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                   2021-03-13
_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  Y  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  N  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  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"  
NCI  InChI             InChI                 1.03   "InChI=1S/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"  
NCI  InChIKey          InChI                 1.03   ZWPUGYBFVBXUSX-FQLXRVMXSA-N  
#   #
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
NCI  "Create component"      2008-10-02  RCSB  
NCI  "Modify aromatic_flag"  2011-06-04  RCSB  
NCI  "Modify descriptor"     2011-06-04  RCSB  
NCI  "Modify synonyms"       2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     NCI
_pdbx_chem_comp_synonyms.name        "N,N'-acridine-3,6-diylbis{3-[(2R)-2-ethylpiperidin-1-yl]propanamide}"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
