data_BO2
# 
_chem_comp.id                                    BO2 
_chem_comp.name                                  N-[(1R)-1-(DIHYDROXYBORYL)-3-METHYLBUTYL]-N-(PYRAZIN-2-YLCARBONYL)-L-PHENYLALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H25 B N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         BORTEZOMIB 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-06 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        384.237 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BO2 
_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        2F16 
_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 
BO2 N1   N1   N 0 1 Y N N 62.634 -135.350 34.666 -3.232 2.476  -0.644 N1   BO2 1  
BO2 C2   C2   C 0 1 Y N N 62.377 -134.360 35.574 -3.442 1.487  0.220  C2   BO2 2  
BO2 C3   C3   C 0 1 Y N N 62.689 -133.030 35.200 -4.685 1.361  0.841  C3   BO2 3  
BO2 N4   N4   N 0 1 Y N N 63.218 -132.770 33.968 -5.649 2.221  0.564  N4   BO2 4  
BO2 C5   C5   C 0 1 Y N N 63.470 -133.760 33.061 -5.436 3.198  -0.300 C5   BO2 5  
BO2 C6   C6   C 0 1 Y N N 63.168 -135.090 33.419 -4.201 3.326  -0.919 C6   BO2 6  
BO2 C7   C7   C 0 1 N N N 61.800 -134.740 36.929 -2.358 0.526  0.528  C7   BO2 7  
BO2 O8   O8   O 0 1 N N N 61.283 -133.830 37.577 -2.550 -0.374 1.322  O8   BO2 8  
BO2 N9   N9   N 0 1 N N N 61.877 -136.010 37.437 -1.158 0.649  -0.073 N9   BO2 9  
BO2 C10  C10  C 0 1 N N S 61.352 -136.240 38.799 -0.085 -0.301 0.231  C10  BO2 10 
BO2 C11  C11  C 0 1 N N N 60.559 -137.570 38.857 -0.236 -1.541 -0.653 C11  BO2 11 
BO2 C12  C12  C 0 1 Y N N 59.202 -137.390 38.165 -1.515 -2.256 -0.301 C12  BO2 12 
BO2 C13  C13  C 0 1 Y N N 58.969 -137.980 36.877 -1.511 -3.240 0.670  C13  BO2 13 
BO2 C14  C14  C 0 1 Y N N 57.704 -137.810 36.223 -2.684 -3.894 0.997  C14  BO2 14 
BO2 C15  C15  C 0 1 Y N N 56.663 -137.060 36.847 -3.860 -3.569 0.346  C15  BO2 15 
BO2 C16  C16  C 0 1 Y N N 56.887 -136.480 38.129 -3.863 -2.589 -0.629 C16  BO2 16 
BO2 C17  C17  C 0 1 Y N N 58.153 -136.640 38.789 -2.690 -1.933 -0.952 C17  BO2 17 
BO2 C18  C18  C 0 1 N N N 62.559 -136.270 39.740 1.250  0.346  -0.035 C18  BO2 18 
BO2 O19  O19  O 0 1 N N N 63.694 -136.180 39.233 1.300  1.488  -0.439 O19  BO2 19 
BO2 N20  N20  N 0 1 N N N 62.375 -136.400 41.088 2.388  -0.345 0.175  N20  BO2 20 
BO2 C21  C21  C 0 1 N N R 63.560 -136.420 41.957 3.685  0.284  -0.083 C21  BO2 21 
BO2 C22  C22  C 0 1 N N N 64.290 -135.000 42.077 4.637  -0.015 1.076  C22  BO2 22 
BO2 C23  C23  C 0 1 N N N 63.536 -133.650 41.792 5.936  0.770  0.885  C23  BO2 23 
BO2 C24  C24  C 0 1 N N N 62.339 -133.370 42.746 5.644  2.269  0.977  C24  BO2 24 
BO2 C25  C25  C 0 1 N N N 64.522 -132.460 41.943 6.935  0.378  1.976  C25  BO2 25 
BO2 B26  B26  B 0 1 N N N 63.207 -137.050 43.372 4.288  -0.288 -1.416 B26  BO2 26 
BO2 O27  O27  O 0 1 N N N 62.353 -136.240 44.024 3.430  -0.616 -2.499 O27  BO2 27 
BO2 O28  O28  O 0 1 N N N 62.626 -138.240 43.153 5.690  -0.477 -1.537 O28  BO2 28 
BO2 H3   H3   H 0 1 N N N 62.508 -132.220 35.891 -4.858 0.563  1.547  H3   BO2 29 
BO2 H5   H5   H 0 1 N N N 63.890 -133.530 32.093 -6.226 3.899  -0.525 H5   BO2 30 
BO2 H6   H6   H 0 1 N N N 63.352 -135.897 32.725 -4.032 4.126  -1.625 H6   BO2 31 
BO2 HN9  HN9  H 0 1 N N N 62.275 -136.756 36.904 -1.004 1.367  -0.707 HN9  BO2 32 
BO2 H10  H10  H 0 1 N N N 60.655 -135.443 39.096 -0.145 -0.593 1.279  H10  BO2 33 
BO2 H111 1H11 H 0 0 N N N 60.399 -137.855 39.907 -0.266 -1.239 -1.700 H111 BO2 34 
BO2 H112 2H11 H 0 0 N N N 61.129 -138.359 38.345 0.610  -2.208 -0.491 H112 BO2 35 
BO2 H13  H13  H 0 1 N N N 59.749 -138.554 36.399 -0.592 -3.494 1.178  H13  BO2 36 
BO2 H14  H14  H 0 1 N N N 57.538 -138.253 35.252 -2.682 -4.659 1.758  H14  BO2 37 
BO2 H15  H15  H 0 1 N N N 55.712 -136.933 36.351 -4.777 -4.082 0.599  H15  BO2 38 
BO2 H16  H16  H 0 1 N N N 56.100 -135.916 38.608 -4.782 -2.335 -1.137 H16  BO2 39 
BO2 H17  H17  H 0 1 N N N 58.314 -136.193 39.759 -2.692 -1.167 -1.714 H17  BO2 40 
BO2 H20  H20  H 0 1 N N N 61.456 -136.480 41.474 2.347  -1.259 0.498  H20  BO2 41 
BO2 H21  H21  H 0 1 N N N 64.301 -137.072 41.472 3.554  1.362  -0.177 H21  BO2 42 
BO2 H221 1H22 H 0 0 N N N 65.027 -135.040 41.261 4.858  -1.083 1.099  H221 BO2 43 
BO2 H222 2H22 H 0 0 N N N 64.631 -134.932 43.121 4.169  0.279  2.016  H222 BO2 44 
BO2 H23  H23  H 0 1 N N N 63.140 -133.750 40.771 6.359  0.541  -0.093 H23  BO2 45 
BO2 H241 1H24 H 0 0 N N N 61.608 -134.188 42.666 4.933  2.549  0.200  H241 BO2 46 
BO2 H242 2H24 H 0 0 N N N 61.860 -132.421 42.464 5.222  2.498  1.955  H242 BO2 47 
BO2 H243 3H24 H 0 0 N N N 62.703 -133.304 43.782 6.569  2.829  0.841  H243 BO2 48 
BO2 H251 1H25 H 0 0 N N N 64.061 -131.548 41.536 6.512  0.606  2.955  H251 BO2 49 
BO2 H252 2H25 H 0 0 N N N 65.449 -132.680 41.392 7.143  -0.690 1.911  H252 BO2 50 
BO2 H253 3H25 H 0 0 N N N 64.755 -132.309 43.007 7.860  0.937  1.840  H253 BO2 51 
BO2 H27  H27  H 0 1 N N N 62.695 -136.049 44.889 2.529  -0.414 -2.213 H27  BO2 52 
BO2 H28  H28  H 0 1 N N N 62.489 -138.359 42.221 5.848  -0.833 -2.423 H28  BO2 53 
# 
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 
BO2 N1  C2   SING Y N 1  
BO2 N1  C6   DOUB Y N 2  
BO2 C2  C3   DOUB Y N 3  
BO2 C2  C7   SING N N 4  
BO2 C3  N4   SING Y N 5  
BO2 C3  H3   SING N N 6  
BO2 N4  C5   DOUB Y N 7  
BO2 C5  C6   SING Y N 8  
BO2 C5  H5   SING N N 9  
BO2 C6  H6   SING N N 10 
BO2 C7  O8   DOUB N N 11 
BO2 C7  N9   SING N N 12 
BO2 N9  C10  SING N N 13 
BO2 N9  HN9  SING N N 14 
BO2 C10 C11  SING N N 15 
BO2 C10 C18  SING N N 16 
BO2 C10 H10  SING N N 17 
BO2 C11 C12  SING N N 18 
BO2 C11 H111 SING N N 19 
BO2 C11 H112 SING N N 20 
BO2 C12 C13  SING Y N 21 
BO2 C12 C17  DOUB Y N 22 
BO2 C13 C14  DOUB Y N 23 
BO2 C13 H13  SING N N 24 
BO2 C14 C15  SING Y N 25 
BO2 C14 H14  SING N N 26 
BO2 C15 C16  DOUB Y N 27 
BO2 C15 H15  SING N N 28 
BO2 C16 C17  SING Y N 29 
BO2 C16 H16  SING N N 30 
BO2 C17 H17  SING N N 31 
BO2 C18 O19  DOUB N N 32 
BO2 C18 N20  SING N N 33 
BO2 N20 C21  SING N N 34 
BO2 N20 H20  SING N N 35 
BO2 C21 C22  SING N N 36 
BO2 C21 B26  SING N N 37 
BO2 C21 H21  SING N N 38 
BO2 C22 C23  SING N N 39 
BO2 C22 H221 SING N N 40 
BO2 C22 H222 SING N N 41 
BO2 C23 C24  SING N N 42 
BO2 C23 C25  SING N N 43 
BO2 C23 H23  SING N N 44 
BO2 C24 H241 SING N N 45 
BO2 C24 H242 SING N N 46 
BO2 C24 H243 SING N N 47 
BO2 C25 H251 SING N N 48 
BO2 C25 H252 SING N N 49 
BO2 C25 H253 SING N N 50 
BO2 B26 O27  SING N N 51 
BO2 B26 O28  SING N N 52 
BO2 O27 H27  SING N N 53 
BO2 O28 H28  SING N N 54 
# 
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 
BO2 SMILES           ACDLabs              10.04 O=C(NC(C(=O)NC(B(O)O)CC(C)C)Cc1ccccc1)c2nccnc2                                                                                                                                          
BO2 InChI            InChI                1.02b InChI=1/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1/f/h23-24H 
BO2 InChIKey         InChI                1.02b GXJABQQUPOEUTA-CPVFBZJHDY                                                                                                                                                               
BO2 SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c2cnccn2)B(O)O                                                                                                                                  
BO2 SMILES           CACTVS               3.341 CC(C)C[CH](NC(=O)[CH](Cc1ccccc1)NC(=O)c2cnccn2)B(O)O                                                                                                                                    
BO2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 B([C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)c2cnccn2)(O)O                                                                                                                                
BO2 SMILES           "OpenEye OEToolkits" 1.5.0 B(C(CC(C)C)NC(=O)C(Cc1ccccc1)NC(=O)c2cnccn2)(O)O                                                                                                                                        
# 
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 
BO2 "SYSTEMATIC NAME" ACDLabs              10.04 N-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-Nalpha-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide      
BO2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R)-3-methyl-1-[[(2S)-3-phenyl-2-(pyrazin-2-ylcarbonylamino)propanoyl]amino]butyl]boronic acid" 
# 
