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-carbo
xamide
;

_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                   2020-06-17
_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  -12.784  70.210  -39.426   1.160   3.781  -1.163  H4    B49  23  
B49  H4A   H4A   H  0  1  N  N  N  -11.798  71.276  -38.368   0.566   3.709   0.513  H4A   B49  24  
B49  H4B   H4B   H  0  1  N  N  N  -12.173  69.597  -37.852   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  -17.840  70.903  -36.488   0.128  -1.739  -2.691  H3    B49  29  
B49  H3A   H3A   H  0  1  N  N  N  -16.863  70.250  -35.130   1.199  -2.039  -1.302  H3A   B49  30  
B49  H3B   H3B   H  0  1  N  N  N  -17.231  72.007  -35.209  -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  C37   C171  C  0  1  N  N  N  -15.550  69.544  -34.299   4.712  -0.088  -0.476  C37   B49  36  
B49  C38   C181  C  0  1  N  N  N  -15.938  69.045  -32.895   5.387  -0.566   0.811  C38   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  C39   C191  C  0  1  N  N  N  -15.135  70.493  -30.961   7.482   0.528   0.285  C39   B49  39  
B49  C40   C201  C  0  1  N  N  N  -17.596  70.493  -31.615   7.464  -1.434   1.704  C40   B49  40  
B49  C41   C211  C  0  1  N  N  N  -17.894  71.504  -30.493   7.119  -2.925   1.666  C41   B49  41  
B49  C42   C221  C  0  1  N  N  N  -15.434  71.504  -29.838   8.851   0.269  -0.347  C42   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  -16.397  70.150  -34.652   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  -15.091  68.439  -32.542   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  -14.411  70.984  -31.629   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  -18.202  69.603  -31.393   7.103  -1.002   2.637  H21   B49  50  
B49  H22   H22   H  0  1  N  N  N  -18.967  71.746  -30.492   7.569  -3.424   2.523  H22   B49  51  
B49  H23   H23   H  0  1  N  N  N  -17.616  71.067  -29.523   6.036  -3.048   1.700  H23   B49  52  
B49  H24   H24   H  0  1  N  N  N  -17.312  72.422  -30.663   7.505  -3.364   0.746  H24   B49  53  
B49  H25   H25   H  0  1  N  N  N  -14.503  71.746  -29.304   8.720  -0.235  -1.305  H25   B49  54  
B49  H26   H26   H  0  1  N  N  N  -15.856  72.422  -30.274   9.365   1.217  -0.503  H26   B49  55  
B49  H27   H27   H  0  1  N  N  N  -16.157  71.066  -29.134   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  C37   SING  N  N  38  
B49  C37  C38   SING  N  N  39  
B49  C38  N4    SING  N  N  40  
B49  N4   C39   SING  N  N  41  
B49  N4   C40   SING  N  N  42  
B49  C40  C41   SING  N  N  43  
B49  C39  C42   SING  N  N  44  
B49  C37  H14   SING  N  N  45  
B49  C37  H15   SING  N  N  46  
B49  C38  H16   SING  N  N  47  
B49  C38  H17   SING  N  N  48  
B49  C39  H18   SING  N  N  49  
B49  C39  H19   SING  N  N  50  
B49  C40  H20   SING  N  N  51  
B49  C40  H21   SING  N  N  52  
B49  C41  H22   SING  N  N  53  
B49  C41  H23   SING  N  N  54  
B49  C41  H24   SING  N  N  55  
B49  C42  H25   SING  N  N  56  
B49  C42  H26   SING  N  N  57  
B49  C42  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               12.01  "O=C(NCCN(CC)CC)c1c(c(nc1C)/C=C3/c2cc(F)ccc2NC3=O)C"  
B49  InChI             InChI                 1.03   "InChI=1S/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-"  
B49  InChIKey          InChI                 1.03   WINHZLLDWRZWRT-ATVHPVEESA-N  
B49  SMILES_CANONICAL  CACTVS                3.370  "CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C/2C(=O)Nc3ccc(F)cc/23)c1C"  
B49  SMILES            CACTVS                3.370  "CCN(CC)CCNC(=O)c1c(C)[nH]c(C=C2C(=O)Nc3ccc(F)cc23)c1C"  
B49  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "CCN(CC)CCNC(=O)c1c(c([nH]c1C)/C=C\2/c3cc(ccc3NC2=O)F)C"  
B49  SMILES            "OpenEye OEToolkits"  1.7.2  "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               12.01  "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"  1.7.2  "N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoranyl-2-oxidanylidene-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
B49  "Create component"          2009-01-29  RCSB  
B49  "Modify descriptor"         2011-06-04  RCSB  
B49  "Modify component atom id"  2011-09-22  RCSB  
B49  "Modify synonyms"           2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     B49
_pdbx_chem_comp_synonyms.name        SUNITINIB
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
