data_5B5
# 
_chem_comp.id                                    5B5 
_chem_comp.name                                  "(3R,3aS,4S,7aS)-3-(ethylamino)hexahydro-4H-furo[2,3-b]pyran-4-yl [(2S,3R)-3-hydroxy-4-{[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino}-1-phenylbutan-2-yl]carbamate" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C31 H45 N3 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-08-31 
_chem_comp.pdbx_modified_date                    2015-10-23 
_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                        619.769 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5B5 
_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        5DGW 
_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 
5B5 C2  C1  C 0 1 Y N N 20.928 27.614 14.705 -7.405 1.565  1.201  C2  5B5 1  
5B5 C3  C2  C 0 1 Y N N 21.524 26.532 15.359 -7.668 0.212  1.040  C3  5B5 2  
5B5 C4  C3  C 0 1 Y N N 20.738 25.454 15.758 -6.631 -0.700 1.075  C4  5B5 3  
5B5 C5  C4  C 0 1 Y N N 19.368 25.462 15.540 -5.333 -0.267 1.270  C5  5B5 4  
5B5 C6  C5  C 0 1 Y N N 18.800 26.498 14.802 -5.068 1.081  1.431  C6  5B5 5  
5B5 C7  C6  C 0 1 Y N N 19.571 27.597 14.411 -6.101 1.997  1.397  C7  5B5 6  
5B5 S8  S1  S 0 1 N N N 18.375 24.078 15.955 -4.013 -1.433 1.314  S8  5B5 7  
5B5 O9  O1  O 0 1 N N N 17.305 23.972 14.912 -3.024 -0.887 2.175  O9  5B5 8  
5B5 O10 O2  O 0 1 N N N 19.236 22.847 15.965 -4.609 -2.706 1.523  O10 5B5 9  
5B5 N11 N1  N 0 1 N N N 17.693 24.180 17.433 -3.344 -1.474 -0.200 N11 5B5 10 
5B5 C12 C7  C 0 1 N N N 18.636 24.520 18.483 -3.762 -2.500 -1.159 C12 5B5 11 
5B5 C13 C8  C 0 1 N N N 18.349 23.773 19.791 -4.482 -1.837 -2.335 C13 5B5 12 
5B5 C14 C9  C 0 1 N N N 18.349 22.252 19.612 -4.844 -2.898 -3.375 C14 5B5 13 
5B5 C15 C10 C 0 1 N N N 19.391 24.155 20.853 -5.758 -1.157 -1.834 C15 5B5 14 
5B5 C16 C11 C 0 1 N N N 16.456 24.932 17.466 -2.334 -0.484 -0.581 C16 5B5 15 
5B5 C17 C12 C 0 1 N N R 15.279 24.052 17.869 -0.937 -1.063 -0.347 C17 5B5 16 
5B5 O18 O3  O 0 1 N N N 14.109 24.832 18.113 -0.729 -2.172 -1.223 O18 5B5 17 
5B5 C19 C13 C 0 1 N N S 14.990 22.908 16.892 0.115  0.012  -0.626 C19 5B5 18 
5B5 N20 N2  N 0 1 N N N 14.131 21.933 17.578 1.443  -0.505 -0.287 N20 5B5 19 
5B5 C21 C14 C 0 1 N N N 14.332 20.619 17.693 2.435  0.348  0.038  C21 5B5 20 
5B5 O22 O4  O 0 1 N N N 15.378 20.080 17.337 2.228  1.545  0.050  O22 5B5 21 
5B5 O23 O5  O 0 1 N N N 13.295 19.909 18.225 3.656  -0.127 0.349  O23 5B5 22 
5B5 C24 C15 C 0 1 N N S 13.539 18.504 18.327 4.676  0.849  0.689  C24 5B5 23 
5B5 C25 C16 C 0 1 N N N 12.555 18.651 20.599 5.778  2.082  2.536  C25 5B5 24 
5B5 O26 O6  O 0 1 N N N 11.361 17.984 20.198 7.017  1.474  2.179  O26 5B5 25 
5B5 C27 C17 C 0 1 N N S 11.122 17.972 18.805 7.193  1.187  0.791  C27 5B5 26 
5B5 O28 O7  O 0 1 N N N 10.553 19.202 18.346 8.321  0.275  0.705  O28 5B5 27 
5B5 C29 C18 C 0 1 N N N 10.617 19.166 16.927 7.847  -1.005 1.164  C29 5B5 28 
5B5 C30 C19 C 0 1 N N R 11.764 18.238 16.549 6.331  -1.058 0.876  C30 5B5 29 
5B5 C31 C20 C 0 1 N N S 12.299 17.744 17.897 6.030  0.323  0.262  C31 5B5 30 
5B5 C32 C21 C 0 1 N N N 14.216 23.395 15.658 0.077  0.390  -2.108 C32 5B5 31 
5B5 C33 C22 C 0 1 Y N N 12.509 21.890 14.545 2.342  1.278  -2.695 C33 5B5 32 
5B5 C34 C23 C 0 1 Y N N 12.153 20.807 13.740 3.211  2.328  -2.931 C34 5B5 33 
5B5 C35 C24 C 0 1 Y N N 13.144 20.065 13.106 2.764  3.632  -2.831 C35 5B5 34 
5B5 C36 C25 C 0 1 Y N N 14.486 20.386 13.299 1.447  3.886  -2.495 C36 5B5 35 
5B5 C37 C26 C 0 1 Y N N 14.835 21.462 14.119 0.578  2.838  -2.259 C37 5B5 36 
5B5 C38 C27 C 0 1 Y N N 13.848 22.212 14.744 1.026  1.533  -2.359 C38 5B5 37 
5B5 O39 O8  O 0 1 N N N 21.695 28.695 14.393 -8.422 2.465  1.162  O39 5B5 38 
5B5 C40 C28 C 0 1 N N N 22.941 28.624 15.093 -8.078 3.841  1.335  C40 5B5 39 
5B5 C51 C29 C 0 1 N N N 13.780 18.200 19.808 4.644  1.107  2.197  C51 5B5 40 
5B5 N52 N3  N 0 1 N N N 11.158 17.092 15.842 6.024  -2.128 -0.083 N52 5B5 41 
5B5 C53 C30 C 0 1 N N N 10.747 17.469 14.483 5.831  -3.411 0.605  C53 5B5 42 
5B5 C54 C31 C 0 1 N N N 10.731 16.214 13.592 5.514  -4.498 -0.424 C54 5B5 43 
5B5 H1  H1  H 0 1 N N N 22.586 26.532 15.553 -8.682 -0.127 0.888  H1  5B5 44 
5B5 H2  H2  H 0 1 N N N 21.199 24.605 16.241 -6.835 -1.753 0.950  H2  5B5 45 
5B5 H3  H3  H 0 1 N N N 17.756 26.452 14.530 -4.054 1.417  1.583  H3  5B5 46 
5B5 H4  H4  H 0 1 N N N 19.116 28.424 13.886 -5.894 3.050  1.523  H4  5B5 47 
5B5 H5  H5  H 0 1 N N N 19.650 24.262 18.144 -2.885 -3.034 -1.525 H5  5B5 48 
5B5 H6  H6  H 0 1 N N N 18.577 25.602 18.674 -4.437 -3.202 -0.669 H6  5B5 49 
5B5 H7  H7  H 0 1 N N N 17.357 24.079 20.154 -3.828 -1.092 -2.788 H7  5B5 50 
5B5 H8  H8  H 0 1 N N N 18.139 21.769 20.577 -5.498 -3.643 -2.922 H8  5B5 51 
5B5 H9  H9  H 0 1 N N N 17.575 21.969 18.884 -5.357 -2.425 -4.213 H9  5B5 52 
5B5 H10 H10 H 0 1 N N N 19.334 21.926 19.246 -3.935 -3.382 -3.732 H10 5B5 53 
5B5 H11 H11 H 0 1 N N N 19.178 23.615 21.787 -6.349 -1.872 -1.261 H11 5B5 54 
5B5 H12 H12 H 0 1 N N N 20.395 23.885 20.495 -5.494 -0.312 -1.198 H12 5B5 55 
5B5 H13 H13 H 0 1 N N N 19.346 25.239 21.037 -6.340 -0.804 -2.685 H13 5B5 56 
5B5 H14 H14 H 0 1 N N N 16.555 25.752 18.193 -2.450 -0.233 -1.636 H14 5B5 57 
5B5 H15 H15 H 0 1 N N N 16.265 25.350 16.466 -2.460 0.415  0.022  H15 5B5 58 
5B5 H16 H16 H 0 1 N N N 15.561 23.578 18.820 -0.851 -1.396 0.688  H16 5B5 59 
5B5 H17 H17 H 0 1 N N N 14.316 25.532 18.720 -0.791 -1.949 -2.162 H17 5B5 60 
5B5 H18 H18 H 0 1 N N N 15.934 22.440 16.577 -0.097 0.894  -0.021 H18 5B5 61 
5B5 H19 H19 H 0 1 N N N 13.303 22.295 18.007 1.609  -1.460 -0.297 H19 5B5 62 
5B5 H20 H20 H 0 1 N N N 14.408 18.195 17.727 4.471  1.780  0.162  H20 5B5 63 
5B5 H21 H21 H 0 1 N N N 12.731 18.446 21.665 5.769  2.296  3.605  H21 5B5 64 
5B5 H22 H22 H 0 1 N N N 12.420 19.733 20.451 5.645  3.007  1.975  H22 5B5 65 
5B5 H23 H23 H 0 1 N N N 10.399 17.171 18.594 7.346  2.092  0.202  H23 5B5 66 
5B5 H24 H24 H 0 1 N N N 10.804 20.176 16.533 8.355  -1.804 0.625  H24 5B5 67 
5B5 H25 H25 H 0 1 N N N 9.671  18.782 16.517 8.028  -1.105 2.234  H25 5B5 68 
5B5 H26 H26 H 0 1 N N N 12.538 18.749 15.957 5.769  -1.197 1.800  H26 5B5 69 
5B5 H27 H27 H 0 1 N N N 12.523 16.669 17.834 6.077  0.262  -0.825 H27 5B5 70 
5B5 H28 H28 H 0 1 N N N 14.842 24.104 15.096 0.376  -0.469 -2.710 H28 5B5 71 
5B5 H29 H29 H 0 1 N N N 13.294 23.899 15.985 -0.934 0.690  -2.381 H29 5B5 72 
5B5 H30 H30 H 0 1 N N N 11.739 22.483 15.017 2.691  0.260  -2.778 H30 5B5 73 
5B5 H31 H31 H 0 1 N N N 11.113 20.546 13.610 4.240  2.128  -3.194 H31 5B5 74 
5B5 H32 H32 H 0 1 N N N 12.873 19.240 12.464 3.442  4.451  -3.015 H32 5B5 75 
5B5 H33 H33 H 0 1 N N N 15.256 19.803 12.815 1.098  4.905  -2.415 H33 5B5 76 
5B5 H34 H34 H 0 1 N N N 15.875 21.711 14.267 -0.450 3.037  -1.997 H34 5B5 77 
5B5 H35 H35 H 0 1 N N N 23.556 29.499 14.837 -8.980 4.451  1.283  H35 5B5 78 
5B5 H36 H36 H 0 1 N N N 22.752 28.612 16.177 -7.604 3.977  2.307  H36 5B5 79 
5B5 H37 H37 H 0 1 N N N 23.472 27.705 14.803 -7.387 4.145  0.549  H37 5B5 80 
5B5 H38 H38 H 0 1 N N N 13.933 17.119 19.945 3.685  1.545  2.476  H38 5B5 81 
5B5 H39 H39 H 0 1 N N N 14.669 18.744 20.159 4.791  0.169  2.734  H39 5B5 82 
5B5 H40 H40 H 0 1 N N N 10.356 16.780 16.352 6.743  -2.199 -0.787 H40 5B5 83 
5B5 H42 H42 H 0 1 N N N 11.458 18.202 14.074 6.740  -3.675 1.144  H42 5B5 84 
5B5 H43 H43 H 0 1 N N N 9.741  17.912 14.513 5.003  -3.325 1.309  H43 5B5 85 
5B5 H44 H44 H 0 1 N N N 10.424 16.491 12.573 4.604  -4.234 -0.963 H44 5B5 86 
5B5 H45 H45 H 0 1 N N N 11.738 15.772 13.564 6.341  -4.584 -1.129 H45 5B5 87 
5B5 H46 H46 H 0 1 N N N 10.020 15.482 14.003 5.370  -5.451 0.086  H46 5B5 88 
# 
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 
5B5 C35 C36 DOUB Y N 1  
5B5 C35 C34 SING Y N 2  
5B5 C36 C37 SING Y N 3  
5B5 C54 C53 SING N N 4  
5B5 C34 C33 DOUB Y N 5  
5B5 C37 C38 DOUB Y N 6  
5B5 O39 C2  SING N N 7  
5B5 O39 C40 SING N N 8  
5B5 C7  C2  DOUB Y N 9  
5B5 C7  C6  SING Y N 10 
5B5 C53 N52 SING N N 11 
5B5 C33 C38 SING Y N 12 
5B5 C2  C3  SING Y N 13 
5B5 C38 C32 SING N N 14 
5B5 C6  C5  DOUB Y N 15 
5B5 O9  S8  DOUB N N 16 
5B5 C3  C4  DOUB Y N 17 
5B5 C5  C4  SING Y N 18 
5B5 C5  S8  SING N N 19 
5B5 C32 C19 SING N N 20 
5B5 N52 C30 SING N N 21 
5B5 S8  O10 DOUB N N 22 
5B5 S8  N11 SING N N 23 
5B5 C30 C29 SING N N 24 
5B5 C30 C31 SING N N 25 
5B5 C19 N20 SING N N 26 
5B5 C19 C17 SING N N 27 
5B5 C29 O28 SING N N 28 
5B5 O22 C21 DOUB N N 29 
5B5 N11 C16 SING N N 30 
5B5 N11 C12 SING N N 31 
5B5 C16 C17 SING N N 32 
5B5 N20 C21 SING N N 33 
5B5 C21 O23 SING N N 34 
5B5 C17 O18 SING N N 35 
5B5 C31 C24 SING N N 36 
5B5 C31 C27 SING N N 37 
5B5 O23 C24 SING N N 38 
5B5 C24 C51 SING N N 39 
5B5 O28 C27 SING N N 40 
5B5 C12 C13 SING N N 41 
5B5 C27 O26 SING N N 42 
5B5 C14 C13 SING N N 43 
5B5 C13 C15 SING N N 44 
5B5 C51 C25 SING N N 45 
5B5 O26 C25 SING N N 46 
5B5 C3  H1  SING N N 47 
5B5 C4  H2  SING N N 48 
5B5 C6  H3  SING N N 49 
5B5 C7  H4  SING N N 50 
5B5 C12 H5  SING N N 51 
5B5 C12 H6  SING N N 52 
5B5 C13 H7  SING N N 53 
5B5 C14 H8  SING N N 54 
5B5 C14 H9  SING N N 55 
5B5 C14 H10 SING N N 56 
5B5 C15 H11 SING N N 57 
5B5 C15 H12 SING N N 58 
5B5 C15 H13 SING N N 59 
5B5 C16 H14 SING N N 60 
5B5 C16 H15 SING N N 61 
5B5 C17 H16 SING N N 62 
5B5 O18 H17 SING N N 63 
5B5 C19 H18 SING N N 64 
5B5 N20 H19 SING N N 65 
5B5 C24 H20 SING N N 66 
5B5 C25 H21 SING N N 67 
5B5 C25 H22 SING N N 68 
5B5 C27 H23 SING N N 69 
5B5 C29 H24 SING N N 70 
5B5 C29 H25 SING N N 71 
5B5 C30 H26 SING N N 72 
5B5 C31 H27 SING N N 73 
5B5 C32 H28 SING N N 74 
5B5 C32 H29 SING N N 75 
5B5 C33 H30 SING N N 76 
5B5 C34 H31 SING N N 77 
5B5 C35 H32 SING N N 78 
5B5 C36 H33 SING N N 79 
5B5 C37 H34 SING N N 80 
5B5 C40 H35 SING N N 81 
5B5 C40 H36 SING N N 82 
5B5 C40 H37 SING N N 83 
5B5 C51 H38 SING N N 84 
5B5 C51 H39 SING N N 85 
5B5 N52 H40 SING N N 86 
5B5 C53 H42 SING N N 87 
5B5 C53 H43 SING N N 88 
5B5 C54 H44 SING N N 89 
5B5 C54 H45 SING N N 90 
5B5 C54 H46 SING N N 91 
# 
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 
5B5 SMILES           ACDLabs              12.01 "c4(ccc(S(=O)(N(CC(O)C(NC(OC1CCOC2OCC(C12)NCC)=O)Cc3ccccc3)CC(C)C)=O)cc4)OC" 
5B5 InChI            InChI                1.03  
"InChI=1S/C31H45N3O8S/c1-5-32-26-20-41-30-29(26)28(15-16-40-30)42-31(36)33-25(17-22-9-7-6-8-10-22)27(35)19-34(18-21(2)3)43(37,38)24-13-11-23(39-4)12-14-24/h6-14,21,25-30,32,35H,5,15-20H2,1-4H3,(H,33,36)/t25-,26-,27+,28-,29-,30-/m0/s1" 
5B5 InChIKey         InChI                1.03  FXVKEZICEPPSOS-BSEVETGLSA-N 
5B5 SMILES_CANONICAL CACTVS               3.385 "CCN[C@H]1CO[C@@H]2OCC[C@H](OC(=O)N[C@@H](Cc3ccccc3)[C@H](O)CN(CC(C)C)[S](=O)(=O)c4ccc(OC)cc4)[C@H]12" 
5B5 SMILES           CACTVS               3.385 "CCN[CH]1CO[CH]2OCC[CH](OC(=O)N[CH](Cc3ccccc3)[CH](O)CN(CC(C)C)[S](=O)(=O)c4ccc(OC)cc4)[CH]12" 
5B5 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCN[C@H]1CO[C@H]2[C@@H]1[C@H](CCO2)OC(=O)N[C@@H](Cc3ccccc3)[C@@H](CN(CC(C)C)S(=O)(=O)c4ccc(cc4)OC)O" 
5B5 SMILES           "OpenEye OEToolkits" 1.9.2 "CCNC1COC2C1C(CCO2)OC(=O)NC(Cc3ccccc3)C(CN(CC(C)C)S(=O)(=O)c4ccc(cc4)OC)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 
5B5 "SYSTEMATIC NAME" ACDLabs              12.01 "(3R,3aS,4S,7aS)-3-(ethylamino)hexahydro-4H-furo[2,3-b]pyran-4-yl [(2S,3R)-3-hydroxy-4-{[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino}-1-phenylbutan-2-yl]carbamate"                     
5B5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "[(3R,3aS,4S,7aS)-3-(ethylamino)-3,3a,4,5,6,7a-hexahydro-2H-furo[2,3-b]pyran-4-yl] N-[(2S,3R)-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-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 
5B5 "Create component" 2015-08-31 RCSB 
5B5 "Initial release"  2015-10-28 RCSB 
# 
