data_CBB
# 
_chem_comp.id                                    CBB 
_chem_comp.name                                  "1-(3-CARBAMIMIDOYL-BENZYL)-1H-INDOLE-2-CARBOXYLIC ACID 3-CARBAMIMIDOYL-BENZYLESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H31 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-05-15 
_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                        433.546 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CBB 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        1LPK 
_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 
CBB C1   C1   C 0 1 Y N N 3.821  9.875  26.113 -5.981 0.708  1.428  C1   CBB 1  
CBB C2   C2   C 0 1 Y N N 4.901  8.990  25.932 -4.629 0.486  1.564  C2   CBB 2  
CBB C3   C3   C 0 1 Y N N 5.331  8.698  24.620 -3.744 1.008  0.626  C3   CBB 3  
CBB C4   C4   C 0 1 Y N N 4.669  9.265  23.482 -4.245 1.760  -0.455 C4   CBB 4  
CBB C5   C5   C 0 1 Y N N 3.594  10.167 23.685 -5.625 1.972  -0.571 C5   CBB 5  
CBB C6   C6   C 0 1 Y N N 3.176  10.478 25.002 -6.473 1.450  0.361  C6   CBB 6  
CBB N7   N7   N 0 1 Y N N 6.346  7.887  24.136 -2.377 0.954  0.490  N7   CBB 7  
CBB C8   C8   C 0 1 Y N N 6.338  7.891  22.788 -2.014 1.660  -0.641 C8   CBB 8  
CBB C9   C9   C 0 1 Y N N 5.305  8.746  22.331 -3.132 2.156  -1.234 C9   CBB 9  
CBB C10  C10  C 0 1 N N N 7.206  7.105  24.998 -1.457 0.262  1.396  C10  CBB 10 
CBB C11  C11  C 0 1 N N N 8.522  7.750  25.298 -1.266 -1.158 0.929  C11  CBB 11 
CBB C14  C14  C 0 1 N N N 9.117  8.870  24.647 -2.218 -2.204 1.337  C14  CBB 12 
CBB C15  C15  C 0 1 N N N 10.385 9.333  25.091 -1.869 -3.482 1.261  C15  CBB 13 
CBB C16  C16  C 0 1 N N N 11.044 8.682  26.163 -0.497 -3.863 0.771  C16  CBB 14 
CBB C17  C17  C 0 1 N N R 10.403 7.583  26.797 -0.043 -2.890 -0.316 C17  CBB 15 
CBB C18  C18  C 0 1 N N N 9.159  7.130  26.349 -0.234 -1.472 0.153  C18  CBB 16 
CBB C19  C19  C 0 1 N N N 10.940 6.868  27.941 -0.859 -3.119 -1.562 C19  CBB 17 
CBB N20  N20  N 0 1 N N N 12.233 6.933  28.254 -0.346 -2.783 -2.787 N20  CBB 18 
CBB N21  N21  N 0 1 N N N 10.037 6.137  28.640 -2.042 -3.633 -1.475 N21  CBB 19 
CBB C31  C31  C 0 1 N N N 7.159  7.101  21.987 -0.640 1.840  -1.128 C31  CBB 20 
CBB O32  O32  O 0 1 N N N 6.710  6.924  20.762 0.392  1.297  -0.451 O32  CBB 21 
CBB C33  C33  C 0 1 N N N 7.481  6.123  19.821 1.750  1.474  -0.933 C33  CBB 22 
CBB C34  C34  C 0 1 N N R 7.476  4.624  20.112 2.723  0.764  0.011  C34  CBB 23 
CBB C37  C37  C 0 1 N N N 6.762  4.010  21.176 2.688  1.440  1.383  C37  CBB 24 
CBB C38  C38  C 0 1 N N N 6.853  2.603  21.375 3.661  0.730  2.326  C38  CBB 25 
CBB C39  C39  C 0 1 N N N 7.650  1.816  20.509 5.077  0.810  1.754  C39  CBB 26 
CBB C40  C40  C 0 1 N N S 8.351  2.433  19.437 5.112  0.134  0.382  C40  CBB 27 
CBB C41  C41  C 0 1 N N N 8.253  3.827  19.244 4.140  0.845  -0.562 C41  CBB 28 
CBB C42  C42  C 0 1 N N N 9.241  1.716  18.526 6.508  0.214  -0.182 C42  CBB 29 
CBB N43  N43  N 0 1 N N N 9.180  1.934  17.220 6.825  1.173  -0.989 N43  CBB 30 
CBB N44  N44  N 0 1 N N N 10.175 0.905  19.014 7.440  -0.730 0.161  N44  CBB 31 
CBB O49  O49  O 0 1 N N N 8.175  6.592  22.353 -0.433 2.478  -2.142 O49  CBB 32 
CBB HC1  HC1  H 0 1 N N N 3.476  10.098 27.137 -6.666 0.302  2.158  HC1  CBB 33 
CBB HC2  HC2  H 0 1 N N N 5.401  8.534  26.803 -4.257 -0.092 2.397  HC2  CBB 34 
CBB HC5  HC5  H 0 1 N N N 3.084  10.625 22.821 -6.017 2.548  -1.397 HC5  CBB 35 
CBB HC6  HC6  H 0 1 N N N 2.349  11.190 25.162 -7.536 1.615  0.270  HC6  CBB 36 
CBB HC9  HC9  H 0 1 N N N 5.046  8.965  21.282 -3.164 2.747  -2.138 HC9  CBB 37 
CBB H101 1H10 H 0 0 N N N 7.359  6.085  24.575 -0.495 0.775  1.399  H101 CBB 38 
CBB H102 2H10 H 0 0 N N N 6.676  6.841  25.943 -1.871 0.260  2.404  H102 CBB 39 
CBB H14  H14  H 0 1 N N N 8.603  9.372  23.810 -3.202 -1.931 1.690  H14  CBB 40 
CBB H15  H15  H 0 1 N N N 10.859 10.201 24.602 -2.569 -4.250 1.554  H15  CBB 41 
CBB H16  H16  H 0 1 N N N 11.308 9.440  26.937 0.206  -3.830 1.604  H16  CBB 42 
CBB H161 1H16 H 0 0 N N N 12.056 8.360  25.821 -0.526 -4.874 0.364  H161 CBB 43 
CBB H17  H17  H 0 1 N N N 11.317 8.156  26.516 1.011  -3.060 -0.536 H17  CBB 44 
CBB H118 18H1 H 0 0 N N N 8.671  6.268  26.834 0.470  -0.708 -0.142 H118 CBB 45 
CBB H201 1H20 H 0 0 N N N 12.484 7.917  28.352 0.542  -2.398 -2.853 H201 CBB 46 
CBB H202 2H20 H 0 0 N N N 12.610 6.431  29.058 -0.871 -2.930 -3.590 H202 CBB 47 
CBB H21  H21  H 0 1 N N N 9.221  6.450  28.114 -2.567 -3.780 -2.278 H21  CBB 48 
CBB H331 1H33 H 0 0 N N N 8.528  6.502  19.755 1.988  2.538  -0.966 H331 CBB 49 
CBB H332 2H33 H 0 0 N N N 7.141  6.317  18.777 1.840  1.051  -1.933 H332 CBB 50 
CBB H334 34H3 H 0 0 N N N 6.742  4.840  20.923 2.432  -0.281 0.113  H334 CBB 51 
CBB H37  H37  H 0 1 N N N 5.685  4.284  21.083 2.980  2.485  1.280  H37  CBB 52 
CBB H371 1H37 H 0 0 N N N 7.040  4.520  22.128 1.679  1.383  1.791  H371 CBB 53 
CBB H38  H38  H 0 1 N N N 5.821  2.181  21.386 3.636  1.211  3.304  H38  CBB 54 
CBB H381 1H38 H 0 0 N N N 7.181  2.416  22.424 3.370  -0.316 2.429  H381 CBB 55 
CBB H39  H39  H 0 1 N N N 7.018  0.997  20.093 5.369  1.856  1.651  H39  CBB 56 
CBB H391 1H39 H 0 0 N N N 8.381  1.242  21.125 5.770  0.304  2.426  H391 CBB 57 
CBB H40  H40  H 0 1 N N N 7.696  1.535  19.523 4.821  -0.911 0.484  H40  CBB 58 
CBB H411 1H41 H 0 0 N N N 9.285  4.248  19.217 4.431  1.890  -0.664 H411 CBB 59 
CBB H412 2H41 H 0 0 N N N 7.906  4.010  18.200 4.165  0.363  -1.539 H412 CBB 60 
CBB H431 1H43 H 0 0 N N N 9.293  2.935  17.057 ?      ?      ?      H431 CBB 61 
CBB H432 2H43 H 0 0 N N N 9.801  1.434  16.584 6.165  1.841  -1.232 H432 CBB 62 
CBB H44  H44  H 0 1 N N N 9.995  -0.026 18.640 7.203  -1.447 0.770  H44  CBB 63 
# 
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 
CBB C1  C2   SING Y N 1  
CBB C1  C6   DOUB Y N 2  
CBB C1  HC1  SING N N 3  
CBB C2  C3   DOUB Y N 4  
CBB C2  HC2  SING N N 5  
CBB C3  C4   SING Y N 6  
CBB C3  N7   SING Y N 7  
CBB C4  C5   DOUB Y N 8  
CBB C4  C9   SING Y N 9  
CBB C5  C6   SING Y N 10 
CBB C5  HC5  SING N N 11 
CBB C6  HC6  SING N N 12 
CBB N7  C8   SING Y N 13 
CBB N7  C10  SING N N 14 
CBB C8  C9   DOUB Y N 15 
CBB C8  C31  SING N N 16 
CBB C9  HC9  SING N N 17 
CBB C10 C11  SING N N 18 
CBB C10 H101 SING N N 19 
CBB C10 H102 SING N N 20 
CBB C11 C14  SING N N 21 
CBB C11 C18  DOUB N N 22 
CBB C14 C15  DOUB N N 23 
CBB C14 H14  SING N N 24 
CBB C15 C16  SING N N 25 
CBB C15 H15  SING N N 26 
CBB C16 C17  SING N N 27 
CBB C16 H16  SING N N 28 
CBB C16 H161 SING N N 29 
CBB C17 C18  SING N N 30 
CBB C17 C19  SING N N 31 
CBB C17 H17  SING N N 32 
CBB C18 H118 SING N N 33 
CBB C19 N20  SING N N 34 
CBB C19 N21  DOUB N E 35 
CBB N20 H201 SING N N 36 
CBB N20 H202 SING N N 37 
CBB N21 H21  SING N N 38 
CBB C31 O32  SING N N 39 
CBB C31 O49  DOUB N N 40 
CBB O32 C33  SING N N 41 
CBB C33 C34  SING N N 42 
CBB C33 H331 SING N N 43 
CBB C33 H332 SING N N 44 
CBB C34 C37  SING N N 45 
CBB C34 C41  SING N N 46 
CBB C34 H334 SING N N 47 
CBB C37 C38  SING N N 48 
CBB C37 H37  SING N N 49 
CBB C37 H371 SING N N 50 
CBB C38 C39  SING N N 51 
CBB C38 H38  SING N N 52 
CBB C38 H381 SING N N 53 
CBB C39 C40  SING N N 54 
CBB C39 H39  SING N N 55 
CBB C39 H391 SING N N 56 
CBB C40 C41  SING N N 57 
CBB C40 C42  SING N N 58 
CBB C40 H40  SING N N 59 
CBB C41 H411 SING N N 60 
CBB C41 H412 SING N N 61 
CBB C42 N43  SING N N 62 
CBB C42 N44  DOUB N N 63 
CBB N43 H431 SING N N 64 
CBB N43 H432 SING N N 65 
CBB N44 H44  SING N N 66 
# 
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 
CBB SMILES           ACDLabs              10.04 O=C(OCC1CC(C(=[N@H])N)CCC1)c3cc2ccccc2n3CC=4C=CCC(C(=[N@H])N)C=4 
CBB InChI            InChI                1.02b 
InChI=1/C25H31N5O2/c26-23(27)19-8-3-5-16(11-19)14-30-21-10-2-1-7-18(21)13-22(30)25(31)32-15-17-6-4-9-20(12-17)24(28)29/h1-3,5,7,10-11,13,17,19-20H,4,6,8-9,12,14-15H2,(H3,26,27)(H3,28,29)/t17-,19-,20+/m1/s1/f/h26,28H,27,29H2/b26-23+,28-24? 
CBB InChIKey         InChI                1.02b SDPCOHPMBQGZNR-SFULATSNDW 
CBB SMILES_CANONICAL CACTVS               3.341 NC(=N)[C@H]1CCC[C@@H](COC(=O)c2cc3ccccc3n2CC4=C[C@@H](CC=C4)C(N)=N)C1 
CBB SMILES           CACTVS               3.341 NC(=N)[CH]1CCC[CH](COC(=O)c2cc3ccccc3n2CC4=C[CH](CC=C4)C(N)=N)C1 
CBB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\C1CC=CC(=C1)Cn2c3ccccc3cc2C(=O)OCC4CCCC(C4)C(=N)N)/N 
CBB SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(C1CC=CC(=C1)Cn2c3ccccc3cc2C(=O)OCC4CCCC(C4)C(=N)N)N 
# 
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 
CBB "SYSTEMATIC NAME" ACDLabs              10.04 "[(1R,3S)-3-carbamimidoylcyclohexyl]methyl 1-{[(3R)-3-carbamimidoylcyclohexa-1,5-dien-1-yl]methyl}-1H-indole-2-carboxylate" 
CBB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3-carbamimidoylcyclohexyl)methyl 1-[(3-carbamimidoyl-1-cyclohexa-1,5-dienyl)methyl]indole-2-carboxylate"                  
# 
