data_CEF
# 
_chem_comp.id                                    CEF 
_chem_comp.name                                  "CEFOTAXIME GROUP" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H19 N5 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        457.481 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CEF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye OEToolkits" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1CEF 
_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 
CEF S1     S1     S 0 1 N N N 17.748 -13.029 42.987 -3.318 -1.172 -0.950 S1     CEF 1  
CEF C2     C2     C 0 1 N N N 18.146 -11.819 44.238 -3.810 0.572  -0.840 C2     CEF 2  
CEF C3     C3     C 0 1 N N N 18.954 -10.717 43.847 -5.107 0.812  -0.089 C3     CEF 3  
CEF "C3'"  "C3'"  C 0 1 N N N 19.840 -10.169 44.694 -5.757 2.120  -0.467 "C3'"  CEF 4  
CEF "C2'"  "C2'"  C 0 1 N N N ?      ?       ?      -6.716 1.919  -1.609 "C2'"  CEF 5  
CEF "O1'"  "O1'"  O 0 1 N N N ?      ?       ?      -6.970 0.860  -2.167 "O1'"  CEF 6  
CEF "O2'"  "O2'"  O 0 1 N N N ?      ?       ?      -7.246 3.138  -1.932 "O2'"  CEF 7  
CEF "C1'"  "C1'"  C 0 1 N N N ?      ?       ?      -8.174 3.139  -3.021 "C1'"  CEF 8  
CEF C4     C4     C 0 1 N N N 18.795 -10.108 42.490 -5.577 -0.065 0.827  C4     CEF 9  
CEF "C4'"  "C4'"  C 0 1 N N N 19.674 -8.923  41.918 -6.870 0.162  1.496  "C4'"  CEF 10 
CEF O4A    O4A    O 0 1 N N N 19.079 -7.876  41.567 -7.804 0.748  0.991  O4A    CEF 11 
CEF O4B    O4B    O 0 1 N N N 20.917 -9.069  41.826 -6.833 -0.378 2.729  O4B    CEF 12 
CEF N5     N5     N 0 1 N N N 17.740 -10.509 41.741 -4.936 -1.226 1.208  N5     CEF 13 
CEF C6     C6     C 0 1 N N R 17.120 -11.852 41.766 -3.608 -1.627 0.788  C6     CEF 14 
CEF C7     C7     C 0 1 N N S 17.117 -12.449 40.274 -3.449 -3.133 0.948  C7     CEF 15 
CEF C8     C8     C 0 1 N N N 16.646 -11.350 39.341 -3.640 -3.565 2.381  C8     CEF 16 
CEF O9     O9     O 0 1 N N N 17.302 -11.031 38.346 -2.913 -3.200 3.302  O9     CEF 17 
CEF N10    N10    N 0 1 N N N 18.436 -12.943 39.903 -4.412 -3.844 0.154  N10    CEF 18 
CEF C11    C11    C 0 1 N N N 18.727 -14.238 39.953 -4.061 -4.754 -0.823 C11    CEF 19 
CEF O12    O12    O 0 1 N N N 17.855 -15.100 40.085 -2.949 -5.109 -1.180 O12    CEF 20 
CEF C13    C13    C 0 1 N N N 20.126 -14.482 39.805 -5.256 -5.364 -1.508 C13    CEF 21 
CEF N16    N16    N 0 1 N N N 20.642 -15.335 38.922 -5.787 -6.456 -1.048 N16    CEF 22 
CEF O17    O17    O 0 1 N N N 19.770 -15.520 37.792 -5.115 -6.921 0.091  O17    CEF 23 
CEF C18    C18    C 0 1 N N N 20.510 -16.198 36.803 -5.756 -8.110 0.526  C18    CEF 24 
CEF C14    C14    C 0 1 Y N N 21.166 -13.841 40.642 -5.808 -4.698 -2.719 C14    CEF 25 
CEF C15    C15    C 0 1 Y N N 20.954 -13.384 41.980 -6.877 -5.191 -3.381 C15    CEF 26 
CEF S16    S16    S 0 1 Y N N 22.206 -12.421 42.535 -7.197 -4.152 -4.707 S16    CEF 27 
CEF C17    C17    C 0 1 Y N N 23.166 -12.860 41.234 -5.867 -3.177 -4.231 C17    CEF 28 
CEF N18    N18    N 0 1 N N N 24.500 -12.464 41.059 -5.560 -2.071 -4.960 N18    CEF 29 
CEF N19    N19    N 0 1 Y N N 22.494 -13.625 40.377 -5.208 -3.566 -3.163 N19    CEF 30 
CEF H21    1H2    H 0 1 N N N 18.615 -12.330 45.111 -3.913 0.927  -1.871 H21    CEF 31 
CEF H22    2H2    H 0 1 N N N 17.204 -11.441 44.700 -3.002 1.147  -0.374 H22    CEF 32 
CEF "H3'1" "1H3'" H 0 0 N N N 20.775 -10.316 45.283 -4.978 2.817  -0.769 "H3'1" CEF 33 
CEF "H3'2" "2H3'" H 0 0 N N N 20.031 -9.804  45.730 -6.288 2.496  0.405  "H3'2" CEF 34 
CEF "H1'1" "1H1'" H 0 0 N N N ?      ?       ?      -8.726 2.196  -3.031 "H1'1" CEF 35 
CEF "H1'2" "2H1'" H 0 0 N N N ?      ?       ?      -7.632 3.265  -3.962 "H1'2" CEF 36 
CEF "H1'3" "3H1'" H 0 0 N N N ?      ?       ?      -8.873 3.968  -2.892 "H1'3" CEF 37 
CEF HO4    HO4    H 0 1 N N N 21.445 -8.358  41.483 -7.680 -0.246 3.206  HO4    CEF 38 
CEF H6     H6     H 0 1 N N N 16.079 -11.696 42.134 -2.859 -1.125 1.409  H6     CEF 39 
CEF H7     H7     H 0 1 N N N 16.428 -13.323 40.206 -2.460 -3.459 0.620  H7     CEF 40 
CEF H88    8H8    H 0 1 N Y N 15.740 -10.723 39.391 -4.541 -4.166 2.599  H88    CEF 41 
CEF HN1    HN1    H 0 1 N N N 19.202 -12.346 39.590 -5.401 -3.657 0.316  HN1    CEF 42 
CEF H181   1H18   H 0 0 N N N 20.959 -17.151 37.169 -6.806 -7.900 0.746  H181   CEF 43 
CEF H182   2H18   H 0 0 N N N 19.835 -16.341 35.928 -5.254 -8.490 1.420  H182   CEF 44 
CEF H183   3H18   H 0 0 N N N 21.463 -15.682 36.540 -5.696 -8.858 -0.268 H183   CEF 45 
CEF H15    H15    H 0 1 N N N 20.024 -13.706 42.478 -7.482 -6.067 -3.192 H15    CEF 46 
CEF HN81   1HN8   H 0 0 N N N 25.003 -12.737 41.903 -4.749 -2.048 -5.587 HN81   CEF 47 
CEF HN82   2HN8   H 0 0 N N N 25.085 -12.731 40.267 -6.070 -1.189 -4.841 HN82   CEF 48 
CEF HN2    HN2    H 0 1 N N N 17.000 -9.890  42.004 -5.381 -1.763 1.947  HN2    CEF 49 
# 
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 
CEF S1    C2     SING N N 1  
CEF S1    C6     SING N N 2  
CEF C2    C3     SING N N 3  
CEF C2    H21    SING N N 4  
CEF C2    H22    SING N N 5  
CEF C3    "C3'"  SING N N 6  
CEF C3    C4     DOUB N N 7  
CEF "C3'" "O2'"  SING N N 8  
CEF "C3'" "H3'1" SING N N 9  
CEF "C3'" "H3'2" SING N N 10 
CEF "C2'" "O1'"  DOUB N N 11 
CEF "C2'" "O2'"  SING N N 12 
CEF "C2'" "C1'"  SING N N 13 
CEF "C1'" "H1'1" SING N N 14 
CEF "C1'" "H1'2" SING N N 15 
CEF "C1'" "H1'3" SING N N 16 
CEF C4    "C4'"  SING N N 17 
CEF C4    N5     SING N N 18 
CEF "C4'" O4A    DOUB N N 19 
CEF "C4'" O4B    SING N N 20 
CEF O4B   HO4    SING N N 21 
CEF N5    C6     SING N N 22 
CEF C6    C7     SING N N 23 
CEF C6    H6     SING N N 24 
CEF C7    C8     SING N N 25 
CEF C7    N10    SING N N 26 
CEF C7    H7     SING N N 27 
CEF C8    O9     DOUB N N 28 
CEF C8    H88    SING N N 29 
CEF N10   C11    SING N N 30 
CEF N10   HN1    SING N N 31 
CEF C11   O12    DOUB N N 32 
CEF C11   C13    SING N N 33 
CEF C13   N16    DOUB N N 34 
CEF C13   C14    SING N N 35 
CEF N16   O17    SING N N 36 
CEF O17   C18    SING N N 37 
CEF C18   H181   SING N N 38 
CEF C18   H182   SING N N 39 
CEF C18   H183   SING N N 40 
CEF C14   C15    DOUB Y N 41 
CEF C14   N19    SING Y N 42 
CEF C15   S16    SING Y N 43 
CEF C15   H15    SING N N 44 
CEF S16   C17    SING Y N 45 
CEF C17   N18    SING N N 46 
CEF C17   N19    DOUB Y N 47 
CEF N18   HN81   SING N N 48 
CEF N18   HN82   SING N N 49 
CEF HN2   N5     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 
CEF SMILES           ACDLabs              10.04 O=CC(NC(=O)/C(=N\OC)c1nc(sc1)N)C2SCC(=C(N2)C(=O)O)COC(=O)C                                                                                                                                              
CEF InChI            InChI                1.02b InChI=1/C16H19N5O7S2/c1-7(23)28-4-8-5-29-14(20-11(8)15(25)26)9(3-22)18-13(24)12(21-27-2)10-6-30-16(17)19-10/h3,6,9,14,20H,4-5H2,1-2H3,(H2,17,19)(H,18,24)(H,25,26)/b21-12-/t9-,14-/m1/s1/f/h18,25H,17H2 
CEF InChIKey         InChI                1.02b YJLHJBLULHXDCF-WSLUPMCTDI                                                                                                                                                                               
CEF SMILES_CANONICAL CACTVS               3.341 CO\N=C(/C(=O)N[C@H](C=O)[C@@H]1NC(=C(COC(C)=O)CS1)C(O)=O)c2csc(N)n2                                                                                                                                     
CEF SMILES           CACTVS               3.341 CON=C(C(=O)N[CH](C=O)[CH]1NC(=C(COC(C)=O)CS1)C(O)=O)c2csc(N)n2                                                                                                                                          
CEF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N[C@H](SC1)[C@@H](C=O)NC(=O)C(=NOC)c2csc(n2)N)C(=O)O                                                                                                                                       
CEF SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(NC(SC1)C(C=O)NC(=O)C(=NOC)c2csc(n2)N)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 
CEF "SYSTEMATIC NAME" ACDLabs              10.04 "(2R)-5-[(acetyloxy)methyl]-2-[(1R)-1-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2-oxoethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid" 
CEF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-5-(acetyloxymethyl)-2-[(1R)-1-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-2-oxo-ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid"      
# 
