data_AV3 # _chem_comp.id AV3 _chem_comp.name "4-[(4-fluoro-2-methyl-3H-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H27 F N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms Cediranib _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-11-26 _chem_comp.pdbx_modified_date 2020-06-17 _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 450.505 _chem_comp.one_letter_code ? _chem_comp.three_letter_code AV3 _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 6IPR _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # # 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 AV3 C01 C1 C 0 1 Y N N 242.979 -44.529 391.271 -6.183 0.174 -0.395 C01 AV3 1 AV3 C02 C2 C 0 1 Y N N 239.255 -40.485 389.171 -0.470 -0.198 0.102 C02 AV3 2 AV3 C03 C3 C 0 1 Y N N 240.202 -41.499 389.204 -1.849 0.083 0.222 C03 AV3 3 AV3 C04 C4 C 0 1 Y N N 241.979 -44.928 392.134 -6.729 0.081 0.888 C04 AV3 4 AV3 C05 C5 C 0 1 Y N N 242.776 -43.364 390.519 -4.870 -0.151 -0.631 C05 AV3 5 AV3 C06 C6 C 0 1 Y N N 238.151 -40.669 388.356 0.442 0.887 0.145 C06 AV3 6 AV3 C07 C7 C 0 1 N N N 244.102 -45.445 391.341 -7.313 0.667 -1.270 C07 AV3 7 AV3 C08 C8 C 0 1 Y N N 239.367 -39.302 389.913 0.011 -1.505 -0.052 C08 AV3 8 AV3 C09 C9 C 0 1 Y N N 241.574 -42.628 390.641 -4.066 -0.587 0.419 C09 AV3 9 AV3 C10 C10 C 0 1 N N N 243.646 -46.387 392.290 -8.466 0.809 -0.296 C10 AV3 10 AV3 C11 C11 C 0 1 Y N N 237.155 -39.716 388.271 1.815 0.637 0.028 C11 AV3 11 AV3 C12 C12 C 0 1 Y N N 238.357 -38.338 389.829 1.355 -1.720 -0.163 C12 AV3 12 AV3 C13 C13 C 0 1 Y N N 237.256 -38.546 388.989 2.258 -0.647 -0.125 C13 AV3 13 AV3 C14 C14 C 0 1 Y N N 238.951 -42.754 387.680 -1.335 2.330 0.395 C14 AV3 14 AV3 C15 C15 C 0 1 Y N N 240.778 -44.207 392.253 -5.912 -0.356 1.937 C15 AV3 15 AV3 C16 C16 C 0 1 Y N N 240.575 -43.065 391.501 -4.597 -0.690 1.697 C16 AV3 16 AV3 C17 C17 C 0 1 N N N 234.957 -34.981 387.010 6.843 0.992 -0.276 C17 AV3 17 AV3 C18 C18 C 0 1 N N N 236.082 -35.983 387.238 5.911 -0.220 -0.331 C18 AV3 18 AV3 C19 C19 C 0 1 N N N 244.568 -47.533 392.620 -9.861 1.273 -0.631 C19 AV3 19 AV3 C20 C20 C 0 1 N N N 234.521 -32.605 387.140 9.148 1.701 -0.606 C20 AV3 20 AV3 C21 C21 C 0 1 N N N 234.870 -33.876 389.174 8.698 -0.133 0.817 C21 AV3 21 AV3 C22 C22 C 0 1 N N N 235.589 -37.380 387.609 4.460 0.245 -0.188 C22 AV3 22 AV3 C23 C23 C 0 1 N N N 239.274 -37.153 391.786 0.855 -4.038 -0.343 C23 AV3 23 AV3 C24 C24 C 0 1 N N N 234.253 -32.524 389.581 10.192 0.201 0.983 C24 AV3 24 AV3 C25 C25 C 0 1 N N N 233.789 -31.876 388.270 10.532 1.130 -0.205 C25 AV3 25 AV3 F01 F1 F 0 1 N N N 243.745 -42.976 389.688 -4.360 -0.049 -1.878 F01 AV3 26 AV3 N01 N1 N 0 1 N N N 242.421 -46.070 392.748 -8.042 0.462 0.865 N01 AV3 27 AV3 N02 N2 N 0 1 Y N N 240.020 -42.607 388.464 -2.221 1.347 0.365 N02 AV3 28 AV3 N03 N3 N 0 1 Y N N 238.020 -41.795 387.630 -0.042 2.129 0.298 N03 AV3 29 AV3 N04 N4 N 0 1 N N N 235.251 -33.744 387.752 8.235 0.545 -0.413 N04 AV3 30 AV3 O01 O1 O 0 1 N N N 241.323 -41.483 389.929 -2.766 -0.911 0.193 O01 AV3 31 AV3 O02 O2 O 0 1 N N N 236.210 -37.668 388.852 3.590 -0.888 -0.238 O02 AV3 32 AV3 O03 O3 O 0 1 N N N 238.494 -37.193 390.584 1.824 -2.987 -0.312 O03 AV3 33 AV3 H1 H1 H 0 1 N N N 244.294 -45.918 390.367 -7.064 1.631 -1.714 H1 AV3 34 AV3 H071 H2 H 0 0 N N N 245.013 -44.936 391.688 -7.550 -0.064 -2.043 H071 AV3 35 AV3 H081 H3 H 0 0 N N N 240.227 -39.136 390.545 -0.677 -2.338 -0.081 H081 AV3 36 AV3 H111 H4 H 0 0 N N N 236.296 -39.889 387.640 2.520 1.454 0.060 H111 AV3 37 AV3 H141 H5 H 0 0 N N N 238.837 -43.648 387.085 -1.692 3.343 0.513 H141 AV3 38 AV3 H151 H6 H 0 0 N N N 240.012 -44.546 392.934 -6.314 -0.434 2.937 H151 AV3 39 AV3 H161 H7 H 0 0 N N N 239.648 -42.517 391.582 -3.973 -1.028 2.511 H161 AV3 40 AV3 H171 H8 H 0 0 N N N 234.877 -34.756 385.936 6.598 1.675 -1.090 H171 AV3 41 AV3 H172 H9 H 0 0 N N N 234.008 -35.407 387.367 6.717 1.504 0.678 H172 AV3 42 AV3 H182 H10 H 0 0 N N N 236.675 -36.057 386.314 6.036 -0.733 -1.285 H182 AV3 43 AV3 H181 H11 H 0 0 N N N 236.719 -35.611 388.054 6.155 -0.903 0.483 H181 AV3 44 AV3 H193 H12 H 0 0 N N N 244.093 -48.182 393.371 -10.475 0.413 -0.900 H193 AV3 45 AV3 H192 H13 H 0 0 N N N 244.770 -48.115 391.709 -10.295 1.773 0.234 H192 AV3 46 AV3 H191 H14 H 0 0 N N N 245.513 -47.139 393.021 -9.821 1.967 -1.470 H191 AV3 47 AV3 H201 H15 H 0 0 N N N 235.231 -31.923 386.649 8.868 2.526 0.049 H201 AV3 48 AV3 H202 H16 H 0 0 N N N 233.797 -32.976 386.400 9.151 2.020 -1.648 H202 AV3 49 AV3 H212 H17 H 0 0 N N N 234.134 -34.684 389.298 8.568 -1.211 0.718 H212 AV3 50 AV3 H211 H18 H 0 0 N N N 235.757 -34.091 389.788 8.138 0.230 1.678 H211 AV3 51 AV3 H221 H19 H 0 0 N N N 234.494 -37.389 387.712 4.335 0.757 0.766 H221 AV3 52 AV3 H222 H20 H 0 0 N N N 235.892 -38.112 386.846 4.216 0.928 -1.002 H222 AV3 53 AV3 H231 H21 H 0 0 N N N 239.237 -36.140 392.214 0.293 -4.041 0.591 H231 AV3 54 AV3 H233 H22 H 0 0 N N N 238.867 -37.873 392.511 0.172 -3.878 -1.177 H233 AV3 55 AV3 H232 H23 H 0 0 N N N 240.317 -37.416 391.555 1.361 -4.995 -0.466 H232 AV3 56 AV3 H241 H24 H 0 0 N N N 235.004 -31.892 390.078 10.361 0.718 1.928 H241 AV3 57 AV3 H242 H25 H 0 0 N N N 233.399 -32.679 390.257 10.791 -0.708 0.937 H242 AV3 58 AV3 H252 H26 H 0 0 N N N 234.048 -30.807 388.262 10.968 0.562 -1.027 H252 AV3 59 AV3 H251 H27 H 0 0 N N N 232.701 -31.991 388.154 11.202 1.930 0.111 H251 AV3 60 # # 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 AV3 C17 C18 SING N N 1 AV3 C17 N04 SING N N 2 AV3 C20 N04 SING N N 3 AV3 C20 C25 SING N N 4 AV3 C18 C22 SING N N 5 AV3 C22 O02 SING N N 6 AV3 N03 C14 DOUB Y N 7 AV3 N03 C06 SING Y N 8 AV3 C14 N02 SING Y N 9 AV3 N04 C21 SING N N 10 AV3 C25 C24 SING N N 11 AV3 C11 C06 SING Y N 12 AV3 C11 C13 DOUB Y N 13 AV3 C06 C02 DOUB Y N 14 AV3 N02 C03 DOUB Y N 15 AV3 O02 C13 SING N N 16 AV3 C13 C12 SING Y N 17 AV3 C02 C03 SING Y N 18 AV3 C02 C08 SING Y N 19 AV3 C21 C24 SING N N 20 AV3 C03 O01 SING N N 21 AV3 F01 C05 SING N N 22 AV3 C12 C08 DOUB Y N 23 AV3 C12 O03 SING N N 24 AV3 O01 C09 SING N N 25 AV3 C05 C09 DOUB Y N 26 AV3 C05 C01 SING Y N 27 AV3 O03 C23 SING N N 28 AV3 C09 C16 SING Y N 29 AV3 C01 C07 SING N N 30 AV3 C01 C04 DOUB Y N 31 AV3 C07 C10 SING N N 32 AV3 C16 C15 DOUB Y N 33 AV3 C04 C15 SING Y N 34 AV3 C04 N01 SING N N 35 AV3 C10 C19 SING N N 36 AV3 C10 N01 DOUB N N 37 AV3 C07 H1 SING N N 38 AV3 C07 H071 SING N N 39 AV3 C08 H081 SING N N 40 AV3 C11 H111 SING N N 41 AV3 C14 H141 SING N N 42 AV3 C15 H151 SING N N 43 AV3 C16 H161 SING N N 44 AV3 C17 H171 SING N N 45 AV3 C17 H172 SING N N 46 AV3 C18 H182 SING N N 47 AV3 C18 H181 SING N N 48 AV3 C19 H193 SING N N 49 AV3 C19 H192 SING N N 50 AV3 C19 H191 SING N N 51 AV3 C20 H201 SING N N 52 AV3 C20 H202 SING N N 53 AV3 C21 H212 SING N N 54 AV3 C21 H211 SING N N 55 AV3 C22 H221 SING N N 56 AV3 C22 H222 SING N N 57 AV3 C23 H231 SING N N 58 AV3 C23 H233 SING N N 59 AV3 C23 H232 SING N N 60 AV3 C24 H241 SING N N 61 AV3 C24 H242 SING N N 62 AV3 C25 H252 SING N N 63 AV3 C25 H251 SING N N 64 # # 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 AV3 SMILES ACDLabs 12.01 "c12CC(C)=Nc1ccc(c2F)Oc4c3cc(OC)c(cc3ncn4)OCCCN5CCCC5" AV3 InChI InChI 1.03 "InChI=1S/C25H27FN4O3/c1-16-12-17-19(29-16)6-7-21(24(17)26)33-25-18-13-22(31-2)23(14-20(18)27-15-28-25)32-11-5-10-30-8-3-4-9-30/h6-7,13-15H,3-5,8-12H2,1-2H3" AV3 InChIKey InChI 1.03 ZOVVOYNGCNKFNN-UHFFFAOYSA-N AV3 SMILES_CANONICAL CACTVS 3.385 "COc1cc2c(Oc3ccc4N=C(C)Cc4c3F)ncnc2cc1OCCCN5CCCC5" AV3 SMILES CACTVS 3.385 "COc1cc2c(Oc3ccc4N=C(C)Cc4c3F)ncnc2cc1OCCCN5CCCC5" AV3 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC1=Nc2ccc(c(c2C1)F)Oc3c4cc(c(cc4ncn3)OCCCN5CCCC5)OC" AV3 SMILES "OpenEye OEToolkits" 2.0.6 "CC1=Nc2ccc(c(c2C1)F)Oc3c4cc(c(cc4ncn3)OCCCN5CCCC5)OC" # # 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 AV3 "SYSTEMATIC NAME" ACDLabs 12.01 "4-[(4-fluoro-2-methyl-3H-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline" AV3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "4-[(4-fluoranyl-2-methyl-3~{H}-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site AV3 "Create component" 2018-11-26 PDBJ AV3 "Initial release" 2020-01-01 RCSB AV3 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id AV3 _pdbx_chem_comp_synonyms.name Cediranib _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##