data_CIO
# 
_chem_comp.id                                    CIO 
_chem_comp.name                                  CILOMILAST 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H25 N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CIS-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANECARBOXYLIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-10-18 
_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                        343.417 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CIO 
_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        ? 
_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 
CIO O25  O25  O 0 1 N N N 7.971  4.724  -6.574  -1.151 -1.439 -5.966 O25  CIO 1  
CIO C23  C23  C 0 1 N N N 7.588  3.525  -6.900  -0.403 -0.460 -5.434 C23  CIO 2  
CIO O24  O24  O 0 1 N N N 8.359  2.507  -6.950  -0.184 0.545  -6.068 O24  CIO 3  
CIO C4   C4   C 0 1 N N N 6.133  3.322  -7.309  0.163  -0.614 -4.046 C4   CIO 4  
CIO C5   C5   C 0 1 N N N 6.054  2.741  -8.704  0.970  0.634  -3.683 C5   CIO 5  
CIO C6   C6   C 0 1 N N N 4.631  2.759  -9.272  1.545  0.477  -2.274 C6   CIO 6  
CIO C3   C3   C 0 1 N N N 5.353  2.360  -6.437  -0.979 -0.791 -3.045 C3   CIO 7  
CIO C2   C2   C 0 1 N N N 3.898  2.380  -6.990  -0.403 -0.948 -1.636 C2   CIO 8  
CIO C1   C1   C 0 1 N N N 3.685  1.909  -8.438  0.402  0.300  -1.273 C1   CIO 9  
CIO C21  C21  C 0 1 N N N 4.102  0.531  -8.648  -0.475 1.481  -1.316 C21  CIO 10 
CIO N22  N22  N 0 1 N N N 4.416  -0.556 -8.897  -1.152 2.392  -1.349 N22  CIO 11 
CIO C7   C7   C 0 1 Y N N 2.234  1.881  -8.947  0.969  0.146  0.114  C7   CIO 12 
CIO C8   C8   C 0 1 Y N N 1.120  2.205  -8.162  2.338  0.179  0.307  C8   CIO 13 
CIO C9   C9   C 0 1 Y N N -0.182 2.133  -8.687  2.863  0.039  1.578  C9   CIO 14 
CIO C10  C10  C 0 1 Y N N -0.437 1.732  -10.026 2.017  -0.135 2.662  C10  CIO 15 
CIO O11  O11  O 0 1 N N N -1.727 1.645  -10.581 2.532  -0.273 3.913  O11  CIO 16 
CIO C12  C12  C 0 1 N N N -2.918 1.883  -9.794  3.953  -0.196 3.786  C12  CIO 17 
CIO C13  C13  C 0 1 Y N N 0.666  1.410  -10.810 0.640  -0.175 2.466  C13  CIO 18 
CIO C20  C20  C 0 1 Y N N 1.976  1.472  -10.275 0.120  -0.028 1.190  C20  CIO 19 
CIO O14  O14  O 0 1 N N N 0.431  1.006  -12.097 -0.194 -0.346 3.526  O14  CIO 20 
CIO C15  C15  C 0 1 N N N 1.608  0.895  -12.972 -1.513 -0.487 2.996  C15  CIO 21 
CIO C16  C16  C 0 1 N N N 1.515  -0.396 -13.722 -2.137 0.903  2.757  C16  CIO 22 
CIO C17  C17  C 0 1 N N N 0.382  -0.108 -14.651 -3.628 0.719  3.133  C17  CIO 23 
CIO C18  C18  C 0 1 N N N 0.467  1.364  -14.932 -3.558 -0.227 4.356  C18  CIO 24 
CIO C19  C19  C 0 1 N N N 1.619  1.886  -14.103 -2.417 -1.206 4.012  C19  CIO 25 
CIO H25  H25  H 0 1 N N N 7.398  5.481  -6.537  -1.514 -1.340 -6.857 H25  CIO 26 
CIO H4   H4   H 0 1 N N N 5.688  4.341  -7.219  0.813  -1.488 -4.014 H4   CIO 27 
CIO H51  1H5  H 0 1 N N N 6.484  1.713  -8.734  0.320  1.508  -3.715 H51  CIO 28 
CIO H52  2H5  H 0 1 N N N 6.766  3.254  -9.392  1.784  0.760  -4.397 H52  CIO 29 
CIO H61  1H6  H 0 1 N N N 4.616  2.453  -10.344 2.120  1.367  -2.016 H61  CIO 30 
CIO H62  2H6  H 0 1 N N N 4.250  3.801  -9.385  2.195  -0.396 -2.243 H62  CIO 31 
CIO H31  1H3  H 0 1 N N N 5.421  2.588  -5.348  -1.554 -1.681 -3.304 H31  CIO 32 
CIO H32  2H3  H 0 1 N N N 5.799  1.339  -6.387  -1.629 0.082  -3.077 H32  CIO 33 
CIO H21  1H2  H 0 1 N N N 3.470  3.402  -6.867  0.246  -1.822 -1.604 H21  CIO 34 
CIO H22  2H2  H 0 1 N N N 3.236  1.794  -6.310  -1.218 -1.074 -0.923 H22  CIO 35 
CIO H8   H8   H 0 1 N N N 1.270  2.521  -7.116  2.998  0.316  -0.536 H8   CIO 36 
CIO H9   H9   H 0 1 N N N -1.027 2.399  -8.030  3.932  0.066  1.727  H9   CIO 37 
CIO H121 1H12 H 0 0 N N N -2.818 2.888  -9.322  4.412  -0.303 4.768  H121 CIO 38 
CIO H122 2H12 H 0 0 N N N -3.940 1.814  -10.234 4.303  -0.996 3.133  H122 CIO 39 
CIO H123 3H12 H 0 0 N N N -2.882 1.205  -8.910  4.228  0.767  3.359  H123 CIO 40 
CIO H20  H20  H 0 1 N N N 2.828  1.191  -10.917 -0.948 -0.054 1.036  H20  CIO 41 
CIO H15  H15  H 0 1 N N N 2.485  1.027  -12.296 -1.482 -1.048 2.062  H15  CIO 42 
CIO H161 1H16 H 0 0 N N N 1.397  -1.308 -13.092 -1.670 1.647  3.403  H161 CIO 43 
CIO H162 2H16 H 0 0 N N N 2.459  -0.735 -14.209 -2.040 1.190  1.710  H162 CIO 44 
CIO H171 1H17 H 0 0 N N N -0.611 -0.436 -14.265 -4.178 0.254  2.315  H171 CIO 45 
CIO H172 2H17 H 0 0 N N N 0.380  -0.742 -15.568 -4.078 1.673  3.408  H172 CIO 46 
CIO H181 1H18 H 0 0 N N N -0.491 1.906  -14.751 -4.499 -0.765 4.476  H181 CIO 47 
CIO H182 2H18 H 0 0 N N N 0.557  1.604  -16.017 -3.321 0.333  5.260  H182 CIO 48 
CIO H191 1H19 H 0 0 N N N 2.590  1.997  -14.640 -2.825 -2.115 3.571  H191 CIO 49 
CIO H192 2H19 H 0 0 N N N 1.555  2.959  -13.807 -1.849 -1.448 4.911  H192 CIO 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 
CIO O25 C23  SING N N 1  
CIO O25 H25  SING N N 2  
CIO C23 O24  DOUB N N 3  
CIO C23 C4   SING N N 4  
CIO C4  C5   SING N N 5  
CIO C4  C3   SING N N 6  
CIO C4  H4   SING N N 7  
CIO C5  C6   SING N N 8  
CIO C5  H51  SING N N 9  
CIO C5  H52  SING N N 10 
CIO C6  C1   SING N N 11 
CIO C6  H61  SING N N 12 
CIO C6  H62  SING N N 13 
CIO C3  C2   SING N N 14 
CIO C3  H31  SING N N 15 
CIO C3  H32  SING N N 16 
CIO C2  C1   SING N N 17 
CIO C2  H21  SING N N 18 
CIO C2  H22  SING N N 19 
CIO C1  C21  SING N N 20 
CIO C1  C7   SING N N 21 
CIO C21 N22  TRIP N N 22 
CIO C7  C8   DOUB Y N 23 
CIO C7  C20  SING Y N 24 
CIO C8  C9   SING Y N 25 
CIO C8  H8   SING N N 26 
CIO C9  C10  DOUB Y N 27 
CIO C9  H9   SING N N 28 
CIO C10 O11  SING N N 29 
CIO C10 C13  SING Y N 30 
CIO O11 C12  SING N N 31 
CIO C12 H121 SING N N 32 
CIO C12 H122 SING N N 33 
CIO C12 H123 SING N N 34 
CIO C13 C20  DOUB Y N 35 
CIO C13 O14  SING N N 36 
CIO C20 H20  SING N N 37 
CIO O14 C15  SING N N 38 
CIO C15 C16  SING N N 39 
CIO C15 C19  SING N N 40 
CIO C15 H15  SING N N 41 
CIO C16 C17  SING N N 42 
CIO C16 H161 SING N N 43 
CIO C16 H162 SING N N 44 
CIO C17 C18  SING N N 45 
CIO C17 H171 SING N N 46 
CIO C17 H172 SING N N 47 
CIO C18 C19  SING N N 48 
CIO C18 H181 SING N N 49 
CIO C18 H182 SING N N 50 
CIO C19 H191 SING N N 51 
CIO C19 H192 SING N N 52 
# 
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 
CIO SMILES           ACDLabs              10.04 O=C(O)C3CCC(C#N)(c2cc(OC1CCCC1)c(OC)cc2)CC3                                                                                                           
CIO InChI            InChI                1.02b InChI=1/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)/t14-,20-/f/h22H 
CIO InChIKey         InChI                1.02b CFBUZOUXXHZCFB-XZBFOCCVDU                                                                                                                             
CIO SMILES_CANONICAL CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[C@]3(CC[C@@H](CC3)C(O)=O)C#N                                                                                                     
CIO SMILES           CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[C]3(CC[CH](CC3)C(O)=O)C#N                                                                                                        
CIO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1ccc(cc1OC2CCCC2)C3(CCC(CC3)C(=O)O)C#N                                                                                                             
CIO SMILES           "OpenEye OEToolkits" 1.5.0 COc1ccc(cc1OC2CCCC2)C3(CCC(CC3)C(=O)O)C#N                                                                                                             
# 
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 
CIO "SYSTEMATIC NAME" ACDLabs              10.04 "cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid" 
CIO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)cyclohexane-1-carboxylic acid"   
# 
