data_TPV
# 
_chem_comp.id                                    TPV 
_chem_comp.name                                  N-(3-{(1R)-1-[(6R)-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-5,6-DIHYDRO-2H-PYRAN-3-YL]PROPYL}PHENYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C31 H33 F3 N2 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         TIPRANAVIR 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-10-06 
_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                        602.664 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TPV 
_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        1D4Y 
_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 
TPV O1   O1   O 0 1 N N N 13.549 21.422 6.078  -1.186 1.261  3.775  O1   TPV 1  
TPV C2   C2   C 0 1 N N N 12.487 22.202 6.119  -0.423 0.662  2.849  C2   TPV 2  
TPV C3   C3   C 0 1 N N N 12.547 23.548 5.488  -0.602 -0.684 2.469  C3   TPV 3  
TPV C4   C4   C 0 1 N N N 13.803 23.939 4.984  -1.507 -1.454 3.107  C4   TPV 4  
TPV C5   C5   C 0 1 N N N 15.030 23.252 5.600  -2.302 -0.831 4.233  C5   TPV 5  
TPV C6   C6   C 0 1 N N R 14.898 22.024 5.886  -1.476 0.324  4.810  C6   TPV 6  
TPV O7   O7   O 0 1 N N N 11.438 21.718 6.484  0.459  1.306  2.315  O7   TPV 7  
TPV O8   O8   O 0 1 N N N 13.993 25.128 4.403  -1.698 -2.741 2.752  O8   TPV 8  
TPV C9   C9   C 0 1 N N N 15.673 21.224 4.793  -2.272 1.017  5.917  C9   TPV 9  
TPV C10  C10  C 0 1 N N N 14.930 20.787 3.808  -3.580 1.562  5.341  C10  TPV 10 
TPV C11  C11  C 0 1 N N N 15.304 19.611 2.940  -4.376 2.255  6.448  C11  TPV 11 
TPV C12  C12  C 0 1 N N N 15.023 21.558 7.303  -0.168 -0.220 5.386  C12  TPV 12 
TPV C13  C13  C 0 1 N N N 16.369 21.839 7.800  0.657  0.934  5.957  C13  TPV 13 
TPV C14  C14  C 0 1 Y N N 17.153 21.043 8.713  1.987  0.411  6.436  C14  TPV 14 
TPV C15  C15  C 0 1 Y N N 16.659 20.012 9.507  3.095  0.482  5.612  C15  TPV 15 
TPV C16  C16  C 0 1 Y N N 17.530 19.281 10.340 4.315  0.003  6.051  C16  TPV 16 
TPV C17  C17  C 0 1 Y N N 18.909 19.597 10.374 4.427  -0.546 7.315  C17  TPV 17 
TPV C18  C18  C 0 1 Y N N 19.422 20.606 9.518  3.319  -0.616 8.139  C18  TPV 18 
TPV C19  C19  C 0 1 Y N N 18.502 21.476 8.905  2.100  -0.133 7.701  C19  TPV 19 
TPV C20  C20  C 0 1 N N S 11.228 24.207 5.108  0.219  -1.264 1.347  C20  TPV 20 
TPV C21  C21  C 0 1 N N N 10.591 24.700 3.760  1.705  -1.059 1.644  C21  TPV 21 
TPV C22  C22  C 0 1 N N N 10.588 23.794 2.551  2.122  -1.962 2.806  C22  TPV 22 
TPV C23  C23  C 0 1 Y N N 10.829 25.104 6.300  -0.135 -0.572 0.055  C23  TPV 23 
TPV C24  C24  C 0 1 Y N N 11.751 25.555 7.216  0.395  0.672  -0.228 C24  TPV 24 
TPV C25  C25  C 0 1 Y N N 11.369 26.489 8.219  0.073  1.311  -1.411 C25  TPV 25 
TPV C26  C26  C 0 1 Y N N 9.996  26.746 8.414  -0.780 0.706  -2.314 C26  TPV 26 
TPV C27  C27  C 0 1 Y N N 9.078  26.343 7.449  -1.314 -0.543 -2.031 C27  TPV 27 
TPV N28  N28  N 0 1 N N N 7.369  26.738 7.833  -2.177 -1.157 -2.942 N28  TPV 28 
TPV C29  C29  C 0 1 Y N N 9.507  25.585 6.353  -0.984 -1.184 -0.844 C29  TPV 29 
TPV S30  S30  S 0 1 N N N 6.964  28.046 6.989  -2.565 -0.394 -4.359 S30  TPV 30 
TPV O31  O31  O 0 1 N N N 8.002  29.091 7.303  -3.302 -1.342 -5.119 O31  TPV 31 
TPV O32  O32  O 0 1 N N N 5.612  28.368 7.312  -3.024 0.898  -3.989 O32  TPV 32 
TPV C33  C33  C 0 1 Y N N 7.125  27.667 5.296  -1.064 -0.134 -5.245 C33  TPV 33 
TPV N34  N34  N 0 1 Y N N 8.271  28.067 4.676  -0.385 0.981  -5.064 N34  TPV 34 
TPV C35  C35  C 0 1 Y N N 8.381  27.822 3.363  0.744  1.216  -5.701 C35  TPV 35 
TPV C36  C36  C 0 1 Y N N 7.436  27.088 2.635  1.255  0.297  -6.597 C36  TPV 36 
TPV C37  C37  C 0 1 Y N N 6.239  26.749 3.244  0.566  -0.885 -6.818 C37  TPV 37 
TPV C38  C38  C 0 1 Y N N 6.079  27.045 4.620  -0.615 -1.100 -6.126 C38  TPV 38 
TPV C39  C39  C 0 1 N N N 7.727  26.758 1.174  2.545  0.577  -7.325 C39  TPV 39 
TPV F40  F40  F 0 1 N N N 8.386  27.915 0.673  3.041  1.825  -6.933 F40  TPV 40 
TPV F41  F41  F 0 1 N N N 6.501  26.511 0.569  3.480  -0.415 -7.014 F41  TPV 41 
TPV F42  F42  F 0 1 N N N 8.595  25.636 1.227  2.310  0.581  -8.705 F42  TPV 42 
TPV H51  1H5  H 0 1 N N N 15.914 23.391 4.935  -2.487 -1.574 5.009  H51  TPV 43 
TPV H52  2H5  H 0 1 N N N 15.365 23.815 6.501  -3.250 -0.452 3.850  H52  TPV 44 
TPV HO81 1HO8 H 0 0 N N N 14.840 25.391 4.063  -1.244 -3.101 1.978  HO81 TPV 45 
TPV H91  1H9  H 0 1 N N N 16.522 21.829 4.398  -1.685 1.840  6.326  H91  TPV 46 
TPV H92  2H9  H 0 1 N N N 16.236 20.381 5.256  -2.494 0.301  6.708  H92  TPV 47 
TPV H101 1H10 H 0 0 N N N 13.916 20.580 4.225  -4.167 0.740  4.932  H101 TPV 48 
TPV H102 2H10 H 0 0 N N N 14.739 21.651 3.129  -3.358 2.279  4.550  H102 TPV 49 
TPV H111 1H11 H 0 0 N N N 14.671 19.238 2.100  -5.308 2.643  6.038  H111 TPV 50 
TPV H112 2H11 H 0 0 N N N 16.317 19.817 2.522  -4.598 1.539  7.239  H112 TPV 51 
TPV H113 3H11 H 0 0 N N N 15.494 18.747 3.618  -3.789 3.077  6.858  H113 TPV 52 
TPV H121 1H12 H 0 0 N N N 14.234 21.994 7.959  -0.390 -0.935 6.179  H121 TPV 53 
TPV H122 2H12 H 0 0 N N N 14.750 20.482 7.416  0.397  -0.716 4.597  H122 TPV 54 
TPV H131 1H13 H 0 0 N N N 17.005 21.980 6.895  0.819  1.683  5.181  H131 TPV 55 
TPV H132 2H13 H 0 0 N N N 16.322 22.859 8.247  0.122  1.385  6.792  H132 TPV 56 
TPV H151 1H15 H 0 0 N N N 15.582 19.775 9.476  3.007  0.912  4.625  H151 TPV 57 
TPV H161 1H16 H 0 0 N N N 17.133 18.462 10.964 5.180  0.057  5.407  H161 TPV 58 
TPV H171 1H17 H 0 0 N N N 19.580 19.059 11.064 5.380  -0.921 7.658  H171 TPV 59 
TPV H181 1H18 H 0 0 N N N 20.504 20.711 9.334  3.407  -1.046 9.126  H181 TPV 60 
TPV H191 1H19 H 0 0 N N N 18.831 22.477 8.581  1.235  -0.188 8.345  H191 TPV 61 
TPV H201 1H20 H 0 0 N N N 10.802 23.235 4.765  0.010  -2.330 1.256  H201 TPV 62 
TPV H211 1H21 H 0 0 N N N 9.542  25.022 3.962  2.291  -1.310 0.760  H211 TPV 63 
TPV H212 2H21 H 0 0 N N N 11.070 25.665 3.475  1.882  -0.017 1.912  H212 TPV 64 
TPV H221 1H22 H 0 0 N N N 10.135 24.144 1.593  3.174  -1.794 3.038  H221 TPV 65 
TPV H222 2H22 H 0 0 N N N 11.636 23.471 2.348  1.516  -1.731 3.682  H222 TPV 66 
TPV H223 3H22 H 0 0 N N N 10.108 22.828 2.835  1.973  -3.005 2.527  H223 TPV 67 
TPV H241 1H24 H 0 0 N N N 12.783 25.172 7.147  1.063  1.147  0.475  H241 TPV 68 
TPV H251 1H25 H 0 0 N N N 12.124 27.005 8.835  0.488  2.283  -1.630 H251 TPV 69 
TPV H261 1H26 H 0 0 N N N 9.640  27.262 9.321  -1.032 1.206  -3.237 H261 TPV 70 
TPV H281 1H28 H 0 0 N N N 7.203  26.845 8.833  -2.550 -2.031 -2.744 H281 TPV 71 
TPV H291 1H29 H 0 0 N N N 8.803  25.366 5.531  -1.397 -2.157 -0.621 H291 TPV 72 
TPV H351 1H35 H 0 0 N N N 9.275  28.236 2.867  1.274  2.140  -5.523 H351 TPV 73 
TPV H371 1H37 H 0 0 N N N 5.443  26.261 2.655  0.942  -1.622 -7.513 H371 TPV 74 
TPV H381 1H38 H 0 0 N N N 5.150  26.793 5.159  -1.177 -2.010 -6.273 H381 TPV 75 
# 
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 
TPV O1  C2   SING N N 1  
TPV O1  C6   SING N N 2  
TPV C2  C3   SING N N 3  
TPV C2  O7   DOUB N N 4  
TPV C3  C4   DOUB N N 5  
TPV C3  C20  SING N N 6  
TPV C4  C5   SING N N 7  
TPV C4  O8   SING N N 8  
TPV C5  C6   SING N N 9  
TPV C5  H51  SING N N 10 
TPV C5  H52  SING N N 11 
TPV C6  C9   SING N N 12 
TPV C6  C12  SING N N 13 
TPV O8  HO81 SING N N 14 
TPV C9  C10  SING N N 15 
TPV C9  H91  SING N N 16 
TPV C9  H92  SING N N 17 
TPV C10 C11  SING N N 18 
TPV C10 H101 SING N N 19 
TPV C10 H102 SING N N 20 
TPV C11 H111 SING N N 21 
TPV C11 H112 SING N N 22 
TPV C11 H113 SING N N 23 
TPV C12 C13  SING N N 24 
TPV C12 H121 SING N N 25 
TPV C12 H122 SING N N 26 
TPV C13 C14  SING N N 27 
TPV C13 H131 SING N N 28 
TPV C13 H132 SING N N 29 
TPV C14 C15  DOUB Y N 30 
TPV C14 C19  SING Y N 31 
TPV C15 C16  SING Y N 32 
TPV C15 H151 SING N N 33 
TPV C16 C17  DOUB Y N 34 
TPV C16 H161 SING N N 35 
TPV C17 C18  SING Y N 36 
TPV C17 H171 SING N N 37 
TPV C18 C19  DOUB Y N 38 
TPV C18 H181 SING N N 39 
TPV C19 H191 SING N N 40 
TPV C20 C21  SING N N 41 
TPV C20 C23  SING N N 42 
TPV C20 H201 SING N N 43 
TPV C21 C22  SING N N 44 
TPV C21 H211 SING N N 45 
TPV C21 H212 SING N N 46 
TPV C22 H221 SING N N 47 
TPV C22 H222 SING N N 48 
TPV C22 H223 SING N N 49 
TPV C23 C24  DOUB Y N 50 
TPV C23 C29  SING Y N 51 
TPV C24 C25  SING Y N 52 
TPV C24 H241 SING N N 53 
TPV C25 C26  DOUB Y N 54 
TPV C25 H251 SING N N 55 
TPV C26 C27  SING Y N 56 
TPV C26 H261 SING N N 57 
TPV C27 N28  SING N N 58 
TPV C27 C29  DOUB Y N 59 
TPV N28 S30  SING N N 60 
TPV N28 H281 SING N N 61 
TPV C29 H291 SING N N 62 
TPV S30 O31  DOUB N N 63 
TPV S30 O32  DOUB N N 64 
TPV S30 C33  SING N N 65 
TPV C33 N34  DOUB Y N 66 
TPV C33 C38  SING Y N 67 
TPV N34 C35  SING Y N 68 
TPV C35 C36  DOUB Y N 69 
TPV C35 H351 SING N N 70 
TPV C36 C37  SING Y N 71 
TPV C36 C39  SING N N 72 
TPV C37 C38  DOUB Y N 73 
TPV C37 H371 SING N N 74 
TPV C38 H381 SING N N 75 
TPV C39 F40  SING N N 76 
TPV C39 F41  SING N N 77 
TPV C39 F42  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 
TPV SMILES           ACDLabs              10.04 FC(F)(F)c1ccc(nc1)S(=O)(=O)Nc2cccc(c2)C(C=3C(=O)OC(CCC)(CC=3O)CCc4ccccc4)CC 
TPV InChI            InChI                1.02b 
InChI=1/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1 
TPV InChIKey         InChI                1.02b SUJUHGSWHZTSEU-FYBSXPHGBO 
TPV SMILES_CANONICAL CACTVS               3.341 CCC[C@@]1(CCc2ccccc2)CC(=C([C@H](CC)c3cccc(N[S](=O)(=O)c4ccc(cn4)C(F)(F)F)c3)C(=O)O1)O 
TPV SMILES           CACTVS               3.341 CCC[C]1(CCc2ccccc2)CC(=C([CH](CC)c3cccc(N[S](=O)(=O)c4ccc(cn4)C(F)(F)F)c3)C(=O)O1)O 
TPV SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC[C@]1(CC(=C(C(=O)O1)[C@H](CC)c2cccc(c2)NS(=O)(=O)c3ccc(cn3)C(F)(F)F)O)CCc4ccccc4 
TPV SMILES           "OpenEye OEToolkits" 1.5.0 CCCC1(CC(=C(C(=O)O1)C(CC)c2cccc(c2)NS(=O)(=O)c3ccc(cn3)C(F)(F)F)O)CCc4ccccc4 
# 
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 
TPV "SYSTEMATIC NAME" ACDLabs              10.04 N-(3-{(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-5,6-dihydro-2H-pyran-3-yl]propyl}phenyl)-5-(trifluoromethyl)pyridine-2-sulfonamide 
TPV "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide                   
# 
