data_CR9
# 
_chem_comp.id                                    CR9 
_chem_comp.name                                  2-{5-[AMINO(IMINIO)METHYL]-6-FLUORO-1H-BENZIMIDAZOL-2-YL}-6-[(2-METHYLCYCLOHEXYL)OXY]BENZENOLATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H23 F N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         CRA_11092 
_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                        382.431 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CR9 
_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        1O2R 
_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 
CR9 C1     C1     C 0  1 Y N N 43.903 -3.169 25.814 -5.345 -0.524 0.184  C1     CR9 1  
CR9 C2     C2     C 0  1 Y N N 43.839 -1.762 25.662 -5.508 0.631  -0.594 C2     CR9 2  
CR9 F2     F2     F 0  1 N N N 43.935 -1.180 24.420 -6.740 0.989  -1.019 F2     CR9 3  
CR9 C3     C3     C 0  1 Y N N 43.649 -0.939 26.768 -4.416 1.403  -0.929 C3     CR9 4  
CR9 C4     C4     C 0  1 Y N N 43.514 -1.532 28.006 -3.148 1.039  -0.495 C4     CR9 5  
CR9 C5     C5     C 0  1 Y N N 43.569 -2.863 28.186 -2.973 -0.119 0.288  C5     CR9 6  
CR9 C6     C6     C 0  1 Y N N 43.767 -3.718 27.095 -4.079 -0.898 0.625  C6     CR9 7  
CR9 C7     C7     C 0  1 N N N 44.107 -4.007 24.708 -6.521 -1.345 0.538  C7     CR9 8  
CR9 N1     N1     N 0  1 N N N 43.687 -5.255 24.711 -7.537 -0.801 1.208  N1     CR9 9  
CR9 N2     N2     N 1  1 N N N 44.742 -3.508 23.668 -6.565 -2.631 0.188  N2     CR9 10 
CR9 N3     N3     N 0  1 Y N N 43.337 -1.043 29.181 -1.892 1.586  -0.658 N3     CR9 11 
CR9 N4     N4     N 0  1 Y N N 43.428 -3.225 29.450 -1.647 -0.225 0.555  N4     CR9 12 
CR9 C8     C8     C 0  1 Y N N 43.289 -2.036 30.017 -1.007 0.779  0.006  C8     CR9 13 
CR9 "C1'"  "C1'"  C 0  1 Y N N 43.042 -1.840 31.398 0.451  1.002  0.086  "C1'"  CR9 14 
CR9 "C2'"  "C2'"  C 0  1 Y N N 42.888 -2.947 32.242 0.955  2.293  0.256  "C2'"  CR9 15 
CR9 "C3'"  "C3'"  C 0  1 Y N N 42.641 -2.779 33.607 2.316  2.498  0.331  "C3'"  CR9 16 
CR9 "C4'"  "C4'"  C 0  1 Y N N 42.549 -1.514 34.142 3.190  1.429  0.239  "C4'"  CR9 17 
CR9 "C5'"  "C5'"  C 0  1 Y N N 42.695 -0.375 33.348 2.705  0.142  0.070  "C5'"  CR9 18 
CR9 "C6'"  "C6'"  C 0  1 Y N N 42.947 -0.540 31.959 1.334  -0.078 -0.013 "C6'"  CR9 19 
CR9 "O6'"  "O6'"  O -1 1 N N N 43.096 0.559  31.123 0.855  -1.339 -0.179 "O6'"  CR9 20 
CR9 "O5'"  "O5'"  O 0  1 N N N 42.577 0.877  33.960 3.569  -0.904 -0.020 "O5'"  CR9 21 
CR9 C1B    "C1''" C 0  1 N N S 42.488 2.505  35.822 5.842  -1.358 -0.703 C1B    CR9 22 
CR9 C2B    "C2''" C 0  1 N N N 43.153 2.944  37.192 7.252  -0.765 -0.748 C2B    CR9 23 
CR9 C3B    "C3''" C 0  1 N N N 44.658 3.124  37.036 7.719  -0.452 0.675  C3B    CR9 24 
CR9 C4B    "C4''" C 0  1 N N N 45.258 1.844  36.380 6.762  0.555  1.316  C4B    CR9 25 
CR9 C5B    "C5''" C 0  1 N N N 44.632 1.595  34.973 5.353  -0.037 1.361  C5B    CR9 26 
CR9 C6B    "C6''" C 0  1 N N S 43.161 1.236  35.230 4.885  -0.351 -0.062 C6B    CR9 27 
CR9 C1A    C1A    C 0  1 N N N 41.050 2.180  36.136 5.375  -1.671 -2.125 C1A    CR9 28 
CR9 HC3    HC3    H 0  1 N N N 43.605 0.137  26.674 -4.547 2.291  -1.529 HC3    CR9 29 
CR9 HC6    HC6    H 0  1 N N N 43.810 -4.785 27.241 -3.955 -1.787 1.225  HC6    CR9 30 
CR9 HH11   HH11   H 0  0 N N N 43.262 -5.600 25.565 -7.505 0.135  1.462  HH11   CR9 31 
CR9 HH12   HH12   H 0  0 N N N 43.782 -5.917 23.971 -8.309 -1.340 1.440  HH12   CR9 32 
CR9 HH21   HH21   H 0  0 N N N 45.119 -2.576 23.701 -7.291 -3.194 0.500  HH21   CR9 33 
CR9 HH22   HH22   H 0  0 N N N 44.918 -4.031 22.840 -5.872 -3.004 -0.378 HH22   CR9 34 
CR9 HN3    HN3    H 0  1 N N N 43.245 -0.098 29.467 -1.676 2.393  -1.151 HN3    CR9 35 
CR9 "HC2'" "HC2'" H 0  0 N N N 42.959 -3.947 31.841 0.278  3.132  0.329  "HC2'" CR9 36 
CR9 "HC3'" "HC3'" H 0  0 N N N 42.522 -3.640 34.252 2.703  3.498  0.463  "HC3'" CR9 37 
CR9 "HC4'" "HC4'" H 0  0 N N N 42.360 -1.414 35.200 4.255  1.598  0.300  "HC4'" CR9 38 
CR9 H1B    H1B    H 0  1 N N N 42.554 3.324  35.122 5.852  -2.275 -0.114 H1B    CR9 39 
CR9 H2A    H2A    H 0  1 N N N 42.749 3.889  37.526 7.933  -1.483 -1.204 H2A    CR9 40 
CR9 H2B    H2B    H 0  1 N N N 42.965 2.206  37.962 7.241  0.152  -1.337 H2B    CR9 41 
CR9 H3A    H3A    H 0  1 N N N 45.103 3.262  38.015 7.729  -1.369 1.264  H3A    CR9 42 
CR9 H3B    H3B    H 0  1 N N N 44.874 3.994  36.439 8.723  -0.029 0.643  H3B    CR9 43 
CR9 H4A    H4A    H 0  1 N N N 46.333 1.927  36.301 7.095  0.779  2.330  H4A    CR9 44 
CR9 H4B    H4B    H 0  1 N N N 45.052 1.006  37.025 6.752  1.472  0.727  H4B    CR9 45 
CR9 H5A    H5A    H 0  1 N N N 45.140 0.769  34.493 5.363  -0.954 1.950  H5A    CR9 46 
CR9 H5B    H5B    H 0  1 N N N 44.724 2.479  34.362 4.671  0.680  1.818  H5B    CR9 47 
CR9 H6B    "H6''" H 0  1 N N N 43.071 0.418  35.932 4.875  0.566  -0.651 H6B    CR9 48 
CR9 H1AA   H1AA   H 0  0 N N N 40.528 1.830  35.261 6.056  -2.389 -2.582 H1AA   CR9 49 
CR9 H1AB   H1AB   H 0  0 N N N 41.003 1.426  36.912 4.370  -2.094 -2.093 H1AB   CR9 50 
CR9 H1AC   H1AC   H 0  0 N N N 40.568 3.078  36.501 5.364  -0.754 -2.715 H1AC   CR9 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 
CR9 C1    C2     DOUB Y N 1  
CR9 C1    C6     SING Y N 2  
CR9 C1    C7     SING N N 3  
CR9 C2    F2     SING N N 4  
CR9 C2    C3     SING Y N 5  
CR9 C3    C4     DOUB Y N 6  
CR9 C3    HC3    SING N N 7  
CR9 C4    C5     SING Y N 8  
CR9 C4    N3     SING Y N 9  
CR9 C5    C6     DOUB Y N 10 
CR9 C5    N4     SING Y N 11 
CR9 C6    HC6    SING N N 12 
CR9 C7    N1     SING N N 13 
CR9 C7    N2     DOUB N N 14 
CR9 N1    HH11   SING N N 15 
CR9 N1    HH12   SING N N 16 
CR9 N2    HH21   SING N N 17 
CR9 N2    HH22   SING N N 18 
CR9 N3    C8     SING Y N 19 
CR9 N3    HN3    SING N N 20 
CR9 N4    C8     DOUB Y N 21 
CR9 C8    "C1'"  SING N N 22 
CR9 "C1'" "C2'"  DOUB Y N 23 
CR9 "C1'" "C6'"  SING Y N 24 
CR9 "C2'" "C3'"  SING Y N 25 
CR9 "C2'" "HC2'" SING N N 26 
CR9 "C3'" "C4'"  DOUB Y N 27 
CR9 "C3'" "HC3'" SING N N 28 
CR9 "C4'" "C5'"  SING Y N 29 
CR9 "C4'" "HC4'" SING N N 30 
CR9 "C5'" "C6'"  DOUB Y N 31 
CR9 "C5'" "O5'"  SING N N 32 
CR9 "C6'" "O6'"  SING N N 33 
CR9 "O5'" C6B    SING N N 34 
CR9 C1B   C2B    SING N N 35 
CR9 C1B   C6B    SING N N 36 
CR9 C1B   C1A    SING N N 37 
CR9 C1B   H1B    SING N N 38 
CR9 C2B   C3B    SING N N 39 
CR9 C2B   H2A    SING N N 40 
CR9 C2B   H2B    SING N N 41 
CR9 C3B   C4B    SING N N 42 
CR9 C3B   H3A    SING N N 43 
CR9 C3B   H3B    SING N N 44 
CR9 C4B   C5B    SING N N 45 
CR9 C4B   H4A    SING N N 46 
CR9 C4B   H4B    SING N N 47 
CR9 C5B   C6B    SING N N 48 
CR9 C5B   H5A    SING N N 49 
CR9 C5B   H5B    SING N N 50 
CR9 C6B   H6B    SING N N 51 
CR9 C1A   H1AA   SING N N 52 
CR9 C1A   H1AB   SING N N 53 
CR9 C1A   H1AC   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 
CR9 SMILES           ACDLabs              10.04 [O-]c4c(OC1CCCCC1C)cccc4c3nc2cc(c(F)cc2n3)\C(=[NH2+])N                                                                                                                                           
CR9 InChI            InChI                1.02b InChI=1/C21H23FN4O2/c1-11-5-2-3-7-17(11)28-18-8-4-6-12(19(18)27)21-25-15-9-13(20(23)24)14(22)10-16(15)26-21/h4,6,8-11,17,27H,2-3,5,7H2,1H3,(H3,23,24)(H,25,26)/t11-,17-/m0/s1/f/h27h,26H,23-24H2 
CR9 InChIKey         InChI                1.02b CMCDWLMEDRBWIR-KGLCFOTRDS                                                                                                                                                                        
CR9 SMILES_CANONICAL CACTVS               3.341 C[C@H]1CCCC[C@@H]1Oc2cccc(c2[O-])c3[nH]c4cc(F)c(cc4n3)C(N)=[NH2+]                                                                                                                                
CR9 SMILES           CACTVS               3.341 C[CH]1CCCC[CH]1Oc2cccc(c2[O-])c3[nH]c4cc(F)c(cc4n3)C(N)=[NH2+]                                                                                                                                   
CR9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1CCCC[C@@H]1Oc2cccc(c2[O-])c3[nH]c4cc(c(cc4n3)C(=[NH2+])N)F                                                                                                                                
CR9 SMILES           "OpenEye OEToolkits" 1.5.0 CC1CCCCC1Oc2cccc(c2[O-])c3[nH]c4cc(c(cc4n3)C(=[NH2+])N)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 
CR9 "SYSTEMATIC NAME" ACDLabs              10.04 2-{5-[amino(iminio)methyl]-6-fluoro-1H-benzimidazol-2-yl}-6-{[(1S,2S)-2-methylcyclohexyl]oxy}phenolate        
CR9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[5-(amino-azaniumylidene-methyl)-6-fluoro-1H-benzimidazol-2-yl]-6-[(1S,2S)-2-methylcyclohexyl]oxy-phenolate 
# 
