data_165
# 
_chem_comp.id                                    165 
_chem_comp.name                                  N-(BENZYLSULFONYL)-3-CYCLOHEXYLALANYL-N-(2-AMINO-1,3-BENZOTHIAZOL-6-YL)PROLINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H35 N5 O4 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-02-17 
_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                        569.739 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     165 
_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        1SB1 
_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 
165 N19  N19  N 0 1 N N N 10.260 -13.702 15.049 -1.888 -1.613 -0.258 N19  165 1  
165 C23  C23  C 0 1 N N S 10.571 -12.390 15.619 -2.367 -1.857 1.114  C23  165 2  
165 C22  C22  C 0 1 N N N 9.590  -12.621 16.825 -2.293 -3.394 1.295  C22  165 3  
165 C21  C21  C 0 1 N N N 8.475  -13.407 16.201 -2.710 -3.894 -0.113 C21  165 4  
165 C20  C20  C 0 1 N N N 9.323  -14.584 15.780 -2.093 -2.836 -1.051 C20  165 5  
165 C24  C24  C 0 1 N N N 11.971 -12.181 16.199 -1.472 -1.168 2.112  C24  165 6  
165 O39  O39  O 0 1 N N N 12.072 -11.438 17.195 -0.304 -0.976 1.848  O39  165 7  
165 N25  N25  N 0 1 N N N 13.098 -12.864 15.519 -1.970 -0.766 3.298  N25  165 8  
165 C26  C26  C 0 1 Y N N 14.489 -12.660 16.030 -1.121 -0.198 4.258  C26  165 9  
165 C31  C31  C 0 1 Y N N 14.988 -11.330 15.374 0.194  -0.627 4.374  C31  165 10 
165 C30  C30  C 0 1 Y N N 15.859 -11.480 14.133 1.009  -0.059 5.320  C30  165 11 
165 S34  S34  S 0 1 Y N N 16.295 -10.069 13.248 2.701  -0.280 5.815  S34  165 12 
165 C33  C33  C 0 1 Y N N 17.192 -11.108 12.059 2.718  0.949  7.113  C33  165 13 
165 N35  N35  N 0 1 N N N 17.831 -10.553 10.981 3.757  1.315  7.944  N35  165 14 
165 N32  N32  N 0 1 Y N N 17.131 -12.374 12.369 1.489  1.411  7.077  N32  165 15 
165 C29  C29  C 0 1 Y N N 16.340 -12.668 13.596 0.568  0.957  6.197  C29  165 16 
165 C28  C28  C 0 1 Y N N 16.097 -14.055 14.190 -0.775 1.370  6.053  C28  165 17 
165 C27  C27  C 0 1 Y N N 15.373 -14.002 15.667 -1.587 0.801  5.107  C27  165 18 
165 C18  C18  C 0 1 N N N 10.797 -14.130 13.697 -1.349 -0.464 -0.711 C18  165 19 
165 O38  O38  O 0 1 N N N 11.527 -13.332 13.029 -1.317 0.513  0.004  O38  165 20 
165 C10  C10  C 0 1 N N R 10.346 -15.548 13.112 -0.787 -0.394 -2.108 C10  165 21 
165 N9   N9   N 0 1 N N N 11.326 -16.473 13.999 0.005  0.828  -2.254 N9   165 22 
165 S8   S8   S 0 1 N N N 13.005 -16.704 13.776 1.577  0.738  -2.769 S8   165 23 
165 O36  O36  O 0 1 N N N 13.759 -16.648 12.580 1.990  2.098  -2.757 O36  165 24 
165 O37  O37  O 0 1 N N N 13.539 -17.455 14.868 2.140  -0.229 -1.895 O37  165 25 
165 C7   C7   C 0 1 N N N 12.227 -18.276 13.068 1.422  0.101  -4.461 C7   165 26 
165 C5   C5   C 0 1 Y N N 13.159 -19.261 12.318 2.794  -0.141 -5.033 C5   165 27 
165 C6   C6   C 0 1 Y N N 12.924 -19.399 10.845 3.443  0.864  -5.724 C6   165 28 
165 C1   C1   C 0 1 Y N N 13.779 -20.281 10.035 4.704  0.641  -6.246 C1   165 29 
165 C2   C2   C 0 1 Y N N 14.892 -21.043 10.685 5.312  -0.589 -6.084 C2   165 30 
165 C3   C3   C 0 1 Y N N 15.121 -20.916 12.141 4.661  -1.596 -5.398 C3   165 31 
165 C4   C4   C 0 1 Y N N 14.245 -20.012 12.974 3.402  -1.373 -4.872 C4   165 32 
165 C11  C11  C 0 1 N N N 10.610 -15.637 11.550 -1.935 -0.382 -3.119 C11  165 33 
165 C12  C12  C 0 1 N N N 9.187  -14.765 11.157 -2.783 0.874  -2.913 C12  165 34 
165 C13  C13  C 0 1 N N N 7.746  -15.526 11.566 -3.593 1.157  -4.179 C13  165 35 
165 C14  C14  C 0 1 N N N 6.422  -14.662 11.224 -4.441 2.413  -3.973 C14  165 36 
165 C15  C15  C 0 1 N N N 6.448  -14.005 9.764  -5.394 2.198  -2.796 C15  165 37 
165 C16  C16  C 0 1 N N N 7.846  -13.347 9.373  -4.584 1.915  -1.529 C16  165 38 
165 C17  C17  C 0 1 N N N 9.069  -14.332 9.657  -3.736 0.658  -1.735 C17  165 39 
165 H23  H23  H 0 1 N N N 10.497 -11.536 14.905 -3.394 -1.511 1.224  H23  165 40 
165 H221 1H22 H 0 0 N N N 10.054 -13.098 17.719 -1.279 -3.711 1.538  H221 165 41 
165 H222 2H22 H 0 0 N N N 9.268  -11.691 17.349 -2.999 -3.732 2.054  H222 165 42 
165 H211 1H21 H 0 0 N N N 7.580  -13.618 16.832 -2.289 -4.879 -0.312 H211 165 43 
165 H212 2H21 H 0 0 N N N 7.869  -12.902 15.412 -3.795 -3.910 -0.211 H212 165 44 
165 H201 1H20 H 0 0 N N N 8.845  -15.436 15.243 -1.138 -3.194 -1.437 H201 165 45 
165 H202 2H20 H 0 0 N N N 9.720  -15.276 16.558 -2.774 -2.630 -1.877 H202 165 46 
165 H25  H25  H 0 1 N N N 12.919 -13.463 14.713 -2.915 -0.869 3.487  H25  165 47 
165 H31  H31  H 0 1 N N N 14.736 -10.331 15.768 0.574  -1.401 3.724  H31  165 48 
165 H351 1H35 H 0 0 N N N 18.334 -11.136 10.313 3.624  2.006  8.612  H351 165 49 
165 H352 2H35 H 0 0 N N N 18.472 -9.838  11.325 4.620  0.879  7.864  H352 165 50 
165 H28  H28  H 0 1 N N N 16.399 -14.959 13.635 -1.167 2.144  6.697  H28  165 51 
165 H27  H27  H 0 1 N N N 15.476 -14.832 16.385 -2.610 1.136  5.018  H27  165 52 
165 H10  H10  H 0 1 N N N 9.264  -15.811 13.182 -0.154 -1.262 -2.288 H10  165 53 
165 HN9  HN9  H 0 1 N N N 10.910 -17.404 13.998 -0.389 1.690  -2.050 HN9  165 54 
165 H71  1H7  H 0 1 N N N 11.692 -18.820 13.880 0.895  0.830  -5.077 H71  165 55 
165 H72  2H7  H 0 1 N N N 11.374 -17.998 12.405 0.862  -0.833 -4.447 H72  165 56 
165 H6   H6   H 0 1 N N N 12.109 -18.843 10.349 2.968  1.825  -5.851 H6   165 57 
165 H1   H1   H 0 1 N N N 13.587 -20.370 8.952  5.213  1.429  -6.782 H1   165 58 
165 H2   H2   H 0 1 N N N 15.546 -21.700 10.088 6.296  -0.763 -6.494 H2   165 59 
165 H3   H3   H 0 1 N N N 15.940 -21.492 12.602 5.135  -2.558 -5.271 H3   165 60 
165 H4   H4   H 0 1 N N N 14.398 -19.900 14.060 2.893  -2.160 -4.336 H4   165 61 
165 H111 1H11 H 0 0 N N N 11.585 -15.271 11.152 -2.556 -1.266 -2.975 H111 165 62 
165 H112 2H11 H 0 0 N N N 10.763 -16.641 11.091 -1.529 -0.383 -4.130 H112 165 63 
165 H12  H12  H 0 1 N N N 9.322  -13.862 11.796 -2.131 1.722  -2.702 H12  165 64 
165 H131 1H13 H 0 0 N N N 7.688  -16.533 11.092 -4.245 0.309  -4.390 H131 165 65 
165 H132 2H13 H 0 0 N N N 7.752  -15.822 12.640 -2.914 1.310  -5.018 H132 165 66 
165 H141 1H14 H 0 0 N N N 5.502  -15.276 11.363 -5.018 2.615  -4.876 H141 165 67 
165 H142 2H14 H 0 0 N N N 6.245  -13.884 12.003 -3.789 3.261  -3.762 H142 165 68 
165 H151 1H15 H 0 0 N N N 6.137  -14.749 8.994  -6.046 1.350  -3.007 H151 165 69 
165 H152 2H15 H 0 0 N N N 5.622  -13.263 9.653  -5.998 3.093  -2.649 H152 165 70 
165 H161 1H16 H 0 0 N N N 7.846  -12.995 8.314  -5.263 1.762  -0.690 H161 165 71 
165 H162 2H16 H 0 0 N N N 7.988  -12.366 9.883  -3.932 2.763  -1.318 H162 165 72 
165 H171 1H17 H 0 0 N N N 10.026 -13.886 9.298  -4.388 -0.188 -1.946 H171 165 73 
165 H172 2H17 H 0 0 N N N 9.019  -15.225 8.991  -3.159 0.457  -0.833 H172 165 74 
# 
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 
165 N19 C23  SING N N 1  
165 N19 C20  SING N N 2  
165 N19 C18  SING N N 3  
165 C23 C22  SING N N 4  
165 C23 C24  SING N N 5  
165 C23 H23  SING N N 6  
165 C22 C21  SING N N 7  
165 C22 H221 SING N N 8  
165 C22 H222 SING N N 9  
165 C21 C20  SING N N 10 
165 C21 H211 SING N N 11 
165 C21 H212 SING N N 12 
165 C20 H201 SING N N 13 
165 C20 H202 SING N N 14 
165 C24 O39  DOUB N N 15 
165 C24 N25  SING N N 16 
165 N25 C26  SING N N 17 
165 N25 H25  SING N N 18 
165 C26 C31  DOUB Y N 19 
165 C26 C27  SING Y N 20 
165 C31 C30  SING Y N 21 
165 C31 H31  SING N N 22 
165 C30 S34  SING Y N 23 
165 C30 C29  DOUB Y N 24 
165 S34 C33  SING Y N 25 
165 C33 N35  SING N N 26 
165 C33 N32  DOUB Y N 27 
165 N35 H351 SING N N 28 
165 N35 H352 SING N N 29 
165 N32 C29  SING Y N 30 
165 C29 C28  SING Y N 31 
165 C28 C27  DOUB Y N 32 
165 C28 H28  SING N N 33 
165 C27 H27  SING N N 34 
165 C18 O38  DOUB N N 35 
165 C18 C10  SING N N 36 
165 C10 N9   SING N N 37 
165 C10 C11  SING N N 38 
165 C10 H10  SING N N 39 
165 N9  S8   SING N N 40 
165 N9  HN9  SING N N 41 
165 S8  O36  DOUB N N 42 
165 S8  O37  DOUB N N 43 
165 S8  C7   SING N N 44 
165 C7  C5   SING N N 45 
165 C7  H71  SING N N 46 
165 C7  H72  SING N N 47 
165 C5  C6   SING Y N 48 
165 C5  C4   DOUB Y N 49 
165 C6  C1   DOUB Y N 50 
165 C6  H6   SING N N 51 
165 C1  C2   SING Y N 52 
165 C1  H1   SING N N 53 
165 C2  C3   DOUB Y N 54 
165 C2  H2   SING N N 55 
165 C3  C4   SING Y N 56 
165 C3  H3   SING N N 57 
165 C4  H4   SING N N 58 
165 C11 C12  SING N N 59 
165 C11 H111 SING N N 60 
165 C11 H112 SING N N 61 
165 C12 C13  SING N N 62 
165 C12 C17  SING N N 63 
165 C12 H12  SING N N 64 
165 C13 C14  SING N N 65 
165 C13 H131 SING N N 66 
165 C13 H132 SING N N 67 
165 C14 C15  SING N N 68 
165 C14 H141 SING N N 69 
165 C14 H142 SING N N 70 
165 C15 C16  SING N N 71 
165 C15 H151 SING N N 72 
165 C15 H152 SING N N 73 
165 C16 C17  SING N N 74 
165 C16 H161 SING N N 75 
165 C16 H162 SING N N 76 
165 C17 H171 SING N N 77 
165 C17 H172 SING N N 78 
# 
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 
165 SMILES           ACDLabs              10.04 O=S(=O)(NC(C(=O)N1CCCC1C(=O)Nc2ccc3nc(sc3c2)N)CC4CCCCC4)Cc5ccccc5 
165 InChI            InChI                1.02b 
InChI=1/C28H35N5O4S2/c29-28-31-22-14-13-21(17-25(22)38-28)30-26(34)24-12-7-15-33(24)27(35)23(16-19-8-3-1-4-9-19)32-39(36,37)18-20-10-5-2-6-11-20/h2,5-6,10-11,13-14,17,19,23-24,32H,1,3-4,7-9,12,15-16,18H2,(H2,29,31)(H,30,34)/t23-,24+/m1/s1/f/h30H,29H2 
165 InChIKey         InChI                1.02b HDSAIJKTEVRQHF-XIWQTDMHDM 
165 SMILES_CANONICAL CACTVS               3.341 Nc1sc2cc(NC(=O)[C@@H]3CCCN3C(=O)[C@@H](CC4CCCCC4)N[S](=O)(=O)Cc5ccccc5)ccc2n1 
165 SMILES           CACTVS               3.341 Nc1sc2cc(NC(=O)[CH]3CCCN3C(=O)[CH](CC4CCCCC4)N[S](=O)(=O)Cc5ccccc5)ccc2n1 
165 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CS(=O)(=O)N[C@H](CC2CCCCC2)C(=O)N3CCC[C@H]3C(=O)Nc4ccc5c(c4)sc(n5)N 
165 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CS(=O)(=O)NC(CC2CCCCC2)C(=O)N3CCCC3C(=O)Nc4ccc5c(c4)sc(n5)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 
165 "SYSTEMATIC NAME" ACDLabs              10.04 N-(benzylsulfonyl)-3-cyclohexyl-D-alanyl-N-(2-amino-1,3-benzothiazol-6-yl)-L-prolinamide                                     
165 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-N-(2-amino-1,3-benzothiazol-6-yl)-1-[(2R)-3-cyclohexyl-2-(phenylmethylsulfonylamino)propanoyl]pyrrolidine-2-carboxamide 
# 
