data_CLS
# 
_chem_comp.id                                    CLS 
_chem_comp.name                                  CEPHALOTHIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H16 N2 O6 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "3-ACETOXYMETHYL-8-OXO-7-(2-THIOPHEN-2-YL-ACETYLAMINO)-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-02-07 
_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                        396.438 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CLS 
_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        1KVL 
_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 
CLS S1     S1     S 0 1 N N N 25.092 8.506  15.860 -1.549 0.771  0.766  S1     CLS 1  
CLS C2     C2     C 0 1 N N N 25.593 9.456  17.310 -1.437 0.724  2.561  C2     CLS 2  
CLS C3     C3     C 0 1 N N N 25.763 8.511  18.539 -0.122 0.217  3.051  C3     CLS 3  
CLS "C3'"  "C3'"  C 0 1 N N N 25.408 9.218  19.860 -0.110 -0.361 4.442  "C3'"  CLS 4  
CLS O20    O20    O 0 1 N N N 25.534 10.672 19.691 -1.420 -0.196 5.047  O20    CLS 5  
CLS C21    C21    C 0 1 N N N 26.831 11.209 19.860 -1.618 -0.549 6.326  C21    CLS 6  
CLS O22    O22    O 0 1 N N N 27.386 11.072 20.890 -0.687 -0.919 7.002  O22    CLS 7  
CLS C23    C23    C 0 1 N N N 27.289 11.915 18.592 -3.002 -0.483 6.921  C23    CLS 8  
CLS C4     C4     C 0 1 N N N 26.191 7.226  18.474 1.037  0.212  2.406  C4     CLS 9  
CLS "C4'"  "C4'"  C 0 1 N N N 26.408 6.289  19.684 2.255  -0.294 3.064  "C4'"  CLS 10 
CLS O4A    O4A    O 0 1 N N N 27.568 6.092  20.124 2.174  -0.868 4.281  O4A    CLS 11 
CLS O4B    O4B    O 0 1 N N N 25.417 5.711  20.155 3.332  -0.194 2.510  O4B    CLS 12 
CLS N5     N5     N 0 1 N N N 26.552 6.570  17.258 1.091  0.694  1.091  N5     CLS 13 
CLS C6     C6     C 0 1 N N R 26.505 7.373  15.936 0.068  1.521  0.396  C6     CLS 14 
CLS C7     C7     C 0 1 N N R 26.186 5.972  15.240 0.694  1.134  -0.932 C7     CLS 15 
CLS C8     C8     C 0 1 N N N 26.252 5.393  16.654 1.794  0.624  -0.031 C8     CLS 16 
CLS O9     O9     O 0 1 N N N 26.053 4.281  17.069 2.932  0.271  -0.257 O9     CLS 17 
CLS N10    N10    N 0 1 N N N 24.942 5.850  14.718 -0.028 0.087  -1.659 N10    CLS 18 
CLS C11    C11    C 0 1 N N N 24.662 6.219  13.467 0.003  0.058  -3.006 C11    CLS 19 
CLS O12    O12    O 0 1 N N N 25.551 6.685  12.727 0.630  0.898  -3.616 O12    CLS 20 
CLS C13    C13    C 0 1 N N N 23.267 6.091  13.144 -0.739 -1.018 -3.754 C13    CLS 21 
CLS C14    C14    C 0 1 Y N N 22.990 6.002  11.615 -0.543 -0.827 -5.236 C14    CLS 22 
CLS C15    C15    C 0 1 Y N N 23.645 6.760  10.564 0.425  -1.328 -6.041 C15    CLS 23 
CLS C16    C16    C 0 1 Y N N 22.928 6.401  9.344  0.404  -1.019 -7.388 C16    CLS 24 
CLS C17    C17    C 0 1 Y N N 22.000 5.524  9.466  -0.579 -0.215 -7.862 C17    CLS 25 
CLS S19    S19    S 0 1 Y N N 21.777 4.963  11.072 -1.523 0.124  -6.386 S19    CLS 26 
CLS H21    1H2    H 0 1 N N N 26.511 10.058 17.117 -2.234 0.089  2.947  H21    CLS 27 
CLS H22    2H2    H 0 1 N N N 24.889 10.294 17.522 -1.574 1.733  2.948  H22    CLS 28 
CLS "H3'1" "1H3'" H 0 0 N N N 24.400 8.924  20.236 0.636  0.155  5.045  "H3'1" CLS 29 
CLS "H3'2" "2H3'" H 0 0 N N N 26.015 8.840  20.715 0.134  -1.422 4.392  "H3'2" CLS 30 
CLS H231   1H23   H 0 0 N N N 28.311 12.338 18.725 -2.982 -0.889 7.932  H231   CLS 31 
CLS H232   2H23   H 0 0 N N N 27.231 11.245 17.702 -3.335 0.553  6.951  H232   CLS 32 
CLS H233   3H23   H 0 0 N N N 26.559 12.691 18.264 -3.688 -1.068 6.308  H233   CLS 33 
CLS HO4    HO4    H 0 1 N N N 27.701 5.516  20.867 2.980  -1.134 4.744  HO4    CLS 34 
CLS H6     H6     H 0 1 N N N 27.331 8.045  15.608 0.116  2.587  0.622  H6     CLS 35 
CLS H7     H7     H 0 1 N N N 26.786 5.608  14.373 0.980  1.978  -1.559 H7     CLS 36 
CLS H10    H10    H 0 1 N N N 24.188 5.466  15.288 -0.529 -0.584 -1.171 H10    CLS 37 
CLS H131   1H13   H 0 0 N N N 22.816 5.222  13.678 -0.356 -1.995 -3.460 H131   CLS 38 
CLS H132   2H13   H 0 0 N N N 22.677 6.917  13.604 -1.801 -0.958 -3.517 H132   CLS 39 
CLS H15    H15    H 0 1 N N N 24.496 7.453  10.668 1.198  -1.965 -5.637 H15    CLS 40 
CLS H16    H16    H 0 1 N N N 23.088 6.794  8.325  1.161  -1.408 -8.052 H16    CLS 41 
CLS H17    H17    H 0 1 N N N 21.535 5.315  8.487  -0.748 0.128  -8.872 H17    CLS 42 
# 
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 
CLS S1    C2     SING N N 1  
CLS S1    C6     SING N N 2  
CLS C2    C3     SING N N 3  
CLS C2    H21    SING N N 4  
CLS C2    H22    SING N N 5  
CLS C3    "C3'"  SING N N 6  
CLS C3    C4     DOUB N N 7  
CLS "C3'" O20    SING N N 8  
CLS "C3'" "H3'1" SING N N 9  
CLS "C3'" "H3'2" SING N N 10 
CLS O20   C21    SING N N 11 
CLS C21   O22    DOUB N N 12 
CLS C21   C23    SING N N 13 
CLS C23   H231   SING N N 14 
CLS C23   H232   SING N N 15 
CLS C23   H233   SING N N 16 
CLS C4    "C4'"  SING N N 17 
CLS C4    N5     SING N N 18 
CLS "C4'" O4A    SING N N 19 
CLS "C4'" O4B    DOUB N N 20 
CLS O4A   HO4    SING N N 21 
CLS N5    C6     SING N N 22 
CLS N5    C8     SING N N 23 
CLS C6    C7     SING N N 24 
CLS C6    H6     SING N N 25 
CLS C7    C8     SING N N 26 
CLS C7    N10    SING N N 27 
CLS C7    H7     SING N N 28 
CLS C8    O9     DOUB N N 29 
CLS N10   C11    SING N N 30 
CLS N10   H10    SING N N 31 
CLS C11   O12    DOUB N N 32 
CLS C11   C13    SING N N 33 
CLS C13   C14    SING N N 34 
CLS C13   H131   SING N N 35 
CLS C13   H132   SING N N 36 
CLS C14   C15    DOUB Y N 37 
CLS C14   S19    SING Y N 38 
CLS C15   C16    SING Y N 39 
CLS C15   H15    SING N N 40 
CLS C16   C17    DOUB Y N 41 
CLS C16   H16    SING N N 42 
CLS C17   S19    SING Y N 43 
CLS C17   H17    SING N N 44 
# 
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 
CLS SMILES           ACDLabs              10.04 O=C2N1C(=C(CSC1C2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O                                                                                                                      
CLS InChI            InChI                1.02b InChI=1/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1/f/h17,22H 
CLS InChIKey         InChI                1.02b XIURVHNZVLADCM-OQJUERBUDY                                                                                                                                            
CLS SMILES_CANONICAL CACTVS               3.341 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)Cc3sccc3)C2=O)C(O)=O                                                                                                            
CLS SMILES           CACTVS               3.341 CC(=O)OCC1=C(N2[CH](SC1)[CH](NC(=O)Cc3sccc3)C2=O)C(O)=O                                                                                                              
CLS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)Cc3cccs3)SC1)C(=O)O                                                                                                          
CLS SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)Cc3cccs3)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 
CLS "SYSTEMATIC NAME" ACDLabs              10.04 "(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" 
CLS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(2-thiophen-2-ylethanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" 
# 
