data_I4A # _chem_comp.id I4A _chem_comp.name "5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H22 N2 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-01-13 _chem_comp.pdbx_modified_date 2011-06-04 _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 362.422 _chem_comp.one_letter_code ? _chem_comp.three_letter_code I4A _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3FR5 _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 I4A O27 O27 O 0 1 N N N 16.907 4.765 2.813 -2.304 -2.580 0.393 O27 I4A 1 I4A C25 C25 C 0 1 N N N 17.587 5.787 2.756 -1.099 -2.461 0.986 C25 I4A 2 I4A O26 O26 O 0 1 N N N 17.200 6.760 1.936 -1.026 -2.332 2.192 O26 I4A 3 I4A C4 C4 C 0 1 Y N N 18.816 5.943 3.589 0.129 -2.487 0.172 C4 I4A 4 I4A C6 C6 C 0 1 Y N N 20.084 5.217 3.317 0.996 -1.382 0.165 C6 I4A 5 I4A C7 C7 C 0 1 Y N N 21.226 5.429 4.237 2.164 -1.429 -0.618 C7 I4A 6 I4A C9 C9 C 0 1 Y N N 22.300 4.584 3.671 2.839 -0.148 -0.408 C9 I4A 7 I4A C10 C10 C 0 1 N N N 23.713 4.350 4.120 4.130 0.303 -1.039 C10 I4A 8 I4A C12 C12 C 0 1 N N N 24.682 4.682 2.990 4.821 1.313 -0.119 C12 I4A 9 I4A C14 C14 C 0 1 N N N 24.850 3.619 1.905 4.335 2.721 -0.454 C14 I4A 10 I4A C13 C13 C 0 1 N N N 23.587 3.633 1.013 2.830 2.835 -0.228 C13 I4A 11 I4A C11 C11 C 0 1 N N N 22.344 2.948 1.582 2.416 1.949 0.949 C11 I4A 12 I4A C8 C8 C 0 1 Y N N 21.659 3.921 2.490 2.085 0.564 0.446 C8 I4A 13 I4A C3 C3 C 0 1 Y N N 21.079 6.299 5.320 2.450 -2.564 -1.378 C3 I4A 14 I4A C2 C2 C 0 1 Y N N 19.870 6.962 5.540 1.588 -3.640 -1.362 C2 I4A 15 I4A C1 C1 C 0 1 Y N N 18.776 6.783 4.690 0.440 -3.612 -0.591 C1 I4A 16 I4A N5 N5 N 0 1 Y N N 20.397 4.316 2.349 0.975 -0.163 0.791 N5 I4A 17 I4A C15 C15 C 0 1 N N N 19.581 3.828 1.260 -0.082 0.297 1.696 C15 I4A 18 I4A C16 C16 C 0 1 Y N N 19.906 4.416 -0.095 -1.081 1.120 0.924 C16 I4A 19 I4A C17 C17 C 0 1 Y N N 19.618 3.630 -1.197 -2.214 0.525 0.412 C17 I4A 20 I4A C18 C18 C 0 1 Y N N 19.906 4.094 -2.474 -3.139 1.289 -0.302 C18 I4A 21 I4A C22 C22 C 0 1 N N N 19.623 3.212 -3.653 -4.356 0.657 -0.853 C22 I4A 22 I4A N24 N24 N 0 1 N N N 20.256 3.506 -4.776 -5.247 1.398 -1.542 N24 I4A 23 I4A O23 O23 O 0 1 N N N 18.879 2.232 -3.554 -4.554 -0.531 -0.686 O23 I4A 24 I4A C19 C19 C 0 1 Y N N 20.461 5.361 -2.676 -2.909 2.652 -0.492 C19 I4A 25 I4A C20 C20 C 0 1 Y N N 20.722 6.159 -1.563 -1.771 3.236 0.026 C20 I4A 26 I4A C21 C21 C 0 1 Y N N 20.464 5.684 -0.271 -0.862 2.474 0.737 C21 I4A 27 I4A HO27 HO27 H 0 0 N N N 16.167 4.843 2.222 -3.080 -2.557 0.969 HO27 I4A 28 I4A H10 H10 H 0 1 N N N 23.930 4.993 4.986 4.782 -0.558 -1.189 H10 I4A 29 I4A H10A H10A H 0 0 N N N 23.833 3.293 4.399 3.920 0.772 -2.001 H10A I4A 30 I4A H12 H12 H 0 1 N N N 24.310 5.593 2.499 4.581 1.082 0.919 H12 I4A 31 I4A H12A H12A H 0 0 N N N 25.669 4.779 3.465 5.900 1.257 -0.264 H12A I4A 32 I4A H14 H14 H 0 1 N N N 25.739 3.842 1.297 4.850 3.440 0.183 H14 I4A 33 I4A H14A H14A H 0 0 N N N 24.979 2.627 2.363 4.559 2.940 -1.498 H14A I4A 34 I4A H13 H13 H 0 1 N N N 23.326 4.687 0.836 2.573 3.871 -0.010 H13 I4A 35 I4A H13A H13A H 0 0 N N N 23.854 3.060 0.113 2.303 2.513 -1.127 H13A I4A 36 I4A H11 H11 H 0 1 N N N 21.668 2.655 0.765 3.236 1.890 1.664 H11 I4A 37 I4A H11A H11A H 0 0 N N N 22.627 2.041 2.136 1.540 2.378 1.436 H11A I4A 38 I4A H3 H3 H 0 1 N N N 21.908 6.460 5.993 3.346 -2.599 -1.980 H3 I4A 39 I4A H2 H2 H 0 1 N N N 19.779 7.628 6.386 1.814 -4.516 -1.953 H2 I4A 40 I4A H1 H1 H 0 1 N N N 17.863 7.321 4.899 -0.223 -4.465 -0.584 H1 I4A 41 I4A H15 H15 H 0 1 N N N 19.727 2.740 1.195 -0.583 -0.565 2.136 H15 I4A 42 I4A H15A H15A H 0 0 N N N 18.547 4.126 1.488 0.357 0.905 2.487 H15A I4A 43 I4A H17 H17 H 0 1 N N N 19.170 2.657 -1.064 -2.386 -0.531 0.563 H17 I4A 44 I4A HN24 HN24 H 0 0 N N N 19.976 2.844 -5.471 -5.089 2.345 -1.676 HN24 I4A 45 I4A HN2A HN2A H 0 0 N N N 20.901 4.259 -4.907 -6.046 0.983 -1.904 HN2A I4A 46 I4A H19 H19 H 0 1 N N N 20.683 5.714 -3.672 -3.621 3.249 -1.043 H19 I4A 47 I4A H20 H20 H 0 1 N N N 21.126 7.151 -1.698 -1.592 4.291 -0.121 H20 I4A 48 I4A H21 H21 H 0 1 N N N 20.696 6.297 0.587 0.027 2.936 1.140 H21 I4A 49 # 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 I4A C25 O27 SING N N 1 I4A O27 HO27 SING N N 2 I4A O26 C25 DOUB N N 3 I4A C25 C4 SING N N 4 I4A C6 C4 DOUB Y N 5 I4A C4 C1 SING Y N 6 I4A N5 C6 SING Y N 7 I4A C6 C7 SING Y N 8 I4A C9 C7 SING Y N 9 I4A C7 C3 DOUB Y N 10 I4A C8 C9 DOUB Y N 11 I4A C9 C10 SING N N 12 I4A C12 C10 SING N N 13 I4A C10 H10 SING N N 14 I4A C10 H10A SING N N 15 I4A C14 C12 SING N N 16 I4A C12 H12 SING N N 17 I4A C12 H12A SING N N 18 I4A C13 C14 SING N N 19 I4A C14 H14 SING N N 20 I4A C14 H14A SING N N 21 I4A C13 C11 SING N N 22 I4A C13 H13 SING N N 23 I4A C13 H13A SING N N 24 I4A C11 C8 SING N N 25 I4A C11 H11 SING N N 26 I4A C11 H11A SING N N 27 I4A N5 C8 SING Y N 28 I4A C3 C2 SING Y N 29 I4A C3 H3 SING N N 30 I4A C1 C2 DOUB Y N 31 I4A C2 H2 SING N N 32 I4A C1 H1 SING N N 33 I4A C15 N5 SING N N 34 I4A C16 C15 SING N N 35 I4A C15 H15 SING N N 36 I4A C15 H15A SING N N 37 I4A C17 C16 DOUB Y N 38 I4A C21 C16 SING Y N 39 I4A C18 C17 SING Y N 40 I4A C17 H17 SING N N 41 I4A C22 C18 SING N N 42 I4A C19 C18 DOUB Y N 43 I4A N24 C22 SING N N 44 I4A C22 O23 DOUB N N 45 I4A N24 HN24 SING N N 46 I4A N24 HN2A SING N N 47 I4A C19 C20 SING Y N 48 I4A C19 H19 SING N N 49 I4A C20 C21 DOUB Y N 50 I4A C20 H20 SING N N 51 I4A C21 H21 SING N N 52 # 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 I4A SMILES ACDLabs 10.04 "O=C(N)c1cc(ccc1)Cn2c4c(c3c2CCCCC3)cccc4C(=O)O" I4A SMILES_CANONICAL CACTVS 3.341 "NC(=O)c1cccc(Cn2c3CCCCCc3c4cccc(C(O)=O)c24)c1" I4A SMILES CACTVS 3.341 "NC(=O)c1cccc(Cn2c3CCCCCc3c4cccc(C(O)=O)c24)c1" I4A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(cc(c1)C(=O)N)Cn2c3c(c4c2c(ccc4)C(=O)O)CCCCC3" I4A SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(cc(c1)C(=O)N)Cn2c3c(c4c2c(ccc4)C(=O)O)CCCCC3" I4A InChI InChI 1.03 "InChI=1S/C22H22N2O3/c23-21(25)15-7-4-6-14(12-15)13-24-19-11-3-1-2-8-16(19)17-9-5-10-18(20(17)24)22(26)27/h4-7,9-10,12H,1-3,8,11,13H2,(H2,23,25)(H,26,27)" I4A InChIKey InChI 1.03 GKBQRPKZHUFGOB-UHFFFAOYSA-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 I4A "SYSTEMATIC NAME" ACDLabs 10.04 "5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid" I4A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[(3-aminocarbonylphenyl)methyl]-7,8,9,10-tetrahydro-6H-cyclohepta[b]indole-4-carboxylic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site I4A "Create component" 2009-01-13 RCSB I4A "Modify aromatic_flag" 2011-06-04 RCSB I4A "Modify descriptor" 2011-06-04 RCSB #