data_I4A
# 
_chem_comp.id                                    I4A 
_chem_comp.name                                  "5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 N2 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-01-13 
_chem_comp.pdbx_modified_date                    2009-03-06 
_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                        362.422 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     I4A 
_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        3FR5 
_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 
I4A O27  O27  O 0 1 N N N 16.907 4.765 2.813  -2.304 -2.580 0.393  O27  I4A 1  
I4A C25  C25  C 0 1 N N N 17.587 5.787 2.756  -1.099 -2.461 0.986  C25  I4A 2  
I4A O26  O26  O 0 1 N N N 17.200 6.760 1.936  -1.026 -2.332 2.192  O26  I4A 3  
I4A C4   C4   C 0 1 Y N N 18.816 5.943 3.589  0.129  -2.487 0.172  C4   I4A 4  
I4A C6   C6   C 0 1 Y N N 20.084 5.217 3.317  0.996  -1.382 0.165  C6   I4A 5  
I4A C7   C7   C 0 1 Y N N 21.226 5.429 4.237  2.164  -1.429 -0.618 C7   I4A 6  
I4A C9   C9   C 0 1 Y N N 22.300 4.584 3.671  2.839  -0.148 -0.408 C9   I4A 7  
I4A C10  C10  C 0 1 N N N 23.713 4.350 4.120  4.130  0.303  -1.039 C10  I4A 8  
I4A C12  C12  C 0 1 N N N 24.682 4.682 2.990  4.821  1.313  -0.119 C12  I4A 9  
I4A C14  C14  C 0 1 N N N 24.850 3.619 1.905  4.335  2.721  -0.454 C14  I4A 10 
I4A C13  C13  C 0 1 N N N 23.587 3.633 1.013  2.830  2.835  -0.228 C13  I4A 11 
I4A C11  C11  C 0 1 N N N 22.344 2.948 1.582  2.416  1.949  0.949  C11  I4A 12 
I4A C8   C8   C 0 1 Y N N 21.659 3.921 2.490  2.085  0.564  0.446  C8   I4A 13 
I4A C3   C3   C 0 1 Y N N 21.079 6.299 5.320  2.450  -2.564 -1.378 C3   I4A 14 
I4A C2   C2   C 0 1 Y N N 19.870 6.962 5.540  1.588  -3.640 -1.362 C2   I4A 15 
I4A C1   C1   C 0 1 Y N N 18.776 6.783 4.690  0.440  -3.612 -0.591 C1   I4A 16 
I4A N5   N5   N 0 1 Y N N 20.397 4.316 2.349  0.975  -0.163 0.791  N5   I4A 17 
I4A C15  C15  C 0 1 N N N 19.581 3.828 1.260  -0.082 0.297  1.696  C15  I4A 18 
I4A C16  C16  C 0 1 Y N N 19.906 4.416 -0.095 -1.081 1.120  0.924  C16  I4A 19 
I4A C17  C17  C 0 1 Y N N 19.618 3.630 -1.197 -2.214 0.525  0.412  C17  I4A 20 
I4A C18  C18  C 0 1 Y N N 19.906 4.094 -2.474 -3.139 1.289  -0.302 C18  I4A 21 
I4A C22  C22  C 0 1 N N N 19.623 3.212 -3.653 -4.356 0.657  -0.853 C22  I4A 22 
I4A N24  N24  N 0 1 N N N 20.256 3.506 -4.776 -5.247 1.398  -1.542 N24  I4A 23 
I4A O23  O23  O 0 1 N N N 18.879 2.232 -3.554 -4.554 -0.531 -0.686 O23  I4A 24 
I4A C19  C19  C 0 1 Y N N 20.461 5.361 -2.676 -2.909 2.652  -0.492 C19  I4A 25 
I4A C20  C20  C 0 1 Y N N 20.722 6.159 -1.563 -1.771 3.236  0.026  C20  I4A 26 
I4A C21  C21  C 0 1 Y N N 20.464 5.684 -0.271 -0.862 2.474  0.737  C21  I4A 27 
I4A HO27 HO27 H 0 0 N N N 16.167 4.843 2.222  -3.080 -2.557 0.969  HO27 I4A 28 
I4A H10  H10  H 0 1 N N N 23.930 4.993 4.986  4.782  -0.558 -1.189 H10  I4A 29 
I4A H10A H10A H 0 0 N N N 23.833 3.293 4.399  3.920  0.772  -2.001 H10A I4A 30 
I4A H12  H12  H 0 1 N N N 24.310 5.593 2.499  4.581  1.082  0.919  H12  I4A 31 
I4A H12A H12A H 0 0 N N N 25.669 4.779 3.465  5.900  1.257  -0.264 H12A I4A 32 
I4A H14  H14  H 0 1 N N N 25.739 3.842 1.297  4.850  3.440  0.183  H14  I4A 33 
I4A H14A H14A H 0 0 N N N 24.979 2.627 2.363  4.559  2.940  -1.498 H14A I4A 34 
I4A H13  H13  H 0 1 N N N 23.326 4.687 0.836  2.573  3.871  -0.010 H13  I4A 35 
I4A H13A H13A H 0 0 N N N 23.854 3.060 0.113  2.303  2.513  -1.127 H13A I4A 36 
I4A H11  H11  H 0 1 N N N 21.668 2.655 0.765  3.236  1.890  1.664  H11  I4A 37 
I4A H11A H11A H 0 0 N N N 22.627 2.041 2.136  1.540  2.378  1.436  H11A I4A 38 
I4A H3   H3   H 0 1 N N N 21.908 6.460 5.993  3.346  -2.599 -1.980 H3   I4A 39 
I4A H2   H2   H 0 1 N N N 19.779 7.628 6.386  1.814  -4.516 -1.953 H2   I4A 40 
I4A H1   H1   H 0 1 N N N 17.863 7.321 4.899  -0.223 -4.465 -0.584 H1   I4A 41 
I4A H15  H15  H 0 1 N N N 19.727 2.740 1.195  -0.583 -0.565 2.136  H15  I4A 42 
I4A H15A H15A H 0 0 N N N 18.547 4.126 1.488  0.357  0.905  2.487  H15A I4A 43 
I4A H17  H17  H 0 1 N N N 19.170 2.657 -1.064 -2.386 -0.531 0.563  H17  I4A 44 
I4A HN24 HN24 H 0 0 N N N 19.976 2.844 -5.471 -5.089 2.345  -1.676 HN24 I4A 45 
I4A HN2A HN2A H 0 0 N N N 20.901 4.259 -4.907 -6.046 0.983  -1.904 HN2A I4A 46 
I4A H19  H19  H 0 1 N N N 20.683 5.714 -3.672 -3.621 3.249  -1.043 H19  I4A 47 
I4A H20  H20  H 0 1 N N N 21.126 7.151 -1.698 -1.592 4.291  -0.121 H20  I4A 48 
I4A H21  H21  H 0 1 N N N 20.696 6.297 0.587  0.027  2.936  1.140  H21  I4A 49 
# 
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 
I4A C25 O27  SING N N 1  
I4A O27 HO27 SING N N 2  
I4A O26 C25  DOUB N N 3  
I4A C25 C4   SING N N 4  
I4A C6  C4   DOUB Y N 5  
I4A C4  C1   SING Y N 6  
I4A N5  C6   SING Y N 7  
I4A C6  C7   SING Y N 8  
I4A C9  C7   SING Y N 9  
I4A C7  C3   DOUB N N 10 
I4A C8  C9   DOUB N N 11 
I4A C9  C10  SING N N 12 
I4A C12 C10  SING N N 13 
I4A C10 H10  SING N N 14 
I4A C10 H10A SING N N 15 
I4A C14 C12  SING N N 16 
I4A C12 H12  SING N N 17 
I4A C12 H12A SING N N 18 
I4A C13 C14  SING N N 19 
I4A C14 H14  SING N N 20 
I4A C14 H14A SING N N 21 
I4A C13 C11  SING N N 22 
I4A C13 H13  SING N N 23 
I4A C13 H13A SING N N 24 
I4A C11 C8   SING N N 25 
I4A C11 H11  SING Y N 26 
I4A C11 H11A SING Y N 27 
I4A N5  C8   SING N N 28 
I4A C3  C2   SING N N 29 
I4A C3  H3   SING Y N 30 
I4A C1  C2   DOUB N N 31 
I4A C2  H2   SING Y N 32 
I4A C1  H1   SING Y N 33 
I4A C15 N5   SING N N 34 
I4A C16 C15  SING N N 35 
I4A C15 H15  SING N N 36 
I4A C15 H15A SING N N 37 
I4A C17 C16  DOUB Y N 38 
I4A C21 C16  SING N N 39 
I4A C18 C17  SING Y N 40 
I4A C17 H17  SING N N 41 
I4A C22 C18  SING N N 42 
I4A C19 C18  DOUB N N 43 
I4A N24 C22  SING N N 44 
I4A C22 O23  DOUB N N 45 
I4A N24 HN24 SING Y N 46 
I4A N24 HN2A SING Y N 47 
I4A C19 C20  SING N N 48 
I4A C19 H19  SING Y N 49 
I4A C20 C21  DOUB N N 50 
I4A C20 H20  SING Y N 51 
I4A C21 H21  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 
I4A SMILES           ACDLabs              10.04 O=C(N)c1cc(ccc1)Cn2c4c(c3c2CCCCC3)cccc4C(=O)O                                                                                                                       
I4A InChI            InChI                1.02b InChI=1/C22H22N2O3/c23-21(25)15-7-4-6-14(12-15)13-24-19-11-3-1-2-8-16(19)17-9-5-10-18(20(17)24)22(26)27/h4-7,9-10,12H,1-3,8,11,13H2,(H2,23,25)(H,26,27)/f/h26H,23H2 
I4A InChIKey         InChI                1.02b GKBQRPKZHUFGOB-LPDQZMHHCQ                                                                                                                                           
I4A SMILES_CANONICAL CACTVS               3.341 NC(=O)c1cccc(Cn2c3CCCCCc3c4cccc(C(O)=O)c24)c1                                                                                                                       
I4A SMILES           CACTVS               3.341 NC(=O)c1cccc(Cn2c3CCCCCc3c4cccc(C(O)=O)c24)c1                                                                                                                       
I4A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)C(=O)N)Cn2c3c(c4c2c(ccc4)C(=O)O)CCCCC3                                                                                                                   
I4A SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)C(=O)N)Cn2c3c(c4c2c(ccc4)C(=O)O)CCCCC3                                                                                                                   
# 
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 
I4A "SYSTEMATIC NAME" ACDLabs              10.04 "5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid"              
I4A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[(3-aminocarbonylphenyl)methyl]-7,8,9,10-tetrahydro-6H-cyclohepta[b]indole-4-carboxylic acid" 
# 
