data_23L
# 
_chem_comp.id                                    23L 
_chem_comp.name                                  "(3S)-tetrahydrofuran-3-yl {(2S,3R)-4-[(4R)-7-fluoro-1,1-dioxido-4-(propan-2-yl)-4,5-dihydro-1,2-benzothiazepin-2(3H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H35 F N2 O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-08-26 
_chem_comp.pdbx_modified_date                    2014-03-28 
_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                        534.640 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     23L 
_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        4MC9 
_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 
23L C1  C1  C 0 1 Y N N 16.439 18.623 2.033  3.107  3.430  1.525  C1  23L 1  
23L C2  C2  C 0 1 Y N N 17.472 18.357 2.902  3.432  3.723  0.211  C2  23L 2  
23L C3  C3  C 0 1 Y N N 17.382 18.653 4.246  3.671  2.706  -0.686 C3  23L 3  
23L C4  C4  C 0 1 Y N N 16.258 19.269 4.768  3.621  1.365  -0.296 C4  23L 4  
23L C5  C5  C 0 1 Y N N 15.229 19.519 3.879  3.351  1.094  1.031  C5  23L 5  
23L C6  C6  C 0 1 Y N N 15.293 19.199 2.538  3.072  2.110  1.926  C6  23L 6  
23L F7  F7  F 0 1 N N N 18.589 17.792 2.425  3.513  5.010  -0.193 F7  23L 7  
23L C8  C8  C 0 1 N N N 16.186 19.558 6.244  3.785  0.371  -1.425 C8  23L 8  
23L S9  S9  S 0 1 N N N 13.725 20.233 4.465  3.384  -0.570 1.606  S9  23L 9  
23L N10 N10 N 0 1 N N N 14.195 21.668 5.207  2.535  -1.458 0.488  N10 23L 10 
23L O11 O11 O 0 1 N N N 12.899 20.549 3.329  4.735  -1.001 1.523  O11 23L 11 
23L O12 O12 O 0 1 N N N 13.212 19.349 5.486  2.625  -0.599 2.807  O12 23L 12 
23L C13 C13 C 0 1 N N N 14.493 22.849 4.373  1.103  -1.721 0.651  C13 23L 13 
23L C14 C14 C 0 1 N N N 14.762 21.593 6.561  3.263  -1.957 -0.642 C14 23L 14 
23L C15 C15 C 0 1 N N R 16.169 21.030 6.625  4.390  -0.960 -0.997 C15 23L 15 
23L C16 C16 C 0 1 N N N 16.630 21.221 8.069  5.231  -1.529 -2.142 C16 23L 16 
23L C17 C17 C 0 1 N N R 13.519 23.970 4.678  0.301  -0.675 -0.125 C17 23L 17 
23L C18 C18 C 0 1 N N S 12.038 23.723 4.401  -1.192 -0.873 0.145  C18 23L 18 
23L O19 O19 O 0 1 N N N 13.957 25.176 4.064  0.555  -0.821 -1.524 O19 23L 19 
23L N20 N20 N 0 1 N N N 11.294 24.769 5.060  -1.952 0.199  -0.502 N20 23L 20 
23L C21 C21 C 0 1 N N N 11.635 23.616 2.933  -1.637 -2.225 -0.419 C21 23L 21 
23L C22 C22 C 0 1 Y N N 10.183 23.319 2.795  -3.076 -2.475 -0.046 C22 23L 22 
23L C23 C23 C 0 1 Y N N 9.722  22.025 2.962  -4.090 -2.052 -0.885 C23 23L 23 
23L C24 C24 C 0 1 Y N N 8.374  21.767 2.854  -5.410 -2.281 -0.543 C24 23L 24 
23L C25 C25 C 0 1 Y N N 7.497  22.798 2.595  -5.715 -2.933 0.637  C25 23L 25 
23L C26 C26 C 0 1 Y N N 7.948  24.085 2.428  -4.701 -3.356 1.475  C26 23L 26 
23L C27 C27 C 0 1 Y N N 9.299  24.346 2.516  -3.381 -3.132 1.131  C27 23L 27 
23L C28 C28 C 0 1 N N N 10.591 24.559 6.212  -3.165 0.547  -0.027 C28 23L 28 
23L O29 O29 O 0 1 N N N 9.934  25.695 6.571  -3.863 1.532  -0.621 O29 23L 29 
23L O30 O30 O 0 1 N N N 10.547 23.524 6.853  -3.628 -0.030 0.937  O30 23L 30 
23L C31 C31 C 0 1 N N S 9.263  25.645 7.838  -5.162 1.853  -0.057 C31 23L 31 
23L C32 C32 C 0 1 N N N 8.358  26.854 7.869  -6.277 1.035  -0.743 C32 23L 32 
23L O33 O33 O 0 1 N N N 9.187  27.891 8.377  -7.400 1.904  -0.928 O33 23L 33 
23L C34 C34 C 0 1 N N N 9.953  27.298 9.414  -7.113 3.201  -0.380 C34 23L 34 
23L C35 C35 C 0 1 N N N 10.253 25.903 8.952  -5.568 3.313  -0.397 C35 23L 35 
23L C36 C36 C 0 1 N N N 18.100 21.010 8.331  6.400  -0.586 -2.433 C36 23L 36 
23L C37 C37 C 0 1 N N N 16.294 22.584 8.619  5.771  -2.904 -1.744 C37 23L 37 
23L H1  H1  H 0 1 N N N 16.524 18.387 0.983  2.890  4.222  2.226  H1  23L 38 
23L H2  H2  H 0 1 N N N 18.202 18.400 4.902  3.902  2.949  -1.713 H2  23L 39 
23L H3  H3  H 0 1 N N N 14.452 19.398 1.890  2.823  1.868  2.950  H3  23L 40 
23L H4  H4  H 0 1 N N N 15.267 19.097 6.635  2.806  0.181  -1.866 H4  23L 41 
23L H5  H5  H 0 1 N N N 17.061 19.095 6.723  4.426  0.814  -2.188 H5  23L 42 
23L H6  H6  H 0 1 N N N 14.408 22.574 3.311  0.870  -2.715 0.269  H6  23L 43 
23L H7  H7  H 0 1 N N N 15.517 23.192 4.582  0.841  -1.669 1.708  H7  23L 44 
23L H8  H8  H 0 1 N N N 14.779 22.609 6.983  3.697  -2.927 -0.398 H8  23L 45 
23L H9  H9  H 0 1 N N N 14.108 20.953 7.172  2.589  -2.063 -1.492 H9  23L 46 
23L H10 H10 H 0 1 N N N 16.827 21.596 5.949  5.025  -0.806 -0.124 H10 23L 47 
23L H11 H11 H 0 1 N N N 16.085 20.484 8.677  4.611  -1.626 -3.034 H11 23L 48 
23L H12 H12 H 0 1 N N N 13.588 24.130 5.764  0.598  0.323  0.196  H12 23L 49 
23L H13 H13 H 0 1 N N N 11.776 22.767 4.877  -1.373 -0.850 1.219  H13 23L 50 
23L H14 H14 H 0 1 N N N 13.342 25.873 4.260  0.314  -1.687 -1.879 H14 23L 51 
23L H15 H15 H 0 1 N N N 11.293 25.684 4.657  -1.583 0.660  -1.271 H15 23L 52 
23L H16 H16 H 0 1 N N N 12.213 22.809 2.460  -1.539 -2.216 -1.504 H16 23L 53 
23L H17 H17 H 0 1 N N N 11.856 24.569 2.430  -1.012 -3.015 -0.004 H17 23L 54 
23L H18 H18 H 0 1 N N N 10.414 21.224 3.175  -3.852 -1.543 -1.807 H18 23L 55 
23L H19 H19 H 0 1 N N N 8.005  20.759 2.972  -6.203 -1.951 -1.198 H19 23L 56 
23L H20 H20 H 0 1 N N N 6.439  22.591 2.522  -6.746 -3.112 0.904  H20 23L 57 
23L H21 H21 H 0 1 N N N 7.250  24.885 2.230  -4.939 -3.870 2.395  H21 23L 58 
23L H22 H22 H 0 1 N N N 9.667  25.351 2.367  -2.588 -3.463 1.786  H22 23L 59 
23L H23 H23 H 0 1 N N N 8.705  24.710 7.994  -5.166 1.687  1.021  H23 23L 60 
23L H24 H24 H 0 1 N N N 7.999  27.100 6.859  -5.927 0.672  -1.709 H24 23L 61 
23L H25 H25 H 0 1 N N N 7.497  26.681 8.532  -6.560 0.193  -0.111 H25 23L 62 
23L H26 H26 H 0 1 N N N 10.886 27.859 9.570  -7.556 3.980  -1.001 H26 23L 63 
23L H27 H27 H 0 1 N N N 9.377  27.276 10.351 -7.488 3.272  0.641  H27 23L 64 
23L H28 H28 H 0 1 N N N 10.110 25.184 9.772  -5.216 4.007  0.367  H28 23L 65 
23L H29 H29 H 0 1 N N N 11.285 25.832 8.578  -5.205 3.602  -1.384 H29 23L 66 
23L H30 H30 H 0 1 N N N 18.310 21.174 9.398  6.957  -0.404 -1.514 H30 23L 67 
23L H31 H31 H 0 1 N N N 18.377 19.981 8.057  7.058  -1.042 -3.173 H31 23L 68 
23L H32 H32 H 0 1 N N N 18.685 21.720 7.729  6.018  0.358  -2.819 H32 23L 69 
23L H33 H33 H 0 1 N N N 16.650 22.659 9.657  6.390  -2.807 -0.852 H33 23L 70 
23L H34 H34 H 0 1 N N N 16.782 23.357 8.007  4.938  -3.576 -1.536 H34 23L 71 
23L H35 H35 H 0 1 N N N 15.204 22.731 8.594  6.370  -3.309 -2.559 H35 23L 72 
# 
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 
23L C1  C6  DOUB Y N 1  
23L C1  C2  SING Y N 2  
23L F7  C2  SING N N 3  
23L C26 C27 DOUB Y N 4  
23L C26 C25 SING Y N 5  
23L C27 C22 SING Y N 6  
23L C6  C5  SING Y N 7  
23L C25 C24 DOUB Y N 8  
23L C22 C21 SING N N 9  
23L C22 C23 DOUB Y N 10 
23L C24 C23 SING Y N 11 
23L C2  C3  DOUB Y N 12 
23L C21 C18 SING N N 13 
23L O11 S9  DOUB N N 14 
23L C5  S9  SING N N 15 
23L C5  C4  DOUB Y N 16 
23L O19 C17 SING N N 17 
23L C3  C4  SING Y N 18 
23L C13 C17 SING N N 19 
23L C13 N10 SING N N 20 
23L C18 C17 SING N N 21 
23L C18 N20 SING N N 22 
23L S9  N10 SING N N 23 
23L S9  O12 DOUB N N 24 
23L C4  C8  SING N N 25 
23L N20 C28 SING N N 26 
23L N10 C14 SING N N 27 
23L C28 O29 SING N N 28 
23L C28 O30 DOUB N N 29 
23L C8  C15 SING N N 30 
23L C14 C15 SING N N 31 
23L O29 C31 SING N N 32 
23L C15 C16 SING N N 33 
23L C31 C32 SING N N 34 
23L C31 C35 SING N N 35 
23L C32 O33 SING N N 36 
23L C16 C36 SING N N 37 
23L C16 C37 SING N N 38 
23L O33 C34 SING N N 39 
23L C35 C34 SING N N 40 
23L C1  H1  SING N N 41 
23L C3  H2  SING N N 42 
23L C6  H3  SING N N 43 
23L C8  H4  SING N N 44 
23L C8  H5  SING N N 45 
23L C13 H6  SING N N 46 
23L C13 H7  SING N N 47 
23L C14 H8  SING N N 48 
23L C14 H9  SING N N 49 
23L C15 H10 SING N N 50 
23L C16 H11 SING N N 51 
23L C17 H12 SING N N 52 
23L C18 H13 SING N N 53 
23L O19 H14 SING N N 54 
23L N20 H15 SING N N 55 
23L C21 H16 SING N N 56 
23L C21 H17 SING N N 57 
23L C23 H18 SING N N 58 
23L C24 H19 SING N N 59 
23L C25 H20 SING N N 60 
23L C26 H21 SING N N 61 
23L C27 H22 SING N N 62 
23L C31 H23 SING N N 63 
23L C32 H24 SING N N 64 
23L C32 H25 SING N N 65 
23L C34 H26 SING N N 66 
23L C34 H27 SING N N 67 
23L C35 H28 SING N N 68 
23L C35 H29 SING N N 69 
23L C36 H30 SING N N 70 
23L C36 H31 SING N N 71 
23L C36 H32 SING N N 72 
23L C37 H33 SING N N 73 
23L C37 H34 SING N N 74 
23L C37 H35 SING N N 75 
# 
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 
23L SMILES           ACDLabs              12.01 "O=C(OC1CCOC1)NC(Cc2ccccc2)C(O)CN4CC(Cc3c(ccc(F)c3)S4(=O)=O)C(C)C" 
23L InChI            InChI                1.03  
"InChI=1S/C27H35FN2O6S/c1-18(2)21-13-20-14-22(28)8-9-26(20)37(33,34)30(15-21)16-25(31)24(12-19-6-4-3-5-7-19)29-27(32)36-23-10-11-35-17-23/h3-9,14,18,21,23-25,31H,10-13,15-17H2,1-2H3,(H,29,32)/t21-,23-,24-,25+/m0/s1" 
23L InChIKey         InChI                1.03  NTBLOIDJWKXDON-BELIEFIBSA-N 
23L SMILES_CANONICAL CACTVS               3.385 "CC(C)[C@@H]1CN(C[C@@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]3CCOC3)[S](=O)(=O)c4ccc(F)cc4C1" 
23L SMILES           CACTVS               3.385 "CC(C)[CH]1CN(C[CH](O)[CH](Cc2ccccc2)NC(=O)O[CH]3CCOC3)[S](=O)(=O)c4ccc(F)cc4C1" 
23L SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC(C)[C@H]1Cc2cc(ccc2S(=O)(=O)N(C1)C[C@H]([C@H](Cc3ccccc3)NC(=O)O[C@H]4CCOC4)O)F" 
23L SMILES           "OpenEye OEToolkits" 1.7.6 "CC(C)C1Cc2cc(ccc2S(=O)(=O)N(C1)CC(C(Cc3ccccc3)NC(=O)OC4CCOC4)O)F" 
# 
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 
23L "SYSTEMATIC NAME" ACDLabs              12.01 "(3S)-tetrahydrofuran-3-yl {(2S,3R)-4-[(4R)-7-fluoro-1,1-dioxido-4-(propan-2-yl)-4,5-dihydro-1,2-benzothiazepin-2(3H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate"               
23L "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4R)-7-fluoranyl-1,1-bis(oxidanylidene)-4-propan-2-yl-4,5-dihydro-3H-1$l^{6},2-benzothiazepin-2-yl]-3-oxidanyl-1-phenyl-butan-2-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 
23L "Create component" 2013-08-26 RCSB 
23L "Initial release"  2014-04-02 RCSB 
# 
