data_920 # _chem_comp.id 920 _chem_comp.name "4-[(1S,5R,6R)-6-amino-1-methyl-3-azabicyclo[3.2.0]hept-3-yl]-6-fluoro-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 "C23 H25 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 2013-05-21 _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 448.496 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 920 _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 4KSG _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 920 F31 F31 F 0 1 N N N 10.193 -1.193 10.269 -4.787 -3.282 -0.172 F31 920 1 920 C6 C6 C 0 1 Y N N 10.945 -2.075 10.961 -3.442 -3.166 -0.118 C6 920 2 920 C1 C1 C 0 1 Y N N 12.301 -2.200 10.604 -2.650 -4.305 -0.107 C1 920 3 920 C5 C5 C 0 1 Y N N 10.348 -2.846 11.985 -2.862 -1.914 -0.081 C5 920 4 920 C4 C4 C 0 1 Y N N 11.144 -3.773 12.663 -1.473 -1.792 -0.025 C4 920 5 920 C9 C9 C 0 1 Y N N 10.929 -4.738 13.759 -0.555 -0.644 0.025 C9 920 6 920 C10 C10 C 0 1 Y N N 9.793 -5.203 14.610 -0.722 0.747 0.035 C10 920 7 920 N22 N22 N 0 1 N N N 8.500 -4.691 14.665 -1.986 1.307 -0.007 N22 920 8 920 C26 C26 C 0 1 N N N 8.162 -3.316 14.315 -2.089 2.306 -1.102 C26 920 9 920 C25 C25 C 0 1 N N R 7.124 -2.982 15.399 -3.305 3.165 -0.684 C25 920 10 920 C28 C28 C 0 1 N N R 7.602 -2.356 16.714 -3.038 4.675 -0.733 C28 920 11 920 N29 N29 N 0 1 N N N 8.927 -1.750 16.757 -2.151 5.078 -1.831 N29 920 12 920 C27 C27 C 0 1 N N N 7.512 -3.729 17.377 -2.318 4.530 0.616 C27 920 13 920 C24 C24 C 0 1 N N S 6.806 -4.274 16.130 -3.149 3.258 0.856 C24 920 14 920 C30 C30 C 0 1 N N N 5.305 -4.488 16.349 -4.435 3.438 1.666 C30 920 15 920 C23 C23 C 0 1 N N N 7.441 -5.417 15.352 -2.280 2.045 1.241 C23 920 16 920 N11 N11 N 0 1 Y N N 10.095 -6.171 15.512 0.362 1.517 0.087 N11 920 17 920 C12 C12 C 0 1 Y N N 11.327 -6.728 15.630 1.574 0.983 0.128 C12 920 18 920 N13 N13 N 0 1 Y N N 12.378 -6.345 14.894 1.773 -0.323 0.119 N13 920 19 920 C8 C8 C 0 1 Y N N 12.232 -5.397 13.961 0.745 -1.170 0.069 C8 920 20 920 N7 N7 N 0 1 Y N N 13.118 -4.867 13.110 0.660 -2.540 0.049 N7 920 21 920 C3 C3 C 0 1 Y N N 12.563 -3.931 12.314 -0.669 -2.940 -0.008 C3 920 22 920 C2 C2 C 0 1 Y N N 13.145 -3.116 11.245 -1.270 -4.199 -0.052 C2 920 23 920 N32 N32 N 0 1 N N N 14.459 -3.324 10.976 -0.480 -5.353 -0.040 N32 920 24 920 C33 C33 C 0 1 N N N 15.112 -2.796 9.791 -1.112 -6.674 -0.085 C33 920 25 920 O14 O14 O 0 1 N N N 11.577 -7.719 16.525 2.648 1.806 0.180 O14 920 26 920 C15 C15 C 0 1 Y N N 10.585 -8.305 17.258 3.885 1.247 0.110 C15 920 27 920 C20 C20 C 0 1 Y N N 10.381 -9.680 17.189 4.392 0.788 -1.101 C20 920 28 920 N19 N19 N 0 1 Y N N 9.411 -10.219 17.954 5.601 0.250 -1.128 N19 920 29 920 C18 C18 C 0 1 Y N N 8.651 -9.439 18.762 6.319 0.147 -0.028 C18 920 30 920 C21 C21 C 0 1 N N N 7.565 -10.054 19.609 7.691 -0.473 -0.106 C21 920 31 920 N17 N17 N 0 1 Y N N 8.845 -8.105 18.834 5.873 0.570 1.137 N17 920 32 920 C16 C16 C 0 1 Y N N 9.801 -7.527 18.099 4.677 1.125 1.246 C16 920 33 920 H1 H1 H 0 1 N N N 12.700 -1.576 9.818 -3.113 -5.280 -0.140 H1 920 34 920 H2 H2 H 0 1 N N N 9.305 -2.722 12.236 -3.482 -1.030 -0.094 H2 920 35 920 H3 H3 H 0 1 N N N 9.039 -2.656 14.379 -1.187 2.915 -1.153 H3 920 36 920 H4 H4 H 0 1 N N N 7.728 -3.251 13.307 -2.276 1.812 -2.056 H4 920 37 920 H5 H5 H 0 1 N N N 6.230 -2.487 14.992 -4.268 2.826 -1.065 H5 920 38 920 H6 H6 H 0 1 N N N 6.835 -1.680 17.120 -3.945 5.279 -0.679 H6 920 39 920 H7 H7 H 0 1 N N N 9.098 -1.386 17.673 -2.001 6.076 -1.827 H7 920 40 920 H8 H8 H 0 1 N N N 9.616 -2.441 16.538 -1.273 4.581 -1.788 H8 920 41 920 H10 H10 H 0 1 N N N 6.896 -3.750 18.288 -1.249 4.339 0.519 H10 920 42 920 H11 H11 H 0 1 N N N 8.487 -4.195 17.582 -2.540 5.335 1.316 H11 920 43 920 H12 H12 H 0 1 N N N 4.892 -3.639 16.914 -5.100 2.593 1.485 H12 920 44 920 H13 H13 H 0 1 N N N 4.799 -4.561 15.375 -4.192 3.489 2.727 H13 920 45 920 H14 H14 H 0 1 N N N 5.146 -5.417 16.916 -4.929 4.361 1.362 H14 920 46 920 H15 H15 H 0 1 N N N 6.733 -5.874 14.645 -2.825 1.402 1.932 H15 920 47 920 H16 H16 H 0 1 N N N 7.844 -6.193 16.020 -1.351 2.384 1.699 H16 920 48 920 H17 H17 H 0 1 N N N 14.081 -5.134 13.069 1.419 -3.143 0.071 H17 920 49 920 H18 H18 H 0 1 N N N 14.580 -4.316 10.940 0.486 -5.279 -0.002 H18 920 50 920 H19 H19 H 0 1 N N N 16.171 -3.094 9.792 -1.766 -6.793 0.779 H19 920 51 920 H20 H20 H 0 1 N N N 14.619 -3.195 8.892 -1.698 -6.765 -1.000 H20 920 52 920 H21 H21 H 0 1 N N N 15.040 -1.698 9.791 -0.343 -7.446 -0.068 H21 920 53 920 H22 H22 H 0 1 N N N 10.984 -10.298 16.540 3.809 0.870 -2.006 H22 920 54 920 H23 H23 H 0 1 N N N 7.538 -11.141 19.439 8.430 0.304 -0.304 H23 920 55 920 H24 H24 H 0 1 N N N 7.771 -9.854 20.671 7.923 -0.962 0.840 H24 920 56 920 H25 H25 H 0 1 N N N 6.594 -9.616 19.335 7.713 -1.208 -0.910 H25 920 57 920 H26 H26 H 0 1 N N N 9.962 -6.461 18.159 4.320 1.474 2.204 H26 920 58 # 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 920 C33 N32 SING N N 1 920 F31 C6 SING N N 2 920 C1 C6 DOUB Y N 3 920 C1 C2 SING Y N 4 920 C6 C5 SING Y N 5 920 N32 C2 SING N N 6 920 C2 C3 DOUB Y N 7 920 C5 C4 DOUB Y N 8 920 C3 C4 SING Y N 9 920 C3 N7 SING Y N 10 920 C4 C9 SING Y N 11 920 N7 C8 SING Y N 12 920 C9 C8 DOUB Y N 13 920 C9 C10 SING Y N 14 920 C8 N13 SING Y N 15 920 C26 N22 SING N N 16 920 C26 C25 SING N N 17 920 C10 N22 SING N N 18 920 C10 N11 DOUB Y N 19 920 N22 C23 SING N N 20 920 N13 C12 DOUB Y N 21 920 C23 C24 SING N N 22 920 C25 C24 SING N N 23 920 C25 C28 SING N N 24 920 N11 C12 SING Y N 25 920 C12 O14 SING N N 26 920 C24 C30 SING N N 27 920 C24 C27 SING N N 28 920 O14 C15 SING N N 29 920 C28 N29 SING N N 30 920 C28 C27 SING N N 31 920 C20 C15 DOUB Y N 32 920 C20 N19 SING Y N 33 920 C15 C16 SING Y N 34 920 N19 C18 DOUB Y N 35 920 C16 N17 DOUB Y N 36 920 C18 N17 SING Y N 37 920 C18 C21 SING N N 38 920 C1 H1 SING N N 39 920 C5 H2 SING N N 40 920 C26 H3 SING N N 41 920 C26 H4 SING N N 42 920 C25 H5 SING N N 43 920 C28 H6 SING N N 44 920 N29 H7 SING N N 45 920 N29 H8 SING N N 46 920 C27 H10 SING N N 47 920 C27 H11 SING N N 48 920 C30 H12 SING N N 49 920 C30 H13 SING N N 50 920 C30 H14 SING N N 51 920 C23 H15 SING N N 52 920 C23 H16 SING N N 53 920 N7 H17 SING N N 54 920 N32 H18 SING N N 55 920 C33 H19 SING N N 56 920 C33 H20 SING N N 57 920 C33 H21 SING N N 58 920 C20 H22 SING N N 59 920 C21 H23 SING N N 60 920 C21 H24 SING N N 61 920 C21 H25 SING N N 62 920 C16 H26 SING N N 63 # 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 920 SMILES ACDLabs 12.01 "Fc4cc3c2c(nc(Oc1cnc(nc1)C)nc2nc3c(NC)c4)N6CC5C(N)CC5(C)C6" 920 InChI InChI 1.03 "InChI=1S/C23H25FN8O/c1-11-27-7-13(8-28-11)33-22-30-20-18(14-4-12(24)5-17(26-3)19(14)29-20)21(31-22)32-9-15-16(25)6-23(15,2)10-32/h4-5,7-8,15-16,26H,6,9-10,25H2,1-3H3,(H,29,30,31)/t15-,16-,23-/m1/s1" 920 InChIKey InChI 1.03 UYSFLJHCRMWPCF-CKNGIIGNSA-N 920 SMILES_CANONICAL CACTVS 3.370 "CNc1cc(F)cc2c1[nH]c3nc(Oc4cnc(C)nc4)nc(N5C[C@@H]6[C@H](N)C[C@]6(C)C5)c23" 920 SMILES CACTVS 3.370 "CNc1cc(F)cc2c1[nH]c3nc(Oc4cnc(C)nc4)nc(N5C[CH]6[CH](N)C[C]6(C)C5)c23" 920 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1ncc(cn1)Oc2nc3c(c4cc(cc(c4[nH]3)NC)F)c(n2)N5C[C@@H]6[C@@H](C[C@@]6(C5)C)N" 920 SMILES "OpenEye OEToolkits" 1.7.6 "Cc1ncc(cn1)Oc2nc3c(c4cc(cc(c4[nH]3)NC)F)c(n2)N5CC6C(CC6(C5)C)N" # 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 920 "SYSTEMATIC NAME" ACDLabs 12.01 "4-[(1S,5R,6R)-6-amino-1-methyl-3-azabicyclo[3.2.0]hept-3-yl]-6-fluoro-N-methyl-2-[(2-methylpyrimidin-5-yl)oxy]-9H-pyrimido[4,5-b]indol-8-amine" 920 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "4-[(1R,5S,7R)-7-azanyl-5-methyl-3-azabicyclo[3.2.0]heptan-3-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 920 "Create component" 2013-05-21 RCSB 920 "Initial release" 2014-01-15 RCSB #