data_8O1
# 
_chem_comp.id                                    8O1 
_chem_comp.name                                  "4-{2-[(cyclopropylmethyl)amino]-5-(ethylsulfonyl)phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 N3 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-02-22 
_chem_comp.pdbx_modified_date                    2017-06-16 
_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                        385.480 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8O1 
_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        5UVS 
_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 
8O1 C4   C1  C 0 1 Y N N 16.288 -10.891 0.857  1.451  -0.313 0.404  C4   8O1 1  
8O1 C5   C2  C 0 1 Y N N 12.191 -14.117 2.456  -1.415 -3.001 -2.579 C5   8O1 2  
8O1 C6   C3  C 0 1 Y N N 13.114 -12.270 1.628  -1.289 -1.722 -0.759 C6   8O1 3  
8O1 C7   C4  C 0 1 Y N N 15.281 -10.938 1.808  0.153  0.157  0.222  C7   8O1 4  
8O1 C8   C5  C 0 1 Y N N 15.597 -10.786 3.157  -0.060 1.513  -0.058 C8   8O1 5  
8O1 C10  C6  C 0 1 Y N N 11.866 -12.396 1.060  -2.386 -2.579 -0.619 C10  8O1 6  
8O1 C13  C7  C 0 1 N N N 11.288 -11.479 0.101  -3.165 -2.500 0.550  C13  8O1 7  
8O1 C15  C8  C 0 1 N N N 12.767 -9.747  6.637  -3.507 5.081  -1.115 C15  8O1 8  
8O1 C17  C9  C 0 1 N N N 18.785 -7.894  -0.320 6.131  -1.072 -1.053 C17  8O1 9  
8O1 C20  C10 C 0 1 N N N 18.479 -9.223  -0.988 4.702  -0.530 -1.121 C20  8O1 10 
8O1 C1   C11 C 0 1 Y N N 16.924 -10.605 3.509  1.022  2.375  -0.150 C1   8O1 11 
8O1 C2   C12 C 0 1 Y N N 17.927 -10.565 2.569  2.306  1.895  0.032  C2   8O1 12 
8O1 C3   C13 C 0 1 Y N N 13.324 -13.350 2.519  -0.698 -2.012 -2.004 C3   8O1 13 
8O1 C9   C14 C 0 1 Y N N 17.600 -10.692 1.241  2.519  0.557  0.309  C9   8O1 14 
8O1 C11  C15 C 0 1 N N N 13.380 -10.296 0.421  -1.802 -0.763 1.417  C11  8O1 15 
8O1 C12  C16 C 0 1 N N N 13.921 -11.162 1.288  -0.997 -0.772 0.322  C12  8O1 16 
8O1 C14  C17 C 0 1 N N N 13.673 -10.191 7.738  -3.739 4.611  0.322  C14  8O1 17 
8O1 C16  C18 C 0 1 N N N 13.727 -10.872 6.404  -3.076 3.676  -0.691 C16  8O1 18 
8O1 C18  C19 C 0 1 N N N 11.688 -9.377  -1.056 -3.699 -1.566 2.718  C18  8O1 19 
8O1 C19  C20 C 0 1 N N N 14.931 -10.642 5.568  -1.577 3.413  -0.534 C19  8O1 20 
8O1 N21  N1  N 0 1 Y N N 11.323 -13.543 1.566  -2.439 -3.355 -1.754 N21  8O1 21 
8O1 N22  N2  N 0 1 N N N 12.127 -10.423 -0.152 -2.862 -1.616 1.517  N22  8O1 22 
8O1 N23  N3  N 0 1 N N N 14.602 -10.813 4.166  -1.357 1.995  -0.242 N23  8O1 23 
8O1 O24  O1  O 0 1 N N N 10.186 -11.632 -0.424 -4.126 -3.240 0.688  O24  8O1 24 
8O1 O25  O2  O 0 1 N N N 20.149 -10.308 0.687  4.004  -1.184 1.370  O25  8O1 25 
8O1 O26  O3  O 0 1 N N N 18.739 -11.861 -0.745 4.887  1.096  0.987  O26  8O1 26 
8O1 S27  S1  S 0 1 N N N 18.905 -10.637 0.022  4.161  -0.041 0.540  S27  8O1 27 
8O1 H4   H1  H 0 1 N N N 16.046 -11.010 -0.189 1.622  -1.357 0.624  H4   8O1 28 
8O1 H5   H2  H 0 1 N N N 12.012 -15.023 3.015  -1.210 -3.440 -3.544 H5   8O1 29 
8O1 H152 H3  H 0 0 N N N 11.688 -9.949  6.698  -4.379 5.165  -1.764 H152 8O1 30 
8O1 H151 H4  H 0 0 N N N 12.931 -8.775  6.149  -2.723 5.819  -1.284 H151 8O1 31 
8O1 H173 H5  H 0 0 N N N 18.500 -7.071  -0.992 6.795  -0.298 -0.667 H173 8O1 32 
8O1 H172 H6  H 0 0 N N N 18.215 -7.815  0.618  6.160  -1.938 -0.391 H172 8O1 33 
8O1 H171 H7  H 0 0 N N N 19.861 -7.833  -0.101 6.457  -1.365 -2.050 H171 8O1 34 
8O1 H1   H10 H 0 1 N N N 17.179 -10.492 4.552  0.862  3.421  -0.365 H1   8O1 35 
8O1 H2   H11 H 0 1 N N N 18.956 -10.436 2.870  3.147  2.569  -0.041 H2   8O1 36 
8O1 H3   H12 H 0 1 N N N 14.199 -13.532 3.125  0.172  -1.531 -2.424 H3   8O1 37 
8O1 H11  H13 H 0 1 N N N 13.967 -9.432  0.148  -1.599 -0.071 2.221  H11  8O1 38 
8O1 H142 H14 H 0 0 N N N 14.504 -9.546  8.060  -3.107 5.040  1.100  H142 8O1 39 
8O1 H141 H15 H 0 0 N N N 13.261 -10.721 8.609  -4.764 4.387  0.619  H141 8O1 40 
8O1 H16  H16 H 0 1 N N N 13.288 -11.880 6.359  -3.665 2.836  -1.060 H16  8O1 41 
8O1 H183 H17 H 0 0 N N N 12.476 -8.614  -1.145 -4.495 -2.306 2.637  H183 8O1 42 
8O1 H181 H18 H 0 0 N N N 11.483 -9.810  -2.046 -3.089 -1.783 3.595  H181 8O1 43 
8O1 H182 H19 H 0 0 N N N 10.772 -8.913  -0.662 -4.135 -0.572 2.816  H182 8O1 44 
8O1 H191 H20 H 0 0 N N N 15.299 -9.619  5.733  -1.064 3.678  -1.459 H191 8O1 45 
8O1 H192 H21 H 0 0 N N N 15.713 -11.363 5.849  -1.186 4.018  0.284  H192 8O1 46 
8O1 H21  H22 H 0 1 N N N 10.425 -13.909 1.323  -3.099 -4.043 -1.937 H21  8O1 47 
8O1 H23  H23 H 0 1 N N N 13.952 -10.087 3.939  -2.113 1.390  -0.178 H23  8O1 48 
8O1 H201 H26 H 0 0 N N N 17.402 -9.263  -1.209 4.674  0.337  -1.782 H201 8O1 49 
8O1 H202 H27 H 0 0 N N N 19.048 -9.281  -1.928 4.038  -1.303 -1.507 H202 8O1 50 
# 
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 
8O1 C4  C7   DOUB Y N 1  
8O1 C4  C9   SING Y N 2  
8O1 C5  C3   DOUB Y N 3  
8O1 C5  N21  SING Y N 4  
8O1 C6  C10  DOUB Y N 5  
8O1 C6  C3   SING Y N 6  
8O1 C6  C12  SING N N 7  
8O1 C7  C8   SING Y N 8  
8O1 C7  C12  SING N N 9  
8O1 C8  C1   DOUB Y N 10 
8O1 C8  N23  SING N N 11 
8O1 C10 C13  SING N N 12 
8O1 C10 N21  SING Y N 13 
8O1 C13 N22  SING N N 14 
8O1 C13 O24  DOUB N N 15 
8O1 C15 C14  SING N N 16 
8O1 C15 C16  SING N N 17 
8O1 C17 C20  SING N N 18 
8O1 C20 S27  SING N N 19 
8O1 C1  C2   SING Y N 20 
8O1 C2  C9   DOUB Y N 21 
8O1 C9  S27  SING N N 22 
8O1 C11 C12  DOUB N N 23 
8O1 C11 N22  SING N N 24 
8O1 C14 C16  SING N N 25 
8O1 C16 C19  SING N N 26 
8O1 C18 N22  SING N N 27 
8O1 C19 N23  SING N N 28 
8O1 O25 S27  DOUB N N 29 
8O1 O26 S27  DOUB N N 30 
8O1 C4  H4   SING N N 31 
8O1 C5  H5   SING N N 32 
8O1 C15 H152 SING N N 33 
8O1 C15 H151 SING N N 34 
8O1 C17 H173 SING N N 35 
8O1 C17 H172 SING N N 36 
8O1 C17 H171 SING N N 37 
8O1 C20 H201 SING N N 38 
8O1 C20 H202 SING N N 39 
8O1 C1  H1   SING N N 40 
8O1 C2  H2   SING N N 41 
8O1 C3  H3   SING N N 42 
8O1 C11 H11  SING N N 43 
8O1 C14 H142 SING N N 44 
8O1 C14 H141 SING N N 45 
8O1 C16 H16  SING N N 46 
8O1 C18 H183 SING N N 47 
8O1 C18 H181 SING N N 48 
8O1 C18 H182 SING N N 49 
8O1 C19 H191 SING N N 50 
8O1 C19 H192 SING N N 51 
8O1 N21 H21  SING N N 52 
8O1 N23 H23  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 
8O1 SMILES           ACDLabs              12.01 "c1c(c(ccc1S(CC)(=O)=O)NCC2CC2)C=3c4c(C(N(C=3)C)=O)ncc4"                                                                                      
8O1 InChI            InChI                1.03  "InChI=1S/C20H23N3O3S/c1-3-27(25,26)14-6-7-18(22-11-13-4-5-13)16(10-14)17-12-23(2)20(24)19-15(17)8-9-21-19/h6-10,12-13,21-22H,3-5,11H2,1-2H3" 
8O1 InChIKey         InChI                1.03  ZQRYCQNBELIIBM-UHFFFAOYSA-N                                                                                                                   
8O1 SMILES_CANONICAL CACTVS               3.385 "CC[S](=O)(=O)c1ccc(NCC2CC2)c(c1)C3=CN(C)C(=O)c4[nH]ccc34"                                                                                    
8O1 SMILES           CACTVS               3.385 "CC[S](=O)(=O)c1ccc(NCC2CC2)c(c1)C3=CN(C)C(=O)c4[nH]ccc34"                                                                                    
8O1 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CCS(=O)(=O)c1ccc(c(c1)C2=CN(C(=O)c3c2cc[nH]3)C)NCC4CC4"                                                                                      
8O1 SMILES           "OpenEye OEToolkits" 2.0.6 "CCS(=O)(=O)c1ccc(c(c1)C2=CN(C(=O)c3c2cc[nH]3)C)NCC4CC4"                                                                                      
# 
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 
8O1 "SYSTEMATIC NAME" ACDLabs              12.01 "4-{2-[(cyclopropylmethyl)amino]-5-(ethylsulfonyl)phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one" 
8O1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "4-[2-(cyclopropylmethylamino)-5-ethylsulfonyl-phenyl]-6-methyl-1~{H}-pyrrolo[2,3-c]pyridin-7-one"             
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
8O1 "Create component" 2017-02-22 RCSB 
8O1 "Initial release"  2017-06-21 RCSB 
# 
