data_CXN
# 
_chem_comp.id                                    CXN 
_chem_comp.name                                  CLOXACILLIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H18 Cl N3 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         [3-(O-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL]PENICILLIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-08-10 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        435.881 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CXN 
_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        1FCM 
_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 
CXN C1   C1   C  0 1 N N N 77.035 4.429 29.214 -0.260 1.763  -2.034 C1   CXN 1  
CXN O1   O1   O  0 1 N N N 77.830 3.560 28.976 -1.264 2.322  -1.647 O1   CXN 2  
CXN C2   C2   C  0 1 N N R 77.481 5.867 29.458 1.146  1.624  -1.489 C2   CXN 3  
CXN C3   C3   C  0 1 N N R 77.368 6.626 28.062 1.484  0.926  -2.807 C3   CXN 4  
CXN N7   N7   N  0 1 N N N 76.909 5.800 26.927 0.035  0.973  -3.116 N7   CXN 5  
CXN C6   C6   C  0 1 N N S 78.020 5.356 26.110 -0.628 -0.360 -3.144 C6   CXN 6  
CXN C8   C8   C  0 1 N N N 77.526 4.622 24.881 -1.738 -0.316 -4.162 C8   CXN 7  
CXN O81  O81  O  0 1 N N N 76.359 4.810 24.499 -2.848 -1.048 -3.977 O81  CXN 8  
CXN O82  O82  O  0 1 N N N 78.283 3.840 24.286 -1.629 0.377  -5.145 O82  CXN 9  
CXN C5   C5   C  0 1 N N N 78.881 6.619 25.857 0.362  -1.495 -3.524 C5   CXN 10 
CXN C51  C51  C  0 1 N N N 80.354 6.317 25.479 0.592  -1.559 -5.035 C51  CXN 11 
CXN C52  C52  C  0 1 N N N 78.303 7.605 24.809 -0.091 -2.848 -2.972 C52  CXN 12 
CXN S4   S4   S  0 1 N N N 78.884 7.420 27.490 1.856  -0.864 -2.635 S4   CXN 13 
CXN N2   N2   N  0 1 N N N 78.811 5.940 30.123 1.240  0.750  -0.317 N2   CXN 14 
CXN C21  C21  C  0 1 N N N 79.008 5.732 31.267 1.533  1.271  0.890  C21  CXN 15 
CXN O21  O21  O  0 1 N N N 78.076 5.695 32.103 1.719  2.467  1.008  O21  CXN 16 
CXN C22  C22  C  0 1 Y N N 80.412 5.499 31.744 1.628  0.391  2.068  C22  CXN 17 
CXN N25  N25  N  0 1 Y N N 82.741 5.513 31.801 1.138  -0.833 3.847  N25  CXN 18 
CXN O24  O24  O  0 1 Y N N 82.260 4.878 32.955 2.329  -0.897 3.666  O24  CXN 19 
CXN C23  C23  C  0 1 Y N N 80.951 4.919 32.844 2.744  -0.194 2.610  C23  CXN 20 
CXN C26  C26  C  0 1 Y N N 81.701 5.874 31.080 0.544  -0.082 2.954  C26  CXN 21 
CXN C27  C27  C  0 1 N N N 80.074 4.317 33.926 4.161  -0.065 2.113  C27  CXN 22 
CXN C28  C28  C  0 1 Y N N 82.127 6.578 29.791 -0.901 0.229  2.856  C28  CXN 23 
CXN C29  C29  C  0 1 Y N N 81.685 7.917 29.493 -1.812 -0.396 3.707  C29  CXN 24 
CXN CL   CL   CL 0 0 N N N 80.626 8.785 30.617 -1.254 -1.537 4.890  CL   CXN 25 
CXN C30  C30  C  0 1 Y N N 82.073 8.564 28.323 -3.157 -0.096 3.615  C30  CXN 26 
CXN C31  C31  C  0 1 Y N N 82.922 7.894 27.411 -3.602 0.811  2.672  C31  CXN 27 
CXN C32  C32  C  0 1 Y N N 83.364 6.557 27.690 -2.704 1.430  1.821  C32  CXN 28 
CXN C33  C33  C  0 1 Y N N 82.966 5.902 28.884 -1.357 1.144  1.908  C33  CXN 29 
CXN H2   H2   H  0 1 N N N 76.821 6.386 30.191 1.659  2.576  -1.351 H2   CXN 30 
CXN H3   H3   H  0 1 N N N 76.599 7.388 28.329 2.146  1.472  -3.480 H3   CXN 31 
CXN H6   H6   H  0 1 N N N 78.664 4.591 26.603 -1.054 -0.574 -2.164 H6   CXN 32 
CXN H81  H81  H  0 1 N N N 76.049 4.349 23.728 -3.560 -1.019 -4.630 H81  CXN 33 
CXN H511 1H51 H  0 0 N N N 80.973 7.225 25.296 1.409  -2.247 -5.250 H511 CXN 34 
CXN H512 2H51 H  0 0 N N N 80.830 5.668 26.250 -0.315 -1.909 -5.526 H512 CXN 35 
CXN H513 3H51 H  0 0 N N N 80.399 5.631 24.600 0.845  -0.566 -5.406 H513 CXN 36 
CXN H521 1H52 H  0 0 N N N 78.922 8.513 24.626 0.702  -3.582 -3.112 H521 CXN 37 
CXN H522 2H52 H  0 0 N N N 78.105 7.074 23.848 -0.312 -2.751 -1.909 H522 CXN 38 
CXN H523 3H52 H  0 0 N N N 77.263 7.896 25.086 -0.986 -3.174 -3.501 H523 CXN 39 
CXN HN2  HN2  H  0 1 N N N 79.726 6.167 29.735 1.092  -0.204 -0.411 HN2  CXN 40 
CXN H271 1H27 H  0 0 N N N 80.517 3.839 34.830 4.825  -0.644 2.755  H271 CXN 41 
CXN H272 2H27 H  0 0 N N N 79.358 5.101 34.265 4.224  -0.441 1.092  H272 CXN 42 
CXN H273 3H27 H  0 0 N N N 79.392 3.577 33.445 4.459  0.982  2.133  H273 CXN 43 
CXN H30  H30  H  0 1 N N N 81.714 9.587 28.122 -3.863 -0.576 4.276  H30  CXN 44 
CXN H31  H31  H  0 1 N N N 83.237 8.410 26.488 -4.656 1.039  2.600  H31  CXN 45 
CXN H32  H32  H  0 1 N N N 84.017 6.026 26.977 -3.058 2.139  1.087  H32  CXN 46 
CXN H33  H33  H  0 1 N N N 83.305 4.876 29.105 -0.657 1.628  1.243  H33  CXN 47 
# 
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 
CXN C1  O1   DOUB N N 1  
CXN C1  C2   SING N N 2  
CXN C1  N7   SING N N 3  
CXN C2  C3   SING N N 4  
CXN C2  N2   SING N N 5  
CXN C2  H2   SING N N 6  
CXN C3  N7   SING N N 7  
CXN C3  S4   SING N N 8  
CXN C3  H3   SING N N 9  
CXN N7  C6   SING N N 10 
CXN C6  C8   SING N N 11 
CXN C6  C5   SING N N 12 
CXN C6  H6   SING N N 13 
CXN C8  O81  SING N N 14 
CXN C8  O82  DOUB N N 15 
CXN O81 H81  SING N N 16 
CXN C5  C51  SING N N 17 
CXN C5  C52  SING N N 18 
CXN C5  S4   SING N N 19 
CXN C51 H511 SING N N 20 
CXN C51 H512 SING N N 21 
CXN C51 H513 SING N N 22 
CXN C52 H521 SING N N 23 
CXN C52 H522 SING N N 24 
CXN C52 H523 SING N N 25 
CXN N2  C21  SING N N 26 
CXN N2  HN2  SING N N 27 
CXN C21 O21  DOUB N N 28 
CXN C21 C22  SING N N 29 
CXN C22 C23  DOUB Y N 30 
CXN C22 C26  SING Y N 31 
CXN N25 O24  SING Y N 32 
CXN N25 C26  DOUB Y N 33 
CXN O24 C23  SING Y N 34 
CXN C23 C27  SING N N 35 
CXN C26 C28  SING N N 36 
CXN C27 H271 SING N N 37 
CXN C27 H272 SING N N 38 
CXN C27 H273 SING N N 39 
CXN C28 C29  DOUB Y N 40 
CXN C28 C33  SING Y N 41 
CXN C29 CL   SING N N 42 
CXN C29 C30  SING Y N 43 
CXN C30 C31  DOUB Y N 44 
CXN C30 H30  SING N N 45 
CXN C31 C32  SING Y N 46 
CXN C31 H31  SING N N 47 
CXN C32 C33  DOUB Y N 48 
CXN C32 H32  SING N N 49 
CXN C33 H33  SING N N 50 
# 
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 
CXN SMILES           ACDLabs              10.04 O=C(O)C3N4C(=O)C(NC(=O)c2c(onc2c1ccccc1Cl)C)C4SC3(C)C                                                                                                                               
CXN InChI            InChI                1.02b InChI=1/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1/f/h21,26H 
CXN InChIKey         InChI                1.02b LQOLIRLGBULYKD-ZEOGXVOZDL                                                                                                                                                           
CXN SMILES_CANONICAL CACTVS               3.341 Cc1onc(c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C(O)=O                                                                                                                  
CXN SMILES           CACTVS               3.341 Cc1onc(c2ccccc2Cl)c1C(=O)N[CH]3[CH]4SC(C)(C)[CH](N4C3=O)C(O)=O                                                                                                                      
CXN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1c(c(no1)c2ccccc2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O                                                                                                              
CXN SMILES           "OpenEye OEToolkits" 1.5.0 Cc1c(c(no1)c2ccccc2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O                                                                                                                           
# 
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 
CXN "SYSTEMATIC NAME" ACDLabs              10.04 "(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid"  
CXN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid" 
# 
