data_QUN
# 
_chem_comp.id                                    QUN 
_chem_comp.name                                  QUINACRINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H30 Cl N3 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         6-CHLORO-9-[[4-(DIETHYLAMINO)-1-METHYLBUTYL]AMINO]-2-METHOXYACRIDINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-08-17 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        399.957 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     QUN 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1JQE 
_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 
QUN C1   C1   C  0 1 Y N N 41.665 -31.129 4.275  2.892  -0.155 1.008  C1   QUN 1  
QUN C2   C2   C  0 1 Y N N 40.436 -30.700 5.025  3.874  -0.231 0.014  C2   QUN 2  
QUN C3   C3   C  0 1 Y N N 39.422 -31.707 5.489  3.543  -0.180 -1.302 C3   QUN 3  
QUN C4   C4   C  0 1 Y N N 39.624 -33.175 5.208  2.191  -0.049 -1.685 C4   QUN 4  
QUN C5   C5   C  0 1 Y N N 40.907 -33.622 4.427  1.198  0.034  -0.675 C5   QUN 5  
QUN C6   C6   C  0 1 Y N N 41.864 -32.568 4.001  1.575  -0.027 0.677  C6   QUN 6  
QUN N1   N1   N  0 1 Y N N 38.651 -34.125 5.656  1.870  0.000  -2.978 N1   QUN 7  
QUN C7   C7   C  0 1 Y N N 38.829 -35.527 5.392  0.609  0.123  -3.383 C7   QUN 8  
QUN C8   C8   C  0 1 Y N N 40.072 -36.078 4.628  -0.474 0.210  -2.402 C8   QUN 9  
QUN C9   C9   C  0 1 Y N N 41.114 -35.162 4.135  -0.159 0.160  -1.032 C9   QUN 10 
QUN C10  C10  C  0 1 Y N N 37.819 -36.502 5.868  0.281  0.173  -4.752 C10  QUN 11 
QUN C11  C11  C  0 1 Y N N 38.008 -37.984 5.599  -1.020 0.299  -5.127 C11  QUN 12 
QUN C12  C12  C  0 1 Y N N 39.188 -38.489 4.867  -2.049 0.382  -4.189 C12  QUN 13 
QUN C13  C13  C  0 1 Y N N 40.205 -37.544 4.385  -1.798 0.339  -2.853 C13  QUN 14 
QUN CL   CL   CL 0 0 N N N 36.882 -39.059 6.137  -1.411 0.359  -6.817 CL   QUN 15 
QUN O    O    O  0 1 N N N 42.693 -30.096 3.794  3.255  -0.209 2.317  O    QUN 16 
QUN C14  C14  C  0 1 N N N 43.596 -29.697 4.770  4.678  -0.342 2.346  C14  QUN 17 
QUN N2   N2   N  0 1 N N N 42.376 -35.855 3.356  -1.145 0.238  -0.070 N2   QUN 18 
QUN C15  C15  C  0 1 N N R 42.994 -35.519 1.983  -1.428 -1.138 0.356  C15  QUN 19 
QUN C16  C16  C  0 1 N N N 43.928 -34.313 2.078  -2.320 -1.821 -0.683 C16  QUN 20 
QUN C17  C17  C  0 1 N N N 41.907 -35.326 1.017  -2.145 -1.116 1.707  C17  QUN 21 
QUN C18  C18  C  0 1 N N N 42.282 -34.968 -0.389 -1.253 -0.432 2.746  C18  QUN 22 
QUN C19  C19  C  0 1 N N N 40.947 -34.886 -0.948 -1.970 -0.410 4.098  C19  QUN 23 
QUN N3   N3   N  0 1 N N N 40.717 -34.495 -2.357 -1.143 0.303  5.079  N3   QUN 24 
QUN C20  C20  C  0 1 N N N 39.247 -34.569 -2.448 -1.282 1.736  4.785  C20  QUN 25 
QUN C21  C21  C  0 1 N N N 41.341 -35.362 -3.401 -1.760 0.080  6.393  C21  QUN 26 
QUN C22  C22  C  0 1 N N N 38.502 -35.959 -2.262 -0.441 2.544  5.776  C22  QUN 27 
QUN C23  C23  C  0 1 N N N 41.026 -34.794 -4.839 -1.310 -1.273 6.945  C23  QUN 28 
QUN H21  1H2  H  0 1 N N N 40.279 -29.652 5.234  4.911  -0.332 0.297  H21  QUN 29 
QUN H31  1H3  H  0 1 N N N 38.545 -31.378 6.026  4.315  -0.241 -2.055 H31  QUN 30 
QUN H61  1H6  H  0 1 N N N 42.751 -32.869 3.463  0.825  0.030  1.452  H61  QUN 31 
QUN H101 1H10 H  0 0 N N N 36.948 -36.158 6.406  1.058  0.112  -5.500 H101 QUN 32 
QUN H121 1H12 H  0 0 N N N 39.303 -39.548 4.687  -3.068 0.481  -4.532 H121 QUN 33 
QUN H131 1H13 H  0 0 N N N 41.063 -37.917 3.846  -2.610 0.404  -2.144 H131 QUN 34 
QUN H141 1H14 H  0 0 N N N 43.629 -30.452 5.569  5.017  -0.389 3.381  H141 QUN 35 
QUN H142 2H14 H  0 0 N N N 43.278 -28.731 5.190  4.968  -1.255 1.826  H142 QUN 36 
QUN H143 3H14 H  0 0 N N N 44.596 -29.591 4.324  5.133  0.517  1.853  H143 QUN 37 
QUN HN21 1HN2 H  0 0 N N N 43.138 -35.717 3.989  -1.976 0.575  -0.534 HN21 QUN 38 
QUN H151 1H15 H  0 0 N N N 43.623 -36.352 1.635  -0.492 -1.689 0.450  H151 QUN 39 
QUN H161 1H16 H  0 0 N N N 43.441 -33.436 1.627  -3.205 -1.210 -0.860 H161 QUN 40 
QUN H162 2H16 H  0 0 N N N 44.863 -34.530 1.541  -1.767 -1.939 -1.614 H162 QUN 41 
QUN H163 3H16 H  0 0 N N N 44.152 -34.105 3.135  -2.623 -2.801 -0.313 H163 QUN 42 
QUN H171 1H17 H  0 0 N N N 41.346 -34.457 1.391  -2.355 -2.137 2.024  H171 QUN 43 
QUN H172 2H17 H  0 0 N N N 41.353 -36.275 0.967  -3.081 -0.565 1.613  H172 QUN 44 
QUN H181 1H18 H  0 0 N N N 42.966 -35.667 -0.892 -1.043 0.588  2.429  H181 QUN 45 
QUN H182 2H18 H  0 0 N N N 42.845 -34.026 -0.464 -0.318 -0.983 2.840  H182 QUN 46 
QUN H191 1H19 H  0 0 N N N 40.501 -34.051 -0.389 -2.136 -1.432 4.438  H191 QUN 47 
QUN H192 2H19 H  0 0 N N N 40.522 -35.896 -0.848 -2.929 0.097  3.992  H192 QUN 48 
QUN H201 1H20 H  0 0 N N N 39.041 -34.306 -3.496 -2.328 2.026  4.876  H201 QUN 49 
QUN H202 2H20 H  0 0 N N N 38.860 -33.909 -1.657 -0.937 1.934  3.770  H202 QUN 50 
QUN H211 1H21 H  0 0 N N N 40.929 -36.379 -3.318 -1.453 0.871  7.078  H211 QUN 51 
QUN H212 2H21 H  0 0 N N N 42.430 -35.384 -3.250 -2.845 0.089  6.291  H212 QUN 52 
QUN H221 1H22 H  0 0 N N N 37.537 -35.793 -1.761 -0.544 3.607  5.557  H221 QUN 53 
QUN H222 2H22 H  0 0 N N N 39.123 -36.629 -1.649 -0.786 2.346  6.791  H222 QUN 54 
QUN H223 3H22 H  0 0 N N N 38.330 -36.418 -3.247 0.605  2.254  5.685  H223 QUN 55 
QUN H231 1H23 H  0 0 N N N 40.073 -35.210 -5.197 -1.773 -1.441 7.917  H231 QUN 56 
QUN H232 2H23 H  0 0 N N N 41.833 -35.079 -5.530 -1.612 -2.064 6.257  H232 QUN 57 
QUN H233 3H23 H  0 0 N N N 40.953 -33.697 -4.793 -0.226 -1.280 7.053  H233 QUN 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 
QUN C1  C2   DOUB Y N 1  
QUN C1  C6   SING Y N 2  
QUN C1  O    SING N N 3  
QUN C2  C3   SING Y N 4  
QUN C2  H21  SING N N 5  
QUN C3  C4   DOUB Y N 6  
QUN C3  H31  SING N N 7  
QUN C4  C5   SING Y N 8  
QUN C4  N1   SING Y N 9  
QUN C5  C6   DOUB Y N 10 
QUN C5  C9   SING Y N 11 
QUN C6  H61  SING N N 12 
QUN N1  C7   DOUB Y N 13 
QUN C7  C8   SING Y N 14 
QUN C7  C10  SING Y N 15 
QUN C8  C9   DOUB Y N 16 
QUN C8  C13  SING Y N 17 
QUN C9  N2   SING N N 18 
QUN C10 C11  DOUB Y N 19 
QUN C10 H101 SING N N 20 
QUN C11 C12  SING Y N 21 
QUN C11 CL   SING N N 22 
QUN C12 C13  DOUB Y N 23 
QUN C12 H121 SING N N 24 
QUN C13 H131 SING N N 25 
QUN O   C14  SING N N 26 
QUN C14 H141 SING N N 27 
QUN C14 H142 SING N N 28 
QUN C14 H143 SING N N 29 
QUN N2  C15  SING N N 30 
QUN N2  HN21 SING N N 31 
QUN C15 C16  SING N N 32 
QUN C15 C17  SING N N 33 
QUN C15 H151 SING N N 34 
QUN C16 H161 SING N N 35 
QUN C16 H162 SING N N 36 
QUN C16 H163 SING N N 37 
QUN C17 C18  SING N N 38 
QUN C17 H171 SING N N 39 
QUN C17 H172 SING N N 40 
QUN C18 C19  SING N N 41 
QUN C18 H181 SING N N 42 
QUN C18 H182 SING N N 43 
QUN C19 N3   SING N N 44 
QUN C19 H191 SING N N 45 
QUN C19 H192 SING N N 46 
QUN N3  C20  SING N N 47 
QUN N3  C21  SING N N 48 
QUN C20 C22  SING N N 49 
QUN C20 H201 SING N N 50 
QUN C20 H202 SING N N 51 
QUN C21 C23  SING N N 52 
QUN C21 H211 SING N N 53 
QUN C21 H212 SING N N 54 
QUN C22 H221 SING N N 55 
QUN C22 H222 SING N N 56 
QUN C22 H223 SING N N 57 
QUN C23 H231 SING N N 58 
QUN C23 H232 SING N N 59 
QUN C23 H233 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 
QUN SMILES           ACDLabs              10.04 Clc2ccc1c(c3c(nc1c2)ccc(OC)c3)NC(C)CCCN(CC)CC                                                                                                                    
QUN InChI            InChI                1.02b InChI=1/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)/t16-/m1/s1/f/h25H 
QUN InChIKey         InChI                1.02b GPKJTRJOBQGKQK-GRXIUPKXDG                                                                                                                                        
QUN SMILES_CANONICAL CACTVS               3.341 CCN(CC)CCC[C@@H](C)Nc1c2ccc(Cl)cc2nc3ccc(OC)cc13                                                                                                                 
QUN SMILES           CACTVS               3.341 CCN(CC)CCC[CH](C)Nc1c2ccc(Cl)cc2nc3ccc(OC)cc13                                                                                                                   
QUN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCN(CC)CCC[C@@H](C)Nc1c2ccc(cc2nc3c1cc(cc3)OC)Cl                                                                                                                 
QUN SMILES           "OpenEye OEToolkits" 1.5.0 CCN(CC)CCCC(C)Nc1c2ccc(cc2nc3c1cc(cc3)OC)Cl                                                                                                                      
# 
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 
QUN "SYSTEMATIC NAME" ACDLabs              10.04 (4R)-N~4~-(6-chloro-2-methoxyacridin-9-yl)-N~1~,N~1~-diethylpentane-1,4-diamine 
QUN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4R)-N'-(6-chloro-2-methoxy-acridin-9-yl)-N,N-diethyl-pentane-1,4-diamine"     
# 
