data_008
# 
_chem_comp.id                                    008 
_chem_comp.name                                  "(S)-2-[(R)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRYL]-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID AMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H22 F N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-06-09 
_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                        355.406 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     008 
_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        2BUC 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
008 F7   F7   F 0 1 N N N -5.722  17.724 4.163  -0.445 1.941  -4.636 F7   008 1  
008 C1   C1   C 0 1 Y N N -7.039  17.928 4.013  -0.500 0.650  -5.031 C1   008 2  
008 C2   C2   C 0 1 Y N N -7.822  16.917 3.458  -0.093 0.299  -6.307 C2   008 3  
008 C3   C3   C 0 1 Y N N -9.193  17.108 3.295  -0.150 -1.020 -6.711 C3   008 4  
008 C4   C4   C 0 1 Y N N -9.775  18.310 3.691  -0.608 -1.991 -5.840 C4   008 5  
008 C5   C5   C 0 1 Y N N -8.991  19.319 4.250  -1.009 -1.642 -4.564 C5   008 6  
008 C6   C6   C 0 1 Y N N -7.618  19.129 4.414  -0.953 -0.323 -4.158 C6   008 7  
008 C8   C8   C 0 1 N N N -6.767  20.227 5.019  -1.391 0.057  -2.767 C8   008 8  
008 C9   C9   C 0 1 N N R -7.136  20.444 6.491  -0.194 -0.019 -1.817 C9   008 9  
008 N10  N10  N 0 1 N N N -6.737  19.273 7.243  0.851  0.907  -2.271 N10  008 10 
008 C11  C11  C 0 1 N N N -6.438  21.670 7.081  -0.639 0.366  -0.405 C11  008 11 
008 C12  C12  C 0 1 N N N -6.954  23.004 6.560  0.539  0.291  0.530  C12  008 12 
008 O13  O13  O 0 1 N N N -7.881  23.049 5.764  1.628  -0.037 0.109  O13  008 13 
008 N14  N14  N 0 1 N N N -6.307  24.103 6.974  0.384  0.591  1.835  N14  008 14 
008 C19  C19  C 0 1 N N N -5.206  24.109 7.940  -0.882 1.120  2.351  C19  008 15 
008 C18  C18  C 0 1 Y N N -5.552  25.059 9.060  -1.240 0.418  3.637  C18  008 16 
008 C20  C20  C 0 1 Y N N -5.421  24.707 10.403 -2.518 0.607  4.144  C20  008 17 
008 C21  C21  C 0 1 Y N N -5.758  25.640 11.387 -2.901 0.000  5.322  C21  008 18 
008 C22  C22  C 0 1 Y N N -6.225  26.905 11.020 -2.004 -0.801 6.003  C22  008 19 
008 C17  C17  C 0 1 Y N N -6.016  26.311 8.697  -0.349 -0.388 4.308  C17  008 20 
008 C23  C23  C 0 1 Y N N -6.350  27.250 9.672  -0.736 -0.994 5.498  C23  008 21 
008 C16  C16  C 0 1 N N N -6.135  26.625 7.221  1.041  -0.667 3.803  C16  008 22 
008 C15  C15  C 0 1 N N S -6.677  25.428 6.417  1.477  0.393  2.801  C15  008 23 
008 C24  C24  C 0 1 N N N -6.210  25.566 4.993  2.719  -0.064 2.081  C24  008 24 
008 O25  O25  O 0 1 N N N -6.992  25.995 4.164  3.661  0.688  1.956  O25  008 25 
008 N26  N26  N 0 1 N N N -4.967  25.216 4.662  2.783  -1.312 1.575  N26  008 26 
008 H2   H2   H 0 1 N N N -7.357  15.966 3.148  0.265  1.057  -6.988 H2   008 27 
008 H3   H3   H 0 1 N N N -9.815  16.311 2.854  0.163  -1.294 -7.708 H3   008 28 
008 H4   H4   H 0 1 N N N -10.859 18.464 3.562  -0.652 -3.023 -6.156 H4   008 29 
008 H5   H5   H 0 1 N N N -9.457  20.269 4.563  -1.366 -2.402 -3.884 H5   008 30 
008 H8C1 1H8C H 0 0 N N N -6.832  21.173 4.432  -2.167 -0.630 -2.430 H8C1 008 31 
008 H8C2 2H8C H 0 0 N N N -5.678  20.026 4.890  -1.785 1.073  -2.775 H8C2 008 32 
008 H9   H9   H 0 1 N N N -8.240  20.575 6.576  0.199  -1.035 -1.809 H9   008 33 
008 H101 1H10 H 0 0 N N N -7.522  19.069 7.862  0.444  1.830  -2.263 H101 008 34 
008 H102 2H10 H 0 0 N N N -6.004  19.595 7.875  1.571  0.901  -1.564 H102 008 35 
008 H111 1H11 H 0 0 N N N -5.335  21.597 6.934  -1.032 1.383  -0.412 H111 008 36 
008 H112 2H11 H 0 0 N N N -6.485  21.644 8.195  -1.414 -0.320 -0.067 H112 008 37 
008 H191 1H19 H 0 0 N N N -4.224  24.346 7.467  -0.779 2.189  2.538  H191 008 38 
008 H192 2H19 H 0 0 N N N -4.956  23.087 8.309  -1.670 0.955  1.616  H192 008 39 
008 H20  H20  H 0 1 N N N -5.056  23.705 10.685 -3.218 1.236  3.613  H20  008 40 
008 H21  H21  H 0 1 N N N -5.655  25.378 12.453 -3.897 0.151  5.711  H21  008 41 
008 H22  H22  H 0 1 N N N -6.497  27.636 11.800 -2.296 -1.276 6.928  H22  008 42 
008 H23  H23  H 0 1 N N N -6.708  28.252 9.383  -0.036 -1.620 6.031  H23  008 43 
008 H161 1H16 H 0 0 N N N -6.751  27.539 7.050  1.734  -0.673 4.644  H161 008 44 
008 H162 2H16 H 0 0 N N N -5.166  26.986 6.805  1.058  -1.643 3.318  H162 008 45 
008 H15  H15  H 0 1 N N N -7.790  25.496 6.417  1.678  1.331  3.321  H15  008 46 
008 H261 1H26 H 0 0 N N N -4.650  25.309 3.697  3.582  -1.607 1.112  H261 008 47 
008 H262 2H26 H 0 0 N N N -4.312  24.857 5.356  2.029  -1.915 1.675  H262 008 48 
# 
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 
008 F7  C1   SING N N 1  
008 C1  C2   DOUB Y N 2  
008 C1  C6   SING Y N 3  
008 C2  C3   SING Y N 4  
008 C2  H2   SING N N 5  
008 C3  C4   DOUB Y N 6  
008 C3  H3   SING N N 7  
008 C4  C5   SING Y N 8  
008 C4  H4   SING N N 9  
008 C5  C6   DOUB Y N 10 
008 C5  H5   SING N N 11 
008 C6  C8   SING N N 12 
008 C8  C9   SING N N 13 
008 C8  H8C1 SING N N 14 
008 C8  H8C2 SING N N 15 
008 C9  N10  SING N N 16 
008 C9  C11  SING N N 17 
008 C9  H9   SING N N 18 
008 N10 H101 SING N N 19 
008 N10 H102 SING N N 20 
008 C11 C12  SING N N 21 
008 C11 H111 SING N N 22 
008 C11 H112 SING N N 23 
008 C12 O13  DOUB N N 24 
008 C12 N14  SING N N 25 
008 N14 C19  SING N N 26 
008 N14 C15  SING N N 27 
008 C19 C18  SING N N 28 
008 C19 H191 SING N N 29 
008 C19 H192 SING N N 30 
008 C18 C20  DOUB Y N 31 
008 C18 C17  SING Y N 32 
008 C20 C21  SING Y N 33 
008 C20 H20  SING N N 34 
008 C21 C22  DOUB Y N 35 
008 C21 H21  SING N N 36 
008 C22 C23  SING Y N 37 
008 C22 H22  SING N N 38 
008 C17 C23  DOUB Y N 39 
008 C17 C16  SING N N 40 
008 C23 H23  SING N N 41 
008 C16 C15  SING N N 42 
008 C16 H161 SING N N 43 
008 C16 H162 SING N N 44 
008 C15 C24  SING N N 45 
008 C15 H15  SING N N 46 
008 C24 O25  DOUB N N 47 
008 C24 N26  SING N N 48 
008 N26 H261 SING N N 49 
008 N26 H262 SING N N 50 
# 
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 
008 SMILES           ACDLabs              10.04 Fc1ccccc1CC(N)CC(=O)N3C(C(=O)N)Cc2c(cccc2)C3                                                                                                               
008 InChI            InChI                1.02b InChI=1/C20H22FN3O2/c21-17-8-4-3-6-14(17)9-16(22)11-19(25)24-12-15-7-2-1-5-13(15)10-18(24)20(23)26/h1-8,16,18H,9-12,22H2,(H2,23,26)/t16-,18+/m1/s1/f/h23H2 
008 InChIKey         InChI                1.02b OEVYDSSAPNIURZ-PRAWBJLQDF                                                                                                                                  
008 SMILES_CANONICAL CACTVS               3.341 N[C@@H](CC(=O)N1Cc2ccccc2C[C@H]1C(N)=O)Cc3ccccc3F                                                                                                          
008 SMILES           CACTVS               3.341 N[CH](CC(=O)N1Cc2ccccc2C[CH]1C(N)=O)Cc3ccccc3F                                                                                                             
008 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)C[C@H](N(C2)C(=O)C[C@@H](Cc3ccccc3F)N)C(=O)N                                                                                                    
008 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)CC(N(C2)C(=O)CC(Cc3ccccc3F)N)C(=O)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 
008 "SYSTEMATIC NAME" ACDLabs              10.04 (3S)-2-[(3R)-3-amino-4-(2-fluorophenyl)butanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
008 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3S)-2-[(3R)-3-amino-4-(2-fluorophenyl)butanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxamide    
# 
