data_A1CI6
# 
_chem_comp.id                                    A1CI6 
_chem_comp.name                                  Icotinib 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H21 N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N-(3-ethynylphenyl)-7,8,10,11,13,14-hexahydro[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2025-07-23 
_chem_comp.pdbx_modified_date                    2025-12-05 
_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                        391.420 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1CI6 
_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        9PMZ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              ? 
# 
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.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
A1CI6 C10  C1  C 0 1 Y N N N N N -52.573 -0.347 22.825 -2.115 0.235  0.408  C10  A1CI6 1  
A1CI6 C15  C2  C 0 1 Y N N N N N -52.437 -1.456 19.296 1.150  1.981  0.673  C15  A1CI6 2  
A1CI6 C17  C3  C 0 1 Y N N N N N -50.616 0.068  19.715 1.526  -0.327 0.070  C17  A1CI6 3  
A1CI6 C21  C4  C 0 1 N N N N N N -49.675 2.045  18.806 3.573  -1.430 0.571  C21  A1CI6 4  
A1CI6 C22  C5  C 0 1 N N N N N N -48.425 2.352  17.974 4.343  -2.695 0.187  C22  A1CI6 5  
A1CI6 C24  C6  C 0 1 N N N N N N -48.784 0.952  16.094 6.130  -1.428 -0.787 C24  A1CI6 6  
A1CI6 C28  C7  C 0 1 N N N N N N -51.693 -1.525 16.595 3.949  1.545  -0.881 C28  A1CI6 7  
A1CI6 C01  C8  C 0 1 N N N N N N -52.361 -3.066 28.495 -7.681 1.588  -1.568 C01  A1CI6 8  
A1CI6 C02  C9  C 0 1 N N N N N N -52.237 -2.015 27.953 -7.014 0.731  -1.123 C02  A1CI6 9  
A1CI6 C03  C10 C 0 1 Y N N N N N -52.094 -0.686 27.225 -6.199 -0.315 -0.581 C03  A1CI6 10 
A1CI6 C04  C11 C 0 1 Y N N N N N -52.014 -0.680 25.840 -4.818 -0.150 -0.491 C04  A1CI6 11 
A1CI6 C05  C12 C 0 1 Y N N N N N -51.885 0.524  25.155 -4.035 -1.166 0.036  C05  A1CI6 12 
A1CI6 C06  C13 C 0 1 Y N N N N N -51.829 1.715  25.870 -4.629 -2.344 0.473  C06  A1CI6 13 
A1CI6 C07  C14 C 0 1 Y N N N N N -51.900 1.706  27.260 -5.998 -2.507 0.384  C07  A1CI6 14 
A1CI6 C08  C15 C 0 1 Y N N N N N -52.031 0.503  27.940 -6.786 -1.500 -0.134 C08  A1CI6 15 
A1CI6 C12  C16 C 0 1 Y N N N N N -54.328 -1.811 22.387 -2.400 2.457  0.985  C12  A1CI6 16 
A1CI6 C14  C17 C 0 1 Y N N N N N -52.850 -1.307 20.641 -0.230 1.743  0.688  C14  A1CI6 17 
A1CI6 C16  C18 C 0 1 Y N N N N N -51.314 -0.764 18.837 2.014  0.952  0.368  C16  A1CI6 18 
A1CI6 C18  C19 C 0 1 Y N N N N N -51.026 0.205  21.017 0.183  -0.581 0.075  C18  A1CI6 19 
A1CI6 C19  C20 C 0 1 Y N N N N N -52.165 -0.494 21.483 -0.716 0.446  0.386  C19  A1CI6 20 
A1CI6 C25  C21 C 0 1 N N N N N N -50.006 0.834  15.182 6.367  -0.099 -0.054 C25  A1CI6 21 
A1CI6 C27  C22 C 0 1 N N N N N N -51.510 -1.009 15.157 5.387  2.008  -0.641 C27  A1CI6 22 
A1CI6 N09  N1  N 0 1 N N N N N N -51.797 0.551  23.698 -2.649 -1.006 0.127  N09  A1CI6 23 
A1CI6 N11  N2  N 0 1 Y N N N N N -53.648 -1.015 23.250 -2.899 1.261  0.713  N11  A1CI6 24 
A1CI6 N13  N3  N 0 1 Y N N N N N -53.937 -1.969 21.101 -1.113 2.711  0.975  N13  A1CI6 25 
A1CI6 O20  O1  O 0 1 N N N N N N -49.477 0.770  19.332 2.397  -1.326 -0.234 O20  A1CI6 26 
A1CI6 O23  O2  O 0 1 N N N N N N -48.741 2.249  16.611 5.744  -2.414 0.173  O23  A1CI6 27 
A1CI6 O26  O3  O 0 1 N N N N N N -50.190 -0.547 14.974 6.292  0.964  -1.007 O26  A1CI6 28 
A1CI6 O29  O4  O 0 1 N N N N N N -50.849 -0.871 17.510 3.353  1.178  0.366  O29  A1CI6 29 
A1CI6 H151 H1  H 0 0 N N N N N N -52.987 -2.102 18.628 1.534  2.965  0.899  H151 A1CI6 30 
A1CI6 H211 H2  H 0 0 N N N N N N -50.572 2.062  18.170 3.290  -1.481 1.622  H211 A1CI6 31 
A1CI6 H212 H3  H 0 0 N N N N N N -49.786 2.781  19.616 4.204  -0.556 0.407  H212 A1CI6 32 
A1CI6 H221 H4  H 0 0 N N N N N N -48.077 3.372  18.195 4.137  -3.480 0.914  H221 A1CI6 33 
A1CI6 H222 H5  H 0 0 N N N N N N -47.631 1.632  18.223 4.029  -3.025 -0.803 H222 A1CI6 34 
A1CI6 H241 H6  H 0 0 N N N N N N -47.869 0.752  15.517 5.339  -1.312 -1.527 H241 A1CI6 35 
A1CI6 H242 H7  H 0 0 N N N N N N -48.864 0.227  16.917 7.048  -1.744 -1.283 H242 A1CI6 36 
A1CI6 H281 H8  H 0 0 N N N N N N -52.738 -1.362 16.899 3.377  2.355  -1.333 H281 A1CI6 37 
A1CI6 H282 H9  H 0 0 N N N N N N -51.469 -2.602 16.615 3.951  0.684  -1.549 H282 A1CI6 38 
A1CI6 H011 H10 H 0 0 N N N N N N -52.472 -4.003 28.978 -8.279 2.354  -1.966 H011 A1CI6 39 
A1CI6 H041 H11 H 0 0 N N N N N N -52.052 -1.611 25.293 -4.358 0.767  -0.832 H041 A1CI6 40 
A1CI6 H061 H12 H 0 0 N N N N N N -51.730 2.653  25.344 -4.018 -3.135 0.883  H061 A1CI6 41 
A1CI6 H071 H13 H 0 0 N N N N N N -51.853 2.635  27.809 -6.454 -3.425 0.725  H071 A1CI6 42 
A1CI6 H081 H14 H 0 0 N N N N N N -52.084 0.492  29.019 -7.856 -1.629 -0.198 H081 A1CI6 43 
A1CI6 H121 H15 H 0 0 N N N N N N -55.206 -2.333 22.736 -3.083 3.258  1.226  H121 A1CI6 44 
A1CI6 H181 H16 H 0 0 N N N N N N -50.478 0.849  21.689 -0.183 -1.569 -0.160 H181 A1CI6 45 
A1CI6 H252 H17 H 0 0 N N N N N N -50.891 1.271  15.667 5.609  0.031  0.718  H252 A1CI6 46 
A1CI6 H251 H18 H 0 0 N N N N N N -49.822 1.345  14.226 7.356  -0.109 0.406  H251 A1CI6 47 
A1CI6 H272 H19 H 0 0 N N N N N N -52.213 -0.183 14.974 5.590  2.892  -1.246 H272 A1CI6 48 
A1CI6 H271 H20 H 0 0 N N N N N N -51.711 -1.826 14.449 5.520  2.251  0.413  H271 A1CI6 49 
A1CI6 H091 H21 H 0 0 N N N N N N -51.179 1.212  23.271 -2.063 -1.767 -0.008 H091 A1CI6 50 
# 
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 
A1CI6 C02 C01  TRIP N N 1  
A1CI6 C03 C02  SING N N 2  
A1CI6 C04 C03  DOUB Y N 3  
A1CI6 C05 C04  SING Y N 4  
A1CI6 C07 C06  SING Y N 5  
A1CI6 C08 C07  DOUB Y N 6  
A1CI6 C06 C05  DOUB Y N 7  
A1CI6 N09 C05  SING N N 8  
A1CI6 C10 N09  SING N N 9  
A1CI6 N11 C10  DOUB Y N 10 
A1CI6 C12 N11  SING Y N 11 
A1CI6 N13 C12  DOUB Y N 12 
A1CI6 C14 N13  SING Y N 13 
A1CI6 C15 C14  DOUB Y N 14 
A1CI6 C16 C15  SING Y N 15 
A1CI6 C17 C16  DOUB Y N 16 
A1CI6 C19 C18  DOUB Y N 17 
A1CI6 C18 C17  SING Y N 18 
A1CI6 O20 C17  SING N N 19 
A1CI6 C21 O20  SING N N 20 
A1CI6 C22 C21  SING N N 21 
A1CI6 O23 C22  SING N N 22 
A1CI6 C24 O23  SING N N 23 
A1CI6 C25 C24  SING N N 24 
A1CI6 O26 C25  SING N N 25 
A1CI6 C27 O26  SING N N 26 
A1CI6 C28 C27  SING N N 27 
A1CI6 O29 C28  SING N N 28 
A1CI6 C03 C08  SING Y N 29 
A1CI6 C10 C19  SING Y N 30 
A1CI6 C14 C19  SING Y N 31 
A1CI6 C16 O29  SING N N 32 
A1CI6 C15 H151 SING N N 33 
A1CI6 C21 H211 SING N N 34 
A1CI6 C21 H212 SING N N 35 
A1CI6 C22 H221 SING N N 36 
A1CI6 C22 H222 SING N N 37 
A1CI6 C24 H241 SING N N 38 
A1CI6 C24 H242 SING N N 39 
A1CI6 C28 H281 SING N N 40 
A1CI6 C28 H282 SING N N 41 
A1CI6 C01 H011 SING N N 42 
A1CI6 C04 H041 SING N N 43 
A1CI6 C06 H061 SING N N 44 
A1CI6 C07 H071 SING N N 45 
A1CI6 C08 H081 SING N N 46 
A1CI6 C12 H121 SING N N 47 
A1CI6 C18 H181 SING N N 48 
A1CI6 C25 H252 SING N N 49 
A1CI6 C25 H251 SING N N 50 
A1CI6 C27 H272 SING N N 51 
A1CI6 C27 H271 SING N N 52 
A1CI6 N09 H091 SING N N 53 
# 
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 
A1CI6 SMILES           ACDLabs              14.52   "C#Cc1cc(ccc1)Nc1ncnc2cc3OCCOCCOCCOc3cc21"                                                                                                         
A1CI6 InChI            InChI                1.06    "InChI=1S/C22H21N3O4/c1-2-16-4-3-5-17(12-16)25-22-18-13-20-21(14-19(18)23-15-24-22)29-11-9-27-7-6-26-8-10-28-20/h1,3-5,12-15H,6-11H2,(H,23,24,25)" 
A1CI6 InChIKey         InChI                1.06    QQLKULDARVNMAL-UHFFFAOYSA-N                                                                                                                        
A1CI6 SMILES_CANONICAL CACTVS               3.385   "C#Cc1cccc(Nc2ncnc3cc4OCCOCCOCCOc4cc23)c1"                                                                                                         
A1CI6 SMILES           CACTVS               3.385   "C#Cc1cccc(Nc2ncnc3cc4OCCOCCOCCOc4cc23)c1"                                                                                                         
A1CI6 SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "C#Cc1cccc(c1)Nc2c3cc4c(cc3ncn2)OCCOCCOCCO4"                                                                                                       
A1CI6 SMILES           "OpenEye OEToolkits" 3.1.0.0 "C#Cc1cccc(c1)Nc2c3cc4c(cc3ncn2)OCCOCCOCCO4"                                                                                                       
# 
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 
A1CI6 "SYSTEMATIC NAME" ACDLabs              14.52   "N-(3-ethynylphenyl)-7,8,10,11,13,14-hexahydro[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine"                  
A1CI6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 3.1.0.0 "~{N}-(3-ethynylphenyl)-2,5,8,11-tetraoxa-15,17-diazatricyclo[10.8.0.0^{14,19}]icosa-1(12),13,15,17,19-pentaen-18-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 
A1CI6 "Create component" 2025-07-23 RCSB 
A1CI6 "Initial release"  2025-12-10 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1CI6 
_pdbx_chem_comp_synonyms.name         "N-(3-ethynylphenyl)-7,8,10,11,13,14-hexahydro[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
