data_655
# 
_chem_comp.id                                    655 
_chem_comp.name                                  2-{5-[AMINO(IMINIO)METHYL]-1H-BENZIMIDAZOL-2-YL}-6-(CYCLOPENTYLOXY)BENZENOLATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H20 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         CRA_10655 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-03-14 
_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                        336.388 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     655 
_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        1O2I 
_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 
655 C1     C1     C 0  1 Y N N 44.291 -2.880 26.677 5.173  0.360  -0.084 C1     655 1  
655 C2     C2     C 0  1 Y N N 44.873 -1.560 26.654 5.275  -0.932 -0.613 C2     655 2  
655 C3     C3     C 0  1 Y N N 44.873 -0.770 27.787 4.164  -1.714 -0.750 C3     655 3  
655 C4     C4     C 0  1 Y N N 44.355 -1.292 28.933 2.919  -1.232 -0.363 C4     655 4  
655 C5     C5     C 0  1 Y N N 43.827 -2.537 29.007 2.798  0.065  0.171  C5     655 5  
655 C6     C6     C 0  1 Y N N 43.774 -3.366 27.881 3.937  0.858  0.314  C6     655 6  
655 C7     C7     C 0  1 N N N 44.318 -3.671 25.494 6.384  1.195  0.059  C7     655 7  
655 N1     N1     N 0  1 N N N 44.178 -4.971 25.588 6.290  2.425  0.562  N1     655 8  
655 N2     N2     N 1  1 N N N 44.491 -3.069 24.321 7.570  0.718  -0.316 N2     655 9  
655 N3     N3     N 0  1 Y N N 44.275 -0.785 30.116 1.646  -1.763 -0.375 N3     655 10 
655 N4     N4     N 0  1 Y N N 43.391 -2.810 30.222 1.486  0.260  0.454  N4     655 11 
655 C8     C8     C 0  1 Y N N 43.686 -1.687 30.869 0.803  -0.812 0.135  C8     655 12 
655 "C1'"  "C1'"  C 0  1 Y N N 43.410 -1.528 32.217 -0.656 -0.970 0.300  "C1'"  655 13 
655 "C2'"  "C2'"  C 0  1 Y N N 43.036 -2.629 32.993 -1.184 -2.185 0.743  "C2'"  655 14 
655 "C3'"  "C3'"  C 0  1 Y N N 42.750 -2.505 34.337 -2.547 -2.329 0.896  "C3'"  655 15 
655 "C4'"  "C4'"  C 0  1 Y N N 42.848 -1.252 34.930 -3.398 -1.274 0.612  "C4'"  655 16 
655 "C5'"  "C5'"  C 0  1 Y N N 43.212 -0.122 34.156 -2.888 -0.064 0.172  "C5'"  655 17 
655 "O5'"  "O5'"  O 0  1 N N N 43.340 1.149  34.674 -3.729 0.968  -0.105 "O5'"  655 18 
655 "C6'"  "C6'"  C 0  1 Y N N 43.495 -0.277 32.801 -1.515 0.097  0.018  "C6'"  655 19 
655 "O6'"  "O6'"  O -1 1 N N N 43.848 0.796  32.007 -1.011 1.283  -0.414 "O6'"  655 20 
655 C1B    "C1''" C 0  1 N N N 42.342 2.768  35.854 -5.928 1.786  0.535  C1B    655 21 
655 C2B    "C2''" C 0  1 N N N 43.005 1.442  36.025 -5.036 0.555  0.298  C2B    655 22 
655 C3B    "C3''" C 0  1 N N N 44.274 1.687  36.796 -5.703 -0.262 -0.827 C3B    655 23 
655 C4B    "C4''" C 0  1 N N N 44.575 3.166  36.573 -7.192 0.161  -0.773 C4B    655 24 
655 C5B    "C5''" C 0  1 N N N 43.188 3.750  36.615 -7.106 1.674  -0.455 C5B    655 25 
655 HC2    HC2    H 0  1 N N N 45.275 -1.151 25.731 6.239  -1.313 -0.916 HC2    655 26 
655 HC3    HC3    H 0  1 N N N 45.307 0.210  27.779 4.253  -2.709 -1.160 HC3    655 27 
655 HC6    HC6    H 0  1 N N N 43.338 -4.351 27.936 3.858  1.853  0.727  HC6    655 28 
655 HH11   HH11   H 0  0 N N N 44.031 -5.397 26.486 5.426  2.772  0.835  HH11   655 29 
655 HH12   HH12   H 0  0 N N N 44.146 -5.577 24.813 7.085  2.973  0.656  HH12   655 30 
655 HH21   HH21   H 0  0 N N N 44.580 -2.058 24.274 8.365  1.267  -0.223 HH21   655 31 
655 HH22   HH22   H 0  0 N N N 44.559 -3.550 23.451 7.640  -0.178 -0.679 HH22   655 32 
655 HN3    HN3    H 0  1 N N N 44.586 0.114  30.325 1.395  -2.647 -0.687 HN3    655 33 
655 "HC2'" "HC2'" H 0  0 N N N 42.964 -3.601 32.534 -0.526 -3.011 0.966  "HC2'" 655 34 
655 "HC3'" "HC3'" H 0  0 N N N 42.460 -3.375 34.915 -2.953 -3.270 1.239  "HC3'" 655 35 
655 "HC4'" "HC4'" H 0  0 N N N 42.630 -1.183 35.983 -4.464 -1.396 0.734  "HC4'" 655 36 
655 H1A    H1A    H 0  1 N N N 42.363 3.049  34.819 -6.300 1.786  1.560  H1A    655 37 
655 H1B    H1B    H 0  1 N N N 41.314 2.736  36.203 -5.364 2.699  0.342  H1B    655 38 
655 H2A    H2A    H 0  1 N N N 42.368 0.707  36.497 -4.975 -0.042 1.208  H2A    655 39 
655 H3A    H3A    H 0  1 N N N 44.057 1.582  37.841 -5.269 -0.006 -1.794 H3A    655 40 
655 H3B    H3B    H 0  1 N N N 45.029 0.980  36.498 -5.603 -1.330 -0.634 H3B    655 41 
655 H4A    H4A    H 0  1 N N N 45.004 3.357  35.588 -7.716 -0.372 0.021  H4A    655 42 
655 H4B    H4B    H 0  1 N N N 45.218 3.587  37.326 -7.676 -0.005 -1.735 H4B    655 43 
655 H5A    H5A    H 0  1 N N N 43.114 4.708  36.135 -8.029 2.019  0.011  H5A    655 44 
655 H5B    H5B    H 0  1 N N N 42.830 3.807  37.626 -6.899 2.243  -1.361 H5B    655 45 
# 
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 
655 C1    C2     DOUB Y N 1  
655 C1    C6     SING Y N 2  
655 C1    C7     SING N N 3  
655 C2    C3     SING Y N 4  
655 C2    HC2    SING N N 5  
655 C3    C4     DOUB Y N 6  
655 C3    HC3    SING N N 7  
655 C4    C5     SING Y N 8  
655 C4    N3     SING Y N 9  
655 C5    C6     DOUB Y N 10 
655 C5    N4     SING Y N 11 
655 C6    HC6    SING N N 12 
655 C7    N1     SING N N 13 
655 C7    N2     DOUB N N 14 
655 N1    HH11   SING N N 15 
655 N1    HH12   SING N N 16 
655 N2    HH21   SING N N 17 
655 N2    HH22   SING N N 18 
655 N3    C8     SING Y N 19 
655 N3    HN3    SING N N 20 
655 N4    C8     DOUB Y N 21 
655 C8    "C1'"  SING N N 22 
655 "C1'" "C2'"  DOUB Y N 23 
655 "C1'" "C6'"  SING Y N 24 
655 "C2'" "C3'"  SING Y N 25 
655 "C2'" "HC2'" SING N N 26 
655 "C3'" "C4'"  DOUB Y N 27 
655 "C3'" "HC3'" SING N N 28 
655 "C4'" "C5'"  SING Y N 29 
655 "C4'" "HC4'" SING N N 30 
655 "C5'" "O5'"  SING N N 31 
655 "C5'" "C6'"  DOUB Y N 32 
655 "O5'" C2B    SING N N 33 
655 "C6'" "O6'"  SING N N 34 
655 C1B   C2B    SING N N 35 
655 C1B   C5B    SING N N 36 
655 C1B   H1A    SING N N 37 
655 C1B   H1B    SING N N 38 
655 C2B   C3B    SING N N 39 
655 C2B   H2A    SING N N 40 
655 C3B   C4B    SING N N 41 
655 C3B   H3A    SING N N 42 
655 C3B   H3B    SING N N 43 
655 C4B   C5B    SING N N 44 
655 C4B   H4A    SING N N 45 
655 C4B   H4B    SING N N 46 
655 C5B   H5A    SING N N 47 
655 C5B   H5B    SING N N 48 
# 
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 
655 SMILES           ACDLabs              10.04 [O-]c4c(OC1CCCC1)cccc4c3nc2cc(ccc2n3)\C(=[NH2+])N                                                                                                                 
655 InChI            InChI                1.02b InChI=1/C19H20N4O2/c20-18(21)11-8-9-14-15(10-11)23-19(22-14)13-6-3-7-16(17(13)24)25-12-4-1-2-5-12/h3,6-10,12,24H,1-2,4-5H2,(H3,20,21)(H,22,23)/f/h24h,22H,20-21H2 
655 InChIKey         InChI                1.02b WCFWDBPDMBXMTQ-LEKGDEFBCJ                                                                                                                                         
655 SMILES_CANONICAL CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cccc(OC4CCCC4)c3[O-]                                                                                                               
655 SMILES           CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cccc(OC4CCCC4)c3[O-]                                                                                                               
655 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c(c(c1)OC2CCCC2)[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])N                                                                                                           
655 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c(c(c1)OC2CCCC2)[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])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 
655 "SYSTEMATIC NAME" ACDLabs              10.04 2-{5-[amino(iminio)methyl]-1H-benzimidazol-2-yl}-6-(cyclopentyloxy)phenolate        
655 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[5-(amino-azaniumylidene-methyl)-1H-benzimidazol-2-yl]-6-cyclopentyloxy-phenolate 
# 
