data_CFX
# 
_chem_comp.id                                    CFX 
_chem_comp.name                                  CEFOXITIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H17 N3 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-02-16 
_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                        427.452 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CFX 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_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                  PDBJ 
# 
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 
CFX C4   C4   C 0 1 N N N 13.584 24.192 -2.494 3.869  -1.406 -0.563 C4   CFX 1  
CFX O5   O5   O 0 1 N N N 14.165 25.099 -1.923 3.365  -2.497 -0.694 O5   CFX 2  
CFX N1   N1   N 0 1 N N N 13.548 24.869 -5.379 3.390  -0.177 -0.274 N1   CFX 3  
CFX C2   C2   C 0 1 N N R 12.518 25.277 -4.469 4.671  0.499  -0.182 C2   CFX 4  
CFX S8   S8   S 0 1 N N N 12.815 26.959 -4.034 4.648  1.932  -1.283 S8   CFX 5  
CFX C9   C9   C 0 1 N N N 13.363 27.890 -5.398 3.259  2.725  -0.402 C9   CFX 6  
CFX C10  C10  C 0 1 N N N 14.398 27.087 -6.018 2.089  1.792  -0.096 C10  CFX 7  
CFX C11  C11  C 0 1 N N N 14.550 25.758 -5.817 2.195  0.442  -0.092 C11  CFX 8  
CFX C15  C15  C 0 1 N N N 15.318 27.864 -6.890 0.816  2.554  0.180  C15  CFX 9  
CFX C12  C12  C 0 1 N N N 15.941 25.120 -6.030 1.011  -0.420 0.047  C12  CFX 10 
CFX O13  O13  O 0 1 N N N 16.112 24.327 -6.989 0.353  -0.833 -0.887 O13  CFX 11 
CFX O14  O14  O 0 1 N N N 16.838 25.512 -5.241 0.788  -0.667 1.352  O14  CFX 12 
CFX C3   C3   C 0 1 N N S 12.299 24.293 -3.297 5.288  -0.796 -0.753 C3   CFX 13 
CFX O16  O16  O 0 1 N N N 12.122 22.984 -3.789 6.280  -1.484 0.033  O16  CFX 14 
CFX C17  C17  C 0 1 N N N 11.067 22.784 -4.711 7.558  -0.911 -0.159 C17  CFX 15 
CFX N18  N18  N 0 1 N N N 11.187 24.678 -2.422 5.648  -0.664 -2.172 N18  CFX 16 
CFX C19  C19  C 0 1 N N N 11.166 24.434 -1.060 5.711  -1.755 -3.005 C19  CFX 17 
CFX O21  O21  O 0 1 N N N 11.966 23.661 -0.535 5.484  -2.919 -2.686 O21  CFX 18 
CFX C20  C20  C 0 1 N N N 10.091 25.150 -0.219 6.099  -1.333 -4.409 C20  CFX 19 
CFX C23  C23  C 0 1 Y N N 9.298  26.147 -0.944 5.041  -1.634 -5.437 C23  CFX 20 
CFX S24  S24  S 0 1 Y N N 7.658  25.910 -1.245 3.493  -0.962 -5.236 S24  CFX 21 
CFX C25  C25  C 0 1 Y N N 7.448  27.397 -1.970 2.947  -1.710 -6.676 C25  CFX 22 
CFX C26  C26  C 0 1 Y N N 8.628  28.108 -2.007 3.938  -2.451 -7.282 C26  CFX 23 
CFX C27  C27  C 0 1 Y N N 9.708  27.376 -1.411 5.162  -2.404 -6.553 C27  CFX 24 
CFX O30  O30  O 0 1 N N N ?      ?      ?      1.007  3.395  1.298  O30  CFX 25 
CFX C31  C31  C 0 1 N N N ?      ?      ?      -0.067 4.160  1.680  C31  CFX 26 
CFX O32  O32  O 0 1 N N N ?      ?      ?      -1.158 4.156  1.119  O32  CFX 27 
CFX N33  N33  N 0 1 N N N ?      ?      ?      0.238  4.932  2.773  N33  CFX 28 
CFX HC2  HC2  H 0 1 N N N 11.534 25.233 -4.958 4.955  0.730  0.853  HC2  CFX 29 
CFX HC91 1HC9 H 0 0 N N N 12.538 28.078 -6.101 2.918  3.544  -1.044 HC91 CFX 30 
CFX HC92 2HC9 H 0 0 N N N 13.740 28.877 -5.093 3.631  3.162  0.531  HC92 CFX 31 
CFX H151 1H15 H 0 0 N N N 15.531 28.710 -7.560 0.010  1.855  0.380  H151 CFX 32 
CFX H152 2H15 H 0 0 N N N 16.214 28.474 -7.080 0.573  3.160  -0.687 H152 CFX 33 
CFX HXT  HXT  H 0 1 N N N 17.667 25.116 -5.482 0.003  -1.240 1.485  HXT  CFX 34 
CFX H171 1H17 H 0 0 N N N 10.111 22.732 -4.169 8.248  -1.671 -0.533 H171 CFX 35 
CFX H172 2H17 H 0 0 N N N 11.039 23.621 -5.424 7.924  -0.507 0.789  H172 CFX 36 
CFX H173 3H17 H 0 0 N N N 11.231 21.843 -5.256 7.479  -0.103 -0.890 H173 CFX 37 
CFX H18  H18  H 0 1 N N N 10.401 25.142 -2.832 5.855  0.246  -2.541 H18  CFX 38 
CFX H201 1H20 H 0 0 N N N 9.398  24.384 0.159  7.033  -1.839 -4.685 H201 CFX 39 
CFX H202 2H20 H 0 0 N N N 10.628 25.696 0.571  6.316  -0.258 -4.404 H202 CFX 40 
CFX H25  H25  H 0 1 N N N 6.508  27.757 -2.361 1.928  -1.574 -7.010 H25  CFX 41 
CFX H26  H26  H 0 1 N N N 8.727  29.096 -2.433 3.793  -3.001 -8.202 H26  CFX 42 
CFX H27  H27  H 0 1 N N N 10.721 27.744 -1.337 6.070  -2.913 -6.851 H27  CFX 43 
CFX H331 1H33 H 0 0 N N N ?      ?      ?      1.166  4.876  3.178  H331 CFX 44 
CFX H332 2H33 H 0 0 N N N ?      ?      ?      -0.446 5.558  3.185  H332 CFX 45 
# 
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 
CFX C4  O5   DOUB N N 1  
CFX C4  N1   SING N N 2  
CFX C4  C3   SING N N 3  
CFX N1  C2   SING N N 4  
CFX N1  C11  SING N N 5  
CFX C2  S8   SING N N 6  
CFX C2  C3   SING N N 7  
CFX C2  HC2  SING N N 8  
CFX S8  C9   SING N N 9  
CFX C9  C10  SING N N 10 
CFX C9  HC91 SING N N 11 
CFX C9  HC92 SING N N 12 
CFX C10 C11  DOUB N N 13 
CFX C10 C15  SING N N 14 
CFX C11 C12  SING N N 15 
CFX C15 O30  SING N N 16 
CFX C15 H151 SING N N 17 
CFX C15 H152 SING N N 18 
CFX C12 O13  DOUB N N 19 
CFX C12 O14  SING N N 20 
CFX O14 HXT  SING N N 21 
CFX C3  O16  SING N N 22 
CFX C3  N18  SING N N 23 
CFX O16 C17  SING N N 24 
CFX C17 H171 SING N N 25 
CFX C17 H172 SING N N 26 
CFX C17 H173 SING N N 27 
CFX N18 C19  SING N N 28 
CFX N18 H18  SING N N 29 
CFX C19 O21  DOUB N N 30 
CFX C19 C20  SING N N 31 
CFX C20 C23  SING N N 32 
CFX C20 H201 SING N N 33 
CFX C20 H202 SING N N 34 
CFX C23 S24  SING Y N 35 
CFX C23 C27  DOUB Y N 36 
CFX S24 C25  SING Y N 37 
CFX C25 C26  DOUB Y N 38 
CFX C25 H25  SING N N 39 
CFX C26 C27  SING Y N 40 
CFX C26 H26  SING N N 41 
CFX C27 H27  SING N N 42 
CFX O30 C31  SING N N 43 
CFX C31 O32  DOUB N N 44 
CFX C31 N33  SING N N 45 
CFX N33 H331 SING N N 46 
CFX N33 H332 SING N N 47 
# 
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 
CFX SMILES           ACDLabs              10.04 O=C2N1C(=C(CSC1C2(OC)NC(=O)Cc3sccc3)COC(=O)N)C(=O)O                                                                                                                                    
CFX InChI            InChI                1.02b InChI=1/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1/f/h18,21H,17H2 
CFX InChIKey         InChI                1.02b WZOZEZRFJCJXNZ-BPLXXLJGDR                                                                                                                                                              
CFX SMILES_CANONICAL CACTVS               3.341 CO[C@]1(NC(=O)Cc2sccc2)[C@H]3SCC(=C(N3C1=O)C(O)=O)COC(N)=O                                                                                                                             
CFX SMILES           CACTVS               3.341 CO[C]1(NC(=O)Cc2sccc2)[CH]3SCC(=C(N3C1=O)C(O)=O)COC(N)=O                                                                                                                               
CFX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)Cc3cccs3                                                                                                                         
CFX SMILES           "OpenEye OEToolkits" 1.5.0 COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)Cc3cccs3                                                                                                                                  
# 
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 
CFX "SYSTEMATIC NAME" ACDLabs              10.04 "(6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid"     
CFX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6R,7S)-3-(aminocarbonyloxymethyl)-7-methoxy-8-oxo-7-(2-thiophen-2-ylethanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" 
# 
