data_DRF
# 
_chem_comp.id                                    DRF 
_chem_comp.name                                  "(2S)-2-ETHOXY-3-{4-[2-(10H-PHENOXAZIN-10-YL)ETHOXY]PHENYL}PROPANOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H25 N O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         RAGAGLITAZAR 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-02-25 
_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                        419.470 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DRF 
_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        1NYX 
_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 
DRF O45  O45  O 0 1 N N N 18.129 63.153 21.231 -2.304 0.653  -7.150 O45  DRF 1  
DRF C44  C44  C 0 1 N N N 18.901 63.053 20.251 -0.997 0.556  -6.860 C44  DRF 2  
DRF O55  O55  O 0 1 N N N 19.975 62.722 20.899 -0.170 0.843  -7.693 O55  DRF 3  
DRF C41  C41  C 0 1 N N S 18.730 63.237 18.967 -0.561 0.091  -5.494 C41  DRF 4  
DRF O46  O46  O 0 1 N N N 20.037 63.780 18.321 0.866  0.072  -5.430 O46  DRF 5  
DRF C48  C48  C 0 1 N N N 19.848 65.035 17.723 1.281  -1.227 -5.854 C48  DRF 6  
DRF C49  C49  C 0 1 N N N 21.132 65.514 17.107 2.808  -1.314 -5.809 C49  DRF 7  
DRF C40  C40  C 0 1 N N N 18.296 62.151 18.162 -1.107 1.047  -4.431 C40  DRF 8  
DRF C33  C33  C 0 1 Y N N 17.829 61.827 16.880 -0.671 0.582  -3.066 C33  DRF 9  
DRF C34  C34  C 0 1 Y N N 18.824 61.567 15.908 0.520  1.035  -2.530 C34  DRF 10 
DRF C35  C35  C 0 1 Y N N 18.450 61.254 14.586 0.922  0.609  -1.279 C35  DRF 11 
DRF C30  C30  C 0 1 Y N N 17.082 61.200 14.237 0.129  -0.272 -0.559 C30  DRF 12 
DRF O27  O27  O 0 1 N N N 16.712 60.901 12.932 0.522  -0.691 0.671  O27  DRF 13 
DRF C24  C24  C 0 1 N N N 16.243 62.096 12.324 -0.490 -1.579 1.148  C24  DRF 14 
DRF C23  C23  C 0 1 N N N 16.092 61.916 10.816 -0.107 -2.090 2.538  C23  DRF 15 
DRF N22  N22  N 0 1 N N N 15.865 63.226 10.184 0.020  -0.957 3.457  N22  DRF 16 
DRF C11  C11  C 0 1 Y N N 14.587 63.711 9.991  -1.066 -0.473 4.210  C11  DRF 17 
DRF C16  C16  C 0 1 Y N N 14.406 65.138 9.851  -0.978 0.793  4.776  C16  DRF 18 
DRF O21  O21  O 0 1 N N N 15.499 65.945 9.910  0.081  1.606  4.600  O21  DRF 19 
DRF C4   C4   C 0 1 Y N N 16.729 65.417 9.644  1.218  0.983  4.234  C4   DRF 20 
DRF C3   C3   C 0 1 Y N N 16.926 63.995 9.785  1.239  -0.281 3.652  C3   DRF 21 
DRF C2   C2   C 0 1 Y N N 18.212 63.448 9.510  2.430  -0.867 3.268  C2   DRF 22 
DRF C1   C1   C 0 1 Y N N 19.272 64.282 9.105  3.625  -0.202 3.476  C1   DRF 23 
DRF C6   C6   C 0 1 Y N N 19.068 65.674 8.970  3.619  1.046  4.068  C6   DRF 24 
DRF C5   C5   C 0 1 Y N N 17.802 66.237 9.238  2.429  1.637  4.445  C5   DRF 25 
DRF C15  C15  C 0 1 Y N N 13.114 65.676 9.660  -2.048 1.256  5.538  C15  DRF 26 
DRF C14  C14  C 0 1 Y N N 11.992 64.818 9.607  -3.173 0.475  5.713  C14  DRF 27 
DRF C13  C13  C 0 1 Y N N 12.155 63.417 9.741  -3.254 -0.777 5.135  C13  DRF 28 
DRF C12  C12  C 0 1 Y N N 13.440 62.866 9.932  -2.195 -1.253 4.381  C12  DRF 29 
DRF C31  C31  C 0 1 Y N N 16.090 61.457 15.221 -1.066 -0.724 -1.099 C31  DRF 30 
DRF C32  C32  C 0 1 Y N N 16.469 61.768 16.533 -1.466 -0.292 -2.348 C32  DRF 31 
DRF H45  H45  H 0 1 N N N 17.343 63.395 20.757 -2.583 0.951  -8.026 H45  DRF 32 
DRF H41  H41  H 0 1 N N N 17.875 63.953 18.968 -0.946 -0.911 -5.312 H41  DRF 33 
DRF H481 1H48 H 0 0 N N N 19.426 65.779 18.439 0.937  -1.404 -6.873 H481 DRF 34 
DRF H482 2H48 H 0 0 N N N 19.011 65.024 16.986 0.854  -1.979 -5.190 H482 DRF 35 
DRF H491 1H49 H 0 0 N N N 21.554 64.770 16.391 3.125  -2.306 -6.132 H491 DRF 36 
DRF H492 2H49 H 0 0 N N N 20.982 66.511 16.632 3.234  -0.562 -6.473 H492 DRF 37 
DRF H493 3H49 H 0 0 N N N 21.969 65.525 17.844 3.152  -1.137 -4.790 H493 DRF 38 
DRF H401 1H40 H 0 0 N N N 17.484 61.727 18.798 -2.195 1.061  -4.480 H401 DRF 39 
DRF H402 2H40 H 0 0 N N N 19.165 61.459 18.253 -0.722 2.050  -4.613 H402 DRF 40 
DRF H34  H34  H 0 1 N N N 19.892 61.608 16.181 1.137  1.721  -3.091 H34  DRF 41 
DRF H35  H35  H 0 1 N N N 19.225 61.052 13.828 1.853  0.963  -0.861 H35  DRF 42 
DRF H241 1H24 H 0 0 N N N 16.893 62.967 12.572 -0.586 -2.422 0.464  H241 DRF 43 
DRF H242 2H24 H 0 0 N N N 15.297 62.453 12.793 -1.441 -1.048 1.205  H242 DRF 44 
DRF H231 1H23 H 0 0 N N N 15.295 61.180 10.558 0.842  -2.621 2.481  H231 DRF 45 
DRF H232 2H23 H 0 0 N N N 16.959 61.377 10.368 -0.880 -2.767 2.902  H232 DRF 46 
DRF H2   H2   H 0 1 N N N 18.389 62.364 9.612  2.428  -1.845 2.808  H2   DRF 47 
DRF H1   H1   H 0 1 N N N 20.262 63.845 8.894  4.559  -0.655 3.177  H1   DRF 48 
DRF H6   H6   H 0 1 N N N 19.901 66.324 8.654  4.551  1.564  4.237  H6   DRF 49 
DRF H5   H5   H 0 1 N N N 17.650 67.324 9.130  2.438  2.613  4.907  H5   DRF 50 
DRF H15  H15  H 0 1 N N N 12.981 66.766 9.552  -1.997 2.233  5.996  H15  DRF 51 
DRF H14  H14  H 0 1 N N N 10.985 65.244 9.461  -3.996 0.845  6.306  H14  DRF 52 
DRF H13  H13  H 0 1 N N N 11.277 62.752 9.696  -4.139 -1.381 5.270  H13  DRF 53 
DRF H12  H12  H 0 1 N N N 13.548 61.773 10.035 -2.251 -2.232 3.927  H12  DRF 54 
DRF H31  H31  H 0 1 N N N 15.018 61.415 14.965 -1.685 -1.411 -0.541 H31  DRF 55 
DRF H32  H32  H 0 1 N N N 15.696 61.967 17.294 -2.396 -0.643 -2.769 H32  DRF 56 
# 
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 
DRF O45 C44  SING N N 1  
DRF O45 H45  SING N N 2  
DRF C44 O55  DOUB N N 3  
DRF C44 C41  SING N N 4  
DRF C41 O46  SING N N 5  
DRF C41 C40  SING N N 6  
DRF C41 H41  SING N N 7  
DRF O46 C48  SING N N 8  
DRF C48 C49  SING N N 9  
DRF C48 H481 SING N N 10 
DRF C48 H482 SING N N 11 
DRF C49 H491 SING N N 12 
DRF C49 H492 SING N N 13 
DRF C49 H493 SING N N 14 
DRF C40 C33  SING N N 15 
DRF C40 H401 SING N N 16 
DRF C40 H402 SING N N 17 
DRF C33 C34  DOUB Y N 18 
DRF C33 C32  SING Y N 19 
DRF C34 C35  SING Y N 20 
DRF C34 H34  SING N N 21 
DRF C35 C30  DOUB Y N 22 
DRF C35 H35  SING N N 23 
DRF C30 O27  SING N N 24 
DRF C30 C31  SING Y N 25 
DRF O27 C24  SING N N 26 
DRF C24 C23  SING N N 27 
DRF C24 H241 SING N N 28 
DRF C24 H242 SING N N 29 
DRF C23 N22  SING N N 30 
DRF C23 H231 SING N N 31 
DRF C23 H232 SING N N 32 
DRF N22 C11  SING N N 33 
DRF N22 C3   SING N N 34 
DRF C11 C16  DOUB Y N 35 
DRF C11 C12  SING Y N 36 
DRF C16 O21  SING N N 37 
DRF C16 C15  SING Y N 38 
DRF O21 C4   SING N N 39 
DRF C4  C3   DOUB Y N 40 
DRF C4  C5   SING Y N 41 
DRF C3  C2   SING Y N 42 
DRF C2  C1   DOUB Y N 43 
DRF C2  H2   SING N N 44 
DRF C1  C6   SING Y N 45 
DRF C1  H1   SING N N 46 
DRF C6  C5   DOUB Y N 47 
DRF C6  H6   SING N N 48 
DRF C5  H5   SING N N 49 
DRF C15 C14  DOUB Y N 50 
DRF C15 H15  SING N N 51 
DRF C14 C13  SING Y N 52 
DRF C14 H14  SING N N 53 
DRF C13 C12  DOUB Y N 54 
DRF C13 H13  SING N N 55 
DRF C12 H12  SING N N 56 
DRF C31 C32  DOUB Y N 57 
DRF C31 H31  SING N N 58 
DRF C32 H32  SING N N 59 
# 
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 
DRF SMILES           ACDLabs              10.04 O=C(O)C(OCC)Cc4ccc(OCCN1c3c(Oc2c1cccc2)cccc3)cc4                                                                                                                       
DRF InChI            InChI                1.02b InChI=1/C25H25NO5/c1-2-29-24(25(27)28)17-18-11-13-19(14-12-18)30-16-15-26-20-7-3-5-9-22(20)31-23-10-6-4-8-21(23)26/h3-14,24H,2,15-17H2,1H3,(H,27,28)/t24-/m0/s1/f/h27H 
DRF InChIKey         InChI                1.02b WMUIIGVAWPWQAW-DNMKONLPDP                                                                                                                                              
DRF SMILES_CANONICAL CACTVS               3.341 CCO[C@@H](Cc1ccc(OCCN2c3ccccc3Oc4ccccc24)cc1)C(O)=O                                                                                                                    
DRF SMILES           CACTVS               3.341 CCO[CH](Cc1ccc(OCCN2c3ccccc3Oc4ccccc24)cc1)C(O)=O                                                                                                                      
DRF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCO[C@@H](Cc1ccc(cc1)OCCN2c3ccccc3Oc4c2cccc4)C(=O)O                                                                                                                    
DRF SMILES           "OpenEye OEToolkits" 1.5.0 CCOC(Cc1ccc(cc1)OCCN2c3ccccc3Oc4c2cccc4)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 
DRF "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-2-ethoxy-3-{4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid" 
DRF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-ethoxy-3-[4-(2-phenoxazin-10-ylethoxy)phenyl]propanoic acid"       
# 
