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 2020-06-17 _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 Y 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 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" CR9 InChI InChI 1.03 "InChI=1S/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" CR9 InChIKey InChI 1.03 CMCDWLMEDRBWIR-GTNSWQLSSA-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 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" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CR9 "Create component" 2003-03-14 RCSB CR9 "Modify aromatic_flag" 2011-06-04 RCSB CR9 "Modify descriptor" 2011-06-04 RCSB CR9 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id CR9 _pdbx_chem_comp_synonyms.name CRA_11092 _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##