data_DFN
# 
_chem_comp.id                                    DFN 
_chem_comp.name                                  3-[3-(2,3-DIHYDROXY-PROPYLAMINO)-PHENYL]-4-(5-FLUORO-1-METHYL-1H-INDOL-3-YL)-PYRROLE-2,5-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H20 F N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-09-21 
_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                        409.410 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DFN 
_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        1R0E 
_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 
DFN C28  C28  C 0 1 N N N 43.265 44.834 35.983 -2.208 3.093  -2.675 C28  DFN 1  
DFN N22  N22  N 0 1 Y N N 43.484 43.419 35.713 -2.437 1.947  -1.792 N22  DFN 2  
DFN C48  C48  C 0 1 Y N N 43.709 42.473 36.676 -1.757 0.775  -1.852 C48  DFN 3  
DFN C21  C21  C 0 1 Y N N 43.515 42.833 34.470 -3.372 1.911  -0.776 C21  DFN 4  
DFN C24  C24  C 0 1 Y N N 43.332 43.409 33.199 -4.306 2.833  -0.315 C24  DFN 5  
DFN C31  C31  C 0 1 Y N N 43.407 42.568 32.081 -5.133 2.507  0.739  C31  DFN 6  
DFN C29  C29  C 0 1 Y N N 43.653 41.211 32.265 -5.047 1.261  1.347  C29  DFN 7  
DFN F39  F39  F 0 1 N N N 43.703 40.415 31.196 -5.864 0.958  2.379  F39  DFN 8  
DFN C20  C20  C 0 1 Y N N 43.763 41.457 34.668 -3.290 0.650  -0.165 C20  DFN 9  
DFN C23  C23  C 0 1 Y N N 43.836 40.639 33.528 -4.130 0.332  0.900  C23  DFN 10 
DFN C19  C19  C 0 1 Y N N 43.870 41.234 36.083 -2.225 -0.079 -0.879 C19  DFN 11 
DFN C01  C01  C 0 1 N N N 44.156 40.060 36.862 -1.758 -1.445 -0.607 C01  DFN 12 
DFN C02  C02  C 0 1 N N N 44.945 38.978 36.627 -0.577 -1.814 0.023  C02  DFN 13 
DFN C03  C03  C 0 1 N N N 44.908 38.127 37.841 -0.571 -3.288 0.054  C03  DFN 14 
DFN O06  O06  O 0 1 N N N 45.506 37.054 37.997 0.306  -3.981 0.530  O06  DFN 15 
DFN N04  N04  N 0 1 N N N 44.116 38.751 38.737 -1.694 -3.738 -0.529 N04  DFN 16 
DFN C05  C05  C 0 1 N N N 43.633 39.905 38.247 -2.456 -2.710 -0.942 C05  DFN 17 
DFN O07  O07  O 0 1 N N N 42.886 40.675 38.837 -3.529 -2.803 -1.503 O07  DFN 18 
DFN C08  C08  C 0 1 Y N N 45.763 38.606 35.465 0.465  -0.911 0.553  C08  DFN 19 
DFN C09  C09  C 0 1 Y N N 46.600 39.560 34.856 1.743  -0.911 -0.008 C09  DFN 20 
DFN C10  C10  C 0 1 Y N N 47.412 39.241 33.745 2.714  -0.057 0.492  C10  DFN 21 
DFN C11  C11  C 0 1 Y N N 47.409 37.931 33.265 2.417  0.787  1.556  C11  DFN 22 
DFN C12  C12  C 0 1 Y N N 46.620 36.956 33.878 1.152  0.782  2.116  C12  DFN 23 
DFN C13  C13  C 0 1 Y N N 45.810 37.290 34.974 0.177  -0.059 1.623  C13  DFN 24 
DFN N15  N15  N 0 1 N N N 48.207 40.146 33.103 3.993  -0.049 -0.070 N15  DFN 25 
DFN C26  C26  C 0 1 N N N 48.339 41.551 33.487 5.021  0.849  0.463  C26  DFN 26 
DFN C34  C34  C 0 1 N N S 47.087 42.279 32.982 6.320  0.661  -0.324 C34  DFN 27 
DFN O41  O41  O 0 1 N N N 47.155 42.400 31.553 6.760  -0.693 -0.201 O41  DFN 28 
DFN C40  C40  C 0 1 N N N 46.988 43.655 33.634 7.393  1.599  0.232  C40  DFN 29 
DFN O45  O45  O 0 1 N N N 48.057 44.486 33.190 8.569  1.509  -0.576 O45  DFN 30 
DFN H281 1H28 H 0 0 N N N 44.133 45.187 36.588 -2.847 3.008  -3.554 H281 DFN 31 
DFN H282 2H28 H 0 0 N N N 43.082 45.605 35.198 -2.443 4.015  -2.144 H282 DFN 32 
DFN H283 3H28 H 0 0 N N N 42.419 44.899 36.706 -1.163 3.109  -2.986 H283 DFN 33 
DFN H48  H48  H 0 1 N N N 43.754 42.677 37.759 -0.969 0.547  -2.556 H48  DFN 34 
DFN H24  H24  H 0 1 N N N 43.136 44.488 33.083 -4.382 3.804  -0.780 H24  DFN 35 
DFN H31  H31  H 0 1 N N N 43.273 42.971 31.063 -5.854 3.228  1.096  H31  DFN 36 
DFN H23  H23  H 0 1 N N N 44.035 39.558 33.624 -4.064 -0.637 1.373  H23  DFN 37 
DFN H04  H04  H 0 1 N N N 43.908 38.394 39.670 -1.926 -4.674 -0.633 H04  DFN 38 
DFN H09  H09  H 0 1 N N N 46.620 40.586 35.261 1.972  -1.567 -0.835 H09  DFN 39 
DFN H11  H11  H 0 1 N N N 48.034 37.665 32.396 3.176  1.448  1.947  H11  DFN 40 
DFN H12  H12  H 0 1 N N N 46.637 35.921 33.496 0.927  1.440  2.942  H12  DFN 41 
DFN H13  H13  H 0 1 N N N 45.202 36.507 35.457 -0.809 -0.059 2.062  H13  DFN 42 
DFN H15  H15  H 0 1 N N N 47.938 40.131 32.119 4.201  -0.637 -0.812 H15  DFN 43 
DFN H261 1H26 H 0 0 N N N 49.288 42.014 33.129 4.685  1.882  0.369  H261 DFN 44 
DFN H262 2H26 H 0 0 N N N 48.515 41.691 34.579 5.196  0.618  1.513  H262 DFN 45 
DFN H34  H34  H 0 1 N N N 46.176 41.696 33.254 6.144  0.892  -1.375 H34  DFN 46 
DFN H41  H41  H 0 1 N N N 46.380 42.851 31.240 6.903  -0.855 0.741  H41  DFN 47 
DFN H401 1H40 H 0 0 N N N 46.947 43.588 34.746 7.022  2.624  0.220  H401 DFN 48 
DFN H402 2H40 H 0 0 N N N 45.993 44.128 33.462 7.632  1.311  1.255  H402 DFN 49 
DFN H45  H45  H 0 1 N N N 47.995 45.343 33.596 9.218  2.114  -0.192 H45  DFN 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 
DFN C28 N22  SING N N 1  
DFN C28 H281 SING N N 2  
DFN C28 H282 SING N N 3  
DFN C28 H283 SING N N 4  
DFN N22 C48  SING Y N 5  
DFN N22 C21  SING Y N 6  
DFN C48 C19  DOUB Y N 7  
DFN C48 H48  SING N N 8  
DFN C21 C24  DOUB Y N 9  
DFN C21 C20  SING Y N 10 
DFN C24 C31  SING Y N 11 
DFN C24 H24  SING N N 12 
DFN C31 C29  DOUB Y N 13 
DFN C31 H31  SING N N 14 
DFN C29 F39  SING N N 15 
DFN C29 C23  SING Y N 16 
DFN C20 C23  DOUB Y N 17 
DFN C20 C19  SING Y N 18 
DFN C23 H23  SING N N 19 
DFN C19 C01  SING N N 20 
DFN C01 C02  DOUB N N 21 
DFN C01 C05  SING N N 22 
DFN C02 C03  SING N N 23 
DFN C02 C08  SING N N 24 
DFN C03 O06  DOUB N N 25 
DFN C03 N04  SING N N 26 
DFN N04 C05  SING N N 27 
DFN N04 H04  SING N N 28 
DFN C05 O07  DOUB N N 29 
DFN C08 C09  DOUB Y N 30 
DFN C08 C13  SING Y N 31 
DFN C09 C10  SING Y N 32 
DFN C09 H09  SING N N 33 
DFN C10 C11  DOUB Y N 34 
DFN C10 N15  SING N N 35 
DFN C11 C12  SING Y N 36 
DFN C11 H11  SING N N 37 
DFN C12 C13  DOUB Y N 38 
DFN C12 H12  SING N N 39 
DFN C13 H13  SING N N 40 
DFN N15 C26  SING N N 41 
DFN N15 H15  SING N N 42 
DFN C26 C34  SING N N 43 
DFN C26 H261 SING N N 44 
DFN C26 H262 SING N N 45 
DFN C34 O41  SING N N 46 
DFN C34 C40  SING N N 47 
DFN C34 H34  SING N N 48 
DFN O41 H41  SING N N 49 
DFN C40 O45  SING N N 50 
DFN C40 H401 SING N N 51 
DFN C40 H402 SING N N 52 
DFN O45 H45  SING N N 53 
# 
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 
DFN SMILES           ACDLabs              10.04 O=C4C(c1cccc(NCC(O)CO)c1)=C(c3c2cc(F)ccc2n(c3)C)C(=O)N4                                                                                                                          
DFN InChI            InChI                1.02b InChI=1/C22H20FN3O4/c1-26-10-17(16-8-13(23)5-6-18(16)26)20-19(21(29)25-22(20)30)12-3-2-4-14(7-12)24-9-15(28)11-27/h2-8,10,15,24,27-28H,9,11H2,1H3,(H,25,29,30)/t15-/m0/s1/f/h25H 
DFN InChIKey         InChI                1.02b RPGZQOOZHIEPJW-PNNQWWITDR                                                                                                                                                        
DFN SMILES_CANONICAL CACTVS               3.341 Cn1cc(c2cc(F)ccc12)C3=C(C(=O)NC3=O)c4cccc(NC[C@H](O)CO)c4                                                                                                                        
DFN SMILES           CACTVS               3.341 Cn1cc(c2cc(F)ccc12)C3=C(C(=O)NC3=O)c4cccc(NC[CH](O)CO)c4                                                                                                                         
DFN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1cc(c2c1ccc(c2)F)C3=C(C(=O)NC3=O)c4cccc(c4)NC[C@@H](CO)O                                                                                                                       
DFN SMILES           "OpenEye OEToolkits" 1.5.0 Cn1cc(c2c1ccc(c2)F)C3=C(C(=O)NC3=O)c4cccc(c4)NCC(CO)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 
DFN "SYSTEMATIC NAME" ACDLabs              10.04 3-(3-{[(2S)-2,3-dihydroxypropyl]amino}phenyl)-4-(5-fluoro-1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 
DFN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[3-[[(2S)-2,3-dihydroxypropyl]amino]phenyl]-4-(5-fluoro-1-methyl-indol-3-yl)pyrrole-2,5-dione        
# 
