data_368
# 
_chem_comp.id                                    368 
_chem_comp.name                                  "(1R)-2-{[AMINO(IMINO)METHYL]AMINO}-1-{4-[(4R)-4-(HYDROXYMETHYL)-1,3,2-DIOXABOROLAN-2-YL]PHENYL}ETHYL NICOTINATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H21 B N4 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-05-20 
_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                        384.194 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     368 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1ZLR 
_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 
368 C01  C01  C 0 1 Y N N 8.911  72.030 84.770 -2.910 0.536  0.430  C01  368 1  
368 C02  C02  C 0 1 Y N N 9.900  71.300 84.030 -2.090 -0.107 -0.496 C02  368 2  
368 C03  C03  C 0 1 Y N N 9.869  71.260 82.610 -0.722 0.059  -0.435 C03  368 3  
368 C04  C04  C 0 1 Y N N 8.855  71.944 81.878 -0.162 0.853  0.550  C04  368 4  
368 C05  C05  C 0 1 Y N N 7.863  72.685 82.616 -0.971 1.494  1.472  C05  368 5  
368 C06  C06  C 0 1 Y N N 7.893  72.725 84.040 -2.341 1.340  1.417  C06  368 6  
368 B07  B07  B 0 1 N N N 8.972  72.049 86.292 -4.468 0.356  0.362  B07  368 7  
368 O08  O08  O 0 1 N N N 8.746  70.736 86.828 -5.408 0.957  1.247  O08  368 8  
368 C09  C09  C 0 1 N N N 7.806  70.841 87.886 -6.720 0.508  0.852  C09  368 9  
368 C10  C10  C 0 1 N N R 6.997  72.087 87.505 -6.418 -0.783 0.050  C10  368 10 
368 O11  O11  O 0 1 N N N 7.977  72.904 86.896 -5.170 -0.432 -0.600 O11  368 11 
368 C12  C12  C 0 1 N N R 8.871  71.848 80.349 1.334  1.026  0.616  C12  368 12 
368 C13  C13  C 0 1 N N N 9.968  72.657 79.645 1.760  2.146  -0.335 C13  368 13 
368 NP4  NP4  N 0 1 N N N 11.198 71.852 79.627 3.214  2.314  -0.271 NP4  368 14 
368 C15  C15  C 0 1 N N N 12.149 71.852 78.688 3.830  3.270  -1.045 C15  368 15 
368 NP6  NP6  N 0 1 N N N 13.440 71.800 79.032 5.194  3.427  -0.985 NP6  368 16 
368 NP7  NP7  N 0 1 N N N 11.799 71.898 77.397 3.120  4.026  -1.834 NP7  368 17 
368 O18  O18  O 0 1 N N N 7.545  72.168 79.807 1.981  -0.213 0.224  O18  368 18 
368 C19  C19  C 0 1 N N N 6.546  71.231 79.803 3.182  -0.538 0.741  C19  368 19 
368 O20  O20  O 0 1 N N N 6.662  70.100 80.234 3.723  0.206  1.534  O20  368 20 
368 C21  C21  C 0 1 Y N N 5.285  71.787 79.199 3.841  -1.799 0.343  C21  368 21 
368 C22  C22  C 0 1 Y N N 5.140  73.170 78.796 5.090  -2.148 0.873  C22  368 22 
368 C23  C23  C 0 1 Y N N 3.911  73.626 78.227 5.664  -3.339 0.467  C23  368 23 
368 C24  C24  C 0 1 Y N N 2.862  72.695 78.076 4.994  -4.140 -0.440 C24  368 24 
368 NP5  NP5  N 0 1 Y N N 2.982  71.387 78.453 3.818  -3.785 -0.923 NP5  368 25 
368 C26  C26  C 0 1 Y N N 4.158  70.950 78.997 3.228  -2.665 -0.564 C26  368 26 
368 C27  C27  C 0 1 N N N 6.400  72.751 88.752 -7.513 -1.057 -0.983 C27  368 27 
368 O28  O28  O 0 1 N N N 6.092  74.095 88.481 -7.264 -2.310 -1.621 O28  368 28 
368 H02  H02  H 0 1 N N N 10.680 70.773 84.560 -2.526 -0.731 -1.263 H02  368 29 
368 H03  H03  H 0 1 N N N 10.625 70.703 82.077 -0.086 -0.439 -1.152 H03  368 30 
368 H05  H05  H 0 1 N N N 7.088  73.216 82.083 -0.529 2.116  2.236  H05  368 31 
368 H06  H06  H 0 1 N N N 7.140  73.285 84.575 -2.971 1.840  2.137  H06  368 32 
368 H091 1H09 H 0 0 N N N 8.278  70.920 88.876 -7.331 0.284  1.726  H091 368 33 
368 H092 2H09 H 0 0 N N N 7.168  69.947 87.954 -7.208 1.250  0.219  H092 368 34 
368 H10  H10  H 0 1 N N N 6.136  71.882 86.852 -6.290 -1.636 0.716  H10  368 35 
368 H12  H12  H 0 1 N N N 9.128  70.801 80.129 1.626  1.283  1.634  H12  368 36 
368 H131 1H13 H 0 0 N N N 10.143 73.602 80.180 1.273  3.077  -0.041 H131 368 37 
368 H132 2H13 H 0 0 N N N 9.658  72.889 78.615 1.468  1.890  -1.353 H132 368 38 
368 HP4  HP4  H 0 1 N N N 11.339 71.237 80.403 3.742  1.751  0.316  HP4  368 39 
368 HP61 1HP6 H 0 0 N N N 13.778 71.759 79.972 5.629  4.101  -1.530 HP61 368 40 
368 HP62 2HP6 H 0 0 N N N 14.021 71.808 78.218 5.722  2.867  -0.394 HP62 368 41 
368 HP7  HP7  H 0 1 N N N 10.804 71.931 77.304 2.157  3.915  -1.876 HP7  368 42 
368 H22  H22  H 0 1 N N N 5.962  73.858 78.926 5.592  -1.503 1.580  H22  368 43 
368 H23  H23  H 0 1 N N N 3.789  74.655 77.921 6.626  -3.641 0.854  H23  368 44 
368 H24  H24  H 0 1 N N N 1.929  73.029 77.646 5.440  -5.071 -0.758 H24  368 45 
368 H26  H26  H 0 1 N N N 4.233  69.913 79.288 2.265  -2.409 -0.981 H26  368 46 
368 H271 1H27 H 0 0 N N N 7.133  72.707 89.571 -8.482 -1.089 -0.485 H271 368 47 
368 H272 2H27 H 0 0 N N N 5.482  72.219 89.042 -7.515 -0.263 -1.730 H272 368 48 
368 H28  H28  H 0 1 N N N 6.022  74.575 89.298 -7.975 -2.444 -2.262 H28  368 49 
# 
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 
368 C01 C02  SING Y N 1  
368 C01 C06  DOUB Y N 2  
368 C01 B07  SING N N 3  
368 C02 C03  DOUB Y N 4  
368 C02 H02  SING N N 5  
368 C03 C04  SING Y N 6  
368 C03 H03  SING N N 7  
368 C04 C05  DOUB Y N 8  
368 C04 C12  SING N N 9  
368 C05 C06  SING Y N 10 
368 C05 H05  SING N N 11 
368 C06 H06  SING N N 12 
368 B07 O08  SING N N 13 
368 B07 O11  SING N N 14 
368 O08 C09  SING N N 15 
368 C09 C10  SING N N 16 
368 C09 H091 SING N N 17 
368 C09 H092 SING N N 18 
368 C10 O11  SING N N 19 
368 C10 C27  SING N N 20 
368 C10 H10  SING N N 21 
368 C12 C13  SING N N 22 
368 C12 O18  SING N N 23 
368 C12 H12  SING N N 24 
368 C13 NP4  SING N N 25 
368 C13 H131 SING N N 26 
368 C13 H132 SING N N 27 
368 NP4 C15  SING N N 28 
368 NP4 HP4  SING N N 29 
368 C15 NP6  SING N N 30 
368 C15 NP7  DOUB N Z 31 
368 NP6 HP61 SING N N 32 
368 NP6 HP62 SING N N 33 
368 NP7 HP7  SING N N 34 
368 O18 C19  SING N N 35 
368 C19 O20  DOUB N N 36 
368 C19 C21  SING N N 37 
368 C21 C22  DOUB Y N 38 
368 C21 C26  SING Y N 39 
368 C22 C23  SING Y N 40 
368 C22 H22  SING N N 41 
368 C23 C24  DOUB Y N 42 
368 C23 H23  SING N N 43 
368 C24 NP5  SING Y N 44 
368 C24 H24  SING N N 45 
368 NP5 C26  DOUB Y N 46 
368 C26 H26  SING N N 47 
368 C27 O28  SING N N 48 
368 C27 H271 SING N N 49 
368 C27 H272 SING N N 50 
368 O28 H28  SING N N 51 
# 
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 
368 SMILES           ACDLabs              10.04 O=C(OC(c1ccc(cc1)B2OCC(O2)CO)CNC(=[N@H])N)c3cccnc3                                                                                                                                 
368 InChI            InChI                1.02b InChI=1/C18H21BN4O5/c20-18(21)23-9-16(27-17(25)13-2-1-7-22-8-13)12-3-5-14(6-4-12)19-26-11-15(10-24)28-19/h1-8,15-16,24H,9-11H2,(H4,20,21,23)/t15-,16+/m1/s1/f/h20,23H,21H2/b20-18- 
368 InChIKey         InChI                1.02b HGLWHYRZHMOCMC-CIVQUGLZDZ                                                                                                                                                          
368 SMILES_CANONICAL CACTVS               3.341 NC(=N)NC[C@H](OC(=O)c1cccnc1)c2ccc(cc2)B3OC[C@@H](CO)O3                                                                                                                            
368 SMILES           CACTVS               3.341 NC(=N)NC[CH](OC(=O)c1cccnc1)c2ccc(cc2)B3OC[CH](CO)O3                                                                                                                               
368 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/N)\NC[C@@H](c1ccc(cc1)B2OC[C@H](O2)CO)OC(=O)c3cccnc3                                                                                                                      
368 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)NCC(c1ccc(cc1)B2OCC(O2)CO)OC(=O)c3cccnc3                                                                                                                                  
# 
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 
368 "SYSTEMATIC NAME" ACDLabs              10.04 "(1R)-2-carbamimidamido-1-{4-[(4R)-4-(hydroxymethyl)-1,3,2-dioxaborolan-2-yl]phenyl}ethyl pyridine-3-carboxylate"   
368 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R)-2-carbamimidamido-1-[4-[(4R)-4-(hydroxymethyl)-1,3,2-dioxaborolan-2-yl]phenyl]ethyl] pyridine-3-carboxylate" 
# 
