data_QUM
# 
_chem_comp.id                                    QUM 
_chem_comp.name                                  "QUINACRINE MUSTARD" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H28 Cl3 N3 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         N-{(1S)-4-[BIS(2-CHLOROETHYL)AMINO]-1-METHYLBUTYL}-N-(6-CHLORO-2-METHOXY-9-ACRIDINYL)AMINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-04-04 
_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                        468.847 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     QUM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1GXF 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
QUM C2   C2   C  0 1 Y N N 23.759 13.555 -2.319 -4.250 1.798  -0.359 C2   QUM 1  
QUM C3   C3   C  0 1 Y N N 23.620 13.194 -0.963 -5.487 1.359  -0.828 C3   QUM 2  
QUM C4   C4   C  0 1 Y N N 22.648 12.337 -0.584 -6.334 0.634  0.009  C4   QUM 3  
QUM C11  C11  C  0 1 Y N N 21.766 11.794 -1.547 -5.952 0.340  1.324  C11  QUM 4  
QUM C12  C12  C  0 1 Y N N 21.900 12.150 -2.907 -4.705 0.785  1.792  C12  QUM 5  
QUM C1   C1   C  0 1 Y N N 22.931 13.054 -3.273 -3.856 1.514  0.949  C1   QUM 6  
QUM N10  N10  N  0 1 Y N N 20.800 10.930 -1.113 -6.798 -0.386 2.168  N10  QUM 7  
QUM C14  C14  C  0 1 Y N N 19.911 10.363 -1.966 -6.482 -0.716 3.492  C14  QUM 8  
QUM C13  C13  C  0 1 Y N N 19.993 10.684 -3.343 -5.255 -0.314 4.053  C13  QUM 9  
QUM C9   C9   C  0 1 Y N N 20.987 11.578 -3.858 -4.303 0.470  3.197  C9   QUM 10 
QUM C5   C5   C  0 1 Y N N 18.931 9.474  -1.457 -7.390 -1.449 4.269  C5   QUM 11 
QUM C6   C6   C  0 1 Y N N 18.052 8.913  -2.340 -7.086 -1.781 5.587  C6   QUM 12 
QUM C7   C7   C  0 1 Y N N 18.114 9.221  -3.697 -5.872 -1.383 6.140  C7   QUM 13 
QUM C8   C8   C  0 1 Y N N 19.042 10.063 -4.196 -4.957 -0.652 5.379  C8   QUM 14 
QUM N18  N18  N  0 1 N N N 21.023 11.838 -5.164 -3.152 0.887  3.619  N18  QUM 15 
QUM C19  C19  C  0 1 N N S 21.745 12.574 -6.143 -2.386 1.628  2.630  C19  QUM 16 
QUM C20  C20  C  0 1 N N N 22.825 13.411 -5.461 -1.085 2.079  3.281  C20  QUM 17 
QUM C21  C21  C  0 1 N N N 22.390 11.537 -7.107 -2.117 0.725  1.420  C21  QUM 18 
QUM C22  C22  C  0 1 N N N 23.618 10.829 -6.530 -1.245 1.416  0.363  C22  QUM 19 
QUM C23  C23  C  0 1 N N N 23.486 9.319  -6.445 -0.921 0.511  -0.829 C23  QUM 20 
QUM N24  N24  N  0 1 N N N 24.612 8.627  -5.812 -0.184 -0.679 -0.425 N24  QUM 21 
QUM C27  C27  C  0 1 N N N 25.239 7.594  -6.673 1.084  -0.311 0.208  C27  QUM 22 
QUM C25  C25  C  0 1 N N N 25.524 9.682  -5.193 0.059  -1.551 -1.576 C25  QUM 23 
QUM C28  C28  C  0 1 N N N 24.974 7.808  -8.138 1.854  -1.517 0.719  C28  QUM 24 
QUM C26  C26  C  0 1 N N N 25.425 9.785  -3.753 -1.227 -2.083 -2.186 C26  QUM 25 
QUM CL1  CL1  CL 0 0 N N N 16.869 7.794  -1.772 -8.207 -2.683 6.530  CL1  QUM 26 
QUM O15  O15  O  0 1 N N N 24.786 14.444 -2.565 -3.425 2.506  -1.178 O15  QUM 27 
QUM C17  C17  C  0 1 N N N 25.912 13.935 -3.262 -3.890 2.763  -2.503 C17  QUM 28 
QUM CL2  CL2  CL 0 0 N Y N 23.758 9.339  -3.237 -0.894 -3.142 -3.579 CL2  QUM 29 
QUM CL3  CL3  CL 0 0 N Y N ?      ?      ?      3.385  -1.031 1.487  CL3  QUM 30 
QUM H3   H3   H  0 1 N N N 24.308 13.613 -0.209 -5.797 1.579  -1.846 H3   QUM 31 
QUM H4   H4   H  0 1 N N N 22.542 12.060 0.478  -7.296 0.299  -0.371 H4   QUM 32 
QUM H1   H1   H  0 1 N N N 23.060 13.349 -4.328 -2.888 1.867  1.293  H1   QUM 33 
QUM H10  H10  H  0 1 N N N 20.746 10.705 -0.119 -7.689 -0.693 1.800  H10  QUM 34 
QUM H5   H5   H  0 1 N N N 18.880 9.242  -0.380 -8.338 -1.762 3.835  H5   QUM 35 
QUM H7   H7   H  0 1 N N N 17.383 8.763  -4.384 -5.621 -1.635 7.167  H7   QUM 36 
QUM H8   H8   H  0 1 N N N 19.063 10.272 -5.279 -4.026 -0.366 5.856  H8   QUM 37 
QUM H19  H19  H  0 1 N N N 21.050 13.238 -6.708 -2.957 2.511  2.319  H19  QUM 38 
QUM H201 1H20 H  0 0 N N N 23.391 13.988 -6.229 -0.494 1.223  3.625  H201 QUM 39 
QUM H202 2H20 H  0 0 N N N 23.496 12.792 -4.821 -1.288 2.710  4.153  H202 QUM 40 
QUM H203 3H20 H  0 0 N N N 22.406 14.069 -4.664 -0.475 2.656  2.579  H203 QUM 41 
QUM H211 1H21 H  0 0 N N N 22.636 12.012 -8.085 -3.069 0.417  0.972  H211 QUM 42 
QUM H212 2H21 H  0 0 N N N 21.632 10.792 -7.445 -1.609 -0.187 1.758  H212 QUM 43 
QUM H221 1H22 H  0 0 N N N 23.880 11.254 -5.533 -0.300 1.727  0.824  H221 QUM 44 
QUM H222 2H22 H  0 0 N N N 24.533 11.108 -7.102 -1.737 2.329  0.006  H222 QUM 45 
QUM H231 1H23 H  0 0 N N N 23.295 8.894  -7.458 -1.855 0.205  -1.312 H231 QUM 46 
QUM H232 2H23 H  0 0 N N N 22.533 9.046  -5.935 -0.335 1.065  -1.571 H232 QUM 47 
QUM H271 1H27 H  0 0 N N N 24.927 6.571  -6.358 1.670  0.257  -0.521 H271 QUM 48 
QUM H272 2H27 H  0 0 N N N 26.334 7.521  -6.473 0.839  0.356  1.041  H272 QUM 49 
QUM H251 1H25 H  0 0 N N N 25.348 10.676 -5.667 0.643  -0.985 -2.308 H251 QUM 50 
QUM H252 2H25 H  0 0 N N N 26.582 9.510  -5.499 0.675  -2.382 -1.219 H252 QUM 51 
QUM H281 1H28 H  0 0 N N N 25.445 7.032  -8.785 2.095  -2.211 -0.092 H281 QUM 52 
QUM H282 2H28 H  0 0 N N N 25.286 8.831  -8.453 1.268  -2.052 1.472  H282 QUM 53 
QUM H261 1H26 H  0 0 N N N 25.728 10.791 -3.380 -1.871 -1.270 -2.535 H261 QUM 54 
QUM H262 2H26 H  0 0 N N N 26.204 9.182  -3.232 -1.780 -2.676 -1.452 H262 QUM 55 
QUM H171 1H17 H  0 0 N N N 26.742 14.653 -3.461 -3.506 1.995  -3.179 H171 QUM 56 
QUM H172 2H17 H  0 0 N N N 25.581 13.470 -4.220 -3.549 3.750  -2.824 H172 QUM 57 
QUM H173 3H17 H  0 0 N N N 26.310 13.041 -2.728 -4.982 2.736  -2.508 H173 QUM 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 
QUM C2  C3   DOUB Y N 1  
QUM C2  C1   SING Y N 2  
QUM C2  O15  SING N N 3  
QUM C3  C4   SING Y N 4  
QUM C3  H3   SING N N 5  
QUM C4  C11  DOUB Y N 6  
QUM C4  H4   SING N N 7  
QUM C11 C12  SING Y N 8  
QUM C11 N10  SING Y N 9  
QUM C12 C1   DOUB Y N 10 
QUM C12 C9   SING Y N 11 
QUM C1  H1   SING N N 12 
QUM N10 C14  SING Y N 13 
QUM N10 H10  SING N N 14 
QUM C14 C13  DOUB Y N 15 
QUM C14 C5   SING Y N 16 
QUM C13 C9   SING Y N 17 
QUM C13 C8   SING Y N 18 
QUM C9  N18  DOUB N Z 19 
QUM C5  C6   DOUB Y N 20 
QUM C5  H5   SING N N 21 
QUM C6  C7   SING Y N 22 
QUM C6  CL1  SING N N 23 
QUM C7  C8   DOUB Y N 24 
QUM C7  H7   SING N N 25 
QUM C8  H8   SING N N 26 
QUM N18 C19  SING N N 27 
QUM C19 C20  SING N N 28 
QUM C19 C21  SING N N 29 
QUM C19 H19  SING N N 30 
QUM C20 H201 SING N N 31 
QUM C20 H202 SING N N 32 
QUM C20 H203 SING N N 33 
QUM C21 C22  SING N N 34 
QUM C21 H211 SING N N 35 
QUM C21 H212 SING N N 36 
QUM C22 C23  SING N N 37 
QUM C22 H221 SING N N 38 
QUM C22 H222 SING N N 39 
QUM C23 N24  SING N N 40 
QUM C23 H231 SING N N 41 
QUM C23 H232 SING N N 42 
QUM N24 C27  SING N N 43 
QUM N24 C25  SING N N 44 
QUM C27 C28  SING N N 45 
QUM C27 H271 SING N N 46 
QUM C27 H272 SING N N 47 
QUM C25 C26  SING N N 48 
QUM C25 H251 SING N N 49 
QUM C25 H252 SING N N 50 
QUM C28 CL3  SING N N 51 
QUM C28 H281 SING N N 52 
QUM C28 H282 SING N N 53 
QUM C26 CL2  SING N N 54 
QUM C26 H261 SING N N 55 
QUM C26 H262 SING N N 56 
QUM O15 C17  SING N N 57 
QUM C17 H171 SING N N 58 
QUM C17 H172 SING N N 59 
QUM C17 H173 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 
QUM SMILES           ACDLabs              10.04 ClCCN(CCCl)CCCC(/N=C2\c1c(ccc(OC)c1)Nc3c2ccc(Cl)c3)C                                                                                                                             
QUM InChI            InChI                1.02b InChI=1/C23H28Cl3N3O/c1-16(4-3-11-29(12-9-24)13-10-25)27-23-19-7-5-17(26)14-22(19)28-21-8-6-18(30-2)15-20(21)23/h5-8,14-16H,3-4,9-13H2,1-2H3,(H,27,28)/t16-/m0/s1/f/h28H/b27-23- 
QUM InChIKey         InChI                1.02b UKOBAUFLOGFCMV-UTOPCPNMDF                                                                                                                                                        
QUM SMILES_CANONICAL CACTVS               3.341 COc1ccc2Nc3cc(Cl)ccc3C(=N[C@@H](C)CCCN(CCCl)CCCl)c2c1                                                                                                                            
QUM SMILES           CACTVS               3.341 COc1ccc2Nc3cc(Cl)ccc3C(=N[CH](C)CCCN(CCCl)CCCl)c2c1                                                                                                                              
QUM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H](CCCN(CCCl)CCCl)/N=C\1/c2ccc(cc2Nc3c1cc(cc3)OC)Cl                                                                                                                         
QUM SMILES           "OpenEye OEToolkits" 1.5.0 CC(CCCN(CCCl)CCCl)N=C1c2ccc(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 
QUM "SYSTEMATIC NAME" ACDLabs              10.04 (4S)-N~1~,N~1~-bis(2-chloroethyl)-N~4~-[(9Z)-6-chloro-2-methoxyacridin-9(10H)-ylidene]pentane-1,4-diamine 
QUM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4S)-N,N-bis(2-chloroethyl)-4-[(6-chloro-2-methoxy-10H-acridin-9-ylidene)amino]pentan-1-amine             
# 
