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 #