data_CIL
# 
_chem_comp.id                                    CIL 
_chem_comp.name                                  CILASTATIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H26 N2 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-02-06 
_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                        358.453 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CIL 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1ITU 
_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 
CIL C1   C1   C 0 1 N N N -11.943 11.023 5.061  5.559  -2.467 -0.934 C1   CIL 1  
CIL C2   C2   C 0 1 N N S -13.254 11.167 4.351  4.156  -1.864 -0.838 C2   CIL 2  
CIL C3   C3   C 0 1 N N N -12.863 12.162 5.395  4.534  -3.063 0.033  C3   CIL 3  
CIL C4   C4   C 0 1 N N N -12.455 13.552 4.966  4.745  -2.813 1.528  C4   CIL 4  
CIL C5   C5   C 0 1 N N N -13.599 12.124 6.708  3.926  -4.420 -0.330 C5   CIL 5  
CIL C6   C6   C 0 1 N N N -13.265 11.556 2.947  4.019  -0.526 -0.157 C6   CIL 6  
CIL N7   N7   N 0 1 N N N -14.478 11.491 2.294  3.687  0.565  -0.876 N7   CIL 7  
CIL C8   C8   C 0 1 N N N -14.645 11.817 0.984  3.457  1.787  -0.230 C8   CIL 8  
CIL C9   C9   C 0 1 N N N -15.549 12.733 0.608  2.271  2.391  -0.345 C9   CIL 9  
CIL O10  O10  O 0 1 N N N -12.246 11.916 2.376  4.207  -0.431 1.037  O10  CIL 10 
CIL C11  C11  C 0 1 N N N -13.814 11.152 -0.108 4.524  2.406  0.578  C11  CIL 11 
CIL O12  O12  O 0 1 N N N -13.429 11.805 -1.082 4.334  3.622  1.126  O12  CIL 12 
CIL O13  O13  O 0 1 N N N -13.531 9.971  -0.026 5.574  1.819  0.749  O13  CIL 13 
CIL C14  C14  C 0 1 N N N -16.434 13.468 1.562  1.144  1.704  -1.073 C14  CIL 14 
CIL C15  C15  C 0 1 N N N -16.062 14.942 1.522  -0.082 1.630  -0.160 C15  CIL 15 
CIL C16  C16  C 0 1 N N N -17.139 15.770 2.218  -1.226 0.934  -0.899 C16  CIL 16 
CIL C17  C17  C 0 1 N N N ?       ?      ?      -2.452 0.860  0.014  C17  CIL 17 
CIL C18  C18  C 0 1 N N N ?       ?      ?      -5.149 0.042  0.361  C18  CIL 18 
CIL C19  C19  C 0 1 N N N ?       ?      ?      -6.387 -0.631 -0.235 C19  CIL 19 
CIL C20  C20  C 0 1 N N N ?       ?      ?      -7.500 -0.624 0.781  C20  CIL 20 
CIL O22  O22  O 0 1 N N N ?       ?      ?      -7.517 -1.538 1.764  O22  CIL 21 
CIL O23  O23  O 0 1 N N N ?       ?      ?      -8.377 0.204  0.711  O23  CIL 22 
CIL N21  N21  N 0 1 N N N ?       ?      ?      -6.814 0.102  -1.434 N21  CIL 23 
CIL S    S    S 0 1 N N N ?       ?      ?      -3.809 0.034  -0.862 S    CIL 24 
CIL H11  H11  H 0 1 N N N -11.545 10.209 5.685  5.799  -3.040 -1.829 H11  CIL 25 
CIL H12A H12A H 0 0 N N N -10.889 10.916 4.766  6.383  -1.896 -0.506 H12A CIL 26 
CIL H2   H2   H 0 1 N N N -14.128 10.519 4.189  3.474  -2.040 -1.669 H2   CIL 27 
CIL H41  H41  H 0 1 N N N -12.356 14.196 5.853  5.550  -2.092 1.666  H41  CIL 28 
CIL H42  H42  H 0 1 N N N -11.491 13.504 4.438  3.826  -2.420 1.963  H42  CIL 29 
CIL H43  H43  H 0 1 N N N -13.221 13.968 4.295  5.007  -3.750 2.019  H43  CIL 30 
CIL H51  H51  H 0 1 N N N -12.874 12.115 7.535  4.281  -5.176 0.370  H51  CIL 31 
CIL H52  H52  H 0 1 N N N -14.242 13.013 6.794  2.839  -4.356 -0.277 H52  CIL 32 
CIL H53  H53  H 0 1 N N N -14.219 11.217 6.754  4.225  -4.693 -1.342 H53  CIL 33 
CIL H7   H7   H 0 1 N N N -15.278 11.188 2.812  3.608  0.504  -1.841 H7   CIL 34 
CIL H9   H9   H 0 1 N N N -15.643 12.952 -0.445 2.120  3.371  0.083  H9   CIL 35 
CIL H12  H12  H 0 1 N N N -12.932 11.243 -1.664 5.063  3.987  1.647  H12  CIL 36 
CIL H141 H141 H 0 0 N N N -17.487 13.340 1.269  0.895  2.269  -1.971 H141 CIL 37 
CIL H142 H142 H 0 0 N N N -16.303 13.073 2.580  1.451  0.696  -1.351 H142 CIL 38 
CIL H151 H151 H 0 0 N N N -15.101 15.089 2.037  0.168  1.066  0.738  H151 CIL 39 
CIL H152 H152 H 0 0 N N N -15.978 15.266 0.474  -0.389 2.639  0.118  H152 CIL 40 
CIL H161 H161 H 0 0 N N N -17.668 16.663 2.583  -1.476 1.498  -1.797 H161 CIL 41 
CIL H162 H162 H 0 0 N N N -18.130 16.189 2.445  -0.919 -0.074 -1.177 H162 CIL 42 
CIL H171 H171 H 0 0 N N N ?       ?      ?      -2.203 0.295  0.912  H171 CIL 43 
CIL H172 H172 H 0 0 N N N ?       ?      ?      -2.760 1.868  0.292  H172 CIL 44 
CIL H181 H181 H 0 0 N N N ?       ?      ?      -5.389 1.071  0.630  H181 CIL 45 
CIL H182 H182 H 0 0 N N N ?       ?      ?      -4.832 -0.502 1.251  H182 CIL 46 
CIL H19  H19  H 0 1 N N N ?       ?      ?      -6.147 -1.660 -0.504 H19  CIL 47 
CIL H22  H22  H 0 1 N N N ?       ?      ?      -8.251 -1.494 2.392  H22  CIL 48 
CIL H211 H211 H 0 0 N N N ?       ?      ?      -7.591 -0.360 -1.882 H211 CIL 49 
CIL H122 H122 H 0 0 N N N ?       ?      ?      -7.042 1.059  -1.210 H122 CIL 50 
# 
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 
CIL C1  C2   SING N N 1  
CIL C1  C3   SING N N 2  
CIL C1  H11  SING N N 3  
CIL C1  H12A SING N N 4  
CIL C2  C3   SING N N 5  
CIL C2  C6   SING N N 6  
CIL C2  H2   SING N N 7  
CIL C3  C4   SING N N 8  
CIL C3  C5   SING N N 9  
CIL C4  H41  SING N N 10 
CIL C4  H42  SING N N 11 
CIL C4  H43  SING N N 12 
CIL C5  H51  SING N N 13 
CIL C5  H52  SING N N 14 
CIL C5  H53  SING N N 15 
CIL C6  N7   SING N N 16 
CIL C6  O10  DOUB N N 17 
CIL N7  C8   SING N N 18 
CIL N7  H7   SING N N 19 
CIL C8  C9   DOUB N Z 20 
CIL C8  C11  SING N N 21 
CIL C9  C14  SING N N 22 
CIL C9  H9   SING N N 23 
CIL C11 O12  SING N N 24 
CIL C11 O13  DOUB N N 25 
CIL O12 H12  SING N N 26 
CIL C14 C15  SING N N 27 
CIL C14 H141 SING N N 28 
CIL C14 H142 SING N N 29 
CIL C15 C16  SING N N 30 
CIL C15 H151 SING N N 31 
CIL C15 H152 SING N N 32 
CIL C16 C17  SING N N 33 
CIL C16 H161 SING N N 34 
CIL C16 H162 SING N N 35 
CIL C17 S    SING N N 36 
CIL C17 H171 SING N N 37 
CIL C17 H172 SING N N 38 
CIL C18 C19  SING N N 39 
CIL C18 S    SING N N 40 
CIL C18 H181 SING N N 41 
CIL C18 H182 SING N N 42 
CIL C19 C20  SING N N 43 
CIL C19 N21  SING N N 44 
CIL C19 H19  SING N N 45 
CIL C20 O22  SING N N 46 
CIL C20 O23  DOUB N N 47 
CIL O22 H22  SING N N 48 
CIL N21 H211 SING N N 49 
CIL N21 H122 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 
CIL SMILES           ACDLabs              10.04 O=C(N\C(=C/CCCCSCC(C(=O)O)N)C(=O)O)C1CC1(C)C                                                                                                                                       
CIL InChI            InChI                1.02b InChI=1/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11?/m1/s1/f/h18,20,22H 
CIL InChIKey         InChI                1.02b DHSUYTOATWAVLW-KILJBIKZDE                                                                                                                                                          
CIL SMILES_CANONICAL CACTVS               3.341 CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSCC(N)C(O)=O)C(O)=O                                                                                                                                  
CIL SMILES           CACTVS               3.341 CC1(C)C[CH]1C(=O)NC(=CCCCCSCC(N)C(O)=O)C(O)=O                                                                                                                                      
CIL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](C(=O)O)N)/C(=O)O)C                                                                                                                             
CIL SMILES           "OpenEye OEToolkits" 1.5.0 CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)O)C                                                                                                                                         
# 
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 
CIL "SYSTEMATIC NAME" ACDLabs              10.04 "(2Z)-7-[(2-amino-2-carboxyethyl)sulfanyl]-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid"         
CIL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(Z)-7-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropyl]carbonylamino]hept-2-enoic acid" 
# 
