data_PIL # _chem_comp.id PIL _chem_comp.name "3-(CYCLOPENTYLOXY)-N-(3,5-DICHLOROPYRIDIN-4-YL)-4-METHOXYBENZAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H18 Cl2 N2 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms PICLAMILAST _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2004-11-17 _chem_comp.pdbx_modified_date 2021-03-01 _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 381.253 _chem_comp.one_letter_code ? _chem_comp.three_letter_code PIL _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 ? _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 PIL CL25 CL25 CL 0 0 N N N 84.236 4.127 62.199 1.701 1.988 -3.739 CL25 PIL 1 PIL C24 C24 C 0 1 Y N N 83.764 3.143 60.869 0.416 0.875 -4.093 C24 PIL 2 PIL C23 C23 C 0 1 Y N N 82.470 3.232 60.430 -0.262 0.949 -5.293 C23 PIL 3 PIL N22 N22 N 0 1 Y N N 82.124 2.492 59.369 -1.239 0.107 -5.570 N22 PIL 4 PIL C21 C21 C 0 1 Y N N 83.022 1.696 58.747 -1.610 -0.834 -4.723 C21 PIL 5 PIL C19 C19 C 0 1 Y N N 84.325 1.614 59.205 -0.978 -0.978 -3.504 C19 PIL 6 PIL CL20 CL20 CL 0 0 N N N 85.460 0.512 58.432 -1.473 -2.221 -2.398 CL20 PIL 7 PIL C18 C18 C 0 1 Y N N 84.721 2.318 60.305 0.056 -0.105 -3.170 C18 PIL 8 PIL N16 N16 N 0 1 N N N 86.025 2.272 60.810 0.718 -0.214 -1.946 N16 PIL 9 PIL C15 C15 C 0 1 N N N 86.273 1.851 62.067 0.030 -0.081 -0.794 C15 PIL 10 PIL O17 O17 O 0 1 N N N 85.393 1.516 62.846 -1.165 0.133 -0.822 O17 PIL 11 PIL C14 C14 C 0 1 Y N N 87.673 1.894 62.601 0.730 -0.196 0.499 C14 PIL 12 PIL C13 C13 C 0 1 Y N N 88.749 2.300 61.816 2.105 -0.443 0.532 C13 PIL 13 PIL C12 C12 C 0 1 Y N N 90.027 2.362 62.355 2.756 -0.549 1.742 C12 PIL 14 PIL C9 C9 C 0 1 Y N N 90.266 2.028 63.684 2.050 -0.412 2.929 C9 PIL 15 PIL O10 O10 O 0 1 N N N 91.522 2.073 64.309 2.697 -0.517 4.118 O10 PIL 16 PIL C11 C11 C 0 1 N N N 92.710 2.426 63.582 4.072 -0.767 3.820 C11 PIL 17 PIL C2 C2 C 0 1 Y N N 89.200 1.630 64.447 0.677 -0.171 2.903 C2 PIL 18 PIL C1 C1 C 0 1 Y N N 87.907 1.557 63.914 0.019 -0.058 1.694 C1 PIL 19 PIL O3 O3 O 0 1 N N N 89.493 1.309 65.738 -0.011 -0.038 4.068 O3 PIL 20 PIL C4 C4 C 0 1 N N N 88.482 0.789 66.603 -1.395 0.049 3.722 C4 PIL 21 PIL C5 C5 C 0 1 N N N 87.486 1.900 66.935 -1.756 1.503 3.354 C5 PIL 22 PIL C6 C6 C 0 1 N N N 87.917 2.363 68.305 -3.183 1.696 3.924 C6 PIL 23 PIL C7 C7 C 0 1 N N N 88.409 1.100 68.949 -3.127 0.911 5.259 C7 PIL 24 PIL C8 C8 C 0 1 N N N 89.143 0.372 67.892 -2.266 -0.327 4.933 C8 PIL 25 PIL H23 H23 H 0 1 N N N 81.726 3.883 60.919 0.009 1.706 -6.014 H23 PIL 26 PIL H21 H21 H 0 1 N N N 82.693 1.115 57.869 -2.415 -1.503 -4.989 H21 PIL 27 PIL H16 H16 H 0 1 N N N 86.823 2.555 60.242 1.672 -0.385 -1.924 H16 PIL 28 PIL H13 H13 H 0 1 N N N 88.588 2.574 60.760 2.657 -0.550 -0.389 H13 PIL 29 PIL H12 H12 H 0 1 N N N 90.867 2.682 61.716 3.819 -0.739 1.766 H12 PIL 30 PIL H111 1H11 H 0 0 N N N 92.534 3.413 63.095 4.635 -0.860 4.749 H111 PIL 31 PIL H112 2H11 H 0 0 N N N 93.708 2.462 64.079 4.158 -1.692 3.249 H112 PIL 32 PIL H113 3H11 H 0 0 N N N 92.789 1.746 62.702 4.473 0.059 3.234 H113 PIL 33 PIL H1 H1 H 0 1 N N N 87.059 1.229 64.539 -1.043 0.132 1.673 H1 PIL 34 PIL H4 H4 H 0 1 N N N 87.962 -0.067 66.112 -1.612 -0.613 2.885 H4 PIL 35 PIL H51 1H5 H 0 1 N N N 86.416 1.596 66.866 -1.061 2.199 3.822 H51 PIL 36 PIL H52 2H5 H 0 1 N N N 87.427 2.710 66.171 -1.757 1.633 2.272 H52 PIL 37 PIL H61 1H6 H 0 1 N N N 87.131 2.904 68.882 -3.928 1.266 3.255 H61 PIL 38 PIL H62 2H6 H 0 1 N N N 88.652 3.201 68.303 -3.387 2.751 4.105 H62 PIL 39 PIL H71 1H7 H 0 1 N N N 87.601 0.498 69.428 -4.128 0.609 5.566 H71 PIL 40 PIL H72 2H7 H 0 1 N N N 89.010 1.274 69.872 -2.652 1.511 6.035 H72 PIL 41 PIL H81 1H8 H 0 1 N N N 90.245 0.539 67.910 -2.907 -1.172 4.683 H81 PIL 42 PIL H82 2H8 H 0 1 N N N 89.179 -0.732 68.045 -1.633 -0.576 5.785 H82 PIL 43 # # 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 PIL CL25 C24 SING N N 1 PIL C24 C23 DOUB Y N 2 PIL C24 C18 SING Y N 3 PIL C23 N22 SING Y N 4 PIL C23 H23 SING N N 5 PIL N22 C21 DOUB Y N 6 PIL C21 C19 SING Y N 7 PIL C21 H21 SING N N 8 PIL C19 CL20 SING N N 9 PIL C19 C18 DOUB Y N 10 PIL C18 N16 SING N N 11 PIL N16 C15 SING N N 12 PIL N16 H16 SING N N 13 PIL C15 O17 DOUB N N 14 PIL C15 C14 SING N N 15 PIL C14 C13 DOUB Y N 16 PIL C14 C1 SING Y N 17 PIL C13 C12 SING Y N 18 PIL C13 H13 SING N N 19 PIL C12 C9 DOUB Y N 20 PIL C12 H12 SING N N 21 PIL C9 O10 SING N N 22 PIL C9 C2 SING Y N 23 PIL O10 C11 SING N N 24 PIL C11 H111 SING N N 25 PIL C11 H112 SING N N 26 PIL C11 H113 SING N N 27 PIL C2 C1 DOUB Y N 28 PIL C2 O3 SING N N 29 PIL C1 H1 SING N N 30 PIL O3 C4 SING N N 31 PIL C4 C5 SING N N 32 PIL C4 C8 SING N N 33 PIL C4 H4 SING N N 34 PIL C5 C6 SING N N 35 PIL C5 H51 SING N N 36 PIL C5 H52 SING N N 37 PIL C6 C7 SING N N 38 PIL C6 H61 SING N N 39 PIL C6 H62 SING N N 40 PIL C7 C8 SING N N 41 PIL C7 H71 SING N N 42 PIL C7 H72 SING N N 43 PIL C8 H81 SING N N 44 PIL C8 H82 SING N N 45 # # 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 PIL SMILES ACDLabs 10.04 "Clc3c(NC(=O)c2ccc(OC)c(OC1CCCC1)c2)c(Cl)cnc3" PIL SMILES_CANONICAL CACTVS 3.341 "COc1ccc(cc1OC2CCCC2)C(=O)Nc3c(Cl)cncc3Cl" PIL SMILES CACTVS 3.341 "COc1ccc(cc1OC2CCCC2)C(=O)Nc3c(Cl)cncc3Cl" PIL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COc1ccc(cc1OC2CCCC2)C(=O)Nc3c(cncc3Cl)Cl" PIL SMILES "OpenEye OEToolkits" 1.5.0 "COc1ccc(cc1OC2CCCC2)C(=O)Nc3c(cncc3Cl)Cl" PIL InChI InChI 1.03 "InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23)" PIL InChIKey InChI 1.03 RRRUXBQSQLKHEL-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 PIL "SYSTEMATIC NAME" ACDLabs 10.04 "3-(cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide" PIL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-cyclopentyloxy-N-(3,5-dichloropyridin-4-yl)-4-methoxy-benzamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site PIL "Create component" 2004-11-17 RCSB PIL "Modify descriptor" 2011-06-04 RCSB PIL "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id PIL _pdbx_chem_comp_synonyms.name PICLAMILAST _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##