data_LZH # _chem_comp.id LZH _chem_comp.name "5-CHLORO-THIOPHENE-2-CARBOXYLIC ACID ((3R,5S)-1-{[2-FLUORO-4-(2-OXO-PYRIDIN-1-YL)-PHENYLCARBAMOYL]-METHYL}-5-HYDROXYMETHYL-PYRROLIDIN-3-YL)-AMIDE" _chem_comp.type non-polymer _chem_comp.pdbx_type ? _chem_comp.formula "C23 H22 Cl F N4 O4 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-06-26 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 504.962 _chem_comp.one_letter_code ? _chem_comp.three_letter_code LZH _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 2VWL _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 LZH F32 F32 F 0 1 N N N 9.309 62.446 1.418 9.309 62.446 1.418 F32 LZH 1 LZH C17 C17 C 0 1 Y N N 8.489 62.010 2.385 8.489 62.010 2.385 C17 LZH 2 LZH C11 C11 C 0 1 Y N N 8.114 60.654 2.397 8.114 60.654 2.397 C11 LZH 3 LZH C9 C9 C 0 1 Y N N 7.286 60.182 3.408 7.286 60.182 3.408 C9 LZH 4 LZH N1 N1 N 0 1 N N N 6.895 58.815 3.390 6.895 58.815 3.390 N1 LZH 5 LZH C21 C21 C 0 1 N N N 7.405 57.915 4.322 7.405 57.915 4.322 C21 LZH 6 LZH C29 C29 C 0 1 N N N 6.947 56.632 4.262 6.947 56.632 4.262 C29 LZH 7 LZH C30 C30 C 0 1 N N N 5.890 56.210 3.409 5.890 56.210 3.409 C30 LZH 8 LZH C23 C23 C 0 1 N N N 5.331 57.139 2.571 5.331 57.139 2.571 C23 LZH 9 LZH C8 C8 C 0 1 N N N 5.793 58.478 2.604 5.793 58.478 2.604 C8 LZH 10 LZH O25 O25 O 0 1 N N N 5.317 59.320 1.804 5.317 59.320 1.804 O25 LZH 11 LZH C26 C26 C 0 1 Y N N 6.853 61.069 4.383 6.853 61.069 4.383 C26 LZH 12 LZH C28 C28 C 0 1 Y N N 7.238 62.412 4.366 7.238 62.412 4.366 C28 LZH 13 LZH C16 C16 C 0 1 Y N N 8.059 62.900 3.358 8.059 62.900 3.358 C16 LZH 14 LZH N15 N15 N 0 1 N N N 8.437 64.232 3.317 8.437 64.232 3.317 N15 LZH 15 LZH C14 C14 C 0 1 N N N 7.993 64.948 2.256 7.993 64.948 2.256 C14 LZH 16 LZH C13 C13 C 0 1 N N R 11.513 67.408 3.641 11.513 67.408 3.641 C13 LZH 17 LZH O27 O27 O 0 1 N N N 7.369 64.424 1.347 7.369 64.424 1.347 O27 LZH 18 LZH C24 C24 C 0 1 N N N 10.514 68.364 4.318 10.514 68.364 4.318 C24 LZH 19 LZH C22 C22 C 0 1 N N N 8.261 66.434 2.143 8.261 66.434 2.143 C22 LZH 20 LZH N4 N4 N 0 1 N N N 9.265 66.810 3.141 9.265 66.810 3.141 N4 LZH 21 LZH C20 C20 C 0 1 N N N 10.669 66.409 2.862 10.669 66.409 2.862 C20 LZH 22 LZH O33 O33 O 0 1 N N N 8.106 68.977 1.505 8.106 68.977 1.505 O33 LZH 23 LZH C34 C34 C 0 1 N N N 9.297 69.160 2.295 9.297 69.160 2.295 C34 LZH 24 LZH N7 N7 N 0 1 N N N 12.200 66.729 4.756 12.200 66.729 4.756 N7 LZH 25 LZH C5 C5 C 0 1 N N N 13.259 65.962 4.523 13.259 65.962 4.523 C5 LZH 26 LZH O24 O24 O 0 1 N N N 13.627 65.785 3.373 13.627 65.785 3.373 O24 LZH 27 LZH C2 C2 C 0 1 Y N N 14.005 65.296 5.653 14.005 65.296 5.653 C2 LZH 28 LZH C12 C12 C 0 1 Y N N 14.026 65.545 7.032 14.026 65.545 7.032 C12 LZH 29 LZH C19 C19 C 0 1 Y N N 14.873 64.686 7.748 14.873 64.686 7.748 C19 LZH 30 LZH S3 S3 S 0 1 Y N N 15.060 64.033 5.099 15.060 64.033 5.099 S3 LZH 31 LZH C10 C10 C 0 1 Y N N 15.470 63.893 6.784 15.470 63.893 6.784 C10 LZH 32 LZH CL1 CL1 CL 0 0 N N N 16.663 62.601 7.205 16.663 62.601 7.205 CL1 LZH 33 LZH C15 C15 C 0 1 N N S 9.236 68.225 3.510 9.236 68.225 3.510 C15 LZH 34 LZH H11 H11 H 0 1 N N N 8.467 59.985 1.626 8.467 59.985 1.626 H11 LZH 35 LZH H26 H26 H 0 1 N N N 6.205 60.714 5.171 6.205 60.714 5.171 H26 LZH 36 LZH H21 H21 H 0 1 N N N 8.132 58.220 5.060 8.132 58.220 5.060 H21 LZH 37 LZH H29 H29 H 0 1 N N N 7.413 55.894 4.898 7.413 55.894 4.898 H29 LZH 38 LZH H30 H30 H 0 1 N N N 5.539 55.189 3.421 5.539 55.189 3.421 H30 LZH 39 LZH H23 H23 H 0 1 N N N 4.543 56.852 1.890 4.543 56.852 1.890 H23 LZH 40 LZH H28 H28 H 0 1 N N N 6.894 63.077 5.144 6.894 63.077 5.144 H28 LZH 41 LZH H15 H15 H 0 1 N N N 9.006 64.642 4.030 9.005 64.642 4.030 H15 LZH 42 LZH H221 1H22 H 0 0 N N N 8.635 66.668 1.135 8.635 66.668 1.135 H221 LZH 43 LZH H222 2H22 H 0 0 N N N 7.332 66.995 2.319 7.332 66.995 2.319 H222 LZH 44 LZH H13 H13 H 0 1 N N N 12.237 67.894 2.970 12.237 67.894 2.970 H13 LZH 45 LZH H241 1H24 H 0 0 N N N 10.350 68.084 5.369 10.349 68.084 5.369 H241 LZH 46 LZH H242 2H24 H 0 0 N N N 10.881 69.401 4.336 10.881 69.401 4.335 H242 LZH 47 LZH H201 1H20 H 0 0 N N N 10.889 66.457 1.785 10.889 66.457 1.785 H201 LZH 48 LZH H202 2H20 H 0 0 N N N 10.872 65.370 3.161 10.872 65.370 3.161 H202 LZH 49 LZH H7 H7 H 0 1 N N N 11.867 66.847 5.691 11.867 66.847 5.692 H7 LZH 50 LZH HA HA H 0 1 N N N 8.310 68.499 4.036 8.310 68.499 4.036 HA LZH 51 LZH H33 H33 H 0 1 N N N 7.349 68.937 2.077 7.349 68.937 2.077 H33 LZH 52 LZH H341 1H34 H 0 0 N N N 10.183 68.922 1.689 10.184 68.922 1.689 H341 LZH 53 LZH H342 2H34 H 0 0 N N N 9.363 70.205 2.632 9.363 70.205 2.632 H342 LZH 54 LZH H12 H12 H 0 1 N N N 13.444 66.325 7.500 13.444 66.326 7.500 H12 LZH 55 LZH H19 H19 H 0 1 N N N 15.026 64.651 8.817 15.026 64.651 8.817 H19 LZH 56 # 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 LZH F32 C17 SING N N 1 LZH C17 C11 SING Y N 2 LZH C17 C16 DOUB Y N 3 LZH C11 C9 DOUB Y N 4 LZH C9 N1 SING N N 5 LZH C9 C26 SING Y N 6 LZH N1 C21 SING N N 7 LZH N1 C8 SING N N 8 LZH C21 C29 DOUB N N 9 LZH C29 C30 SING N N 10 LZH C30 C23 DOUB N N 11 LZH C23 C8 SING N N 12 LZH C8 O25 DOUB N N 13 LZH C26 C28 DOUB Y N 14 LZH C28 C16 SING Y N 15 LZH C16 N15 SING N N 16 LZH N15 C14 SING N N 17 LZH C14 O27 DOUB N N 18 LZH C14 C22 SING N N 19 LZH C13 C24 SING N N 20 LZH C13 C20 SING N N 21 LZH C13 N7 SING N N 22 LZH C24 C15 SING N N 23 LZH C22 N4 SING N N 24 LZH N4 C20 SING N N 25 LZH N4 C15 SING N N 26 LZH O33 C34 SING N N 27 LZH C34 C15 SING N N 28 LZH N7 C5 SING N N 29 LZH C5 O24 DOUB N N 30 LZH C5 C2 SING N N 31 LZH C2 C12 DOUB Y N 32 LZH C2 S3 SING Y N 33 LZH C12 C19 SING Y N 34 LZH C19 C10 DOUB Y N 35 LZH S3 C10 SING Y N 36 LZH C10 CL1 SING N N 37 LZH C11 H11 SING N N 38 LZH C26 H26 SING N N 39 LZH C21 H21 SING N N 40 LZH C29 H29 SING N N 41 LZH C30 H30 SING N N 42 LZH C23 H23 SING N N 43 LZH C28 H28 SING N N 44 LZH N15 H15 SING N N 45 LZH C22 H221 SING N N 46 LZH C22 H222 SING N N 47 LZH C13 H13 SING N N 48 LZH C24 H241 SING N N 49 LZH C24 H242 SING N N 50 LZH C20 H201 SING N N 51 LZH C20 H202 SING N N 52 LZH N7 H7 SING N N 53 LZH C15 HA SING N N 54 LZH O33 H33 SING N N 55 LZH C34 H341 SING N N 56 LZH C34 H342 SING N N 57 LZH C12 H12 SING N N 58 LZH C19 H19 SING N N 59 # 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 LZH SMILES ACDLabs 10.04 "O=C(NC3CC(N(CC(=O)Nc2ccc(N1C=CC=CC1=O)cc2F)C3)CO)c4sc(Cl)cc4" LZH SMILES_CANONICAL CACTVS 3.341 "OC[C@@H]1C[C@H](CN1CC(=O)Nc2ccc(cc2F)N3C=CC=CC3=O)NC(=O)c4sc(Cl)cc4" LZH SMILES CACTVS 3.341 "OC[CH]1C[CH](CN1CC(=O)Nc2ccc(cc2F)N3C=CC=CC3=O)NC(=O)c4sc(Cl)cc4" LZH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c(cc1N2C=CC=CC2=O)F)NC(=O)C[N@]3C[C@@H](C[C@H]3CO)NC(=O)c4ccc(s4)Cl" LZH SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(c(cc1N2C=CC=CC2=O)F)NC(=O)CN3CC(CC3CO)NC(=O)c4ccc(s4)Cl" LZH InChI InChI 1.03 "InChI=1S/C23H22ClFN4O4S/c24-20-7-6-19(34-20)23(33)26-14-9-16(13-30)28(11-14)12-21(31)27-18-5-4-15(10-17(18)25)29-8-2-1-3-22(29)32/h1-8,10,14,16,30H,9,11-13H2,(H,26,33)(H,27,31)/t14-,16+/m1/s1" LZH InChIKey InChI 1.03 FMLMGXAAZAZCMG-ZBFHGGJFSA-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 LZH "SYSTEMATIC NAME" ACDLabs 10.04 "5-chloro-N-[(3R,5S)-1-(2-{[2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl]amino}-2-oxoethyl)-5-(hydroxymethyl)pyrrolidin-3-yl]thiophene-2-carboxamide" LZH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-chloro-N-[(1R,3R,5S)-1-[2-[[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]amino]-2-oxo-ethyl]-5-(hydroxymethyl)pyrrolidin-3-yl]thiophene-2-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site LZH "Create component" 2008-06-26 EBI LZH "Modify aromatic_flag" 2011-06-04 RCSB LZH "Modify descriptor" 2011-06-04 RCSB #