data_WSH
# 
_chem_comp.id                                    WSH 
_chem_comp.name                                  "BENZYL [(4R)-1-METHYL-6-PHENYL-4H-[1,2,4]TRIAZOLO[4,3-A][1,4]BENZODIAZEPIN-4-YL]CARBAMATE" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H21 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2011-03-24 
_chem_comp.pdbx_modified_date                    2011-06-10 
_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                        423.467 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     WSH 
_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        2YDW 
_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 
WSH C17  C17  C 0 1 Y N N 43.859 -1.477 0.853  4.540  -4.177 -0.229 C17  WSH 1  
WSH C10  C10  C 0 1 Y N N 41.233 6.257  -8.135 -7.220 -0.745 1.512  C10  WSH 2  
WSH C18  C18  C 0 1 Y N N 44.255 -0.834 -0.297 4.662  -3.194 0.737  C18  WSH 3  
WSH C16  C16  C 0 1 Y N N 43.482 -0.736 1.949  3.597  -4.054 -1.234 C16  WSH 4  
WSH C22  C22  C 0 1 Y N N 46.128 3.605  3.564  1.426  -0.300 3.309  C22  WSH 5  
WSH C11  C11  C 0 1 Y N N 40.655 5.379  -7.250 -6.974 0.481  0.922  C11  WSH 6  
WSH C9   C9   C 0 1 Y N N 42.574 6.545  -8.030 -6.446 -1.841 1.177  C9   WSH 7  
WSH C23  C23  C 0 1 Y N N 45.524 4.723  4.091  1.441  1.078  3.440  C23  WSH 8  
WSH C19  C19  C 0 1 Y N N 44.270 0.542  -0.346 3.843  -2.084 0.703  C19  WSH 9  
WSH C15  C15  C 0 1 Y N N 43.495 0.640  1.896  2.773  -2.948 -1.279 C15  WSH 10 
WSH C21  C21  C 0 1 Y N N 45.587 2.989  2.462  1.592  -0.881 2.073  C21  WSH 11 
WSH C12  C12  C 0 1 Y N N 41.409 4.785  -6.263 -5.954 0.610  -0.002 C12  WSH 12 
WSH C8   C8   C 0 1 Y N N 43.331 5.957  -7.041 -5.427 -1.711 0.252  C8   WSH 13 
WSH C24  C24  C 0 1 Y N N 44.377 5.226  3.516  1.614  1.874  2.327  C24  WSH 14 
WSH C14  C14  C 0 1 Y N N 43.890 1.288  0.748  2.891  -1.954 -0.308 C14  WSH 15 
WSH C20  C20  C 0 1 Y N N 44.437 3.479  1.874  1.780  -0.087 0.931  C20  WSH 16 
WSH C7   C7   C 0 1 Y N N 42.751 5.072  -6.156 -5.181 -0.486 -0.338 C7   WSH 17 
WSH C25  C25  C 0 1 Y N N 43.831 4.603  2.415  1.772  1.302  1.069  C25  WSH 18 
WSH C3   C3   C 0 1 Y N N 42.443 5.353  0.474  1.360  1.931  -1.266 C3   WSH 19 
WSH C2   C2   C 0 1 Y N N 41.577 5.797  2.427  2.511  3.355  -0.100 C2   WSH 20 
WSH C13  C13  C 0 1 N N N 43.896 2.779  0.695  2.008  -0.765 -0.349 C13  WSH 21 
WSH C5   C5   C 0 1 N N N 44.042 4.864  -2.809 -1.743 0.175  -1.428 C5   WSH 22 
WSH C4   C4   C 0 1 N N S 43.472 4.766  -0.465 0.626  0.684  -1.688 C4   WSH 23 
WSH C1   C1   C 0 1 N N N 41.345 5.878  3.879  3.290  4.023  1.004  C1   WSH 24 
WSH C6   C6   C 0 1 N N N 43.564 4.439  -5.075 -4.071 -0.344 -1.346 C6   WSH 25 
WSH N2   N2   N 0 1 Y N N 41.342 6.028  0.277  1.617  2.983  -1.990 N2   WSH 26 
WSH N1   N1   N 0 1 Y N N 40.794 6.310  1.508  2.307  3.824  -1.303 N1   WSH 27 
WSH N4   N4   N 0 1 N N N 43.446 3.305  -0.383 1.535  -0.453 -1.505 N4   WSH 28 
WSH N5   N5   N 0 1 Y N N 42.646 5.175  1.834  1.886  2.149  -0.035 N5   WSH 29 
WSH N3   N3   N 0 1 N N N 43.187 5.151  -1.814 -0.567 0.505  -0.857 N3   WSH 30 
WSH O1   O1   O 0 1 N N N 45.107 4.282  -2.689 -1.813 0.027  -2.632 O1   WSH 31 
WSH O2   O2   O 0 1 N N N 43.558 5.330  -3.974 -2.839 0.010  -0.664 O2   WSH 32 
WSH H17  H17  H 0 1 N N N 43.844 -2.556 0.895  5.186  -5.042 -0.201 H17  WSH 33 
WSH H18  H18  H 0 1 N N N 44.554 -1.408 -1.161 5.400  -3.296 1.519  H18  WSH 34 
WSH H16  H16  H 0 1 N N N 43.174 -1.236 2.856  3.507  -4.824 -1.985 H16  WSH 35 
WSH H10  H10  H 0 1 N N N 40.638 6.719  -8.909 -8.014 -0.845 2.237  H10  WSH 36 
WSH H11  H11  H 0 1 N N N 39.602 5.153  -7.329 -7.578 1.337  1.183  H11  WSH 37 
WSH H9   H9   H 0 1 N N N 43.034 7.233  -8.724 -6.639 -2.799 1.638  H9   WSH 38 
WSH H19  H19  H 0 1 N N N 44.583 1.041  -1.251 3.939  -1.318 1.458  H19  WSH 39 
WSH H15  H15  H 0 1 N N N 43.194 1.214  2.760  2.037  -2.853 -2.064 H15  WSH 40 
WSH H22  H22  H 0 1 N N N 47.027 3.212  4.016  1.286  -0.922 4.181  H22  WSH 41 
WSH H23  H23  H 0 1 N N N 45.950 5.208  4.957  1.319  1.530  4.413  H23  WSH 42 
WSH H21  H21  H 0 1 N N N 46.066 2.112  2.051  1.578  -1.957 1.981  H21  WSH 43 
WSH H12  H12  H 0 1 N N N 40.948 4.094  -5.573 -5.762 1.568  -0.463 H12  WSH 44 
WSH H8   H8   H 0 1 N N N 44.382 6.190  -6.958 -4.824 -2.567 -0.009 H8   WSH 45 
WSH H24  H24  H 0 1 N N N 43.907 6.107  3.928  1.625  2.949  2.432  H24  WSH 46 
WSH H61C H61C H 0 0 N N N 43.126 3.472  -4.785 -3.936 -1.289 -1.872 H61C WSH 47 
WSH H62C H62C H 0 0 N N N 44.594 4.269  -5.422 -4.327 0.437  -2.062 H62C WSH 48 
WSH H4   H4   H 0 1 N N N 44.463 5.143  -0.172 0.338  0.762  -2.737 H4   WSH 49 
WSH H11C H11C H 0 0 N N N 40.416 6.434  4.072  2.620  4.646  1.596  H11C WSH 50 
WSH H12C H12C H 0 0 N N N 41.257 4.863  4.293  3.739  3.262  1.643  H12C WSH 51 
WSH H13C H13C H 0 0 N N N 42.189 6.398  4.357  4.075  4.642  0.571  H13C WSH 52 
WSH H3   H3   H 0 1 N N N 42.339 5.641  -2.018 -0.511 0.623  0.104  H3   WSH 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 
WSH C17 C18  SING Y N 1  
WSH C17 C16  DOUB Y N 2  
WSH C10 C11  SING Y N 3  
WSH C10 C9   DOUB Y N 4  
WSH C18 C19  DOUB Y N 5  
WSH C16 C15  SING Y N 6  
WSH C22 C23  SING Y N 7  
WSH C22 C21  DOUB Y N 8  
WSH C11 C12  DOUB Y N 9  
WSH C9  C8   SING Y N 10 
WSH C23 C24  DOUB Y N 11 
WSH C19 C14  SING Y N 12 
WSH C15 C14  DOUB Y N 13 
WSH C21 C20  SING Y N 14 
WSH C12 C7   SING Y N 15 
WSH C8  C7   DOUB Y N 16 
WSH C24 C25  SING Y N 17 
WSH C14 C13  SING N N 18 
WSH C20 C25  DOUB Y N 19 
WSH C20 C13  SING N N 20 
WSH C7  C6   SING N N 21 
WSH C25 N5   SING Y N 22 
WSH C3  C4   SING N N 23 
WSH C3  N2   DOUB Y N 24 
WSH C3  N5   SING Y N 25 
WSH C2  C1   SING N N 26 
WSH C2  N1   DOUB Y N 27 
WSH C2  N5   SING Y N 28 
WSH C13 N4   DOUB N N 29 
WSH C5  N3   SING N N 30 
WSH C5  O1   DOUB N N 31 
WSH C5  O2   SING N N 32 
WSH C4  N4   SING N N 33 
WSH C4  N3   SING N N 34 
WSH C6  O2   SING N N 35 
WSH N2  N1   SING Y N 36 
WSH C17 H17  SING N N 37 
WSH C18 H18  SING N N 38 
WSH C16 H16  SING N N 39 
WSH C10 H10  SING N N 40 
WSH C11 H11  SING N N 41 
WSH C9  H9   SING N N 42 
WSH C19 H19  SING N N 43 
WSH C15 H15  SING N N 44 
WSH C22 H22  SING N N 45 
WSH C23 H23  SING N N 46 
WSH C21 H21  SING N N 47 
WSH C12 H12  SING N N 48 
WSH C8  H8   SING N N 49 
WSH C24 H24  SING N N 50 
WSH C6  H61C SING N N 51 
WSH C6  H62C SING N N 52 
WSH C4  H4   SING N N 53 
WSH C1  H11C SING N N 54 
WSH C1  H12C SING N N 55 
WSH C1  H13C SING N N 56 
WSH N3  H3   SING N N 57 
# 
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 
WSH SMILES           ACDLabs              12.01 "O=C(OCc1ccccc1)NC4N=C(c2ccccc2n3c4nnc3C)c5ccccc5"                                                                                                                   
WSH SMILES_CANONICAL CACTVS               3.370 "Cc1nnc2[C@H](NC(=O)OCc3ccccc3)N=C(c4ccccc4)c5ccccc5n12"                                                                                                             
WSH SMILES           CACTVS               3.370 "Cc1nnc2[CH](NC(=O)OCc3ccccc3)N=C(c4ccccc4)c5ccccc5n12"                                                                                                              
WSH SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "Cc1nnc2n1-c3ccccc3C(=N[C@H]2NC(=O)OCc4ccccc4)c5ccccc5"                                                                                                              
WSH SMILES           "OpenEye OEToolkits" 1.7.0 "Cc1nnc2n1-c3ccccc3C(=NC2NC(=O)OCc4ccccc4)c5ccccc5"                                                                                                                  
WSH InChI            InChI                1.03  "InChI=1S/C25H21N5O2/c1-17-28-29-24-23(27-25(31)32-16-18-10-4-2-5-11-18)26-22(19-12-6-3-7-13-19)20-14-8-9-15-21(20)30(17)24/h2-15,23H,16H2,1H3,(H,27,31)/t23-/m0/s1" 
WSH InChIKey         InChI                1.03  TUWDLUFFAHHNEF-QHCPKHFHSA-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 
WSH "SYSTEMATIC NAME" ACDLabs              12.01 "benzyl [(4R)-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]carbamate"         
WSH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "phenylmethyl N-[(4R)-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]carbamate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
WSH "Create component"     2011-03-24 EBI  
WSH "Modify aromatic_flag" 2011-06-04 RCSB 
WSH "Modify descriptor"    2011-06-04 RCSB 
# 
