data_653
# 
_chem_comp.id                                    653 
_chem_comp.name                                  "5-(2-AMINOETHYL)-3-{5-[AMINO(IMINIO)METHYL]-1H-BENZIMIDAZOL-2-YL}-1,1'-BIPHENYL-2-OLATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 N5 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         CRA_23653 
_chem_comp.pdbx_formal_charge                    1 
_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                        372.443 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     653 
_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        1O38 
_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 
653 C1     C1     C 0  1 Y N N 44.022 -3.031 26.234 5.337  0.361  0.073  C1     653 1  
653 C2     C2     C 0  1 Y N N 44.333 -1.625 26.242 5.072  1.547  -0.623 C2     653 2  
653 C3     C3     C 0  1 Y N N 44.231 -0.821 27.373 3.794  1.872  -0.976 C3     653 3  
653 C4     C4     C 0  1 Y N N 43.817 -1.434 28.514 2.742  1.026  -0.647 C4     653 4  
653 C5     C5     C 0  1 Y N N 43.517 -2.750 28.575 2.990  -0.171 0.052  C5     653 5  
653 C6     C6     C 0  1 Y N N 43.591 -3.604 27.467 4.298  -0.502 0.406  C6     653 6  
653 C7     C7     C 0  1 N N N 44.153 -3.791 25.043 6.726  0.022  0.450  C7     653 7  
653 N1     N1     N 0  1 N N N 43.929 -5.095 25.062 6.980  -1.106 1.111  N1     653 8  
653 N2     N2     N 1  1 N N N 44.495 -3.164 23.927 7.723  0.845  0.127  N2     653 9  
653 N3     N3     N 0  1 Y N N 43.652 -0.951 29.699 1.380  1.073  -0.857 N3     653 10 
653 N4     N4     N 0  1 Y N N 43.150 -3.116 29.790 1.794  -0.785 0.232  N4     653 11 
653 C8     C8     C 0  1 Y N N 43.256 -1.952 30.426 0.843  -0.058 -0.301 C8     653 12 
653 "C1'"  "C1'"  C 0  1 Y N N 43.009 -1.840 31.818 -0.594 -0.405 -0.301 "C1'"  653 13 
653 "C2'"  "C2'"  C 0  1 Y N N 42.656 -2.971 32.593 -0.995 -1.726 -0.510 "C2'"  653 14 
653 "C3'"  "C3'"  C 0  1 Y N N 42.406 -2.887 33.964 -2.336 -2.051 -0.510 "C3'"  653 15 
653 "CV'"  "C31'" C 0  1 N N N 42.043 -4.149 34.816 -2.760 -3.479 -0.737 "CV'"  653 16 
653 "CW'"  "C32'" C 0  1 N N N 40.537 -4.558 34.655 -2.845 -4.205 0.607  "CW'"  653 17 
653 "NX'"  "N33'" N 1  1 N N N 40.338 -5.959 35.203 -3.259 -5.597 0.386  "NX'"  653 18 
653 "C4'"  "C4'"  C 0  1 Y N N 42.506 -1.643 34.575 -3.293 -1.075 -0.303 "C4'"  653 19 
653 "C5'"  "C5'"  C 0  1 Y N N 42.849 -0.484 33.872 -2.911 0.248  -0.092 "C5'"  653 20 
653 "C6'"  "C6'"  C 0  1 Y N N 43.094 -0.605 32.498 -1.556 0.588  -0.086 "C6'"  653 21 
653 "O6'"  "O6'"  O -1 1 N N N 43.433 0.529  31.809 -1.175 1.874  0.119  "O6'"  653 22 
653 C1B    "C1''" C 0  1 Y N N 42.928 0.728  34.573 -3.940 1.293  0.130  C1B    653 23 
653 C2B    "C2''" C 0  1 Y N N 44.121 1.467  34.685 -3.831 2.164  1.212  C2B    653 24 
653 C3B    "C3''" C 0  1 Y N N 44.173 2.663  35.421 -4.791 3.134  1.414  C3B    653 25 
653 C4B    "C4''" C 0  1 Y N N 43.042 3.158  36.062 -5.862 3.242  0.544  C4B    653 26 
653 C5B    "C5''" C 0  1 Y N N 41.845 2.445  35.966 -5.976 2.380  -0.531 C5B    653 27 
653 C6B    "C6''" C 0  1 Y N N 41.792 1.251  35.228 -5.018 1.410  -0.747 C6B    653 28 
653 HC2    HC2    H 0  1 N N N 44.676 -1.150 25.346 5.885  2.210  -0.881 HC2    653 29 
653 HC3    HC3    H 0  1 N N N 44.461 0.230  27.361 3.600  2.789  -1.512 HC3    653 30 
653 HC6    HC6    H 0  1 N N N 43.334 -4.653 27.553 4.503  -1.420 0.937  HC6    653 31 
653 HH11   HH11   H 0  0 N N N 43.688 -5.517 25.952 7.891  -1.328 1.359  HH11   653 32 
653 HH12   HH12   H 0  0 N N N 43.979 -5.719 24.287 6.254  -1.704 1.346  HH12   653 33 
653 HH21   HH21   H 0  0 N N N 44.641 -2.164 23.931 7.538  1.666  -0.355 HH21   653 34 
653 HH22   HH22   H 0  0 N N N 44.650 -3.632 23.060 8.634  0.624  0.378  HH22   653 35 
653 HN3    HN3    H 0  1 N N N 43.757 -0.029 30.023 0.892  1.776  -1.314 HN3    653 36 
653 "HC2'" "HC2'" H 0  0 N N N 42.574 -3.936 32.111 -0.254 -2.495 -0.672 "HC2'" 653 37 
653 H31A   H31A   H 0  0 N N N 42.276 -3.950 35.863 -3.737 -3.495 -1.221 H31A   653 38 
653 H31B   H31B   H 0  0 N N N 42.697 -4.958 34.521 -2.030 -3.978 -1.374 H31B   653 39 
653 H32A   H32A   H 0  0 N N N 40.227 -4.506 33.620 -1.869 -4.189 1.091  H32A   653 40 
653 H32B   H32B   H 0  0 N N N 39.912 -3.859 35.199 -3.575 -3.706 1.245  H32B   653 41 
653 H33A   H33A   H 0  0 N N N 40.281 -6.682 34.451 -4.163 -5.613 -0.062 H33A   653 42 
653 H33B   H33B   H 0  0 N N N 39.473 -6.037 35.783 -2.583 -6.059 -0.204 H33B   653 43 
653 H33C   H33C   H 0  0 N N N 41.148 -6.192 35.806 -3.315 -6.076 1.272  H33C   653 44 
653 "HC4'" "HC4'" H 0  0 N N N 42.312 -1.567 35.637 -4.340 -1.339 -0.305 "HC4'" 653 45 
653 H2B    "H2''" H 0  1 N N N 45.017 1.109  34.195 -2.996 2.080  1.892  H2B    653 46 
653 H3B    "H3''" H 0  1 N N N 45.101 3.214  35.499 -4.708 3.810  2.252  H3B    653 47 
653 H4B    "H4''" H 0  1 N N N 43.088 4.080  36.632 -6.611 4.003  0.706  H4B    653 48 
653 H5B    "H5''" H 0  1 N N N 40.955 2.814  36.458 -6.814 2.469  -1.207 H5B    653 49 
653 H6B    "H6''" H 0  1 N N N 40.852 0.718  35.170 -5.107 0.738  -1.587 H6B    653 50 
# 
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 
653 C1    C2     DOUB Y N 1  
653 C1    C6     SING Y N 2  
653 C1    C7     SING N N 3  
653 C2    C3     SING Y N 4  
653 C2    HC2    SING N N 5  
653 C3    C4     DOUB Y N 6  
653 C3    HC3    SING N N 7  
653 C4    C5     SING Y N 8  
653 C4    N3     SING Y N 9  
653 C5    C6     DOUB Y N 10 
653 C5    N4     SING Y N 11 
653 C6    HC6    SING N N 12 
653 C7    N1     SING N N 13 
653 C7    N2     DOUB N N 14 
653 N1    HH11   SING N N 15 
653 N1    HH12   SING N N 16 
653 N2    HH21   SING N N 17 
653 N2    HH22   SING N N 18 
653 N3    C8     SING Y N 19 
653 N3    HN3    SING N N 20 
653 N4    C8     DOUB Y N 21 
653 C8    "C1'"  SING N N 22 
653 "C1'" "C2'"  DOUB Y N 23 
653 "C1'" "C6'"  SING Y N 24 
653 "C2'" "C3'"  SING Y N 25 
653 "C2'" "HC2'" SING N N 26 
653 "C3'" "CV'"  SING N N 27 
653 "C3'" "C4'"  DOUB Y N 28 
653 "CV'" "CW'"  SING N N 29 
653 "CV'" H31A   SING N N 30 
653 "CV'" H31B   SING N N 31 
653 "CW'" "NX'"  SING N N 32 
653 "CW'" H32A   SING N N 33 
653 "CW'" H32B   SING N N 34 
653 "NX'" H33A   SING N N 35 
653 "NX'" H33B   SING N N 36 
653 "NX'" H33C   SING N N 37 
653 "C4'" "C5'"  SING Y N 38 
653 "C4'" "HC4'" SING N N 39 
653 "C5'" "C6'"  DOUB Y N 40 
653 "C5'" C1B    SING N N 41 
653 "C6'" "O6'"  SING N N 42 
653 C1B   C2B    DOUB Y N 43 
653 C1B   C6B    SING Y N 44 
653 C2B   C3B    SING Y N 45 
653 C2B   H2B    SING N N 46 
653 C3B   C4B    DOUB Y N 47 
653 C3B   H3B    SING N N 48 
653 C4B   C5B    SING Y N 49 
653 C4B   H4B    SING N N 50 
653 C5B   C6B    DOUB Y N 51 
653 C5B   H5B    SING N N 52 
653 C6B   H6B    SING N N 53 
# 
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 
653 SMILES           ACDLabs              10.04 [O-]c4c(c1ccccc1)cc(cc4c3nc2cc(ccc2n3)\C(=[NH2+])N)CC[NH3+]                                                                                                                                  
653 InChI            InChI                1.02b InChI=1/C22H21N5O/c23-9-8-13-10-16(14-4-2-1-3-5-14)20(28)17(11-13)22-26-18-7-6-15(21(24)25)12-19(18)27-22/h1-7,10-12,28H,8-9,23H2,(H3,24,25)(H,26,27)/p+1/fC22H22N5O/h28h,23,26H,24-25H2/q+1 
653 InChIKey         InChI                1.02b YYUZFCLHOQHMPT-GMUWGWGFCP                                                                                                                                                                    
653 SMILES_CANONICAL CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cc(CC[NH3+])cc(c3[O-])c4ccccc4                                                                                                                                
653 SMILES           CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cc(CC[NH3+])cc(c3[O-])c4ccccc4                                                                                                                                
653 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)c2cc(cc(c2[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])N)CC[NH3+]                                                                                                                              
653 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)c2cc(cc(c2[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])N)CC[NH3+]                                                                                                                              
# 
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 
653 "SYSTEMATIC NAME" ACDLabs              10.04 3-{5-[amino(iminio)methyl]-1H-benzimidazol-2-yl}-5-(2-ammonioethyl)biphenyl-2-olate              
653 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[5-(amino-azaniumylidene-methyl)-1H-benzimidazol-2-yl]-4-(2-azaniumylethyl)-6-phenyl-phenolate 
# 
