data_E5S
# 
_chem_comp.id                                    E5S 
_chem_comp.name                                  "(3R)-3-({2-benzyl-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridin-3-yl}ethynyl)-1-azabicyclo[2.2.2]octan-3-ol" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H31 N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-06-13 
_chem_comp.pdbx_modified_date                    2014-06-13 
_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                        433.543 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     E5S 
_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        3WCC 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
E5S CAO CAO C 0 1 N N N 82.400 0.863  46.619 -4.623 1.578  -2.190 CAO E5S 1  
E5S CAM CAM C 0 1 N N N 83.383 1.202  45.465 -4.115 0.182  -1.821 CAM E5S 2  
E5S CBB CBB C 0 1 N N N 84.115 2.524  45.822 -4.685 -0.206 -0.451 CBB E5S 3  
E5S CAN CAN C 0 1 N N N 84.885 2.319  47.159 -6.217 -0.180 -0.533 CAN E5S 4  
E5S CAP CAP C 0 1 N N N 83.844 2.019  48.269 -6.666 1.227  -0.938 CAP E5S 5  
E5S NBD NBD N 0 1 N N N 82.459 1.931  47.687 -5.486 2.083  -1.114 NBD E5S 6  
E5S CAT CAT C 0 1 N N N 82.071 3.272  47.109 -4.738 2.214  0.145  CAT E5S 7  
E5S CBF CBF C 0 1 N N R 83.068 3.671  45.995 -4.233 0.836  0.580  CBF E5S 8  
E5S OAC OAC O 0 1 N N N 83.754 4.883  46.374 -4.777 0.510  1.861  OAC E5S 9  
E5S CAE CAE C 0 1 N N N 82.299 3.883  44.730 -2.763 0.848  0.657  CAE E5S 10 
E5S CAD CAD C 0 1 N N N 81.614 4.106  43.724 -1.591 0.858  0.718  CAD E5S 11 
E5S CAX CAX C 0 1 Y N N 80.726 4.380  42.608 -0.161 0.870  0.792  CAX E5S 12 
E5S CAK CAK C 0 1 Y N N 81.012 5.469  41.740 0.498  1.743  1.668  CAK E5S 13 
E5S CAL CAL C 0 1 Y N N 80.160 5.762  40.641 1.878  1.718  1.705  CAL E5S 14 
E5S CAY CAY C 0 1 Y N N 79.010 4.946  40.456 2.565  0.834  0.877  CAY E5S 15 
E5S NBE NBE N 0 1 N N N 78.136 5.145  39.458 3.953  0.804  0.909  NBE E5S 16 
E5S CAS CAS C 0 1 N N N 78.251 6.076  38.293 4.482  -0.196 -0.037 CAS E5S 17 
E5S CAR CAR C 0 1 N N N 76.895 4.318  39.277 4.520  2.125  0.564  CAR E5S 18 
E5S CBA CBA C 0 1 N N R 76.245 4.952  38.060 5.837  1.806  -0.187 CBA E5S 19 
E5S OAB OAB O 0 1 N N N 75.456 6.113  38.414 6.892  1.515  0.731  OAB E5S 20 
E5S CBC CBC C 0 1 N N S 77.482 5.243  37.277 5.438  0.544  -0.996 CBC E5S 21 
E5S OAV OAV O 0 1 N N N 77.152 5.916  36.040 6.587  -0.257 -1.280 OAV E5S 22 
E5S CAA CAA C 0 1 N N N 78.233 5.829  35.098 6.492  -0.999 -2.497 CAA E5S 23 
E5S NAU NAU N 0 1 Y N N 78.775 3.916  41.303 1.912  0.021  0.060  NAU E5S 24 
E5S CAZ CAZ C 0 1 Y N N 79.561 3.592  42.359 0.596  0.009  -0.002 CAZ E5S 25 
E5S CAQ CAQ C 0 1 N N N 79.191 2.472  43.139 -0.098 -0.936 -0.948 CAQ E5S 26 
E5S CAW CAW C 0 1 Y N N 79.553 1.284  42.447 -0.368 -2.242 -0.246 CAW E5S 27 
E5S CAI CAI C 0 1 Y N N 78.664 0.681  41.514 0.572  -3.254 -0.283 CAI E5S 28 
E5S CAG CAG C 0 1 Y N N 79.034 -0.497 40.813 0.326  -4.450 0.366  CAG E5S 29 
E5S CAF CAF C 0 1 Y N N 80.299 -1.097 41.027 -0.860 -4.634 1.051  CAF E5S 30 
E5S CAH CAH C 0 1 Y N N 81.193 -0.503 41.953 -1.800 -3.621 1.089  CAH E5S 31 
E5S CAJ CAJ C 0 1 Y N N 80.826 0.673  42.655 -1.554 -2.425 0.440  CAJ E5S 32 
E5S H1  H1  H 0 1 N N N 81.377 0.805  46.219 -3.775 2.250  -2.322 H1  E5S 33 
E5S H2  H2  H 0 1 N N N 82.677 -0.106 47.059 -5.193 1.525  -3.118 H2  E5S 34 
E5S H3  H3  H 0 1 N N N 82.825 1.328  44.526 -4.445 -0.537 -2.571 H3  E5S 35 
E5S H4  H4  H 0 1 N N N 84.116 0.390  45.350 -3.026 0.190  -1.774 H4  E5S 36 
E5S H5  H5  H 0 1 N N N 84.823 2.786  45.022 -4.331 -1.196 -0.164 H5  E5S 37 
E5S H6  H6  H 0 1 N N N 85.582 1.474  47.063 -6.555 -0.900 -1.279 H6  E5S 38 
E5S H7  H7  H 0 1 N N N 85.447 3.231  47.410 -6.639 -0.433 0.439  H7  E5S 39 
E5S H8  H8  H 0 1 N N N 84.095 1.063  48.751 -7.222 1.176  -1.874 H8  E5S 40 
E5S H9  H9  H 0 1 N N N 83.871 2.825  49.017 -7.305 1.643  -0.158 H9  E5S 41 
E5S H11 H11 H 0 1 N N N 82.089 4.032  47.904 -3.890 2.882  -0.004 H11 E5S 42 
E5S H12 H12 H 0 1 N N N 81.058 3.208  46.686 -5.392 2.623  0.915  H12 E5S 43 
E5S H13 H13 H 0 1 N N N 84.238 4.735  47.178 -4.530 1.128  2.562  H13 E5S 44 
E5S H14 H14 H 0 1 N N N 81.885 6.079  41.918 -0.060 2.419  2.299  H14 E5S 45 
E5S H15 H15 H 0 1 N N N 80.379 6.578  39.968 2.418  2.377  2.368  H15 E5S 46 
E5S H16 H16 H 0 1 N N N 79.296 6.239  37.992 5.025  -0.969 0.506  H16 E5S 47 
E5S H17 H17 H 0 1 N N N 77.769 7.046  38.486 3.662  -0.644 -0.600 H17 E5S 48 
E5S H18 H18 H 0 1 N N N 76.240 4.388  40.158 3.836  2.673  -0.084 H18 E5S 49 
E5S H19 H19 H 0 1 N N N 77.145 3.263  39.089 4.726  2.697  1.469  H19 E5S 50 
E5S H20 H20 H 0 1 N N N 75.630 4.206  37.535 6.115  2.625  -0.851 H20 E5S 51 
E5S H21 H21 H 0 1 N N N 74.692 5.839  38.908 7.110  2.246  1.325  H21 E5S 52 
E5S H22 H22 H 0 1 N N N 78.028 4.309  37.077 4.924  0.821  -1.916 H22 E5S 53 
E5S H23 H23 H 0 1 N N N 77.954 6.348  34.169 5.636  -1.672 -2.447 H23 E5S 54 
E5S H24 H24 H 0 1 N N N 79.131 6.300  35.526 6.365  -0.311 -3.333 H24 E5S 55 
E5S H25 H25 H 0 1 N N N 78.443 4.772  34.878 7.403  -1.581 -2.641 H25 E5S 56 
E5S H26 H26 H 0 1 N N N 79.713 2.508  44.107 -1.041 -0.497 -1.274 H26 E5S 57 
E5S H27 H27 H 0 1 N N N 78.104 2.483  43.308 0.538  -1.115 -1.815 H27 E5S 58 
E5S H28 H28 H 0 1 N N N 77.696 1.125  41.337 1.499  -3.111 -0.819 H28 E5S 59 
E5S H29 H29 H 0 1 N N N 78.344 -0.940 40.110 1.061  -5.241 0.336  H29 E5S 60 
E5S H30 H30 H 0 1 N N N 80.578 -1.993 40.493 -1.052 -5.568 1.558  H30 E5S 61 
E5S H31 H31 H 0 1 N N N 82.161 -0.950 42.125 -2.727 -3.764 1.625  H31 E5S 62 
E5S H32 H32 H 0 1 N N N 81.519 1.112  43.357 -2.287 -1.633 0.473  H32 E5S 63 
# 
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 
E5S CAA OAV SING N N 1  
E5S OAV CBC SING N N 2  
E5S CBC CBA SING N N 3  
E5S CBC CAS SING N N 4  
E5S CBA OAB SING N N 5  
E5S CBA CAR SING N N 6  
E5S CAS NBE SING N N 7  
E5S CAR NBE SING N N 8  
E5S NBE CAY SING N N 9  
E5S CAY CAL DOUB Y N 10 
E5S CAY NAU SING Y N 11 
E5S CAL CAK SING Y N 12 
E5S CAG CAF DOUB Y N 13 
E5S CAG CAI SING Y N 14 
E5S CAF CAH SING Y N 15 
E5S NAU CAZ DOUB Y N 16 
E5S CAI CAW DOUB Y N 17 
E5S CAK CAX DOUB Y N 18 
E5S CAH CAJ DOUB Y N 19 
E5S CAZ CAX SING Y N 20 
E5S CAZ CAQ SING N N 21 
E5S CAW CAJ SING Y N 22 
E5S CAW CAQ SING N N 23 
E5S CAX CAD SING N N 24 
E5S CAD CAE TRIP N N 25 
E5S CAE CBF SING N N 26 
E5S CAM CBB SING N N 27 
E5S CAM CAO SING N N 28 
E5S CBB CBF SING N N 29 
E5S CBB CAN SING N N 30 
E5S CBF OAC SING N N 31 
E5S CBF CAT SING N N 32 
E5S CAO NBD SING N N 33 
E5S CAT NBD SING N N 34 
E5S CAN CAP SING N N 35 
E5S NBD CAP SING N N 36 
E5S CAO H1  SING N N 37 
E5S CAO H2  SING N N 38 
E5S CAM H3  SING N N 39 
E5S CAM H4  SING N N 40 
E5S CBB H5  SING N N 41 
E5S CAN H6  SING N N 42 
E5S CAN H7  SING N N 43 
E5S CAP H8  SING N N 44 
E5S CAP H9  SING N N 45 
E5S CAT H11 SING N N 46 
E5S CAT H12 SING N N 47 
E5S OAC H13 SING N N 48 
E5S CAK H14 SING N N 49 
E5S CAL H15 SING N N 50 
E5S CAS H16 SING N N 51 
E5S CAS H17 SING N N 52 
E5S CAR H18 SING N N 53 
E5S CAR H19 SING N N 54 
E5S CBA H20 SING N N 55 
E5S OAB H21 SING N N 56 
E5S CBC H22 SING N N 57 
E5S CAA H23 SING N N 58 
E5S CAA H24 SING N N 59 
E5S CAA H25 SING N N 60 
E5S CAQ H26 SING N N 61 
E5S CAQ H27 SING N N 62 
E5S CAI H28 SING N N 63 
E5S CAG H29 SING N N 64 
E5S CAF H30 SING N N 65 
E5S CAH H31 SING N N 66 
E5S CAJ H32 SING N N 67 
# 
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 
E5S SMILES           ACDLabs              12.01 "OC5(C#Cc1ccc(nc1Cc2ccccc2)N3CC(O)C(OC)C3)C4CCN(CC4)C5"                                                                                                                                
E5S InChI            InChI                1.03  "InChI=1S/C26H31N3O3/c1-32-24-17-29(16-23(24)30)25-8-7-20(22(27-25)15-19-5-3-2-4-6-19)9-12-26(31)18-28-13-10-21(26)11-14-28/h2-8,21,23-24,30-31H,10-11,13-18H2,1H3/t23-,24+,26-/m1/s1" 
E5S InChIKey         InChI                1.03  NDEOTZXSBKCQLS-RMTZWNOUSA-N                                                                                                                                                            
E5S SMILES_CANONICAL CACTVS               3.370 "CO[C@H]1CN(C[C@H]1O)c2ccc(C#C[C@@]3(O)CN4CCC3CC4)c(Cc5ccccc5)n2"                                                                                                                      
E5S SMILES           CACTVS               3.370 "CO[CH]1CN(C[CH]1O)c2ccc(C#C[C]3(O)CN4CCC3CC4)c(Cc5ccccc5)n2"                                                                                                                          
E5S SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CO[C@H]1CN(C[C@H]1O)c2ccc(c(n2)Cc3ccccc3)C#C[C@]4(CN5CCC4CC5)O"                                                                                                                       
E5S SMILES           "OpenEye OEToolkits" 1.7.6 "COC1CN(CC1O)c2ccc(c(n2)Cc3ccccc3)C#CC4(CN5CCC4CC5)O"                                                                                                                                  
# 
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 
E5S "SYSTEMATIC NAME" ACDLabs              12.01 "(3R)-3-({2-benzyl-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridin-3-yl}ethynyl)-1-azabicyclo[2.2.2]octan-3-ol"             
E5S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(3R)-3-[2-[6-[(3S,4R)-3-methoxy-4-oxidanyl-pyrrolidin-1-yl]-2-(phenylmethyl)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
E5S "Create component" 2013-06-13 PDBJ 
E5S "Initial release"  2014-06-18 RCSB 
# 
