data_8U2
#

_chem_comp.id                                   8U2
_chem_comp.name                                 "2-{1-[4-(12-Amino-3-chloro-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolin-9-yl)butyl]-1H-1,2,3-triazol-4-yl}-N-[4-hydroxy-3-methoxybenzyl]acetamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C32 H37 Cl N6 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2017-03-09
_chem_comp.pdbx_modified_date                   2021-10-01
_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                       589.128
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    8U2
_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       5NDS
_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
8U2  CAN  C1   C   0  1  N  N  N  -17.888  -11.184  39.458    8.529  -0.592   0.535  CAN  8U2   1  
8U2  CAM  C2   C   0  1  N  N  R  -18.253  -10.749  40.866    7.719  -0.168  -0.692  CAM  8U2   2  
8U2  CAS  C3   C   0  1  N  N  N  -18.833   -9.309  40.932    7.382  -1.429  -1.506  CAS  8U2   3  
8U2  CAH  C4   C   0  1  Y  N  N  -18.177  -11.738  41.895    6.415   0.451  -0.250  CAH  8U2   4  
8U2  CAI  C5   C   0  1  Y  N  N  -17.797  -11.442  43.150    5.781   1.319  -1.133  CAI  8U2   5  
8U2  NAL  N1   N   0  1  N  N  N  -17.434  -10.178  43.399    6.340   1.610  -2.368  NAL  8U2   6  
8U2  CAB  C6   C   0  1  Y  N  N  -17.709  -12.366  44.152    4.553   1.896  -0.740  CAB  8U2   7  
8U2  CAA  C7   C   0  1  Y  N  N  -17.306  -11.821  45.311    3.858   2.784  -1.572  CAA  8U2   8  
8U2  CAF  C8   C   0  1  Y  N  N  -17.162  -12.651  46.372    2.674   3.313  -1.153  CAF  8U2   9  
8U2  CAE  C9   C   0  1  Y  N  N  -17.481  -13.988  46.263    2.146   2.981   0.093  CAE  8U2  10  
8U2  CL1  CL1  CL  0  0  N  N  N  -17.257  -14.707  47.788    0.633   3.672   0.591  CL1  8U2  11  
8U2  CAD  C10  C   0  1  Y  N  N  -17.934  -14.597  45.073    2.798   2.122   0.926  CAD  8U2  12  
8U2  CAC  C11  C   0  1  Y  N  N  -18.051  -13.713  43.981    4.023   1.559   0.529  CAC  8U2  13  
8U2  NAJ  N2   N   0  1  Y  N  N  -18.479  -14.064  42.703    4.689   0.721   1.325  NAJ  8U2  14  
8U2  CAG  C12  C   0  1  Y  N  N  -18.543  -13.096  41.637    5.846   0.180   0.981  CAG  8U2  15  
8U2  CAP  C13  C   0  1  N  N  N  -18.986  -13.312  40.230    6.509  -0.714   1.997  CAP  8U2  16  
8U2  CAO  C14  C   0  1  N  N  S  -19.181  -11.835  39.706    7.659  -1.503   1.400  CAO  8U2  17  
8U2  CAQ  C15  C   0  1  N  N  N  -20.364  -10.984  39.645    7.184  -2.719   0.623  CAQ  8U2  18  
8U2  CAR  C16  C   0  1  N  N  R  -20.189   -9.666  40.337    6.457  -2.305  -0.655  CAR  8U2  19  
8U2  CAT  C17  C   0  1  N  N  N  -21.405   -8.846  40.547    5.197  -1.516  -0.293  CAT  8U2  20  
8U2  CAU  C18  C   0  1  N  N  N  -22.693   -9.786  40.510    3.959  -2.352  -0.623  CAU  8U2  21  
8U2  CAV  C19  C   0  1  N  N  N  -22.997  -10.455  41.885    2.707  -1.628  -0.123  CAV  8U2  22  
8U2  CAW  C20  C   0  1  N  N  N  -21.811  -11.323  42.370    1.462  -2.405  -0.556  CAW  8U2  23  
8U2  NAZ  N3   N   0  1  Y  N  N  -22.046  -12.889  42.286    0.263  -1.712  -0.077  NAZ  8U2  24  
8U2  CAX  C21  C   0  1  Y  N  N  -21.358  -14.022  41.920   -0.777  -1.307  -0.841  CAX  8U2  25  
8U2  NBA  N4   N   0  1  Y  N  N  -23.373  -13.445  42.808    0.016  -1.390   1.144  NBA  8U2  26  
8U2  NBB  N5   N   0  1  Y  N  N  -23.280  -14.812  42.686   -1.121  -0.793   1.224  NBB  8U2  27  
8U2  CAY  C22  C   0  1  Y  N  N  -22.119  -15.109  42.142   -1.657  -0.717   0.001  CAY  8U2  28  
8U2  CBC  C23  C   0  1  N  N  N  -21.676  -16.582  41.845   -2.982  -0.100  -0.366  CBC  8U2  29  
8U2  CBD  C24  C   0  1  N  N  N  -22.066  -16.916  40.382   -4.075  -0.725   0.463  CBD  8U2  30  
8U2  OBM  O1   O   0  1  N  N  N  -23.110  -16.439  39.903   -3.804  -1.587   1.272  OBM  8U2  31  
8U2  NBL  N6   N   0  1  N  N  N  -21.159  -17.715  39.743   -5.352  -0.326   0.305  NBL  8U2  32  
8U2  CBE  C25  C   0  1  N  N  N  -21.195  -18.303  38.374   -6.414  -0.934   1.110  CBE  8U2  33  
8U2  CBF  C26  C   0  1  Y  N  N  -20.806  -19.624  38.664   -7.739  -0.316   0.743  CBF  8U2  34  
8U2  CBK  C27  C   0  1  Y  N  N  -21.476  -20.700  38.098   -8.503  -0.872  -0.266  CBK  8U2  35  
8U2  CBG  C28  C   0  1  Y  N  N  -19.786  -19.882  39.612   -8.190   0.802   1.420  CBG  8U2  36  
8U2  CBH  C29  C   0  1  Y  N  N  -19.410  -21.191  39.950   -9.405   1.372   1.087  CBH  8U2  37  
8U2  CBI  C30  C   0  1  Y  N  N  -20.079  -22.289  39.374  -10.173   0.822   0.073  CBI  8U2  38  
8U2  OBN  O2   O   0  1  N  N  N  -19.755  -23.621  39.687  -11.368   1.382  -0.256  OBN  8U2  39  
8U2  CBJ  C31  C   0  1  Y  N  N  -21.113  -22.006  38.437   -9.722  -0.306  -0.605  CBJ  8U2  40  
8U2  OBO  O3   O   0  1  N  N  N  -21.792  -23.039  37.849  -10.474  -0.852  -1.597  OBO  8U2  41  
8U2  CBP  C32  C   0  1  N  N  N  -22.670  -23.666  38.824   -9.948  -2.009  -2.249  CBP  8U2  42  
8U2  H1   H1   H   0  1  N  N  N  -17.861  -10.403  38.684    9.420  -1.133   0.216  H1   8U2  43  
8U2  H2   H2   H   0  1  N  N  N  -17.011  -11.839  39.348    8.817   0.290   1.106  H2   8U2  44  
8U2  H3   H3   H   0  1  N  N  N  -17.232  -10.393  41.068    8.294   0.530  -1.300  H3   8U2  45  
8U2  H4   H4   H   0  1  N  N  N  -18.906   -8.926  41.960    6.877  -1.147  -2.430  H4   8U2  46  
8U2  H5   H5   H   0  1  N  N  N  -18.271   -8.594  40.313    8.297  -1.974  -1.737  H5   8U2  47  
8U2  H6   H6   H   0  1  N  N  N  -17.175  -10.088  44.361    7.184   1.206  -2.626  H6   8U2  48  
8U2  H7   H7   H   0  1  N  N  N  -16.655   -9.935  42.821    5.888   2.217  -2.974  H7   8U2  49  
8U2  H8   H8   H   0  1  N  N  N  -17.105  -10.763  45.394    4.259   3.048  -2.539  H8   8U2  50  
8U2  H9   H9   H   0  1  N  N  N  -16.795  -12.262  47.310    2.139   3.997  -1.795  H9   8U2  51  
8U2  H10  H10  H   0  1  N  N  N  -18.170  -15.649  45.005    2.375   1.874   1.888  H10  8U2  52  
8U2  H11  H11  H   0  1  N  N  N  -18.218  -13.843  39.648    6.887  -0.101   2.815  H11  8U2  53  
8U2  H12  H12  H   0  1  N  N  N  -19.930  -13.876  40.192    5.769  -1.411   2.392  H12  8U2  54  
8U2  H13  H13  H   0  1  N  N  N  -19.286  -12.160  38.660    8.275  -1.868   2.222  H13  8U2  55  
8U2  H14  H14  H   0  1  N  N  N  -20.602  -10.793  38.588    8.045  -3.335   0.361  H14  8U2  56  
8U2  H15  H15  H   0  1  N  N  N  -21.201  -11.517  40.119    6.506  -3.300   1.248  H15  8U2  57  
8U2  H16  H16  H   0  1  N  N  N  -19.955   -9.154  39.392    6.179  -3.195  -1.220  H16  8U2  58  
8U2  H17  H17  H   0  1  N  N  N  -21.345   -8.345  41.524    5.206  -1.286   0.772  H17  8U2  59  
8U2  H18  H18  H   0  1  N  N  N  -21.480   -8.090  39.751    5.172  -0.589  -0.865  H18  8U2  60  
8U2  H19  H19  H   0  1  N  N  N  -23.562   -9.179  40.215    3.891  -2.491  -1.702  H19  8U2  61  
8U2  H20  H20  H   0  1  N  N  N  -22.529  -10.577  39.764    4.036  -3.324  -0.136  H20  8U2  62  
8U2  H21  H21  H   0  1  N  N  N  -23.192   -9.669  42.629    2.735  -1.564   0.965  H21  8U2  63  
8U2  H22  H22  H   0  1  N  N  N  -23.888  -11.092  41.783    2.674  -0.624  -0.546  H22  8U2  64  
8U2  H23  H23  H   0  1  N  N  N  -20.934  -11.076  41.754    1.434  -2.470  -1.644  H23  8U2  65  
8U2  H24  H24  H   0  1  N  N  N  -21.606  -11.065  43.419    1.495  -3.409  -0.133  H24  8U2  66  
8U2  H25  H25  H   0  1  N  N  N  -20.357  -14.037  41.515   -0.884  -1.430  -1.909  H25  8U2  67  
8U2  H26  H26  H   0  1  N  N  N  -20.587  -16.677  41.972   -2.949   0.973  -0.174  H26  8U2  68  
8U2  H27  H27  H   0  1  N  N  N  -22.187  -17.271  42.534   -3.183  -0.273  -1.423  H27  8U2  69  
8U2  H28  H28  H   0  1  N  N  N  -20.344  -17.940  40.278   -5.569   0.363  -0.343  H28  8U2  70  
8U2  H29  H29  H   0  1  N  N  N  -22.204  -18.261  37.938   -6.448  -2.006   0.918  H29  8U2  71  
8U2  H30  H30  H   0  1  N  N  N  -20.483  -17.807  37.698   -6.213  -0.760   2.167  H30  8U2  72  
8U2  H31  H31  H   0  1  N  N  N  -22.278  -20.528  37.395   -8.150  -1.748  -0.790  H31  8U2  73  
8U2  H32  H32  H   0  1  N  N  N  -19.285  -19.051  40.086   -7.592   1.231   2.210  H32  8U2  74  
8U2  H33  H33  H   0  1  N  N  N  -18.607  -21.357  40.653   -9.755   2.245   1.617  H33  8U2  75  
8U2  H34  H34  H   0  1  N  N  N  -20.318  -24.208  39.196  -11.309   2.063  -0.939  H34  8U2  76  
8U2  H35  H35  H   0  1  N  N  N  -23.214  -24.495  38.348  -10.645  -2.342  -3.018  H35  8U2  77  
8U2  H36  H36  H   0  1  N  N  N  -22.071  -24.053  39.661   -8.991  -1.763  -2.709  H36  8U2  78  
8U2  H37  H37  H   0  1  N  N  N  -23.389  -22.924  39.200   -9.806  -2.805  -1.518  H37  8U2  79  
#   #
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
8U2  CAN  CAM  SING  N  N   1  
8U2  CAN  CAO  SING  N  N   2  
8U2  CAM  CAS  SING  N  N   3  
8U2  CAM  CAH  SING  N  N   4  
8U2  CAS  CAR  SING  N  N   5  
8U2  CAH  CAI  DOUB  Y  N   6  
8U2  CAH  CAG  SING  Y  N   7  
8U2  CAI  NAL  SING  N  N   8  
8U2  CAI  CAB  SING  Y  N   9  
8U2  CAB  CAA  DOUB  Y  N  10  
8U2  CAB  CAC  SING  Y  N  11  
8U2  CAA  CAF  SING  Y  N  12  
8U2  CAF  CAE  DOUB  Y  N  13  
8U2  CAE  CL1  SING  N  N  14  
8U2  CAE  CAD  SING  Y  N  15  
8U2  CAD  CAC  DOUB  Y  N  16  
8U2  CAC  NAJ  SING  Y  N  17  
8U2  NAJ  CAG  DOUB  Y  N  18  
8U2  CAG  CAP  SING  N  N  19  
8U2  CAP  CAO  SING  N  N  20  
8U2  CAO  CAQ  SING  N  N  21  
8U2  CAQ  CAR  SING  N  N  22  
8U2  CAR  CAT  SING  N  N  23  
8U2  CAT  CAU  SING  N  N  24  
8U2  CAU  CAV  SING  N  N  25  
8U2  CAV  CAW  SING  N  N  26  
8U2  CAW  NAZ  SING  N  N  27  
8U2  NAZ  CAX  SING  Y  N  28  
8U2  NAZ  NBA  SING  Y  N  29  
8U2  CAX  CAY  DOUB  Y  N  30  
8U2  NBA  NBB  DOUB  Y  N  31  
8U2  NBB  CAY  SING  Y  N  32  
8U2  CAY  CBC  SING  N  N  33  
8U2  CBC  CBD  SING  N  N  34  
8U2  CBD  OBM  DOUB  N  N  35  
8U2  CBD  NBL  SING  N  N  36  
8U2  NBL  CBE  SING  N  N  37  
8U2  CBE  CBF  SING  N  N  38  
8U2  CBF  CBK  DOUB  Y  N  39  
8U2  CBF  CBG  SING  Y  N  40  
8U2  CBK  CBJ  SING  Y  N  41  
8U2  CBG  CBH  DOUB  Y  N  42  
8U2  CBH  CBI  SING  Y  N  43  
8U2  CBI  OBN  SING  N  N  44  
8U2  CBI  CBJ  DOUB  Y  N  45  
8U2  CBJ  OBO  SING  N  N  46  
8U2  OBO  CBP  SING  N  N  47  
8U2  CAN  H1   SING  N  N  48  
8U2  CAN  H2   SING  N  N  49  
8U2  CAM  H3   SING  N  N  50  
8U2  CAS  H4   SING  N  N  51  
8U2  CAS  H5   SING  N  N  52  
8U2  NAL  H6   SING  N  N  53  
8U2  NAL  H7   SING  N  N  54  
8U2  CAA  H8   SING  N  N  55  
8U2  CAF  H9   SING  N  N  56  
8U2  CAD  H10  SING  N  N  57  
8U2  CAP  H11  SING  N  N  58  
8U2  CAP  H12  SING  N  N  59  
8U2  CAO  H13  SING  N  N  60  
8U2  CAQ  H14  SING  N  N  61  
8U2  CAQ  H15  SING  N  N  62  
8U2  CAR  H16  SING  N  N  63  
8U2  CAT  H17  SING  N  N  64  
8U2  CAT  H18  SING  N  N  65  
8U2  CAU  H19  SING  N  N  66  
8U2  CAU  H20  SING  N  N  67  
8U2  CAV  H21  SING  N  N  68  
8U2  CAV  H22  SING  N  N  69  
8U2  CAW  H23  SING  N  N  70  
8U2  CAW  H24  SING  N  N  71  
8U2  CAX  H25  SING  N  N  72  
8U2  CBC  H26  SING  N  N  73  
8U2  CBC  H27  SING  N  N  74  
8U2  NBL  H28  SING  N  N  75  
8U2  CBE  H29  SING  N  N  76  
8U2  CBE  H30  SING  N  N  77  
8U2  CBK  H31  SING  N  N  78  
8U2  CBG  H32  SING  N  N  79  
8U2  CBH  H33  SING  N  N  80  
8U2  OBN  H34  SING  N  N  81  
8U2  CBP  H35  SING  N  N  82  
8U2  CBP  H36  SING  N  N  83  
8U2  CBP  H37  SING  N  N  84  
#   #
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
8U2  InChI             InChI                 1.03   "InChI=1S/C32H37ClN6O3/c1-42-29-14-20(5-8-28(29)40)17-35-30(41)16-24-18-39(38-37-24)9-3-2-4-19-10-21-12-22(11-19)31-27(13-21)36-26-15-23(33)6-7-25(26)32(31)34/h5-8,14-15,18-19,21-22,40H,2-4,9-13,16-17H2,1H3,(H2,34,36)(H,35,41)/t19-,21+,22-/m1/s1"  
8U2  InChIKey          InChI                 1.03   ACGLNWGWENJFEC-BAGYTPMASA-N  
8U2  SMILES_CANONICAL  CACTVS                3.385  "COc1cc(CNC(=O)Cc2cn(CCCC[C@@H]3C[C@H]4C[C@@H](C3)c5c(N)c6ccc(Cl)cc6nc5C4)nn2)ccc1O"  
8U2  SMILES            CACTVS                3.385  "COc1cc(CNC(=O)Cc2cn(CCCC[CH]3C[CH]4C[CH](C3)c5c(N)c6ccc(Cl)cc6nc5C4)nn2)ccc1O"  
8U2  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "COc1cc(ccc1O)CNC(=O)Cc2cn(nn2)CCCCC3CC4Cc5c(c(c6ccc(cc6n5)Cl)N)C(C4)C3"  
8U2  SMILES            "OpenEye OEToolkits"  2.0.6  "COc1cc(ccc1O)CNC(=O)Cc2cn(nn2)CCCCC3CC4Cc5c(c(c6ccc(cc6n5)Cl)N)C(C4)C3"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
8U2  "Create component"  2017-03-09  RCSB  
8U2  "Initial release"   2021-10-06  RCSB  
##
