data_CE3
# 
_chem_comp.id                                    CE3 
_chem_comp.name                                  "(6S,7S)-3-[(ACETYLOXY)METHYL]-7-{[(2E)-2-(2-AMINO-1,3-THIAZOL-4-YL)-2-(METHOXYIMINO)ETHANOYL]AMINO}-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H17 N5 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         CEFOTAXIME 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-12-07 
_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                        455.465 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CE3 
_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        2F50 
_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 
CE3 C    C    C 0 1 N N R -2.569 -2.331 2.911  0.449  -1.442 -1.641 C    CE3 1  
CE3 C1   C1   C 0 1 N N R -2.117 -2.460 4.392  -0.879 -1.904 -1.049 C1   CE3 2  
CE3 S    S    S 0 1 N N N -4.255 -1.950 2.428  0.676  0.363  -1.733 S    CE3 3  
CE3 C2   C2   C 0 1 N N N -3.854 -1.300 0.788  2.474  0.417  -1.484 C2   CE3 4  
CE3 C3   C3   C 0 1 N N N -2.846 -0.142 0.790  2.929  -0.459 -0.365 C3   CE3 5  
CE3 C4   C4   C 0 1 N N N -1.787 -0.106 1.746  2.309  -1.509 0.156  C4   CE3 6  
CE3 N    N    N 0 1 N N N -1.831 -1.093 2.831  1.045  -1.885 -0.341 N    CE3 7  
CE3 C5   C5   C 0 1 N N N -1.357 -1.185 4.066  -0.064 -2.527 0.072  C5   CE3 8  
CE3 O    O    O 0 1 N N N -0.506 -0.579 4.711  -0.317 -3.275 0.992  O    CE3 9  
CE3 N1   N1   N 0 1 N N N -3.199 -2.256 5.348  -1.742 -0.805 -0.608 N1   CE3 10 
CE3 C6   C6   C 0 1 N N N -3.037 -1.974 6.647  -3.073 -0.991 -0.511 C6   CE3 11 
CE3 O2   O2   O 0 1 N N N -4.009 -1.798 7.376  -3.569 -2.039 -0.875 O2   CE3 12 
CE3 C7   C7   C 0 1 N N N -1.635 -1.866 7.261  -3.932 0.083  0.040  C7   CE3 13 
CE3 N2   N2   N 0 1 N N N -0.857 -2.984 7.449  -5.199 -0.139 0.250  N2   CE3 14 
CE3 O1   O1   O 0 1 N N N -1.246 -4.134 7.159  -5.777 -1.369 -0.148 O1   CE3 15 
CE3 C8   C8   C 0 1 N N N -2.024 -4.694 8.207  -7.159 -1.311 0.213  C8   CE3 16 
CE3 C14  C14  C 0 1 Y N N -1.098 -0.496 7.684  -3.353 1.407  0.352  C14  CE3 17 
CE3 N3   N3   N 0 1 Y N N 0.130  -0.304 8.354  -2.089 1.682  0.033  N3   CE3 18 
CE3 C15  C15  C 0 1 Y N N 0.392  1.032  8.665  -1.558 2.860  0.300  C15  CE3 19 
CE3 N4   N4   N 0 1 N N N 1.542  1.469  9.426  -0.278 3.322  0.043  N4   CE3 20 
CE3 S1   S1   S 0 1 Y N N -0.899 2.129  8.124  -2.924 3.701  1.089  S1   CE3 21 
CE3 C13  C13  C 0 1 Y N N -1.756 0.698  7.472  -4.107 2.365  0.977  C13  CE3 22 
CE3 C9   C9   C 0 1 N N N -3.007 0.944  -0.277 4.259  -0.106 0.250  C9   CE3 23 
CE3 O3   O3   O 0 1 N N N -4.133 0.741  -1.123 4.772  1.104  -0.368 O3   CE3 24 
CE3 C10  C10  C 0 1 N N N -3.894 -0.153 -2.141 5.995  1.554  -0.048 C10  CE3 25 
CE3 O4   O4   O 0 1 N N N -2.840 -0.754 -2.351 6.706  0.905  0.683  O4   CE3 26 
CE3 C11  C11  C 0 1 N N N -5.073 -0.391 -3.076 6.483  2.868  -0.601 C11  CE3 27 
CE3 C12  C12  C 0 1 N N N -0.712 0.821  1.682  2.940  -2.289 1.236  C12  CE3 28 
CE3 O5   O5   O 0 1 N N N 0.218  0.731  2.508  2.408  -3.302 1.644  O5   CE3 29 
CE3 O6   O6   O 0 1 N N N -0.618 1.642  0.743  4.107  -1.878 1.771  O6   CE3 30 
CE3 HC   HC   H 0 1 N N N -2.441 -3.252 2.324  0.780  -1.984 -2.527 HC   CE3 31 
CE3 H1   H1   H 0 1 N N N -1.664 -3.363 4.827  -1.404 -2.634 -1.666 H1   CE3 32 
CE3 H21  1H2  H 0 1 N N N -4.790 -0.902 0.369  2.966  0.097  -2.402 H21  CE3 33 
CE3 H22  2H2  H 0 1 N N N -3.422 -2.121 0.197  2.768  1.444  -1.269 H22  CE3 34 
CE3 HN1  HN1  H 0 1 N N N -4.136 -2.333 5.007  -1.355 0.056  -0.387 HN1  CE3 35 
CE3 H81  1H8  H 0 1 N N N -2.430 -5.664 7.884  -7.649 -2.241 -0.076 H81  CE3 36 
CE3 H82  2H8  H 0 1 N N N -2.852 -4.013 8.453  -7.248 -1.173 1.290  H82  CE3 37 
CE3 H83  3H8  H 0 1 N N N -1.393 -4.839 9.096  -7.634 -0.475 -0.301 H83  CE3 38 
CE3 H41  1H4  H 0 1 N N N 2.252  0.872  9.800  -0.025 4.221  0.304  H41  CE3 39 
CE3 H42  2H4  H 0 1 N N N 1.512  2.464  9.518  0.366  2.745  -0.397 H42  CE3 40 
CE3 H13  H13  H 0 1 N N N -2.704 0.764  6.958  -5.133 2.324  1.310  H13  CE3 41 
CE3 H91  1H9  H 0 1 N N N -2.110 0.914  -0.913 4.133  0.057  1.320  H91  CE3 42 
CE3 H92  2H9  H 0 1 N N N -3.130 1.911  0.233  4.962  -0.923 0.087  H92  CE3 43 
CE3 H111 1H11 H 0 0 N N N -4.924 -1.336 -3.620 5.869  3.678  -0.207 H111 CE3 44 
CE3 H112 2H11 H 0 0 N N N -5.144 0.439  -3.794 7.521  3.024  -0.307 H112 CE3 45 
CE3 H113 3H11 H 0 0 N N N -6.001 -0.448 -2.489 6.412  2.854  -1.688 H113 CE3 46 
CE3 HO6  HO6  H 0 1 N N N 0.209  2.105  0.808  4.557  -2.426 2.428  HO6  CE3 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 
CE3 C   C1   SING N N 1  
CE3 C   S    SING N N 2  
CE3 C   N    SING N N 3  
CE3 C   HC   SING N N 4  
CE3 C1  C5   SING N N 5  
CE3 C1  N1   SING N N 6  
CE3 C1  H1   SING N N 7  
CE3 S   C2   SING N N 8  
CE3 C2  C3   SING N N 9  
CE3 C2  H21  SING N N 10 
CE3 C2  H22  SING N N 11 
CE3 C3  C4   DOUB N N 12 
CE3 C3  C9   SING N N 13 
CE3 C4  N    SING N N 14 
CE3 C4  C12  SING N N 15 
CE3 N   C5   SING N N 16 
CE3 C5  O    DOUB N N 17 
CE3 N1  C6   SING N N 18 
CE3 N1  HN1  SING N N 19 
CE3 C6  O2   DOUB N N 20 
CE3 C6  C7   SING N N 21 
CE3 C7  N2   DOUB N Z 22 
CE3 C7  C14  SING N N 23 
CE3 N2  O1   SING N N 24 
CE3 O1  C8   SING N N 25 
CE3 C8  H81  SING N N 26 
CE3 C8  H82  SING N N 27 
CE3 C8  H83  SING N N 28 
CE3 C14 N3   SING Y N 29 
CE3 C14 C13  DOUB Y N 30 
CE3 N3  C15  DOUB Y N 31 
CE3 C15 N4   SING N N 32 
CE3 C15 S1   SING Y N 33 
CE3 N4  H41  SING N N 34 
CE3 N4  H42  SING N N 35 
CE3 S1  C13  SING Y N 36 
CE3 C13 H13  SING N N 37 
CE3 C9  O3   SING N N 38 
CE3 C9  H91  SING N N 39 
CE3 C9  H92  SING N N 40 
CE3 O3  C10  SING N N 41 
CE3 C10 O4   DOUB N N 42 
CE3 C10 C11  SING N N 43 
CE3 C11 H111 SING N N 44 
CE3 C11 H112 SING N N 45 
CE3 C11 H113 SING N N 46 
CE3 C12 O5   DOUB N N 47 
CE3 C12 O6   SING N N 48 
CE3 O6  HO6  SING N N 49 
# 
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 
CE3 SMILES           ACDLabs              10.04 O=C2N1C(=C(CSC1C2NC(=O)C(=N\OC)/c3nc(sc3)N)COC(=O)C)C(=O)O                                                                                                                                            
CE3 InChI            InChI                1.02b InChI=1/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1/f/h19,25H,17H2 
CE3 InChIKey         InChI                1.02b GPRBEKHLDVQUJE-IGPBGJDODM                                                                                                                                                                             
CE3 SMILES_CANONICAL CACTVS               3.341 CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(O)=O)COC(C)=O)c3csc(N)n3                                                                                                                                    
CE3 SMILES           CACTVS               3.341 CON=C(C(=O)N[CH]1[CH]2SCC(=C(N2C1=O)C(O)=O)COC(C)=O)c3csc(N)n3                                                                                                                                        
CE3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/c3csc(n3)N)SC1)C(=O)O                                                                                                                               
CE3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)c3csc(n3)N)SC1)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 
CE3 "SYSTEMATIC NAME" ACDLabs              10.04 "(6R,7R)-3-[(acetyloxy)methyl]-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" 
CE3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid"  
# 
