data_GRL
# 
_chem_comp.id                                    GRL 
_chem_comp.name                                  "(3AS,5R,6AR)-HEXAHYDRO-2H-CYCLOPENTA[B]FURAN-5-YL (2S,3S)-3-HYDROXY-4-(4-(HYDROXYMETHYL)-N-ISOBUTYLPHENYLSULFONAMIDO)-1-PHENYLBUTAN-2-YLCARBAMATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H40 N2 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-06-19 
_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                         UIC 
_chem_comp.formula_weight                        560.702 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GRL 
_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        ? 
_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 
GRL C11  C11  C 0 1 N N R -8.823  15.761 22.420 5.664   0.053  0.129  C11  GRL 1  
GRL C12  C12  C 0 1 N N N -7.404  15.157 22.217 6.827   0.125  -0.891 C12  GRL 2  
GRL O1   O1   O 0 1 N N N -7.400  18.506 21.330 8.015   -2.410 0.451  O1   GRL 3  
GRL C14  C14  C 0 1 N N N -6.049  18.528 21.813 9.292   -2.183 -0.181 C14  GRL 4  
GRL C15  C15  C 0 1 N N S -6.619  16.255 21.475 8.078   -0.079 -0.005 C15  GRL 5  
GRL C16  C16  C 0 1 N N N -9.017  16.583 21.139 6.095   -1.046 1.121  C16  GRL 6  
GRL C2   C2   C 0 1 N N N -5.760  17.136 22.390 9.166   -0.790 -0.836 C2   GRL 7  
GRL C1   C1   C 0 1 N N R -7.629  17.165 20.804 7.631   -1.132 1.046  C1   GRL 8  
GRL O13  O13  O 0 1 N N N -8.860  16.703 23.502 4.428   -0.318 -0.535 O13  GRL 9  
GRL C21  C21  C 0 1 N N N -8.789  16.302 24.880 3.246   0.088  -0.034 C21  GRL 10 
GRL C22  C22  C 0 1 N N S -9.019  17.259 27.166 0.812   0.185  -0.106 C22  GRL 11 
GRL C23  C23  C 0 1 N N N -7.912  18.050 27.931 0.496   1.590  -0.621 C23  GRL 12 
GRL C24  C24  C 0 1 Y N N -6.600  17.936 27.215 1.513   2.564  -0.083 C24  GRL 13 
GRL C25  C25  C 0 1 Y N N -5.780  16.776 27.430 1.284   3.209  1.118  C25  GRL 14 
GRL C26  C26  C 0 1 Y N N -4.536  16.673 26.738 2.218   4.099  1.614  C26  GRL 15 
GRL C27  C27  C 0 1 Y N N -4.137  17.726 25.843 3.378   4.350  0.904  C27  GRL 16 
GRL C28  C28  C 0 1 Y N N -4.968  18.889 25.637 3.604   3.708  -0.299 C28  GRL 17 
GRL C29  C29  C 0 1 Y N N -6.208  18.994 26.327 2.672   2.815  -0.793 C29  GRL 18 
GRL O21  O21  O 0 1 N N N -8.546  15.139 25.273 3.214   0.765  0.974  O21  GRL 19 
GRL N21  N21  N 0 1 N N N -8.951  17.385 25.677 2.098   -0.257 -0.651 N21  GRL 20 
GRL C31  C31  C 0 1 N N R -10.422 17.717 27.622 -0.289  -0.781 -0.549 C31  GRL 21 
GRL C32  C32  C 0 1 N N N -10.681 17.423 29.125 -1.608  -0.392 0.121  C32  GRL 22 
GRL C33  C33  C 0 1 N N N -11.465 15.075 28.528 -2.685  -2.650 0.543  C33  GRL 23 
GRL C34  C34  C 0 1 N N N -12.495 14.290 29.351 -3.013  -2.363 2.010  C34  GRL 24 
GRL C35  C35  C 0 1 N N N -12.451 12.767 29.122 -4.424  -1.782 2.113  C35  GRL 25 
GRL C36  C36  C 0 1 N N N -13.891 14.796 29.035 -2.937  -3.663 2.813  C36  GRL 26 
GRL O31  O31  O 0 1 N N N -10.516 19.119 27.338 -0.437  -0.715 -1.968 O31  GRL 27 
GRL O32  O32  O 0 1 N N N -7.992  15.988 30.054 -3.124  -0.119 -2.246 O32  GRL 28 
GRL O33  O33  O 0 1 N N N -9.205  13.812 29.938 -4.195  -2.367 -1.826 O33  GRL 29 
GRL N31  N31  N 0 1 N N N -10.530 15.952 29.359 -2.632  -1.390 -0.201 N31  GRL 30 
GRL S31  S31  S 0 1 N N N -9.185  15.224 30.261 -3.728  -1.092 -1.405 S31  GRL 31 
GRL C41  C41  C 0 1 Y N N -9.505  15.248 32.007 -5.115  -0.293 -0.669 C41  GRL 32 
GRL C42  C42  C 0 1 Y N N -9.691  13.982 32.669 -5.152  1.086  -0.580 C42  GRL 33 
GRL C43  C43  C 0 1 Y N N -9.944  13.969 34.065 -6.240  1.713  -0.003 C43  GRL 34 
GRL C44  C44  C 0 1 Y N N -10.007 15.217 34.774 -7.292  0.961  0.485  C44  GRL 35 
GRL C45  C45  C 0 1 Y N N -9.816  16.465 34.100 -7.257  -0.418 0.395  C45  GRL 36 
GRL C46  C46  C 0 1 Y N N -9.560  16.484 32.693 -6.170  -1.045 -0.186 C46  GRL 37 
GRL C3   C3   C 0 1 N N N -10.277 15.248 36.275 -8.478  1.644  1.115  C3   GRL 38 
GRL O2   O2   O 0 1 N N N -11.576 15.765 36.650 -9.456  1.924  0.111  O2   GRL 39 
GRL H11  H11  H 0 1 N N N -9.565  14.976 22.626 5.548   1.007  0.644  H11  GRL 40 
GRL H121 1H12 H 0 0 N N N -7.431  14.212 21.654 6.743   -0.672 -1.629 H121 GRL 41 
GRL H122 2H12 H 0 0 N N N -6.934  14.916 23.182 6.853   1.101  -1.377 H122 GRL 42 
GRL H141 1H14 H 0 0 N N N -5.919  19.306 22.580 9.481   -2.943 -0.939 H141 GRL 43 
GRL H142 2H14 H 0 0 N N N -5.353  18.754 20.992 10.089  -2.182 0.563  H142 GRL 44 
GRL H15  H15  H 0 1 N N N -5.941  15.746 20.774 8.430   0.848  0.447  H15  GRL 45 
GRL H161 1H16 H 0 0 N N N -9.766  17.377 21.277 5.785   -0.796 2.135  H161 GRL 46 
GRL H162 2H16 H 0 0 N N N -9.381  15.947 20.319 5.654   -1.996 0.820  H162 GRL 47 
GRL H21  1H2  H 0 1 N N N -5.993  17.035 23.460 8.852   -0.884 -1.875 H21  GRL 48 
GRL H22A 2H2  H 0 0 N N N -4.692  16.875 22.341 10.111  -0.250 -0.769 H22A GRL 49 
GRL H1   H1   H 0 1 N N N -7.546  17.228 19.709 8.103   -0.978 2.017  H1   GRL 50 
GRL H22  H22  H 0 1 N N N -8.836  16.203 27.416 0.865   0.201  0.983  H22  GRL 51 
GRL H231 1H23 H 0 0 N N N -7.806  17.629 28.942 0.530   1.594  -1.710 H231 GRL 52 
GRL H232 2H23 H 0 0 N N N -8.201  19.110 27.990 -0.500  1.884  -0.288 H232 GRL 53 
GRL H25  H25  H 0 1 N N N -6.100  15.995 28.104 0.378   3.013  1.672  H25  GRL 54 
GRL H26  H26  H 0 1 N N N -3.900  15.812 26.885 2.042   4.600  2.554  H26  GRL 55 
GRL H27  H27  H 0 1 N N N -3.198  17.645 25.315 4.107   5.047  1.290  H27  GRL 56 
GRL H28  H28  H 0 1 N N N -4.651  19.673 24.965 4.510   3.904  -0.854 H28  GRL 57 
GRL H29  H29  H 0 1 N N N -6.844  19.855 26.185 2.849   2.314  -1.733 H29  GRL 58 
GRL HN21 HN21 H 0 0 N N N -9.027  18.291 25.260 2.124   -0.798 -1.456 HN21 GRL 59 
GRL H31  H31  H 0 1 N N N -11.195 17.154 27.079 -0.019  -1.796 -0.258 H31  GRL 60 
GRL H321 1H32 H 0 0 N N N -11.697 17.744 29.400 -1.926  0.585  -0.243 H321 GRL 61 
GRL H322 2H32 H 0 0 N N N -9.955  17.974 29.742 -1.469  -0.350 1.201  H322 GRL 62 
GRL H331 1H33 H 0 0 N N N -12.033 15.750 27.871 -1.719  -3.152 0.478  H331 GRL 63 
GRL H332 2H33 H 0 0 N N N -10.847 14.349 27.979 -3.457  -3.291 0.117  H332 GRL 64 
GRL H34  H34  H 0 1 N N N -12.235 14.460 30.406 -2.295  -1.647 2.409  H34  GRL 65 
GRL H351 1H35 H 0 0 N N N -13.339 12.302 29.576 -5.130  -2.454 1.626  H351 GRL 66 
GRL H352 2H35 H 0 0 N N N -11.543 12.353 29.584 -4.695  -1.669 3.163  H352 GRL 67 
GRL H353 3H35 H 0 0 N N N -12.441 12.558 28.042 -4.453  -0.808 1.624  H353 GRL 68 
GRL H361 1H36 H 0 0 N N N -14.405 14.071 28.387 -3.655  -4.380 2.414  H361 GRL 69 
GRL H362 2H36 H 0 0 N N N -13.822 15.765 28.519 -1.931  -4.078 2.740  H362 GRL 70 
GRL H363 3H36 H 0 0 N N N -14.458 14.918 29.970 -3.170  -3.459 3.858  H363 GRL 71 
GRL HO31 HO31 H 0 0 N N N -10.537 19.607 28.153 -0.675  0.198  -2.182 HO31 GRL 72 
GRL H42  H42  H 0 1 N N N -9.639  13.058 32.112 -4.329  1.674  -0.961 H42  GRL 73 
GRL H43  H43  H 0 1 N N N -10.087 13.034 34.587 -6.268  2.790  0.068  H43  GRL 74 
GRL H45  H45  H 0 1 N N N -9.865  17.391 34.653 -8.079  -1.005 0.775  H45  GRL 75 
GRL H46  H46  H 0 1 N N N -9.413  17.417 32.169 -6.142  -2.122 -0.257 H46  GRL 76 
GRL H31A 1H3  H 0 0 N N N -9.532  15.930 36.712 -8.913  0.993  1.874  H31A GRL 77 
GRL H32  2H3  H 0 1 N N N -10.207 14.216 36.649 -8.157  2.577  1.578  H32  GRL 78 
GRL HO2  HO2  H 0 1 N N N -11.612 15.878 37.593 -10.196 2.360  0.555  HO2  GRL 79 
# 
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 
GRL C11 C12  SING N N 1  
GRL C11 C16  SING N N 2  
GRL C11 O13  SING N N 3  
GRL C11 H11  SING N N 4  
GRL C12 C15  SING N N 5  
GRL C12 H121 SING N N 6  
GRL C12 H122 SING N N 7  
GRL O1  C14  SING N N 8  
GRL O1  C1   SING N N 9  
GRL C14 C2   SING N N 10 
GRL C14 H141 SING N N 11 
GRL C14 H142 SING N N 12 
GRL C15 C2   SING N N 13 
GRL C15 C1   SING N N 14 
GRL C15 H15  SING N N 15 
GRL C16 C1   SING N N 16 
GRL C16 H161 SING N N 17 
GRL C16 H162 SING N N 18 
GRL C2  H21  SING N N 19 
GRL C2  H22A SING N N 20 
GRL C1  H1   SING N N 21 
GRL O13 C21  SING N N 22 
GRL C21 O21  DOUB N N 23 
GRL C21 N21  SING N N 24 
GRL C22 C23  SING N N 25 
GRL C22 N21  SING N N 26 
GRL C22 C31  SING N N 27 
GRL C22 H22  SING N N 28 
GRL C23 C24  SING N N 29 
GRL C23 H231 SING N N 30 
GRL C23 H232 SING N N 31 
GRL C24 C25  SING Y N 32 
GRL C24 C29  DOUB Y N 33 
GRL C25 C26  DOUB Y N 34 
GRL C25 H25  SING N N 35 
GRL C26 C27  SING Y N 36 
GRL C26 H26  SING N N 37 
GRL C27 C28  DOUB Y N 38 
GRL C27 H27  SING N N 39 
GRL C28 C29  SING Y N 40 
GRL C28 H28  SING N N 41 
GRL C29 H29  SING N N 42 
GRL N21 HN21 SING N N 43 
GRL C31 C32  SING N N 44 
GRL C31 O31  SING N N 45 
GRL C31 H31  SING N N 46 
GRL C32 N31  SING N N 47 
GRL C32 H321 SING N N 48 
GRL C32 H322 SING N N 49 
GRL C33 C34  SING N N 50 
GRL C33 N31  SING N N 51 
GRL C33 H331 SING N N 52 
GRL C33 H332 SING N N 53 
GRL C34 C35  SING N N 54 
GRL C34 C36  SING N N 55 
GRL C34 H34  SING N N 56 
GRL C35 H351 SING N N 57 
GRL C35 H352 SING N N 58 
GRL C35 H353 SING N N 59 
GRL C36 H361 SING N N 60 
GRL C36 H362 SING N N 61 
GRL C36 H363 SING N N 62 
GRL O31 HO31 SING N N 63 
GRL O32 S31  DOUB N N 64 
GRL O33 S31  DOUB N N 65 
GRL N31 S31  SING N N 66 
GRL S31 C41  SING N N 67 
GRL C41 C42  DOUB Y N 68 
GRL C41 C46  SING Y N 69 
GRL C42 C43  SING Y N 70 
GRL C42 H42  SING N N 71 
GRL C43 C44  DOUB Y N 72 
GRL C43 H43  SING N N 73 
GRL C44 C45  SING Y N 74 
GRL C44 C3   SING N N 75 
GRL C45 C46  DOUB Y N 76 
GRL C45 H45  SING N N 77 
GRL C46 H46  SING N N 78 
GRL C3  O2   SING N N 79 
GRL C3  H31A SING N N 80 
GRL C3  H32  SING N N 81 
GRL O2  HO2  SING N N 82 
# 
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 
GRL SMILES           ACDLabs              10.04 O=S(=O)(c1ccc(cc1)CO)N(CC(C)C)CC(O)C(NC(=O)OC3CC2C(OCC2)C3)Cc4ccccc4 
GRL InChI            InChI                1.02b 
InChI=1/C29H40N2O7S/c1-20(2)17-31(39(35,36)25-10-8-22(19-32)9-11-25)18-27(33)26(14-21-6-4-3-5-7-21)30-29(34)38-24-15-23-12-13-37-28(23)16-24/h3-11,20,23-24,26-28,32-33H,12-19H2,1-2H3,(H,30,34)/t23-,24+,26-,27+,28+/m0/s1/f/h30H 
GRL InChIKey         InChI                1.02b VYBDPVQMILRSMK-OOSHRCTGDC 
GRL SMILES_CANONICAL CACTVS               3.341 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@@H]2C[C@@H]3CCO[C@@H]3C2)[S](=O)(=O)c4ccc(CO)cc4 
GRL SMILES           CACTVS               3.341 CC(C)CN(C[CH](O)[CH](Cc1ccccc1)NC(=O)O[CH]2C[CH]3CCO[CH]3C2)[S](=O)(=O)c4ccc(CO)cc4 
GRL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)CN(C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@@H]2C[C@@H]3CCO[C@@H]3C2)O)S(=O)(=O)c4ccc(cc4)CO 
GRL SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CN(CC(C(Cc1ccccc1)NC(=O)OC2CC3CCOC3C2)O)S(=O)(=O)c4ccc(cc4)CO 
# 
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 
GRL "SYSTEMATIC NAME" ACDLabs              10.04 "(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yl {(1S,2R)-1-benzyl-2-hydroxy-3-[{[4-(hydroxymethyl)phenyl]sulfonyl}(2-methylpropyl)amino]propyl}carbamate"                       
GRL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3aS,5R,6aR)-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]furan-5-yl] N-[(2S,3R)-3-hydroxy-4-[[4-(hydroxymethyl)phenyl]sulfonyl-(2-methylpropyl)amino]-1-phenyl-butan-2-yl]carbamate" 
# 
