data_693
# 
_chem_comp.id                                    693 
_chem_comp.name                                  "2-(5-{5-[AMINO(IMINIO)METHYL]-1H-BENZIMIDAZOL-2-YL}-2'-FLUORO-6-OXIDO-1,1'-BIPHENYL-3-YL)SUCCINATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H17 F N4 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         CRA_17693 
_chem_comp.pdbx_formal_charge                    -2 
_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                        460.414 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     693 
_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        1O30 
_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 
693 C1     C1     C 0  1 Y N N 43.979 -3.132 26.009 5.900  0.127  0.017  C1     693 1  
693 C2     C2     C 0  1 Y N N 44.166 -1.715 25.988 5.777  1.239  -0.825 C2     693 2  
693 C3     C3     C 0  1 Y N N 44.026 -0.921 27.125 4.544  1.717  -1.164 C3     693 3  
693 C4     C4     C 0  1 Y N N 43.696 -1.569 28.290 3.398  1.102  -0.675 C4     693 4  
693 C5     C5     C 0  1 Y N N 43.508 -2.893 28.369 3.503  -0.017 0.172  C5     693 5  
693 C6     C6     C 0  1 Y N N 43.637 -3.722 27.260 4.765  -0.506 0.512  C6     693 6  
693 C7     C7     C 0  1 N N N 44.143 -3.881 24.829 7.242  -0.381 0.376  C7     693 7  
693 N1     N1     N 0  1 N N N 43.829 -5.162 24.809 7.361  -1.439 1.177  N1     693 8  
693 N2     N2     N 1  1 N N N 44.619 -3.272 23.754 8.331  0.220  -0.101 N2     693 9  
693 N3     N3     N 0  1 Y N N 43.508 -1.099 29.471 2.048  1.342  -0.830 N3     693 10 
693 N4     N4     N 0  1 Y N N 43.193 -3.287 29.591 2.241  -0.400 0.488  N4     693 11 
693 C8     C8     C 0  1 Y N N 43.215 -2.120 30.209 1.381  0.396  -0.099 C8     693 12 
693 "C1'"  "C1'"  C 0  1 Y N N 42.999 -1.984 31.601 -0.089 0.289  0.012  "C1'"  693 13 
693 "C2'"  "C2'"  C 0  1 Y N N 42.679 -3.093 32.396 -0.703 -0.965 0.007  "C2'"  693 14 
693 "C3'"  "C3'"  C 0  1 Y N N 42.455 -3.014 33.778 -2.075 -1.066 0.111  "C3'"  693 15 
693 CVX    "C31'" C 0  1 N N R 42.081 -4.306 34.559 -2.729 -2.423 0.105  CVX    693 16 
693 CWX    "C32'" C 0  1 N N N 40.576 -4.484 34.251 -2.212 -3.235 1.264  CWX    693 17 
693 OXX    "O33'" O 0  1 N N N 40.254 -5.317 33.419 -1.389 -2.756 2.026  OXX    693 18 
693 OYX    "O34'" O -1 1 N N N 39.788 -3.772 34.842 -2.617 -4.372 1.441  OYX    693 19 
693 C6X    "C42'" C 0  1 N N N 42.382 -4.210 36.126 -2.401 -3.141 -1.206 C6X    693 20 
693 C7X    "C43'" C 0  1 N N N 43.111 -5.440 36.776 -3.153 -4.445 -1.267 C7X    693 21 
693 O8X    "O44'" O 0  1 N N N 42.980 -6.555 36.293 -3.917 -4.786 -0.304 O8X    693 22 
693 O9X    "O45'" O -1 1 N N N 43.797 -5.222 37.774 -3.026 -5.209 -2.280 O9X    693 23 
693 "C4'"  "C4'"  C 0  1 Y N N 42.566 -1.772 34.374 -2.853 0.071  0.221  "C4'"  693 24 
693 "C5'"  "C5'"  C 0  1 Y N N 42.888 -0.619 33.655 -2.259 1.330  0.228  "C5'"  693 25 
693 "C6'"  "C6'"  C 0  1 Y N N 43.093 -0.729 32.271 -0.870 1.444  0.129  "C6'"  693 26 
693 "O6'"  "O6'"  O -1 1 N N N 43.360 0.441  31.578 -0.282 2.667  0.135  "O6'"  693 27 
693 C1B    "C1''" C 0  1 Y N N 43.041 0.586  34.341 -3.097 2.548  0.346  C1B    693 28 
693 C2B    "C2''" C 0  1 Y N N 44.277 1.260  34.335 -3.156 3.463  -0.706 C2B    693 29 
693 C3B    "C3''" C 0  1 Y N N 44.449 2.428  35.045 -3.945 4.593  -0.591 C3B    693 30 
693 C4B    "C4''" C 0  1 Y N N 43.399 2.967  35.781 -4.664 4.822  0.568  C4B    693 31 
693 C5B    "C5''" C 0  1 Y N N 42.174 2.332  35.796 -4.604 3.920  1.615  C5B    693 32 
693 C6B    "C6''" C 0  1 Y N N 41.999 1.156  35.086 -3.825 2.786  1.511  C6B    693 33 
693 F2B    "F2''" F 0  1 N N N 45.369 0.773  33.592 -2.453 3.240  -1.838 F2B    693 34 
693 HC2    HC2    H 0  1 N N N 44.425 -1.226 25.068 6.664  1.722  -1.208 HC2    693 35 
693 HC3    HC3    H 0  1 N N N 44.162 0.149  27.094 4.460  2.576  -1.814 HC3    693 36 
693 HC6    HC6    H 0  1 N N N 43.479 -4.785 27.350 4.859  -1.367 1.157  HC6    693 37 
693 HH11   HH11   H 0  0 N N N 43.493 -5.566 25.673 8.241  -1.771 1.413  HH11   693 38 
693 HH12   HH12   H 0  0 N N N 43.896 -5.789 24.038 6.568  -1.876 1.524  HH12   693 39 
693 HH21   HH21   H 0  0 N N N 44.900 -2.305 23.798 8.244  0.991  -0.684 HH21   693 40 
693 HH22   HH22   H 0  0 N N N 44.772 -3.735 22.888 9.211  -0.110 0.138  HH22   693 41 
693 HN3    HN3    H 0  1 N N N 43.556 -0.163 29.795 1.647  2.049  -1.359 HN3    693 42 
693 "HC2'" "HC2'" H 0  0 N N N 42.599 -4.058 31.918 -0.102 -1.858 -0.079 "HC2'" 693 43 
693 H31B   H31B   H 0  0 N N N 42.632 -5.133 34.134 -3.809 -2.307 0.195  H31B   693 44 
693 H42A   H42A   H 0  0 N N N 43.017 -3.358 36.303 -2.695 -2.513 -2.048 H42A   693 45 
693 H42B   H42B   H 0  0 N N N 41.468 -4.040 36.673 -1.330 -3.336 -1.256 H42B   693 46 
693 "HC4'" "HC4'" H 0  0 N N N 42.396 -1.679 35.435 -3.927 -0.017 0.302  "HC4'" 693 47 
693 H3B    "H3''" H 0  1 N N N 45.407 2.922  35.029 -3.996 5.300  -1.406 H3B    693 48 
693 H4B    "H4''" H 0  1 N N N 43.539 3.882  36.337 -5.275 5.708  0.655  H4B    693 49 
693 H5B    "H5''" H 0  1 N N N 41.352 2.746  36.360 -5.169 4.105  2.517  H5B    693 50 
693 H6B    "H6''" H 0  1 N N N 41.031 0.677  35.113 -3.780 2.083  2.330  H6B    693 51 
# 
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 
693 C1    C2     DOUB Y N 1  
693 C1    C6     SING Y N 2  
693 C1    C7     SING N N 3  
693 C2    C3     SING Y N 4  
693 C2    HC2    SING N N 5  
693 C3    C4     DOUB Y N 6  
693 C3    HC3    SING N N 7  
693 C4    C5     SING Y N 8  
693 C4    N3     SING Y N 9  
693 C5    C6     DOUB Y N 10 
693 C5    N4     SING Y N 11 
693 C6    HC6    SING N N 12 
693 C7    N1     SING N N 13 
693 C7    N2     DOUB N N 14 
693 N1    HH11   SING N N 15 
693 N1    HH12   SING N N 16 
693 N2    HH21   SING N N 17 
693 N2    HH22   SING N N 18 
693 N3    C8     SING Y N 19 
693 N3    HN3    SING N N 20 
693 N4    C8     DOUB Y N 21 
693 C8    "C1'"  SING N N 22 
693 "C1'" "C2'"  DOUB Y N 23 
693 "C1'" "C6'"  SING Y N 24 
693 "C2'" "C3'"  SING Y N 25 
693 "C2'" "HC2'" SING N N 26 
693 "C3'" CVX    SING N N 27 
693 "C3'" "C4'"  DOUB Y N 28 
693 CVX   CWX    SING N N 29 
693 CVX   C6X    SING N N 30 
693 CVX   H31B   SING N N 31 
693 CWX   OXX    DOUB N N 32 
693 CWX   OYX    SING N N 33 
693 C6X   C7X    SING N N 34 
693 C6X   H42A   SING N N 35 
693 C6X   H42B   SING N N 36 
693 C7X   O8X    DOUB N N 37 
693 C7X   O9X    SING N N 38 
693 "C4'" "C5'"  SING Y N 39 
693 "C4'" "HC4'" SING N N 40 
693 "C5'" "C6'"  DOUB Y N 41 
693 "C5'" C1B    SING N N 42 
693 "C6'" "O6'"  SING N N 43 
693 C1B   C2B    DOUB Y N 44 
693 C1B   C6B    SING Y N 45 
693 C2B   C3B    SING Y N 46 
693 C2B   F2B    SING N N 47 
693 C3B   C4B    DOUB Y N 48 
693 C3B   H3B    SING N N 49 
693 C4B   C5B    SING Y N 50 
693 C4B   H4B    SING N N 51 
693 C5B   C6B    DOUB Y N 52 
693 C5B   H5B    SING N N 53 
693 C6B   H6B    SING N N 54 
# 
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 
693 SMILES           ACDLabs              10.04 [O-]C(=O)CC(C([O-])=O)c4cc(c2nc1cc(ccc1n2)\C(=[NH2+])N)c([O-])c(c3ccccc3F)c4 
693 InChI            InChI                1.02b 
InChI=1/C24H19FN4O5/c25-17-4-2-1-3-13(17)15-7-12(14(24(33)34)10-20(30)31)8-16(21(15)32)23-28-18-6-5-11(22(26)27)9-19(18)29-23/h1-9,14,32H,10H2,(H3,26,27)(H,28,29)(H,30,31)(H,33,34)/p-2/t14-/m1/s1/fC24H17FN4O5/h32h,28H,26-27H2/q-2 
693 InChIKey         InChI                1.02b XCOFROALSAFROV-LRBUTBSWDG 
693 SMILES_CANONICAL CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cc(cc(c3[O-])c4ccccc4F)[C@@H](CC([O-])=O)C([O-])=O 
693 SMILES           CACTVS               3.341 NC(=[NH2+])c1ccc2[nH]c(nc2c1)c3cc(cc(c3[O-])c4ccccc4F)[CH](CC([O-])=O)C([O-])=O 
693 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(c(c1)c2cc(cc(c2[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])N)[C@@H](CC(=O)[O-])C(=O)[O-])F 
693 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(c(c1)c2cc(cc(c2[O-])c3[nH]c4ccc(cc4n3)C(=[NH2+])N)C(CC(=O)[O-])C(=O)[O-])F 
# 
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 
693 "SYSTEMATIC NAME" ACDLabs              10.04 "(2R)-2-(5-{5-[amino(iminio)methyl]-1H-benzimidazol-2-yl}-2'-fluoro-6-oxidobiphenyl-3-yl)butanedioate"          
693 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-2-[3-[5-(amino-azaniumylidene-methyl)-1H-benzimidazol-2-yl]-5-(2-fluorophenyl)-4-oxido-phenyl]butanedioate 
# 
