data_12C
# 
_chem_comp.id                                    12C 
_chem_comp.name                                  4-[(3S)-1-AZABICYCLO[2.2.2]OCT-3-YLAMINO]-3-(1H-BENZIMIDAZOL-2-YL)-6-CHLOROQUINOLIN-2(1H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 Cl N5 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-03-27 
_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                        419.907 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     12C 
_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        ? 
_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 
12C C1   C1   C  0 1 Y N N 4.919  -1.474 46.017 -2.067 1.087  -0.141 C1   12C 1  
12C C2   C2   C  0 1 Y N N 5.724  -2.323 45.228 -3.091 0.163  -0.366 C2   12C 2  
12C C3   C3   C  0 1 Y N N 7.050  -2.002 44.931 -4.405 0.564  -0.266 C3   12C 3  
12C CL   CL   CL 0 0 N N N 7.982  -3.080 43.971 -5.682 -0.577 -0.550 CL   12C 4  
12C C4   C4   C  0 1 Y N N 7.619  -0.819 45.408 -4.714 1.877  0.067  C4   12C 5  
12C C5   C5   C  0 1 Y N N 6.846  0.047  46.200 -3.715 2.798  0.296  C5   12C 6  
12C C6   C6   C  0 1 Y N N 5.511  -0.284 46.498 -2.381 2.415  0.195  C6   12C 7  
12C N1   N1   N  0 1 Y N N 4.761  0.587  47.301 -1.369 3.327  0.422  N1   12C 8  
12C C7   C7   C  0 1 Y N N 3.451  0.351  47.664 -0.074 2.980  0.329  C7   12C 9  
12C O1   O1   O  0 1 N N N 2.841  1.155  48.375 0.783  3.821  0.538  O1   12C 10 
12C C8   C8   C  0 1 Y N N 2.801  -0.905 47.148 0.318  1.662  -0.005 C8   12C 11 
12C C9   C9   C  0 1 Y N N 1.428  -1.221 47.490 1.746  1.316  -0.099 C9   12C 12 
12C C10  C10  C  0 1 Y N N 3.502  -1.781 46.362 -0.656 0.692  -0.246 C10  12C 13 
12C N2   N2   N  0 1 N N N 2.896  -2.940 45.868 -0.306 -0.596 -0.572 N2   12C 14 
12C C11  C11  C  0 1 N N S 2.812  -3.502 44.528 -0.737 -1.709 0.276  C11  12C 15 
12C N3   N3   N  0 1 Y N N 0.691  -2.272 47.133 2.744  1.872  0.659  N3   12C 16 
12C C12  C12  C  0 1 Y N N -0.541 -2.094 47.709 3.932  1.281  0.267  C12  12C 17 
12C C13  C13  C  0 1 Y N N -0.581 -0.905 48.435 3.600  0.362  -0.743 C13  12C 18 
12C N4   N4   N  0 1 Y N N 0.674  -0.369 48.281 2.256  0.425  -0.918 N4   12C 19 
12C C14  C14  C  0 1 Y N N -1.691 -2.913 47.650 5.253  1.427  0.662  C14  12C 20 
12C C15  C15  C  0 1 Y N N -2.847 -2.502 48.334 6.238  0.670  0.062  C15  12C 21 
12C C16  C16  C  0 1 Y N N -2.859 -1.300 49.060 5.916  -0.238 -0.936 C16  12C 22 
12C C17  C17  C  0 1 Y N N -1.721 -0.471 49.129 4.610  -0.397 -1.341 C17  12C 23 
12C C18  C18  C  0 1 N N N 1.417  -3.186 43.915 0.286  -1.932 1.389  C18  12C 24 
12C N5   N5   N  0 1 N N N 0.718  -4.495 43.542 0.855  -3.272 1.323  N5   12C 25 
12C C19  C19  C  0 1 N N N 1.540  -5.244 42.506 1.529  -3.458 0.046  C19  12C 26 
12C C20  C20  C  0 1 N N N 2.913  -5.570 43.113 0.557  -3.301 -1.124 C20  12C 27 
12C C21  C21  C  0 1 N N N 0.515  -5.369 44.776 -0.201 -4.263 1.476  C21  12C 28 
12C C22  C22  C  0 1 N N N 1.883  -5.698 45.382 -1.249 -4.138 0.364  C22  12C 29 
12C C23  C23  C  0 1 N N N 3.010  -5.040 44.564 -0.842 -2.988 -0.567 C23  12C 30 
12C H2   H2   H  0 1 N N N 5.305  -3.242 44.845 -2.854 -0.860 -0.622 H2   12C 31 
12C H4   H4   H  0 1 N N N 8.643  -0.572 45.170 -5.748 2.179  0.147  H4   12C 32 
12C H5   H5   H  0 1 N N N 7.275  0.963  46.579 -3.967 3.816  0.554  H5   12C 33 
12C HN1  HN1  H  0 1 N N N 5.199  1.424  47.628 -1.598 4.241  0.653  HN1  12C 34 
12C HN2  HN2  H  0 1 N N N 3.363  -3.663 46.377 0.227  -0.767 -1.364 HN2  12C 35 
12C H11  H11  H  0 1 N N N 3.606  -3.053 43.914 -1.709 -1.480 0.714  H11  12C 36 
12C HN3  HN3  H  0 1 N N N 0.979  -3.039 46.559 2.637  2.552  1.342  HN3  12C 37 
12C H14  H14  H  0 1 N N N -1.681 -3.837 47.090 5.511  2.133  1.438  H14  12C 38 
12C H15  H15  H  0 1 N N N -3.735 -3.116 48.301 7.266  0.785  0.370  H15  12C 39 
12C H16  H16  H  0 1 N N N -3.760 -1.004 49.577 6.696  -0.825 -1.399 H16  12C 40 
12C H17  H17  H  0 1 N N N -1.726 0.453  49.688 4.366  -1.107 -2.119 H17  12C 41 
12C H181 1H18 H  0 0 N N N 1.543  -2.567 43.014 1.087  -1.199 1.289  H181 12C 42 
12C H182 2H18 H  0 0 N N N 0.807  -2.641 44.651 -0.201 -1.798 2.354  H182 12C 43 
12C H191 1H19 H  0 0 N N N 1.665  -4.624 41.606 2.324  -2.718 -0.049 H191 12C 44 
12C H192 2H19 H  0 0 N N N 1.026  -6.176 42.226 1.967  -4.456 0.015  H192 12C 45 
12C H201 1H20 H  0 0 N N N 3.692  -5.086 42.506 0.886  -2.484 -1.765 H201 12C 46 
12C H202 2H20 H  0 0 N N N 3.053  -6.661 43.119 0.523  -4.228 -1.697 H202 12C 47 
12C H211 1H21 H  0 0 N N N 0.000  -6.299 44.493 0.237  -5.261 1.444  H211 12C 48 
12C H212 2H21 H  0 0 N N N -0.097 -4.830 45.514 -0.687 -4.119 2.441  H212 12C 49 
12C H221 1H22 H  0 0 N N N 2.025  -6.789 45.369 -2.225 -3.928 0.800  H221 12C 50 
12C H222 2H22 H  0 0 N N N 1.920  -5.320 46.414 -1.291 -5.069 -0.201 H222 12C 51 
12C H23  H23  H  0 1 N N N 3.984  -5.274 45.018 -1.560 -2.862 -1.378 H23  12C 52 
# 
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 
12C C1  C2   SING Y N 1  
12C C1  C6   DOUB Y N 2  
12C C1  C10  SING Y N 3  
12C C2  C3   DOUB Y N 4  
12C C2  H2   SING N N 5  
12C C3  CL   SING N N 6  
12C C3  C4   SING Y N 7  
12C C4  C5   DOUB Y N 8  
12C C4  H4   SING N N 9  
12C C5  C6   SING Y N 10 
12C C5  H5   SING N N 11 
12C C6  N1   SING Y N 12 
12C N1  C7   SING Y N 13 
12C N1  HN1  SING N N 14 
12C C7  O1   DOUB N N 15 
12C C7  C8   SING Y N 16 
12C C8  C9   SING N N 17 
12C C8  C10  DOUB Y N 18 
12C C9  N3   SING Y N 19 
12C C9  N4   DOUB Y N 20 
12C C10 N2   SING N N 21 
12C N2  C11  SING N N 22 
12C N2  HN2  SING N N 23 
12C C11 C18  SING N N 24 
12C C11 C23  SING N N 25 
12C C11 H11  SING N N 26 
12C N3  C12  SING Y N 27 
12C N3  HN3  SING N N 28 
12C C12 C13  SING Y N 29 
12C C12 C14  DOUB Y N 30 
12C C13 N4   SING Y N 31 
12C C13 C17  DOUB Y N 32 
12C C14 C15  SING Y N 33 
12C C14 H14  SING N N 34 
12C C15 C16  DOUB Y N 35 
12C C15 H15  SING N N 36 
12C C16 C17  SING Y N 37 
12C C16 H16  SING N N 38 
12C C17 H17  SING N N 39 
12C C18 N5   SING N N 40 
12C C18 H181 SING N N 41 
12C C18 H182 SING N N 42 
12C N5  C19  SING N N 43 
12C N5  C21  SING N N 44 
12C C19 C20  SING N N 45 
12C C19 H191 SING N N 46 
12C C19 H192 SING N N 47 
12C C20 C23  SING N N 48 
12C C20 H201 SING N N 49 
12C C20 H202 SING N N 50 
12C C21 C22  SING N N 51 
12C C21 H211 SING N N 52 
12C C21 H212 SING N N 53 
12C C22 C23  SING N N 54 
12C C22 H221 SING N N 55 
12C C22 H222 SING N N 56 
12C C23 H23  SING N N 57 
# 
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 
12C SMILES           ACDLabs              10.04 Clc1ccc6c(c1)C(NC3C2CCN(CC2)C3)=C(c4nc5ccccc5n4)C(=O)N6                                                                                                                                         
12C InChI            InChI                1.02b InChI=1/C23H22ClN5O/c24-14-5-6-16-15(11-14)21(25-19-12-29-9-7-13(19)8-10-29)20(23(30)28-16)22-26-17-3-1-2-4-18(17)27-22/h1-6,11,13,19H,7-10,12H2,(H,26,27)(H2,25,28,30)/t19-/m1/s1/f/h25-26,28H 
12C InChIKey         InChI                1.02b MOVBBVMDHIRCTG-XNQRRJCQDJ                                                                                                                                                                       
12C SMILES_CANONICAL CACTVS               3.341 Clc1ccc2NC(=O)C(=C(N[C@@H]3CN4CCC3CC4)c2c1)c5[nH]c6ccccc6n5                                                                                                                                     
12C SMILES           CACTVS               3.341 Clc1ccc2NC(=O)C(=C(N[CH]3CN4CCC3CC4)c2c1)c5[nH]c6ccccc6n5                                                                                                                                       
12C SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)[nH]c(n2)C3=C(c4cc(ccc4NC3=O)Cl)N[C@@H]5CN6CCC5CC6                                                                                                                                   
12C SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)[nH]c(n2)C3=C(c4cc(ccc4NC3=O)Cl)NC5CN6CCC5CC6                                                                                                                                        
# 
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 
12C "SYSTEMATIC NAME" ACDLabs              10.04 4-[(3S)-1-azabicyclo[2.2.2]oct-3-ylamino]-3-(1H-benzimidazol-2-yl)-6-chloroquinolin-2(1H)-one     
12C "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[[(8S)-1-azabicyclo[2.2.2]octan-8-yl]amino]-3-(1H-benzimidazol-2-yl)-6-chloro-1H-quinolin-2-one 
# 
