data_669 # _chem_comp.id 669 _chem_comp.name "1-(5-CARBOXYPENTYL)-5-(2,6-DICHLOROBENZYLOXY)-1H-INDOLE-2-CARBOXYLIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H21 Cl2 N O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-10-10 _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 450.312 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 669 _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 1MZS _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 669 O01 O01 O 0 1 N N N 29.552 7.420 34.225 8.715 -3.897 -0.658 O01 669 1 669 C02 C02 C 0 1 N N N 30.463 7.685 33.252 7.673 -3.221 -0.150 C02 669 2 669 O03 O03 O 0 1 N N N 31.183 6.789 32.767 7.301 -3.443 0.978 O03 669 3 669 C04 C04 C 0 1 N N N 30.433 9.160 32.885 6.967 -2.185 -0.986 C04 669 4 669 C05 C05 C 0 1 N N N 29.019 9.666 32.490 5.825 -1.568 -0.176 C05 669 5 669 C06 C06 C 0 1 N N N 28.305 8.708 31.527 5.107 -0.517 -1.024 C06 669 6 669 C07 C07 C 0 1 N N N 27.101 9.323 30.855 3.965 0.100 -0.214 C07 669 7 669 C08 C08 C 0 1 N N N 25.906 9.503 31.808 3.248 1.152 -1.063 C08 669 8 669 N09 N09 N 0 1 Y N N 25.966 10.762 32.594 2.155 1.743 -0.288 N09 669 9 669 C10 C10 C 0 1 Y N N 25.873 10.870 34.023 2.254 2.856 0.524 C10 669 10 669 C11 C11 C 0 1 Y N N 26.053 12.233 34.341 1.040 3.110 1.082 C11 669 11 669 C12 C12 C 0 1 Y N N 26.209 12.886 33.139 0.135 2.129 0.612 C12 669 12 669 C13 C13 C 0 1 Y N N 26.385 14.280 32.922 -1.226 1.889 0.841 C13 669 13 669 C14 C14 C 0 1 Y N N 26.492 14.752 31.578 -1.845 0.824 0.222 C14 669 14 669 O15 O15 O 0 1 N N N 26.646 16.084 31.324 -3.167 0.589 0.442 O15 669 15 669 C16 C16 C 0 1 N N N 27.052 16.981 32.377 -3.514 -0.565 -0.326 C16 669 16 669 C17 C17 C 0 1 Y N N 26.768 18.364 31.852 -4.974 -0.881 -0.125 C17 669 17 669 C18 C18 C 0 1 Y N N 27.780 19.077 31.096 -5.364 -1.733 0.893 C18 669 18 669 CL9 CL9 CL 0 0 N N N 29.349 18.424 30.724 -4.172 -2.433 1.944 CL9 669 19 669 C20 C20 C 0 1 Y N N 27.486 20.366 30.577 -6.705 -2.019 1.080 C20 669 20 669 C21 C21 C 0 1 Y N N 26.211 20.957 30.780 -7.653 -1.462 0.243 C21 669 21 669 C22 C22 C 0 1 Y N N 25.209 20.267 31.514 -7.264 -0.615 -0.778 C22 669 22 669 C23 C23 C 0 1 Y N N 25.466 18.977 32.054 -5.924 -0.324 -0.962 C23 669 23 669 CL4 CL4 CL 0 0 N N N 24.164 18.230 32.931 -5.435 0.739 -2.244 CL4 669 24 669 C25 C25 C 0 1 Y N N 26.429 13.893 30.463 -1.125 -0.013 -0.628 C25 669 25 669 C26 C26 C 0 1 Y N N 26.267 12.521 30.688 0.213 0.210 -0.861 C26 669 26 669 C27 C27 C 0 1 Y N N 26.158 12.020 32.037 0.857 1.283 -0.252 C27 669 27 669 C28 C28 C 0 1 N N N 25.581 9.774 34.939 3.476 3.640 0.749 C28 669 28 669 O29 O29 O 0 1 N N N 24.865 8.813 34.725 4.625 3.288 0.138 O29 669 29 669 O30 O30 O 0 1 N N N 26.198 9.915 36.134 3.451 4.606 1.487 O30 669 30 669 H01 H01 H 0 1 N N N 29.004 8.102 34.594 9.169 -4.562 -0.122 H01 669 31 669 H041 1H04 H 0 0 N N N 31.172 9.383 32.081 7.673 -1.405 -1.271 H041 669 32 669 H042 2H04 H 0 0 N N N 30.861 9.781 33.706 6.563 -2.655 -1.883 H042 669 33 669 H051 1H05 H 0 0 N N N 29.063 10.699 32.071 5.119 -2.349 0.109 H051 669 34 669 H052 2H05 H 0 0 N N N 28.397 9.867 33.393 6.228 -1.098 0.721 H052 669 35 669 H061 1H06 H 0 0 N N N 28.028 7.760 32.045 5.813 0.263 -1.309 H061 669 36 669 H062 2H06 H 0 0 N N N 29.017 8.304 30.770 4.704 -0.987 -1.921 H062 669 37 669 H071 1H07 H 0 0 N N N 26.806 8.737 29.953 3.259 -0.680 0.070 H071 669 38 669 H072 2H07 H 0 0 N N N 27.369 10.289 30.366 4.369 0.570 0.682 H072 669 39 669 H081 1H08 H 0 0 N N N 25.800 8.621 32.481 3.954 1.932 -1.348 H081 669 40 669 H082 2H08 H 0 0 N N N 24.942 9.428 31.253 2.845 0.682 -1.960 H082 669 41 669 H11 H11 H 0 1 N N N 26.069 12.700 35.340 0.808 3.917 1.762 H11 669 42 669 H13 H13 H 0 1 N N N 26.437 14.978 33.775 -1.788 2.536 1.499 H13 669 43 669 H161 1H16 H 0 0 N N N 28.106 16.835 32.711 -3.326 -0.369 -1.381 H161 669 44 669 H162 2H16 H 0 0 N N N 26.573 16.766 33.361 -2.911 -1.413 -0.001 H162 669 45 669 H20 H20 H 0 1 N N N 28.257 20.914 30.010 -7.010 -2.680 1.877 H20 669 46 669 H21 H21 H 0 1 N N N 25.998 21.957 30.366 -8.699 -1.689 0.386 H21 669 47 669 H22 H22 H 0 1 N N N 24.223 20.737 31.666 -8.006 -0.180 -1.431 H22 669 48 669 H25 H25 H 0 1 N N N 26.505 14.286 29.435 -1.620 -0.844 -1.107 H25 669 49 669 H26 H26 H 0 1 N N N 26.226 11.846 29.817 0.762 -0.445 -1.522 H26 669 50 669 H29 H29 H 0 1 N N N 24.675 8.099 35.322 5.429 3.804 0.286 H29 669 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 669 O01 C02 SING N N 1 669 O01 H01 SING N N 2 669 C02 O03 DOUB N N 3 669 C02 C04 SING N N 4 669 C04 C05 SING N N 5 669 C04 H041 SING N N 6 669 C04 H042 SING N N 7 669 C05 C06 SING N N 8 669 C05 H051 SING N N 9 669 C05 H052 SING N N 10 669 C06 C07 SING N N 11 669 C06 H061 SING N N 12 669 C06 H062 SING N N 13 669 C07 C08 SING N N 14 669 C07 H071 SING N N 15 669 C07 H072 SING N N 16 669 C08 N09 SING N N 17 669 C08 H081 SING N N 18 669 C08 H082 SING N N 19 669 N09 C10 SING Y N 20 669 N09 C27 SING Y N 21 669 C10 C11 DOUB Y N 22 669 C10 C28 SING N N 23 669 C11 C12 SING Y N 24 669 C11 H11 SING N N 25 669 C12 C13 SING Y N 26 669 C12 C27 DOUB Y N 27 669 C13 C14 DOUB Y N 28 669 C13 H13 SING N N 29 669 C14 O15 SING N N 30 669 C14 C25 SING Y N 31 669 O15 C16 SING N N 32 669 C16 C17 SING N N 33 669 C16 H161 SING N N 34 669 C16 H162 SING N N 35 669 C17 C18 SING Y N 36 669 C17 C23 DOUB Y N 37 669 C18 CL9 SING N N 38 669 C18 C20 DOUB Y N 39 669 C20 C21 SING Y N 40 669 C20 H20 SING N N 41 669 C21 C22 DOUB Y N 42 669 C21 H21 SING N N 43 669 C22 C23 SING Y N 44 669 C22 H22 SING N N 45 669 C23 CL4 SING N N 46 669 C25 C26 DOUB Y N 47 669 C25 H25 SING N N 48 669 C26 C27 SING Y N 49 669 C26 H26 SING N N 50 669 C28 O29 SING N N 51 669 C28 O30 DOUB N N 52 669 O29 H29 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 669 SMILES ACDLabs 10.04 "Clc1cccc(Cl)c1COc2cc3c(cc2)n(c(c3)C(=O)O)CCCCCC(=O)O" 669 SMILES_CANONICAL CACTVS 3.341 "OC(=O)CCCCCn1c(cc2cc(OCc3c(Cl)cccc3Cl)ccc12)C(O)=O" 669 SMILES CACTVS 3.341 "OC(=O)CCCCCn1c(cc2cc(OCc3c(Cl)cccc3Cl)ccc12)C(O)=O" 669 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c(c(c1)Cl)COc2ccc3c(c2)cc(n3CCCCCC(=O)O)C(=O)O)Cl" 669 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(c(c(c1)Cl)COc2ccc3c(c2)cc(n3CCCCCC(=O)O)C(=O)O)Cl" 669 InChI InChI 1.03 "InChI=1S/C22H21Cl2NO5/c23-17-5-4-6-18(24)16(17)13-30-15-8-9-19-14(11-15)12-20(22(28)29)25(19)10-3-1-2-7-21(26)27/h4-6,8-9,11-12H,1-3,7,10,13H2,(H,26,27)(H,28,29)" 669 InChIKey InChI 1.03 JTGPYFFQVOIJKR-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 669 "SYSTEMATIC NAME" ACDLabs 10.04 "1-(5-carboxypentyl)-5-[(2,6-dichlorobenzyl)oxy]-1H-indole-2-carboxylic acid" 669 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[(2,6-dichlorophenyl)methoxy]-1-(6-hydroxy-6-oxo-hexyl)indole-2-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 669 "Create component" 2002-10-10 RCSB 669 "Modify descriptor" 2011-06-04 RCSB #