  -0.014 -1.168 N19 DOO 28 
DOO C18 C18 C 0 1 Y N N 8.541  -9.433  18.811 6.251  -0.123 -0.063 C18 DOO 29 
DOO C21 C21 C 0 1 N N N 7.490  -10.069 19.686 7.583  -0.827 -0.115 C21 DOO 30 
DOO N17 N17 N 0 1 Y N N 8.723  -8.097  18.871 5.831  0.366  1.087  N17 DOO 31 
DOO C16 C16 C 0 1 Y N N 9.660  -7.519  18.111 4.671  0.996  1.172  C16 DOO 32 
DOO H1  H1  H 0 1 N N N 12.630 -1.690  9.810  -3.495 -4.965 -0.012 H1  DOO 33 
DOO H2  H2  H 0 1 N N N 9.236  -2.743  12.260 -3.603 -0.701 -0.116 H2  DOO 34 
DOO H3  H3  H 0 1 N N N 6.516  -5.474  14.871 -2.587 1.710  1.922  H3  DOO 35 
DOO H4  H4  H 0 1 N N N 7.713  -6.072  16.069 -1.307 2.860  1.428  H4  DOO 36 
DOO H5  H5  H 0 1 N N N 5.959  -3.914  16.531 -4.297 3.053  0.994  H5  DOO 37 
DOO H6  H6  H 0 1 N N N 6.966  -4.310  18.572 -3.581 5.018  2.097  H6  DOO 38 
DOO H7  H7  H 0 1 N N N 8.524  -4.785  17.816 -1.880 4.773  1.582  H7  DOO 39 
DOO H8  H8  H 0 1 N N N 9.186  -2.690  18.655 -4.211 5.939  -0.041 H8  DOO 40 
DOO H9  H9  H 0 1 N N N 7.521  -2.020  18.580 -2.561 6.606  0.167  H9  DOO 41 
DOO H10 H10 H 0 1 N N N 9.454  -2.399  16.468 -1.680 4.934  -1.180 H10 DOO 42 
DOO H12 H12 H 0 1 N N N 6.776  -2.065  15.534 -4.063 3.280  -1.363 H12 DOO 43 
DOO H13 H13 H 0 1 N N N 9.190  -2.670  14.233 -1.045 3.072  -1.259 H13 DOO 44 
DOO H14 H14 H 0 1 N N N 7.564  -3.051  13.571 -2.206 2.047  -2.157 H14 DOO 45 
DOO H15 H15 H 0 1 N N N 13.983 -5.223  13.094 1.160  -3.102 0.138  H15 DOO 46 
DOO H16 H16 H 0 1 N N N 14.450 -4.442  10.861 0.097  -5.178 0.138  H16 DOO 47 
DOO H17 H17 H 0 1 N N N 16.071 -3.198  9.781  -2.172 -6.563 -0.814 H17 DOO 48 
DOO H18 H18 H 0 1 N N N 14.509 -3.189  8.894  -0.862 -7.292 0.146  H18 DOO 49 
DOO H19 H19 H 0 1 N N N 14.986 -1.770  9.887  -2.244 -6.524 0.964  H19 DOO 50 
DOO H20 H20 H 0 1 N N N 10.792 -10.290 16.523 3.792  0.684  -2.072 H20 DOO 51 
DOO H21 H21 H 0 1 N N N 7.481  -11.156 19.518 8.368  -0.105 -0.337 H21 DOO 52 
DOO H22 H22 H 0 1 N N N 7.718  -9.863  20.742 7.783  -1.297 0.848  H22 DOO 53 
DOO H23 H23 H 0 1 N N N 6.503  -9.652  19.436 7.560  -1.590 -0.894 H23 DOO 54 
DOO H24 H24 H 0 1 N N N 9.824  -6.453  18.165 4.335  1.399  2.116  H24 DOO 55 
# 
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 
DOO C32 N31 SING N N 1  
DOO F30 C6  SING N N 2  
DOO C1  C6  DOUB Y N 3  
DOO C1  C2  SING Y N 4  
DOO N31 C2  SING N N 5  
DOO C6  C5  SING Y N 6  
DOO C2  C3  DOUB Y N 7  
DOO C5  C4  DOUB Y N 8  
DOO C3  C4  SING Y N 9  
DOO C3  N9  SING Y N 10 
DOO C4  C7  SING Y N 11 
DOO N9  C8  SING Y N 12 
DOO C7  C8  DOUB Y N 13 
DOO C7  C13 SING Y N 14 
DOO C8  N10 SING Y N 15 
DOO C23 N22 SING N N 16 
DOO C23 C24 SING N N 17 
DOO C13 N22 SING N N 18 
DOO C13 N12 DOUB Y N 19 
DOO N22 C26 SING N N 20 
DOO N10 C11 DOUB Y N 21 
DOO C26 C25 SING N N 22 
DOO N12 C11 SING Y N 23 
DOO C11 O14 SING N N 24 
DOO C24 C25 SING N N 25 
DOO C24 N29 SING N N 26 
DOO C25 C27 SING N N 27 
DOO O14 C15 SING N N 28 
DOO N29 C28 SING N N 29 
DOO C20 C15 DOUB Y N 30 
DOO C20 N19 SING Y N 31 
DOO C15 C16 SING Y N 32 
DOO C27 C28 SING N N 33 
DOO N19 C18 DOUB Y N 34 
DOO C16 N17 DOUB Y N 35 
DOO C18 N17 SING Y N 36 
DOO C18 C21 SING N N 37 
DOO C1  H1  SING N N 38 
DOO C5  H2  SING N N 39 
DOO C26 H3  SING N N 40 
DOO C26 H4  SING N N 41 
DOO C25 H5  SING N N 42 
DOO C27 H6  SING N N 43 
DOO C27 H7  SING N N 44 
DOO C28 H8  SING N N 45 
DOO C28 H9  SING N N 46 
DOO N29 H10 SING N N 47 
DOO C24 H12 SING N N 48 
DOO C23 H13 SING N N 49 
DOO C23 H14 SING N N 50 
DOO N9  H15 SING N N 51 
DOO N31 H16 SING N N 52 
DOO C32 H17 SING N N 53 
DOO C32 H18 SING N N 54 
DOO C32 H19 SING N N 55 
DOO C20 H20 SING N N 56 
DOO C21 H21 SING N N 57 
DOO C21 H22 SING N N 58 
DOO C21 H23 SING N N 59 
DOO C16 H24 SING N N 60 
# 
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 
DOO SMILES           ACDLabs              12.01 "Fc4cc3c2c(nc(Oc1cnc(nc1)C)nc2nc3c(NC)c4)N6CC5CCNC5C6"                                                                                                                                         
DOO InChI            InChI                1.03  "InChI=1S/C22H23FN8O/c1-11-26-7-14(8-27-11)32-22-29-20-18(15-5-13(23)6-16(24-2)19(15)28-20)21(30-22)31-9-12-3-4-25-17(12)10-31/h5-8,12,17,24-25H,3-4,9-10H2,1-2H3,(H,28,29,30)/t12-,17+/m1/s1" 
DOO InChIKey         InChI                1.03  ACMIJDVJWLMBCX-PXAZEXFGSA-N                                                                                                                                                                    
DOO SMILES_CANONICAL CACTVS               3.370 "CNc1cc(F)cc2c1[nH]c3nc(Oc4cnc(C)nc4)nc(N5C[C@H]6CCN[C@H]6C5)c23"                                                                                                                              
DOO SMILES           CACTVS               3.370 "CNc1cc(F)cc2c1[nH]c3nc(Oc4cnc(C)nc4)nc(N5C[CH]6CCN[CH]6C5)c23"                                                                                                                                
DOO SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1ncc(cn1)Oc2nc3c(c4cc(cc(c4[nH]3)NC)F)c(n2)N5C[C@H]6CCN[C@H]6C5"                                                                                                                            
DOO SMILES           "OpenEye OEToolkits" 1.7.6 "Cc1ncc(cn1)Oc2nc3c(c4cc(cc(c4[nH]3)NC)F)c(n2)N5CC6CCNC6C5"                                                                                                                                    
# 
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 
DOO "SYSTEMATIC NAME" ACDLabs              12.01 "6-fluoro-4-[(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl]-N-methyl-2-[(2-methylpyrimidin-5-yl)oxy]-9H-pyrimido[4,5-b]indol-8-amine"                
DOO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "4-[(3aR,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrol-5-yl]-6-fluoranyl-N-methyl-2-(2-methylpyrimidin-5-yl)oxy-9H-pyrimido[4,5-b]indol-8-amine" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
DOO "Create component" 2013-04-23 RCSB 
DOO "Initial release"  2014-01-15 RCSB 
# 
