data_CP0
# 
_chem_comp.id                                    CP0 
_chem_comp.name                                  
;(4S)-4,11-DIETHYL-4-HYDROXY-3,14-DIOXO-3,4,12,14-TETRAHYDRO-1H-PYRANO[3',4':6,7]INDOLIZINO[1,2-B]QUINOLIN-9-YL 1,4'-BIPIPERIDINE-1'-CARBOXYLATE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C33 H38 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "IRINOTECAN, CPT-11" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-02 
_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                        586.678 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CP0 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1U65 
_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 
CP0 N1   N1   N 0 1 Y N N -17.188 113.198 39.692 -10.202 -2.653 6.455  N1   CP0 1  
CP0 N4   N4   N 0 1 Y N N -14.792 114.665 41.913 -12.708 -4.016 4.263  N4   CP0 2  
CP0 O1   O1   O 0 1 N N N -22.393 109.692 38.469 -7.272  2.456  5.615  O1   CP0 3  
CP0 O2   O2   O 0 1 N N N -22.340 110.742 40.483 -5.878  0.645  5.244  O2   CP0 4  
CP0 O18  O18  O 0 1 N N N -13.147 115.667 43.335 -14.341 -4.874 2.869  O18  CP0 5  
CP0 O19  O19  O 0 1 N N N -10.634 116.617 39.758 -15.947 -7.203 6.016  O19  CP0 6  
CP0 O22  O22  O 0 1 N N N -10.253 116.594 37.536 -15.491 -8.116 8.016  O22  CP0 7  
CP0 O23  O23  O 0 1 N N N -12.075 114.316 37.606 -13.565 -6.383 8.509  O23  CP0 8  
CP0 C13  C13  C 0 1 Y N N -18.457 112.588 39.982 -9.164  -1.855 6.130  C13  CP0 9  
CP0 C10  C10  C 0 1 Y N N -21.051 111.355 40.403 -6.968  -0.184 5.531  C10  CP0 10 
CP0 C14  C14  C 0 1 Y N N -14.525 114.556 39.477 -12.726 -4.468 6.595  C14  CP0 11 
CP0 C6   C6   C 0 1 Y N N -16.858 113.631 42.147 -10.841 -2.661 4.111  C6   CP0 12 
CP0 C8   C8   C 0 1 Y N N -19.014 112.467 41.401 -8.918  -1.427 4.794  C8   CP0 13 
CP0 C7   C7   C 0 1 Y N N -18.154 113.019 42.488 -9.785  -1.848 3.773  C7   CP0 14 
CP0 C37  C37  C 0 1 N N N -22.999 109.990 39.426 -6.163  2.011  5.321  C37  CP0 15 
CP0 C3   C3   C 0 1 Y N N -15.268 114.287 40.596 -12.172 -3.878 5.533  C3   CP0 16 
CP0 C9   C9   C 0 1 Y N N -20.351 111.821 41.540 -7.822  -0.596 4.512  C9   CP0 17 
CP0 C12  C12  C 0 1 Y N N -19.175 112.097 38.746 -8.292  -1.425 7.124  C12  CP0 18 
CP0 C11  C11  C 0 1 Y N N -20.419 111.513 39.013 -7.203  -0.599 6.836  C11  CP0 19 
CP0 C2   C2   C 0 1 Y N N -16.511 113.655 40.739 -10.996 -3.024 5.442  C2   CP0 20 
CP0 C16  C16  C 0 1 Y N N -12.715 115.646 40.875 -14.465 -5.421 5.186  C16  CP0 21 
CP0 C15  C15  C 0 1 Y N N -13.222 115.250 39.606 -13.917 -5.282 6.406  C15  CP0 22 
CP0 C23  C23  C 0 1 Y N N -13.483 115.372 42.155 -13.845 -4.753 3.986  C23  CP0 23 
CP0 C17  C17  C 0 1 N N N -11.347 116.371 41.037 -15.707 -6.221 4.985  C17  CP0 24 
CP0 C5   C5   C 0 1 N N N -15.762 114.281 42.983 -11.915 -3.265 3.268  C5   CP0 25 
CP0 C21  C21  C 0 1 N N N -11.006 116.296 38.464 -15.354 -7.178 7.233  C21  CP0 26 
CP0 C28  C28  C 0 1 N N N -13.348 116.190 37.233 -15.492 -4.947 8.331  C28  CP0 27 
CP0 C20  C20  C 0 1 N N S -12.408 115.556 38.269 -14.569 -5.924 7.600  C20  CP0 28 
CP0 C31  C31  C 0 1 N N N -18.666 112.934 43.955 -9.606  -1.449 2.345  C31  CP0 29 
CP0 C32  C32  C 0 1 N N N -19.449 114.185 44.546 -10.344 -0.157 2.008  C32  CP0 30 
CP0 C33  C33  C 0 1 N N N -13.885 117.495 37.552 -16.108 -5.599 9.543  C33  CP0 31 
CP0 N2   N2   N 0 1 N N N -24.308 109.675 39.658 -5.050  2.804  5.027  N2   CP0 32 
CP0 N3   N3   N 0 1 N N N -25.918 105.827 38.985 -2.865  4.969  2.130  N3   CP0 33 
CP0 C25  C25  C 0 1 N N N -24.443 107.394 40.298 -3.230  2.878  3.366  C25  CP0 34 
CP0 C22  C22  C 0 1 N N N -25.712 109.806 39.126 -5.138  4.263  5.102  C22  CP0 35 
CP0 C24  C24  C 0 1 N N N -25.768 107.253 39.576 -3.262  4.411  3.422  C24  CP0 36 
CP0 C26  C26  C 0 1 N N N -24.246 108.832 40.841 -3.729  2.271  4.677  C26  CP0 37 
CP0 C29  C29  C 0 1 N N N -27.082 105.730 37.909 -2.893  6.438  2.173  C29  CP0 38 
CP0 C34  C34  C 0 1 N N N -26.859 104.457 37.148 -2.527  7.037  0.814  C34  CP0 39 
CP0 C35  C35  C 0 1 N N N -26.205 104.809 40.048 -1.537  4.474  1.742  C35  CP0 40 
CP0 C27  C27  C 0 1 N N N -26.335 103.352 39.528 -1.128  5.009  0.369  C27  CP0 41 
CP0 C30  C30  C 0 1 N N N -27.049 103.230 38.094 -1.172  6.532  0.332  C30  CP0 42 
CP0 C36  C36  C 0 1 N N N ?       ?       ?      -4.665  4.905  3.800  C36  CP0 43 
CP0 H23  H23  H 0 1 N N N -11.590 114.498 36.809 -12.959 -6.932 7.990  H23  CP0 44 
CP0 H14  H14  H 0 1 N N N -14.956 114.228 38.516 -12.311 -4.345 7.589  H14  CP0 45 
CP0 H9   H9   H 0 1 N N N -20.839 111.682 42.519 -7.617  -0.257 3.499  H9   CP0 46 
CP0 H12  H12  H 0 1 N N N -18.811 112.161 37.706 -8.451  -1.735 8.155  H12  CP0 47 
CP0 H11  H11  H 0 1 N N N -20.919 111.164 38.094 -6.543  -0.283 7.640  H11  CP0 48 
CP0 H171 1H17 H 0 0 N N N -10.692 115.815 41.748 -16.585 -5.569 4.928  H171 CP0 49 
CP0 H172 2H17 H 0 0 N N N -11.474 117.323 41.602 -15.647 -6.786 4.049  H172 CP0 50 
CP0 H51  1H5  H 0 1 N N N -15.347 113.653 43.806 -12.559 -2.516 2.798  H51  CP0 51 
CP0 H52  2H5  H 0 1 N N N -16.093 115.108 43.652 -11.528 -3.968 2.524  H52  CP0 52 
CP0 H281 1H28 H 0 0 N N N -12.839 116.227 36.241 -16.257 -4.631 7.629  H281 CP0 53 
CP0 H282 2H28 H 0 0 N N N -14.183 115.487 37.008 -14.898 -4.085 8.615  H282 CP0 54 
CP0 H311 1H31 H 0 0 N N N -19.295 112.021 44.069 -8.536  -1.325 2.114  H311 CP0 55 
CP0 H312 2H31 H 0 0 N N N -17.810 112.687 44.626 -9.958  -2.251 1.677  H312 CP0 56 
CP0 H321 1H32 H 0 0 N N N -19.815 114.124 45.597 -11.421 -0.263 2.181  H321 CP0 57 
CP0 H322 2H32 H 0 0 N N N -18.819 115.097 44.431 -10.194 0.110  0.957  H322 CP0 58 
CP0 H323 3H32 H 0 0 N N N -20.304 114.431 43.874 -9.985  0.673  2.624  H323 CP0 59 
CP0 H331 1H33 H 0 0 N N N -14.567 117.955 36.799 -16.706 -6.474 9.268  H331 CP0 60 
CP0 H332 2H33 H 0 0 N N N -14.393 117.457 38.543 -15.344 -5.926 10.256 H332 CP0 61 
CP0 H333 3H33 H 0 0 N N N -13.049 118.197 37.776 -16.762 -4.881 10.046 H333 CP0 62 
CP0 H251 1H25 H 0 0 N N N -24.334 106.633 41.106 -2.212  2.526  3.164  H251 CP0 63 
CP0 H252 2H25 H 0 0 N N N -23.590 107.080 39.651 -3.865  2.522  2.543  H252 CP0 64 
CP0 H221 1H22 H 0 0 N N N -26.599 110.058 39.751 -4.509  4.585  5.940  H221 CP0 65 
CP0 H222 2H22 H 0 0 N N N -26.061 110.639 38.473 -6.163  4.578  5.320  H222 CP0 66 
CP0 H24  H24  H 0 1 N N N -26.318 108.213 39.709 -2.546  4.757  4.177  H24  CP0 67 
CP0 H261 1H26 H 0 0 N N N -23.321 108.967 41.449 -3.746  1.181  4.591  H261 CP0 68 
CP0 H262 2H26 H 0 0 N N N -24.964 109.118 41.643 -3.049  2.524  5.499  H262 CP0 69 
CP0 H291 1H29 H 0 0 N N N -28.101 105.803 38.355 -2.206  6.817  2.942  H291 CP0 70 
CP0 H292 2H29 H 0 0 N N N -27.151 106.628 37.252 -3.900  6.778  2.441  H292 CP0 71 
CP0 H341 1H34 H 0 0 N N N -27.507 104.391 36.243 -2.511  8.131  0.884  H341 CP0 72 
CP0 H342 2H34 H 0 0 N N N -25.867 104.442 36.638 -3.298  6.775  0.078  H342 CP0 73 
CP0 H351 1H35 H 0 0 N N N -25.438 104.865 40.855 -1.554  3.378  1.695  H351 CP0 74 
CP0 H352 2H35 H 0 0 N N N -27.114 105.097 40.625 -0.784  4.757  2.489  H352 CP0 75 
CP0 H271 1H27 H 0 0 N N N -25.338 102.851 39.512 -1.800  4.604  -0.399 H271 CP0 76 
CP0 H272 2H27 H 0 0 N N N -26.855 102.713 40.279 -0.117  4.663  0.124  H272 CP0 77 
CP0 H301 1H30 H 0 0 N N N -28.134 103.011 38.224 -0.978  6.889  -0.686 H301 CP0 78 
CP0 H302 2H30 H 0 0 N N N -26.720 102.296 37.580 -0.381  6.937  0.973  H302 CP0 79 
CP0 H11A 1H1  H 0 0 N N N 0.234   -1.023  -0.375 -5.376  4.656  3.000  H11A CP0 80 
CP0 H12A 2H1  H 0 0 N N N 0.251   -1.022  -0.367 -4.669  5.996  3.907  H12A CP0 81 
# 
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 
CP0 N1  C13  SING Y N 1  
CP0 N1  C2   DOUB Y N 2  
CP0 N4  C3   SING Y N 3  
CP0 N4  C23  SING Y N 4  
CP0 N4  C5   SING N N 5  
CP0 O1  C37  DOUB N N 6  
CP0 O2  C10  SING N N 7  
CP0 O2  C37  SING N N 8  
CP0 O18 C23  DOUB N N 9  
CP0 O19 C17  SING N N 10 
CP0 O19 C21  SING N N 11 
CP0 O22 C21  DOUB N N 12 
CP0 O23 C20  SING N N 13 
CP0 O23 H23  SING N N 14 
CP0 C13 C8   DOUB Y N 15 
CP0 C13 C12  SING Y N 16 
CP0 C10 C9   DOUB Y N 17 
CP0 C10 C11  SING Y N 18 
CP0 C14 C3   DOUB Y N 19 
CP0 C14 C15  SING Y N 20 
CP0 C14 H14  SING N N 21 
CP0 C6  C7   DOUB Y N 22 
CP0 C6  C2   SING Y N 23 
CP0 C6  C5   SING N N 24 
CP0 C8  C7   SING Y N 25 
CP0 C8  C9   SING Y N 26 
CP0 C7  C31  SING N N 27 
CP0 C37 N2   SING N N 28 
CP0 C3  C2   SING N N 29 
CP0 C9  H9   SING N N 30 
CP0 C12 C11  DOUB Y N 31 
CP0 C12 H12  SING N N 32 
CP0 C11 H11  SING N N 33 
CP0 C16 C15  DOUB Y N 34 
CP0 C16 C23  SING Y N 35 
CP0 C16 C17  SING N N 36 
CP0 C15 C20  SING N N 37 
CP0 C17 H171 SING N N 38 
CP0 C17 H172 SING N N 39 
CP0 C5  H51  SING N N 40 
CP0 C5  H52  SING N N 41 
CP0 C21 C20  SING N N 42 
CP0 C28 C20  SING N N 43 
CP0 C28 C33  SING N N 44 
CP0 C28 H281 SING N N 45 
CP0 C28 H282 SING N N 46 
CP0 C31 C32  SING N N 47 
CP0 C31 H311 SING N N 48 
CP0 C31 H312 SING N N 49 
CP0 C32 H321 SING N N 50 
CP0 C32 H322 SING N N 51 
CP0 C32 H323 SING N N 52 
CP0 C33 H331 SING N N 53 
CP0 C33 H332 SING N N 54 
CP0 C33 H333 SING N N 55 
CP0 N2  C22  SING N N 56 
CP0 N2  C26  SING N N 57 
CP0 N3  C24  SING N N 58 
CP0 N3  C29  SING N N 59 
CP0 N3  C35  SING N N 60 
CP0 C25 C24  SING N N 61 
CP0 C25 C26  SING N N 62 
CP0 C25 H251 SING N N 63 
CP0 C25 H252 SING N N 64 
CP0 C22 C36  SING N N 65 
CP0 C22 H221 SING N N 66 
CP0 C22 H222 SING N N 67 
CP0 C24 C36  SING N N 68 
CP0 C24 H24  SING N N 69 
CP0 C26 H261 SING N N 70 
CP0 C26 H262 SING N N 71 
CP0 C29 C34  SING N N 72 
CP0 C29 H291 SING N N 73 
CP0 C29 H292 SING N N 74 
CP0 C34 C30  SING N N 75 
CP0 C34 H341 SING N N 76 
CP0 C34 H342 SING N N 77 
CP0 C35 C27  SING N N 78 
CP0 C35 H351 SING N N 79 
CP0 C35 H352 SING N N 80 
CP0 C27 C30  SING N N 81 
CP0 C27 H271 SING N N 82 
CP0 C27 H272 SING N N 83 
CP0 C30 H301 SING N N 84 
CP0 C30 H302 SING N N 85 
CP0 C36 H11A SING N N 86 
CP0 C36 H12A SING N N 87 
# 
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 
CP0 SMILES           ACDLabs              10.04 O=C7OCC=6C(=O)N2C(c1nc5c(c(c1C2)CC)cc(OC(=O)N4CCC(N3CCCCC3)CC4)cc5)=CC=6C7(O)CC 
CP0 InChI            InChI                1.02b 
InChI=1/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1 
CP0 InChIKey         InChI                1.02b UWKQSNNFCGGAFS-XIFFEERXBR 
CP0 SMILES_CANONICAL CACTVS               3.341 CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(OC(=O)N6CCC(CC6)N7CCCCC7)cc15)[C@@](O)(CC)C(=O)OC4 
CP0 SMILES           CACTVS               3.341 CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(OC(=O)N6CCC(CC6)N7CCCCC7)cc15)[C](O)(CC)C(=O)OC4 
CP0 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1c2cc(ccc2nc3c1CN4C3=CC5=C(C4=O)COC(=O)[C@@]5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7 
CP0 SMILES           "OpenEye OEToolkits" 1.5.0 CCc1c2cc(ccc2nc3c1CN4C3=CC5=C(C4=O)COC(=O)C5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7 
# 
_pdbx_chem_comp_identifier.comp_id           CP0 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        
;(4S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 1,4'-bipiperidine-1'-carboxylate
;
# 
