data_LGZ
# 
_chem_comp.id                                    LGZ 
_chem_comp.name                                  "CARBAMIC ACID 1-{5-BENZYL-5-[2-HYDROXY-4-PHENYL-3-(TETRAHYDRO-FURAN- 3-YLOXYCARBONYLAMINO)-BUTYL]-4-OXO-4,5-DIHYDRO-1H-PYRROL-3-YL}- INDAN-2-YL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C36 H39 N3 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "LGZ479 INHIBITOR" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-01-21 
_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                        625.711 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LGZ 
_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        1NPW 
_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 
LGZ O01 O01 O 0 1 N N N 16.359 20.230 4.858  4.906  -1.737 0.038  O01 LGZ 1  
LGZ C02 C02 C 0 1 N N N 15.289 20.848 5.226  4.055  -0.721 0.274  C02 LGZ 2  
LGZ O03 O03 O 0 1 N N N 14.215 20.333 5.151  4.329  0.122  1.105  O03 LGZ 3  
LGZ NP4 NP4 N 0 1 N N N 15.580 22.128 5.674  2.898  -0.639 -0.413 NP4 LGZ 4  
LGZ C05 C05 C 0 1 N N S 14.683 23.101 6.360  1.971  0.467  -0.157 C05 LGZ 5  
LGZ C06 C06 C 0 1 N N S 13.969 24.087 5.414  0.552  0.042  -0.540 C06 LGZ 6  
LGZ O07 O07 O 0 1 N N N 14.965 24.822 4.679  0.515  -0.299 -1.927 O07 LGZ 7  
LGZ C08 C08 C 0 1 N N N 13.208 23.351 4.234  0.140  -1.172 0.295  C08 LGZ 8  
LGZ C09 C09 C 0 1 N N S 11.912 24.124 3.833  -1.320 -1.520 0.003  C09 LGZ 9  
LGZ C10 C10 C 0 1 N N N 11.270 23.545 2.554  -1.769 -2.705 0.861  C10 LGZ 10 
LGZ C11 C11 C 0 1 Y N N 9.845  24.049 2.393  -3.185 -3.078 0.502  C11 LGZ 11 
LGZ C12 C12 C 0 1 Y N N 9.655  25.268 1.757  -3.422 -4.007 -0.494 C12 LGZ 12 
LGZ C13 C13 C 0 1 Y N N 8.414  25.791 1.575  -4.720 -4.349 -0.824 C13 LGZ 13 
LGZ C14 C14 C 0 1 Y N N 7.339  25.114 2.052  -5.781 -3.763 -0.158 C14 LGZ 14 
LGZ C15 C15 C 0 1 Y N N 7.524  23.888 2.686  -5.543 -2.834 0.838  C15 LGZ 15 
LGZ C16 C16 C 0 1 Y N N 8.764  23.348 2.870  -4.244 -2.495 1.171  C16 LGZ 16 
LGZ C17 C17 C 0 1 N N N 10.904 23.989 4.999  -2.206 -0.314 0.243  C17 LGZ 17 
LGZ O18 O18 O 0 1 N N N 10.542 22.929 5.451  -2.371 0.282  1.289  O18 LGZ 18 
LGZ C19 C19 C 0 1 N N S 9.525  25.500 6.535  -3.776 1.084  -1.252 C19 LGZ 19 
LGZ C20 C20 C 0 1 N N R 8.189  26.120 6.024  -3.151 2.440  -0.861 C20 LGZ 20 
LGZ O1  O1  O 0 1 N N N 8.576  27.284 5.255  -2.146 2.267  0.173  O1  LGZ 21 
LGZ C22 C22 C 0 1 N N N 7.444  26.654 7.260  -4.365 3.225  -0.320 C22 LGZ 22 
LGZ C23 C23 C 0 1 Y N N 8.637  27.161 8.010  -5.329 2.170  0.180  C23 LGZ 23 
LGZ C24 C24 C 0 1 Y N N 8.632  28.111 9.031  -6.414 2.278  1.034  C24 LGZ 24 
LGZ C25 C25 C 0 1 Y N N 9.822  28.370 9.688  -7.160 1.161  1.353  C25 LGZ 25 
LGZ C26 C26 C 0 1 Y N N 11.007 27.710 9.318  -6.824 -0.069 0.820  C26 LGZ 26 
LGZ C27 C27 C 0 1 Y N N 11.011 26.775 8.276  -5.742 -0.179 -0.031 C27 LGZ 27 
LGZ C28 C28 C 0 1 Y N N 9.817  26.507 7.623  -4.992 0.940  -0.353 C28 LGZ 28 
LGZ N29 N29 N 0 1 N N N 12.173 25.564 3.821  -1.502 -1.821 -1.426 N29 LGZ 29 
LGZ C30 C30 C 0 1 N N N 11.270 26.157 4.797  -2.378 -0.913 -1.929 C30 LGZ 30 
LGZ C35 C35 C 0 1 N N N 10.556 25.287 5.478  -2.803 -0.038 -0.997 C35 LGZ 31 
LGZ C36 C36 C 0 1 N N N 15.481 23.750 7.490  2.383  1.681  -0.992 C36 LGZ 32 
LGZ C37 C37 C 0 1 Y N N 16.046 22.646 8.405  3.730  2.175  -0.530 C37 LGZ 33 
LGZ C38 C38 C 0 1 Y N N 15.137 21.896 9.169  4.883  1.677  -1.107 C38 LGZ 34 
LGZ C39 C39 C 0 1 Y N N 15.579 20.792 9.916  6.119  2.130  -0.684 C39 LGZ 35 
LGZ C40 C40 C 0 1 Y N N 16.933 20.434 9.964  6.201  3.081  0.316  C40 LGZ 36 
LGZ C41 C41 C 0 1 Y N N 17.857 21.214 9.259  5.048  3.579  0.893  C41 LGZ 37 
LGZ C42 C42 C 0 1 Y N N 17.412 22.310 8.481  3.812  3.129  0.467  C42 LGZ 38 
LGZ C44 C44 C 0 1 N N S 16.397 19.188 3.924  6.153  -1.826 0.778  C44 LGZ 39 
LGZ C45 C45 C 0 1 N N N 17.558 18.269 3.874  7.296  -1.141 -0.004 C45 LGZ 40 
LGZ O46 O46 O 0 1 N N N 17.844 18.428 2.515  8.455  -1.972 0.237  O46 LGZ 41 
LGZ C47 C47 C 0 1 N N N 16.614 18.410 1.753  7.970  -3.332 0.176  C47 LGZ 42 
LGZ C48 C48 C 0 1 N N N 15.514 18.835 2.758  6.606  -3.298 0.900  C48 LGZ 43 
LGZ C1  C1  C 0 1 N N N 7.818  27.918 4.365  -1.129 3.143  0.276  C1  LGZ 44 
LGZ N1  N1  N 0 1 N N N 6.548  27.557 4.316  -0.196 2.982  1.236  N1  LGZ 45 
LGZ O2  O2  O 0 1 N N N 8.249  28.863 3.762  -1.053 4.079  -0.495 O2  LGZ 46 
LGZ H1  H1  H 0 1 N N N 16.556 22.373 5.652  2.679  -1.311 -1.077 H1  LGZ 47 
LGZ H2  H2  H 0 1 N N N 13.942 22.431 6.807  2.000  0.727  0.901  H2  LGZ 48 
LGZ H3  H3  H 0 1 N N N 13.228 24.500 6.177  -0.137 0.865  -0.349 H3  LGZ 49 
LGZ H4  H4  H 0 1 N N N 14.940 25.740 4.322  1.137  -1.028 -2.052 H4  LGZ 50 
LGZ H5  H5  H 0 1 N N N 12.892 22.395 4.619  0.254  -0.940 1.354  H5  LGZ 51 
LGZ H6  H6  H 0 1 N N N 13.761 23.024 3.343  0.775  -2.021 0.039  H6  LGZ 52 
LGZ H7  H7  H 0 1 N N N 11.268 22.466 2.592  -1.112 -3.555 0.680  H7  LGZ 53 
LGZ H8  H8  H 0 1 N N N 11.843 23.852 1.699  -1.723 -2.428 1.915  H8  LGZ 54 
LGZ H9  H9  H 0 1 N N N 10.507 25.864 1.455  -2.594 -4.465 -1.014 H9  LGZ 55 
LGZ H10 H10 H 0 1 N N N 8.310  26.768 1.111  -4.906 -5.074 -1.602 H10 LGZ 56 
LGZ H11 H11 H 0 1 N N N 6.362  25.561 1.944  -6.795 -4.030 -0.417 H11 LGZ 57 
LGZ H12 H12 H 0 1 N N N 6.637  23.385 3.050  -6.371 -2.376 1.358  H12 LGZ 58 
LGZ H13 H13 H 0 1 N N N 8.891  22.380 3.335  -4.059 -1.770 1.949  H13 LGZ 59 
LGZ H14 H14 H 0 1 N N N 9.291  24.553 7.004  -4.078 1.091  -2.299 H14 LGZ 60 
LGZ H15 H15 H 0 1 N N N 7.614  25.436 5.406  -2.726 2.937  -1.733 H15 LGZ 61 
LGZ H16 H16 H 0 1 N N N 6.983  25.840 7.808  -4.059 3.877  0.499  H16 LGZ 62 
LGZ H17 H17 H 0 1 N N N 6.702  27.409 7.075  -4.824 3.809  -1.118 H17 LGZ 63 
LGZ H18 H18 H 0 1 N N N 7.701  28.593 9.314  -6.677 3.239  1.451  H18 LGZ 64 
LGZ H19 H19 H 0 1 N N N 9.794  29.119 10.467 -8.006 1.249  2.020  H19 LGZ 65 
LGZ H20 H20 H 0 1 N N N 11.947 27.982 9.769  -7.407 -0.944 1.069  H20 LGZ 66 
LGZ H21 H21 H 0 1 N N N 11.931 26.290 7.971  -5.480 -1.140 -0.448 H21 LGZ 67 
LGZ H22 H22 H 0 1 N N N 13.092 25.766 4.185  -1.075 -2.539 -1.919 H22 LGZ 68 
LGZ H23 H23 H 0 1 N N N 11.148 27.204 4.931  -2.699 -0.895 -2.960 H23 LGZ 69 
LGZ H24 H24 H 0 1 N N N 14.884 24.432 8.064  2.441  1.397  -2.042 H24 LGZ 70 
LGZ H25 H25 H 0 1 N N N 16.324 24.301 7.106  1.644  2.473  -0.870 H25 LGZ 71 
LGZ H26 H26 H 0 1 N N N 14.085 22.149 9.195  4.819  0.935  -1.889 H26 LGZ 72 
LGZ H27 H27 H 0 1 N N N 14.856 20.217 10.485 7.020  1.741  -1.134 H27 LGZ 73 
LGZ H28 H28 H 0 1 N N N 17.224 19.570 10.557 7.166  3.434  0.648  H28 LGZ 74 
LGZ H29 H29 H 0 1 N N N 18.903 20.926 9.259  5.112  4.321  1.675  H29 LGZ 75 
LGZ H30 H30 H 0 1 N N N 18.142 22.837 7.874  2.911  3.518  0.917  H30 LGZ 76 
LGZ H31 H31 H 0 1 N N N 16.824 20.016 3.356  6.043  -1.377 1.765  H31 LGZ 77 
LGZ H32 H32 H 0 1 N N N 17.308 17.244 4.108  7.063  -1.115 -1.068 H32 LGZ 78 
LGZ H33 H33 H 0 1 N N N 18.385 18.563 4.496  7.467  -0.133 0.373  H33 LGZ 79 
LGZ H34 H34 H 0 1 N N N 16.453 17.386 1.450  8.657  -4.003 0.691  H34 LGZ 80 
LGZ H35 H35 H 0 1 N N N 16.686 19.033 0.881  7.842  -3.642 -0.861 H35 LGZ 81 
LGZ H36 H36 H 0 1 N N N 14.866 19.629 2.410  6.723  -3.576 1.947  H36 LGZ 82 
LGZ H37 H37 H 0 1 N N N 14.922 17.988 3.075  5.895  -3.959 0.405  H37 LGZ 83 
LGZ H38 H38 H 0 1 N N N 6.069  28.108 3.642  0.536  3.614  1.310  H38 LGZ 84 
LGZ H39 H39 H 0 1 N N N 6.131  26.849 4.885  -0.260 2.237  1.854  H39 LGZ 85 
# 
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 
LGZ O01 C02 SING N N 1  
LGZ O01 C44 SING N N 2  
LGZ C02 O03 DOUB N N 3  
LGZ C02 NP4 SING N N 4  
LGZ NP4 C05 SING N N 5  
LGZ NP4 H1  SING N N 6  
LGZ C05 C06 SING N N 7  
LGZ C05 C36 SING N N 8  
LGZ C05 H2  SING N N 9  
LGZ C06 O07 SING N N 10 
LGZ C06 C08 SING N N 11 
LGZ C06 H3  SING N N 12 
LGZ O07 H4  SING N N 13 
LGZ C08 C09 SING N N 14 
LGZ C08 H5  SING N N 15 
LGZ C08 H6  SING N N 16 
LGZ C09 C10 SING N N 17 
LGZ C09 C17 SING N N 18 
LGZ C09 N29 SING N N 19 
LGZ C10 C11 SING N N 20 
LGZ C10 H7  SING N N 21 
LGZ C10 H8  SING N N 22 
LGZ C11 C12 DOUB Y N 23 
LGZ C11 C16 SING Y N 24 
LGZ C12 C13 SING Y N 25 
LGZ C12 H9  SING N N 26 
LGZ C13 C14 DOUB Y N 27 
LGZ C13 H10 SING N N 28 
LGZ C14 C15 SING Y N 29 
LGZ C14 H11 SING N N 30 
LGZ C15 C16 DOUB Y N 31 
LGZ C15 H12 SING N N 32 
LGZ C16 H13 SING N N 33 
LGZ C17 O18 DOUB N N 34 
LGZ C17 C35 SING N N 35 
LGZ C19 C20 SING N N 36 
LGZ C19 C28 SING N N 37 
LGZ C19 C35 SING N N 38 
LGZ C19 H14 SING N N 39 
LGZ C20 O1  SING N N 40 
LGZ C20 C22 SING N N 41 
LGZ C20 H15 SING N N 42 
LGZ O1  C1  SING N N 43 
LGZ C22 C23 SING N N 44 
LGZ C22 H16 SING N N 45 
LGZ C22 H17 SING N N 46 
LGZ C23 C24 DOUB Y N 47 
LGZ C23 C28 SING Y N 48 
LGZ C24 C25 SING Y N 49 
LGZ C24 H18 SING N N 50 
LGZ C25 C26 DOUB Y N 51 
LGZ C25 H19 SING N N 52 
LGZ C26 C27 SING Y N 53 
LGZ C26 H20 SING N N 54 
LGZ C27 C28 DOUB Y N 55 
LGZ C27 H21 SING N N 56 
LGZ N29 C30 SING N N 57 
LGZ N29 H22 SING N N 58 
LGZ C30 C35 DOUB N N 59 
LGZ C30 H23 SING N N 60 
LGZ C36 C37 SING N N 61 
LGZ C36 H24 SING N N 62 
LGZ C36 H25 SING N N 63 
LGZ C37 C38 DOUB Y N 64 
LGZ C37 C42 SING Y N 65 
LGZ C38 C39 SING Y N 66 
LGZ C38 H26 SING N N 67 
LGZ C39 C40 DOUB Y N 68 
LGZ C39 H27 SING N N 69 
LGZ C40 C41 SING Y N 70 
LGZ C40 H28 SING N N 71 
LGZ C41 C42 DOUB Y N 72 
LGZ C41 H29 SING N N 73 
LGZ C42 H30 SING N N 74 
LGZ C44 C45 SING N N 75 
LGZ C44 C48 SING N N 76 
LGZ C44 H31 SING N N 77 
LGZ C45 O46 SING N N 78 
LGZ C45 H32 SING N N 79 
LGZ C45 H33 SING N N 80 
LGZ O46 C47 SING N N 81 
LGZ C47 C48 SING N N 82 
LGZ C47 H34 SING N N 83 
LGZ C47 H35 SING N N 84 
LGZ C48 H36 SING N N 85 
LGZ C48 H37 SING N N 86 
LGZ C1  N1  SING N N 87 
LGZ C1  O2  DOUB N N 88 
LGZ N1  H38 SING N N 89 
LGZ N1  H39 SING N N 90 
# 
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 
LGZ SMILES           ACDLabs              10.04 O=C(OC1CCOC1)NC(Cc2ccccc2)C(O)CC3(C(=O)C(=CN3)C5c4ccccc4CC5OC(=O)N)Cc6ccccc6 
LGZ InChI            InChI                1.02b 
;InChI=1/C36H39N3O7/c37-34(42)46-31-18-25-13-7-8-14-27(25)32(31)28-21-38-36(33(28)41,19-24-11-5-2-6-12-24)20-30(40)29(17-23-9-3-1-4-10-23)39-35(43)45-26-15-16-44-22-26/h1-14,21,26,29-32,38,40H,15-20,22H2,(H2,37,42)(H,39,43)/t26-,29+,30+,31-,32-,36+/m1/s1/f/h39H,37H2
;
LGZ InChIKey         InChI                1.02b LIIUTXFOEDWJEK-FBNQABSKDY 
LGZ SMILES_CANONICAL CACTVS               3.341 NC(=O)O[C@@H]1Cc2ccccc2[C@@H]1C3=CN[C@](C[C@H](O)[C@H](Cc4ccccc4)NC(=O)O[C@@H]5CCOC5)(Cc6ccccc6)C3=O 
LGZ SMILES           CACTVS               3.341 NC(=O)O[CH]1Cc2ccccc2[CH]1C3=CN[C](C[CH](O)[CH](Cc4ccccc4)NC(=O)O[CH]5CCOC5)(Cc6ccccc6)C3=O 
LGZ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)C[C@@H]([C@H](C[C@]2(C(=O)C(=CN2)[C@H]3c4ccccc4C[C@H]3OC(=O)N)Cc5ccccc5)O)NC(=O)OC6CCOC6 
LGZ SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CC(C(CC2(C(=O)C(=CN2)C3c4ccccc4CC3OC(=O)N)Cc5ccccc5)O)NC(=O)OC6CCOC6 
# 
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 
LGZ "SYSTEMATIC NAME" ACDLabs              10.04 "(3R)-tetrahydrofuran-3-yl [(1S,2S)-1-benzyl-3-{(2S)-2-benzyl-4-[(1R,2R)-2-(carbamoyloxy)-2,3-dihydro-1H-inden-1-yl]-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-2-hydroxypropyl]carbamate" 
LGZ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "oxolan-3-yl N-[(2S,3S)-4-[(2S)-4-[(1R,2R)-2-aminocarbonyloxy-2,3-dihydro-1H-inden-1-yl]-3-oxo-2-(phenylmethyl)-1H-pyrrol-2-yl]-3-hydroxy-1-phenyl-butan-2-yl]carbamate"          
# 
