data_133
# 
_chem_comp.id                                    133 
_chem_comp.name                                  6-FLUORO-2-(2-HYDROXY-3-ISOBUTOXY-PHENYL)-1H-BENZOIMIDAZOLE-5-CARBOXAMIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H19 F N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-05-09 
_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                        342.367 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     133 
_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 
133 C1     C1     C 0 1 Y N N 8.702  1.906  24.721 0.600  -0.066 -4.598 C1     133 1  
133 C2     C2     C 0 1 Y N N 9.502  1.701  23.546 -0.710 0.387  -4.804 C2     133 2  
133 F2     F2     F 0 1 N N N 9.723  0.474  23.074 -1.130 0.684  -6.053 F2     133 3  
133 C3     C3     C 0 1 Y N N 10.089 2.746  22.809 -1.571 0.532  -3.738 C3     133 4  
133 C4     C4     C 0 1 Y N N 9.894  3.985  23.327 -1.142 0.227  -2.452 C4     133 5  
133 C5     C5     C 0 1 Y N N 9.143  4.222  24.436 0.171  -0.229 -2.234 C5     133 6  
133 C6     C6     C 0 1 Y N N 8.561  3.236  25.176 1.039  -0.374 -3.316 C6     133 7  
133 C7     C7     C 0 1 N N N 8.096  0.866  25.444 1.517  -0.218 -5.748 C7     133 8  
133 N1     N1     N 0 1 N N N 7.622  1.129  26.630 2.805  -0.665 -5.548 N1     133 9  
133 N2     N2     N 0 1 N N N 7.969  -0.341 24.955 1.106  0.068  -6.952 N2     133 10 
133 N3     N3     N 0 1 Y N N 10.280 5.133  22.905 -1.747 0.266  -1.213 N3     133 11 
133 N4     N4     N 0 1 Y N N 9.073  5.487  24.759 0.305  -0.437 -0.900 N4     133 12 
133 C8     C8     C 0 1 Y N N 9.789  5.975  23.763 -0.821 -0.153 -0.295 C8     133 13 
133 "C1'"  "C1'"  C 0 1 Y N N 10.024 7.330  23.661 -1.056 -0.263 1.159  "C1'"  133 14 
133 "C2'"  "C2'"  C 0 1 Y N N 9.607  8.195  24.673 -2.274 -0.749 1.638  "C2'"  133 15 
133 "C3'"  "C3'"  C 0 1 Y N N 9.842  9.542  24.587 -2.489 -0.851 2.996  "C3'"  133 16 
133 "C4'"  "C4'"  C 0 1 Y N N 10.430 10.058 23.443 -1.503 -0.472 3.891  "C4'"  133 17 
133 "C5'"  "C5'"  C 0 1 Y N N 10.856 9.220  22.407 -0.289 0.011  3.429  "C5'"  133 18 
133 "C6'"  "C6'"  C 0 1 Y N N 10.619 7.869  22.509 -0.060 0.124  2.062  "C6'"  133 19 
133 "O6'"  "O6'"  O 0 1 N N N 11.036 7.053  21.474 1.127  0.598  1.606  "O6'"  133 20 
133 "O5'"  "O5'"  O 0 1 N N N 11.457 9.700  21.255 0.676  0.380  4.313  "O5'"  133 21 
133 C10    C10    C 0 1 N N N 12.269 10.858 21.478 0.146  0.155  5.621  C10    133 22 
133 C20    C20    C 0 1 N N N 12.855 11.354 20.157 1.188  0.552  6.669  C20    133 23 
133 C30    C30    C 0 1 N N N 14.152 10.607 19.824 0.620  0.311  8.069  C30    133 24 
133 C40    C40    C 0 1 N N N 11.826 11.215 19.047 2.450  -0.290 6.478  C40    133 25 
133 HC3    HC3    H 0 1 N N N 10.651 2.575  21.902 -2.579 0.882  -3.902 HC3    133 26 
133 HC6    HC6    H 0 1 N N N 8.012  3.463  26.078 2.048  -0.724 -3.158 HC6    133 27 
133 HH11   1HH1   H 0 0 N N N 7.653  2.023  27.077 3.406  -0.765 -6.302 HH11   133 28 
133 HH12   2HH1   H 0 0 N N N 7.223  0.302  27.025 3.110  -0.879 -4.652 HH12   133 29 
133 HH21   1HH2   H 0 0 N N N 8.370  -0.378 24.040 1.708  -0.031 -7.706 HH21   133 30 
133 HN3    HN3    H 0 1 N N N 10.834 5.334  22.097 -2.659 0.540  -1.026 HN3    133 31 
133 "HC'2" "2HC'" H 0 0 N N N 9.092  7.798  25.535 -3.047 -1.046 0.945  "HC'2" 133 32 
133 "HC'3" "3HC'" H 0 0 N N N 9.572  10.196 25.403 -3.432 -1.227 3.364  "HC'3" 133 33 
133 "HC'4" "4HC'" H 0 0 N N N 10.562 11.126 23.350 -1.679 -0.555 4.953  "HC'4" 133 34 
133 "HO'6" "6HO'" H 0 0 N N N 11.132 7.569  20.682 1.031  1.556  1.519  "HO'6" 133 35 
133 H101   1H10   H 0 0 N N N 13.091 10.594 22.159 -0.100 -0.900 5.736  H101   133 36 
133 H102   2H10   H 0 0 N N N 11.652 11.653 21.922 -0.753 0.756  5.757  H102   133 37 
133 H20    H20    H 0 1 N N N 13.108 12.420 20.255 1.435  1.608  6.553  H20    133 38 
133 H301   1H30   H 0 0 N N N 14.167 9.644  20.355 1.363  0.595  8.815  H301   133 39 
133 H302   2H30   H 0 0 N N N 15.015 11.213 20.138 -0.278 0.912  8.205  H302   133 40 
133 H303   3H30   H 0 0 N N N 14.205 10.428 18.740 0.373  -0.743 8.184  H303   133 41 
133 H401   1H40   H 0 0 N N N 12.014 10.287 18.487 2.203  -1.345 6.593  H401   133 42 
133 H402   2H40   H 0 0 N N N 11.902 12.076 18.367 2.854  -0.118 5.480  H402   133 43 
133 H403   3H40   H 0 0 N N N 10.817 11.181 19.484 3.192  -0.007 7.224  H403   133 44 
# 
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 
133 C1    C2     DOUB Y N 1  
133 C1    C6     SING Y N 2  
133 C1    C7     SING N N 3  
133 C2    F2     SING N N 4  
133 C2    C3     SING Y N 5  
133 C3    C4     DOUB Y N 6  
133 C3    HC3    SING N N 7  
133 C4    C5     SING Y N 8  
133 C4    N3     SING Y N 9  
133 C5    C6     DOUB Y N 10 
133 C5    N4     SING Y N 11 
133 C6    HC6    SING N N 12 
133 C7    N1     SING N N 13 
133 C7    N2     DOUB N E 14 
133 N1    HH11   SING N N 15 
133 N1    HH12   SING N N 16 
133 N2    HH21   SING N N 17 
133 N3    C8     SING Y N 18 
133 N3    HN3    SING N N 19 
133 N4    C8     DOUB Y N 20 
133 C8    "C1'"  SING N N 21 
133 "C1'" "C2'"  DOUB Y N 22 
133 "C1'" "C6'"  SING Y N 23 
133 "C2'" "C3'"  SING Y N 24 
133 "C2'" "HC'2" SING N N 25 
133 "C3'" "C4'"  DOUB Y N 26 
133 "C3'" "HC'3" SING N N 27 
133 "C4'" "C5'"  SING Y N 28 
133 "C4'" "HC'4" SING N N 29 
133 "C5'" "C6'"  DOUB Y N 30 
133 "C5'" "O5'"  SING N N 31 
133 "C6'" "O6'"  SING N N 32 
133 "O6'" "HO'6" SING N N 33 
133 "O5'" C10    SING N N 34 
133 C10   C20    SING N N 35 
133 C10   H101   SING N N 36 
133 C10   H102   SING N N 37 
133 C20   C30    SING N N 38 
133 C20   C40    SING N N 39 
133 C20   H20    SING N N 40 
133 C30   H301   SING N N 41 
133 C30   H302   SING N N 42 
133 C30   H303   SING N N 43 
133 C40   H401   SING N N 44 
133 C40   H402   SING N N 45 
133 C40   H403   SING N N 46 
# 
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 
133 SMILES           ACDLabs              10.04 Fc3cc1c(nc(n1)c2cccc(OCC(C)C)c2O)cc3C(=[N@H])N                                                                                                                  
133 InChI            InChI                1.02b InChI=1/C18H19FN4O2/c1-9(2)8-25-15-5-3-4-10(16(15)24)18-22-13-6-11(17(20)21)12(19)7-14(13)23-18/h3-7,9,24H,8H2,1-2H3,(H3,20,21)(H,22,23)/f/h20,23H,21H2/b20-17+ 
133 InChIKey         InChI                1.02b NSUDDASMRZSVON-XSMBQKCDDY                                                                                                                                       
133 SMILES_CANONICAL CACTVS               3.341 CC(C)COc1cccc(c1O)c2[nH]c3cc(F)c(cc3n2)C(N)=N                                                                                                                   
133 SMILES           CACTVS               3.341 CC(C)COc1cccc(c1O)c2[nH]c3cc(F)c(cc3n2)C(N)=N                                                                                                                   
133 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1cc2c(cc1F)[nH]c(n2)c3cccc(c3O)OCC(C)C)/N                                                                                                             
133 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1cc2c(cc1F)[nH]c(n2)c3cccc(c3O)OCC(C)C)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 
133 "SYSTEMATIC NAME" ACDLabs              10.04 6-fluoro-2-[2-hydroxy-3-(2-methylpropoxy)phenyl]-1H-benzimidazole-5-carboximidamide 
133 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-fluoro-2-[2-hydroxy-3-(2-methylpropoxy)phenyl]-1H-benzimidazole-5-carboximidamide 
# 
