data_B49
# 
_chem_comp.id                                    B49 
_chem_comp.name                                  N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C22 H27 F N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         SUNITINIB 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-01-29 
_chem_comp.pdbx_modified_date                    2009-02-20 
_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                        398.474 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     B49 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3G0F 
_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 
B49 C4   C4   C 0 1 N N N -12.557 70.480 -38.384 1.117  3.173  -0.259 C4   B49 1  
B49 C5   C5   C 0 1 Y N N -17.220 78.912 -37.041 -7.489 -0.699 0.742  C5   B49 2  
B49 C6   C6   C 0 1 Y N N -15.949 78.688 -37.629 -6.728 0.133  1.538  C6   B49 3  
B49 C7   C7   C 0 1 Y N N -17.461 76.483 -36.545 -5.593 -1.142 -0.659 C7   B49 4  
B49 C13  C13  C 0 1 Y N N -15.752 71.336 -36.595 0.025  -0.263 -1.153 C13  B49 5  
B49 C15  C15  C 0 1 Y N N -17.958 77.808 -36.503 -6.927 -1.337 -0.354 C15  B49 6  
B49 C17  C17  C 0 1 Y N N -16.207 76.272 -37.131 -4.819 -0.304 0.138  C17  B49 7  
B49 C20  C20  C 0 1 N N N -15.394 75.075 -37.360 -3.399 0.111  0.094  C20  B49 8  
B49 C21  C21  C 0 1 N N N -14.131 75.547 -38.050 -3.230 1.016  1.239  C21  B49 9  
B49 C22  C22  C 0 1 N N N -14.904 68.882 -36.682 2.477  0.520  -1.233 C22  B49 10 
B49 C3   C3   C 0 1 N N N -17.005 71.109 -35.803 0.213  -1.688 -1.606 C3   B49 11 
B49 C12  C12  C 0 1 N N N -15.845 73.861 -36.972 -2.442 -0.269 -0.825 C12  B49 12 
B49 C14  C14  C 0 1 Y N N -13.806 70.966 -37.709 0.421  1.871  -0.562 C14  B49 13 
B49 C16  C16  C 0 1 Y N N -15.474 77.362 -37.656 -5.385 0.341  1.246  C16  B49 14 
B49 C18  C18  C 0 1 Y N N -15.288 72.553 -37.082 -1.169 0.342  -0.812 C18  B49 15 
B49 C19  C19  C 0 1 Y N N -14.808 70.319 -36.989 1.036  0.709  -0.991 C19  B49 16 
B49 N23  N23  N 0 1 Y N N -14.126 72.302 -37.744 -0.900 1.647  -0.456 N23  B49 17 
B49 N24  N24  N 0 1 N N N -14.272 76.918 -38.180 -4.411 1.113  1.871  N24  B49 18 
B49 N25  N25  N 0 1 N N N -15.265 68.579 -35.370 3.279  0.100  -0.235 N25  B49 19 
B49 O27  O27  O 0 1 N N N -13.194 74.889 -38.421 -2.198 1.579  1.559  O27  B49 20 
B49 O28  O28  O 0 1 N N N -14.663 68.027 -37.535 2.943  0.743  -2.334 O28  B49 21 
B49 F29  F29  F 0 1 N N N -19.147 78.017 -35.944 -7.683 -2.149 -1.124 F29  B49 22 
B49 H4   H4   H 0 1 N N N -12.744 70.361 -39.461 1.160  3.781  -1.163 H4   B49 23 
B49 H4A  H4A  H 0 1 N N N -11.749 71.211 -38.231 0.566  3.709  0.513  H4A  B49 24 
B49 H4B  H4B  H 0 1 N N N -12.262 69.511 -37.954 2.130  2.970  0.091  H4B  B49 25 
B49 H5   H5   H 0 1 N N N -17.630 79.910 -36.999 -8.531 -0.859 0.978  H5   B49 26 
B49 H6   H6   H 0 1 N N N -15.369 79.501 -38.039 -7.178 0.624  2.388  H6   B49 27 
B49 H7   H7   H 0 1 N N N -18.031 75.661 -36.138 -5.153 -1.638 -1.511 H7   B49 28 
B49 H3   H3   H 0 1 N N N -16.758 71.053 -34.733 0.128  -1.739 -2.691 H3   B49 29 
B49 H3A  H3A  H 0 1 N N N -17.703 71.941 -35.975 1.199  -2.039 -1.302 H3A  B49 30 
B49 H3B  H3B  H 0 1 N N N -17.473 70.166 -36.120 -0.552 -2.318 -1.152 H3B  B49 31 
B49 H12  H12  H 0 1 N N N -16.810 73.887 -36.487 -2.666 -1.035 -1.554 H12  B49 32 
B49 HN23 HN23 H 0 0 N N N -13.575 73.001 -38.199 -1.559 2.300  -0.175 HN23 B49 33 
B49 HN24 HN24 H 0 0 N N N -13.589 77.515 -38.601 -4.566 1.652  2.662  HN24 B49 34 
B49 HN25 HN25 H 0 0 N N N -15.337 67.610 -35.135 2.908  -0.079 0.643  HN25 B49 35 
B49 C171 C171 C 0 0 N N N -15.550 69.544 -34.299 4.712  -0.088 -0.476 C171 B49 36 
B49 C181 C181 C 0 0 N N N -15.938 69.045 -32.895 5.387  -0.566 0.811  C181 B49 37 
B49 N4   N4   N 0 1 N N N -16.223 70.010 -31.823 6.824  -0.754 0.570  N4   B49 38 
B49 C191 C191 C 0 0 N N N -15.135 70.493 -30.961 7.482  0.528  0.285  C191 B49 39 
B49 C201 C201 C 0 0 N N N -17.596 70.493 -31.615 7.464  -1.434 1.704  C201 B49 40 
B49 C211 C211 C 0 0 N N N -17.894 71.504 -30.493 7.119  -2.925 1.666  C211 B49 41 
B49 C221 C221 C 0 0 N N N -15.434 71.504 -29.838 8.851  0.269  -0.347 C221 B49 42 
B49 H14  H14  H 0 1 N N N -14.632 70.136 -34.169 4.854  -0.833 -1.259 H14  B49 43 
B49 H15  H15  H 0 1 N N N -16.456 70.060 -34.650 5.155  0.858  -0.789 H15  B49 44 
B49 H16  H16  H 0 1 N N N -16.856 68.454 -33.025 5.245  0.178  1.594  H16  B49 45 
B49 H17  H17  H 0 1 N N N -15.032 68.529 -32.544 4.944  -1.512 1.124  H17  B49 46 
B49 H18  H18  H 0 1 N N N -14.719 69.603 -30.467 6.867  1.107  -0.404 H18  B49 47 
B49 H19  H19  H 0 1 N N N -14.487 71.054 -31.650 7.610  1.084  1.214  H19  B49 48 
B49 H20  H20  H 0 1 N N N -17.893 70.983 -32.554 8.545  -1.310 1.639  H20  B49 49 
B49 H21  H21  H 0 1 N N N -18.144 69.591 -31.305 7.103  -1.002 2.637  H21  B49 50 
B49 H22  H22  H 0 1 N N N -17.965 70.975 -29.531 7.569  -3.424 2.523  H22  B49 51 
B49 H23  H23  H 0 1 N N N -17.084 72.246 -30.444 6.036  -3.048 1.700  H23  B49 52 
B49 H24  H24  H 0 1 N N N -18.846 72.013 -30.702 7.505  -3.364 0.746  H24  B49 53 
B49 H25  H25  H 0 1 N N N -15.505 70.974 -28.877 8.720  -0.235 -1.305 H25  B49 54 
B49 H26  H26  H 0 1 N N N -14.624 72.247 -29.788 9.365  1.217  -0.503 H26  B49 55 
B49 H27  H27  H 0 1 N N N -16.386 72.013 -30.047 9.444  -0.361 0.316  H27  B49 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 
B49 C4   C14  SING N N 1  
B49 C4   H4   SING N N 2  
B49 C4   H4A  SING N N 3  
B49 C4   H4B  SING N N 4  
B49 C5   C6   DOUB Y N 5  
B49 C5   C15  SING Y N 6  
B49 C5   H5   SING N N 7  
B49 C6   C16  SING Y N 8  
B49 C6   H6   SING N N 9  
B49 C7   C15  DOUB Y N 10 
B49 C7   C17  SING Y N 11 
B49 C7   H7   SING N N 12 
B49 C13  C3   SING N N 13 
B49 C13  C18  DOUB Y N 14 
B49 C13  C19  SING Y N 15 
B49 C15  F29  SING N N 16 
B49 C17  C20  SING N N 17 
B49 C17  C16  DOUB Y N 18 
B49 C20  C21  SING N N 19 
B49 C20  C12  DOUB N Z 20 
B49 C21  N24  SING N N 21 
B49 C21  O27  DOUB N N 22 
B49 C22  C19  SING N N 23 
B49 C22  N25  SING N N 24 
B49 C22  O28  DOUB N N 25 
B49 C3   H3   SING N N 26 
B49 C3   H3A  SING N N 27 
B49 C3   H3B  SING N N 28 
B49 C12  C18  SING N N 29 
B49 C12  H12  SING N N 30 
B49 C14  C19  DOUB Y N 31 
B49 C14  N23  SING Y N 32 
B49 C16  N24  SING N N 33 
B49 C18  N23  SING Y N 34 
B49 N23  HN23 SING N N 35 
B49 N24  HN24 SING N N 36 
B49 N25  HN25 SING N N 37 
B49 N25  C171 SING N N 38 
B49 C171 C181 SING N N 39 
B49 C181 N4   SING N N 40 
B49 N4   C191 SING N N 41 
B49 N4   C201 SING N N 42 
B49 C201 C211 SING N N 43 
B49 C191 C221 SING N N 44 
B49 C171 H14  SING N N 45 
B49 C171 H15  SING N N 46 
B49 C181 H16  SING N N 47 
B49 C181 H17  SING N N 48 
B49 C191 H18  SING N N 49 
B49 C191 H19  SING N N 50 
B49 C201 H20  SING N N 51 
B49 C201 H21  SING N N 52 
B49 C211 H22  SING N N 53 
B49 C211 H23  SING N N 54 
B49 C211 H24  SING N N 55 
B49 C221 H25  SING N N 56 
B49 C221 H26  SING N N 57 
B49 C221 H27  SING N N 58 
# 
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 
B49 SMILES           ACDLabs              10.04 O=C(NCCN(CC)CC)c1c(c(nc1C)/C=C3/c2cc(F)ccc2NC3=O)C                                                                                                                               
B49 InChI            InChI                1.02b InChI=1/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-/f/h24,26H 
B49 InChIKey         InChI                1.02b WINHZLLDWRZWRT-IUQVRHKZDC                                                                                                                                                        
B49 SMILES_CANONICAL CACTVS               3.341 CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C/2C(=O)Nc3ccc(F)cc/23)c1C                                                                                                                         
B49 SMILES           CACTVS               3.341 CCN(CC)CCNC(=O)c1c(C)[nH]c(C=C2C(=O)Nc3ccc(F)cc23)c1C                                                                                                                            
B49 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCN(CC)CCNC(=O)c1c(c([nH]c1C)\C=C/2\c3cc(ccc3NC2=O)F)C                                                                                                                           
B49 SMILES           "OpenEye OEToolkits" 1.5.0 CCN(CC)CCNC(=O)c1c(c([nH]c1C)C=C2c3cc(ccc3NC2=O)F)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 
B49 "SYSTEMATIC NAME" ACDLabs              10.04 N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide 
B49 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide               
# 
