data_NCI
# 
_chem_comp.id                                    NCI 
_chem_comp.name                                  3,6-Bis{3-[(2R)-(2-ethylpiperidino)]propionamido}acridine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C33 H45 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N,N'-acridine-3,6-diylbis{3-[(2R)-2-ethylpiperidin-1-yl]propanamide}" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-10-02 
_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                        543.743 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     NCI 
_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        3EQW 
_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 
NCI O39  O39  O 0 1 N N N 12.815 -2.855 -11.189 -5.882  -1.106 0.308  O39  NCI 1  
NCI C9   C9   C 0 1 N N N 14.002 -3.108 -11.240 -5.879  -0.066 -0.317 C9   NCI 2  
NCI C10  C10  C 0 1 N N N 14.858 -2.580 -12.377 -7.155  0.720  -0.476 C10  NCI 3  
NCI C13  C13  C 0 1 N N N 14.042 -2.314 -13.638 -8.295  -0.006 0.241  C13  NCI 4  
NCI N16  N16  N 0 1 N N N 14.722 -1.404 -14.569 -9.538  0.761  0.086  N16  NCI 5  
NCI C18  C18  C 0 1 N N R 15.295 -2.090 -15.751 -10.681 0.030  0.647  C18  NCI 6  
NCI C20  C20  C 0 1 N N N 16.313 -3.131 -15.311 -10.748 -1.366 0.024  C20  NCI 7  
NCI C23  C23  C 0 1 N N N 17.682 -2.767 -15.862 -10.821 -1.242 -1.499 C23  NCI 8  
NCI C27  C27  C 0 1 N N N 16.080 -1.085 -16.601 -11.974 0.788  0.339  C27  NCI 9  
NCI C30  C30  C 0 1 N N N 15.243 0.107  -17.022 -11.894 2.191  0.947  C30  NCI 10 
NCI C33  C33  C 0 1 N N N 14.634 0.754  -15.789 -10.668 2.914  0.383  C33  NCI 11 
NCI C36  C36  C 0 1 N N N 13.866 -0.271 -14.956 -9.413  2.094  0.689  C36  NCI 12 
NCI N7   N7   N 0 1 N N N 14.621 -3.863 -10.324 -4.735  0.388  -0.865 N7   NCI 13 
NCI C6   C6   C 0 1 Y N N 14.096 -4.414 -9.137  -3.535  -0.289 -0.636 C6   NCI 14 
NCI C40  C40  C 0 1 Y N N 14.968 -5.148 -8.318  -3.545  -1.687 -0.544 C40  NCI 15 
NCI C42  C42  C 0 1 Y N N 14.539 -5.672 -7.099  -2.406  -2.390 -0.322 C42  NCI 16 
NCI C4   C4   C 0 1 Y N N 12.787 -4.181 -8.707  -2.375  0.430  -0.512 C4   NCI 17 
NCI C3   C3   C 0 1 Y N N 12.346 -4.704 -7.488  -1.160  -0.244 -0.281 C3   NCI 18 
NCI N1   N1   N 0 1 Y N N 11.064 -4.490 -7.084  -0.020  0.430  -0.157 N1   NCI 19 
NCI C44  C44  C 0 1 Y N N 13.228 -5.445 -6.680  -1.180  -1.707 -0.180 C44  NCI 20 
NCI C45  C45  C 0 1 Y N N 12.787 -5.960 -5.464  0.011   -2.399 0.049  C45  NCI 21 
NCI C2   C2   C 0 1 Y N N 11.474 -5.736 -5.069  1.185   -1.655 0.179  C2   NCI 22 
NCI C47  C47  C 0 1 Y N N 11.011 -6.251 -3.859  2.426   -2.283 0.413  C47  NCI 23 
NCI C49  C49  C 0 1 Y N N 9.688  -5.995 -3.485  3.548   -1.530 0.535  C49  NCI 24 
NCI C51  C51  C 0 1 Y N N 8.811  -5.260 -4.307  3.505   -0.133 0.434  C51  NCI 25 
NCI C85  C85  C 0 1 Y N N 9.289  -4.743 -5.517  2.330   0.535  0.209  C85  NCI 26 
NCI C87  C87  C 0 1 Y N N 10.613 -4.985 -5.905  1.134   -0.194 0.061  C87  NCI 27 
NCI N52  N52  N 0 1 N N N 7.497  -4.995 -3.834  4.689   0.596  0.567  N52  NCI 28 
NCI C54  C54  C 0 1 N N N 6.510  -4.340 -4.471  5.849   0.088  0.106  C54  NCI 29 
NCI O84  O84  O 0 1 N N N 6.575  -3.955 -5.631  5.851   -0.958 -0.507 O84  NCI 30 
NCI C55  C55  C 0 1 N N N 5.232  -4.124 -3.679  7.143   0.821  0.352  C55  NCI 31 
NCI C58  C58  C 0 1 N N N 4.176  -3.361 -4.498  8.299   0.036  -0.271 C58  NCI 32 
NCI N61  N61  N 0 1 N N N 3.628  -2.217 -3.743  9.560   0.750  -0.032 N61  NCI 33 
NCI C63  C63  C 0 1 N N R 2.407  -1.666 -4.373  10.714  -0.083 -0.396 C63  NCI 34 
NCI C77  C77  C 0 1 N N N 2.704  -1.357 -5.836  10.627  -1.423 0.338  C77  NCI 35 
NCI C80  C80  C 0 1 N N N 1.474  -1.451 -6.721  10.529  -1.174 1.844  C80  NCI 36 
NCI C66  C66  C 0 1 N N N 2.086  -0.320 -3.720  12.007  0.633  0.002  C66  NCI 37 
NCI C69  C69  C 0 1 N N N 1.922  -0.470 -2.215  12.080  1.982  -0.719 C69  NCI 38 
NCI C72  C72  C 0 1 N N N 3.228  -0.999 -1.633  10.843  2.810  -0.361 C72  NCI 39 
NCI C75  C75  C 0 1 N N N 3.535  -2.348 -2.283  9.584   2.032  -0.748 C75  NCI 40 
NCI H10  H10  H 0 1 N N N 15.324 -1.637 -12.056 -7.026  1.712  -0.042 H10  NCI 41 
NCI H10A H10A H 0 0 N N N 15.612 -3.344 -12.616 -7.393  0.815  -1.535 H10A NCI 42 
NCI H13  H13  H 0 1 N N N 13.871 -3.272 -14.150 -8.423  -0.998 -0.193 H13  NCI 43 
NCI H13A H13A H 0 0 N N N 13.099 -1.837 -13.332 -8.056  -0.101 1.300  H13A NCI 44 
NCI H18  H18  H 0 1 N N N 14.463 -2.545 -16.308 -10.561 -0.060 1.726  H18  NCI 45 
NCI H20  H20  H 0 1 N N N 16.356 -3.160 -14.212 -9.858  -1.931 0.300  H20  NCI 46 
NCI H20A H20A H 0 0 N N N 16.015 -4.119 -15.693 -11.635 -1.885 0.389  H20A NCI 47 
NCI H23  H23  H 0 1 N N N 17.626 -2.679 -16.957 -10.778 -2.235 -1.947 H23  NCI 48 
NCI H23A H23A H 0 0 N N N 18.006 -1.807 -15.433 -11.757 -0.757 -1.780 H23A NCI 49 
NCI H23B H23B H 0 0 N N N 18.405 -3.551 -15.594 -9.982  -0.646 -1.856 H23B NCI 50 
NCI H27  H27  H 0 1 N N N 16.931 -0.719 -16.008 -12.102 0.866  -0.740 H27  NCI 51 
NCI H27A H27A H 0 0 N N N 16.405 -1.604 -17.515 -12.821 0.253  0.769  H27A NCI 52 
NCI H30  H30  H 0 1 N N N 15.879 0.837  -17.544 -12.795 2.750  0.694  H30  NCI 53 
NCI H30A H30A H 0 0 N N N 14.441 -0.226 -17.697 -11.805 2.114  2.031  H30A NCI 54 
NCI H33  H33  H 0 1 N N N 15.440 1.182  -15.175 -10.776 3.026  -0.696 H33  NCI 55 
NCI H33A H33A H 0 0 N N N 13.934 1.539  -16.113 -10.582 3.898  0.844  H33A NCI 56 
NCI H36  H36  H 0 1 N N N 13.023 -0.651 -15.552 -9.298  1.995  1.769  H36  NCI 57 
NCI H36A H36A H 0 0 N N N 13.512 0.224  -14.039 -8.539  2.599  0.276  H36A NCI 58 
NCI HN7  HN7  H 0 1 N N N 15.584 -4.063 -10.506 -4.744  1.184  -1.418 HN7  NCI 59 
NCI H40  H40  H 0 1 N N N 15.987 -5.309 -8.637  -4.480  -2.216 -0.651 H40  NCI 60 
NCI H42  H42  H 0 1 N N N 15.215 -6.248 -6.485  -2.438  -3.467 -0.255 H42  NCI 61 
NCI H4   H4   H 0 1 N N N 12.115 -3.596 -9.317  -2.392  1.507  -0.591 H4   NCI 62 
NCI H45  H45  H 0 1 N N N 13.458 -6.527 -4.835  0.023   -3.477 0.124  H45  NCI 63 
NCI H47  H47  H 0 1 N N N 11.660 -6.835 -3.224  2.483   -3.359 0.494  H47  NCI 64 
NCI H49  H49  H 0 1 N N N 9.328  -6.372 -2.539  4.495   -2.018 0.714  H49  NCI 65 
NCI H85  H85  H 0 1 N N N 8.638  -4.159 -6.150  2.323   1.612  0.136  H85  NCI 66 
NCI HN52 HN52 H 0 0 N N N 7.281  -5.336 -2.919  4.676   1.468  0.992  HN52 NCI 67 
NCI H55  H55  H 0 1 N N N 4.820  -5.105 -3.399  7.091   1.811  -0.100 H55  NCI 68 
NCI H55A H55A H 0 0 N N N 5.476  -3.525 -2.789  7.306   0.919  1.425  H55A NCI 69 
NCI H58  H58  H 0 1 N N N 4.645  -2.985 -5.419  8.351   -0.955 0.181  H58  NCI 70 
NCI H58A H58A H 0 0 N N N 3.351  -4.051 -4.727  8.135   -0.062 -1.344 H58A NCI 71 
NCI H63  H63  H 0 1 N N N 1.584  -2.388 -4.264  10.711  -0.257 -1.472 H63  NCI 72 
NCI H77  H77  H 0 1 N N N 3.099  -0.332 -5.900  9.743   -1.965 0.001  H77  NCI 73 
NCI H77A H77A H 0 0 N N N 3.428  -2.104 -6.193  11.518  -2.013 0.124  H77A NCI 74 
NCI H80  H80  H 0 1 N N N 0.571  -1.474 -6.093  9.595   -0.659 2.068  H80  NCI 75 
NCI H80A H80A H 0 0 N N N 1.435  -0.577 -7.388  10.554  -2.128 2.372  H80A NCI 76 
NCI H80B H80B H 0 0 N N N 1.525  -2.370 -7.323  11.370  -0.559 2.166  H80B NCI 77 
NCI H66  H66  H 0 1 N N N 2.909  0.381  -3.922  12.017  0.795  1.079  H66  NCI 78 
NCI H66A H66A H 0 0 N N N 1.143  0.058  -4.140  12.863  0.021  -0.283 H66A NCI 79 
NCI H69  H69  H 0 1 N N N 1.684  0.506  -1.768  12.978  2.514  -0.406 H69  NCI 80 
NCI H69A H69A H 0 0 N N N 1.103  -1.170 -1.995  12.109  1.818  -1.796 H69A NCI 81 
NCI H72  H72  H 0 1 N N N 4.043  -0.290 -1.841  10.835  3.007  0.711  H72  NCI 82 
NCI H72A H72A H 0 0 N N N 3.135  -1.118 -0.543  10.868  3.755  -0.904 H72A NCI 83 
NCI H75  H75  H 0 1 N N N 2.729  -3.055 -2.038  9.586   1.848  -1.822 H75  NCI 84 
NCI H75A H75A H 0 0 N N N 4.500  -2.712 -1.900  8.701   2.613  -0.481 H75A NCI 85 
# 
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 
NCI C9  O39  DOUB N N 1  
NCI C10 C9   SING N N 2  
NCI C9  N7   SING N N 3  
NCI C13 C10  SING N N 4  
NCI C10 H10  SING N N 5  
NCI C10 H10A SING N N 6  
NCI N16 C13  SING N N 7  
NCI C13 H13  SING N N 8  
NCI C13 H13A SING N N 9  
NCI C18 N16  SING N N 10 
NCI C36 N16  SING N N 11 
NCI C27 C18  SING N N 12 
NCI C18 C20  SING N N 13 
NCI C18 H18  SING N N 14 
NCI C23 C20  SING N N 15 
NCI C20 H20  SING N N 16 
NCI C20 H20A SING N N 17 
NCI C23 H23  SING N N 18 
NCI C23 H23A SING N N 19 
NCI C23 H23B SING N N 20 
NCI C30 C27  SING N N 21 
NCI C27 H27  SING N N 22 
NCI C27 H27A SING N N 23 
NCI C30 C33  SING N N 24 
NCI C30 H30  SING N N 25 
NCI C30 H30A SING N N 26 
NCI C33 C36  SING N N 27 
NCI C33 H33  SING N N 28 
NCI C33 H33A SING N N 29 
NCI C36 H36  SING N N 30 
NCI C36 H36A SING N N 31 
NCI N7  C6   SING N N 32 
NCI N7  HN7  SING N N 33 
NCI C6  C4   DOUB Y N 34 
NCI C6  C40  SING Y N 35 
NCI C40 C42  DOUB Y N 36 
NCI C40 H40  SING N N 37 
NCI C42 C44  SING Y N 38 
NCI C42 H42  SING N N 39 
NCI C4  C3   SING Y N 40 
NCI C4  H4   SING N N 41 
NCI C3  N1   DOUB Y N 42 
NCI C3  C44  SING Y N 43 
NCI N1  C87  SING Y N 44 
NCI C44 C45  DOUB Y N 45 
NCI C45 C2   SING Y N 46 
NCI C45 H45  SING N N 47 
NCI C87 C2   SING Y N 48 
NCI C2  C47  DOUB Y N 49 
NCI C47 C49  SING N N 50 
NCI C47 H47  SING N N 51 
NCI C51 C49  DOUB Y N 52 
NCI C49 H49  SING N N 53 
NCI C85 C51  SING Y N 54 
NCI C51 N52  SING N N 55 
NCI C87 C85  DOUB Y N 56 
NCI C85 H85  SING Y N 57 
NCI C54 N52  SING N N 58 
NCI N52 HN52 SING N N 59 
NCI O84 C54  DOUB N N 60 
NCI C54 C55  SING N N 61 
NCI C58 C55  SING N N 62 
NCI C55 H55  SING N N 63 
NCI C55 H55A SING N N 64 
NCI C58 N61  SING N N 65 
NCI C58 H58  SING N N 66 
NCI C58 H58A SING N N 67 
NCI C63 N61  SING N N 68 
NCI N61 C75  SING N N 69 
NCI C77 C63  SING N N 70 
NCI C63 C66  SING N N 71 
NCI C63 H63  SING N N 72 
NCI C80 C77  SING N N 73 
NCI C77 H77  SING N N 74 
NCI C77 H77A SING N N 75 
NCI C80 H80  SING N N 76 
NCI C80 H80A SING N N 77 
NCI C80 H80B SING N N 78 
NCI C66 C69  SING N N 79 
NCI C66 H66  SING N N 80 
NCI C66 H66A SING N N 81 
NCI C69 C72  SING N N 82 
NCI C69 H69  SING N N 83 
NCI C69 H69A SING N N 84 
NCI C75 C72  SING N N 85 
NCI C72 H72  SING N N 86 
NCI C72 H72A SING N N 87 
NCI C75 H75  SING N N 88 
NCI C75 H75A SING N N 89 
# 
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 
NCI SMILES           ACDLabs              10.04 O=C(Nc3cc2nc1cc(ccc1cc2cc3)NC(=O)CCN4C(CCCC4)CC)CCN5C(CC)CCCC5 
NCI InChI            InChI                1.02b 
InChI=1/C33H45N5O2/c1-3-28-9-5-7-17-37(28)19-15-32(39)34-26-13-11-24-21-25-12-14-27(23-31(25)36-30(24)22-26)35-33(40)16-20-38-18-8-6-10-29(38)4-2/h11-14,21-23,28-29H,3-10,15-20H2,1-2H3,(H,34,39)(H,35,40)/t28-,29-/m1/s1/f/h34-35H 
NCI InChIKey         InChI                1.02b ZWPUGYBFVBXUSX-DASMLCOGDS 
NCI SMILES_CANONICAL CACTVS               3.341 CC[C@@H]1CCCCN1CCC(=O)Nc2ccc3cc4ccc(NC(=O)CCN5CCCC[C@H]5CC)cc4nc3c2 
NCI SMILES           CACTVS               3.341 CC[CH]1CCCCN1CCC(=O)Nc2ccc3cc4ccc(NC(=O)CCN5CCCC[CH]5CC)cc4nc3c2 
NCI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H]1CCCC[N@]1CCC(=O)Nc2ccc3cc4ccc(cc4nc3c2)NC(=O)CC[N@@]5CCCC[C@H]5CC 
NCI SMILES           "OpenEye OEToolkits" 1.5.0 CCC1CCCCN1CCC(=O)Nc2ccc3cc4ccc(cc4nc3c2)NC(=O)CCN5CCCCC5CC 
# 
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 
NCI "SYSTEMATIC NAME" ACDLabs              10.04 "N,N'-acridine-3,6-diylbis{3-[(2R)-2-ethylpiperidin-1-yl]propanamide}"                                           
NCI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[(1S,2R)-2-ethylpiperidin-1-yl]-N-[6-[3-[(1S,2R)-2-ethylpiperidin-1-yl]propanoylamino]acridin-3-yl]propanamide 
# 
