data_545
# 
_chem_comp.id                                    545 
_chem_comp.name                                  "[2-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONYLAMINO]-(1,3,4,5-TETRAHYDROXY-4-HYDROXYMETHYL-PIPERIDIN-2-YL)- ACETIC ACID BUTYL ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H33 N3 O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         SB-243545 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-07-05 
_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                        471.501 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     545 
_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        1JIK 
_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 
545 C8   C8   C 0 1 Y N N 28.648 8.051  82.237 -0.667 -1.159 -5.792 C8   545 1  
545 C7   C7   C 0 1 Y N N 27.372 7.590  82.542 -0.525 -0.769 -7.109 C7   545 2  
545 C12  C12  C 0 1 Y N N 26.735 8.081  83.660 -0.725 0.556  -7.465 C12  545 3  
545 C11  C11  C 0 1 Y N N 27.247 9.189  84.336 -1.068 1.487  -6.495 C11  545 4  
545 C10  C10  C 0 1 Y N N 28.425 9.796  83.888 -1.215 1.091  -5.180 C10  545 5  
545 C9   C9   C 0 1 Y N N 29.136 9.230  82.838 -1.009 -0.229 -4.828 C9   545 6  
545 C14  C14  C 0 1 N N N 30.444 9.876  82.355 -1.164 -0.657 -3.391 C14  545 7  
545 C15  C15  C 0 1 N N S 30.520 11.412 82.225 0.180  -0.529 -2.673 C15  545 8  
545 C17  C17  C 0 1 N N N 31.992 11.896 82.080 0.026  -0.957 -1.236 C17  545 9  
545 N19  N19  N 0 1 N N N 32.800 11.551 83.061 -0.306 -0.051 -0.295 N19  545 10 
545 C20  C20  C 0 1 N N S 34.170 12.125 83.264 -0.460 -0.468 1.100  C20  545 11 
545 C21  C21  C 0 1 N N N 35.197 11.433 82.315 -1.731 0.114  1.661  C21  545 12 
545 O23  O23  O 0 1 N N N 34.951 10.078 82.110 -2.215 -0.332 2.831  O23  545 13 
545 C24  C24  C 0 1 N N N 35.858 9.314  81.309 -3.440 0.229  3.372  C24  545 14 
545 C25  C25  C 0 1 N N N 37.349 9.735  81.576 -3.768 -0.450 4.703  C25  545 15 
545 C26  C26  C 0 1 N N N 38.372 8.616  81.239 -5.059 0.141  5.273  C26  545 16 
545 C27  C27  C 0 1 N N N 39.166 8.152  82.492 -5.387 -0.538 6.604  C27  545 17 
545 O18  O18  O 0 1 N N N 32.372 12.520 81.105 0.201  -2.116 -0.927 O18  545 18 
545 N16  N16  N 0 1 N N N 29.636 11.876 81.115 1.173  -1.386 -3.335 N16  545 19 
545 O22  O22  O 0 1 N N N 36.133 12.062 81.828 -2.315 0.983  1.058  O22  545 20 
545 C6   C6   C 0 1 N N S 34.642 12.277 84.731 0.733  0.031  1.915  C6   545 21 
545 N5   N5   N 0 1 N N N 33.467 12.720 85.620 0.876  1.480  1.733  N5   545 22 
545 C4   C4   C 0 1 N N N 33.766 13.385 86.944 1.938  1.931  2.639  C4   545 23 
545 C3   C3   C 0 1 N N S 34.890 14.412 86.787 3.276  1.329  2.205  C3   545 24 
545 C2   C2   C 0 1 N N S 36.129 13.714 86.241 3.191  -0.198 2.287  C2   545 25 
545 C1   C1   C 0 1 N N S 35.824 13.295 84.789 2.005  -0.675 1.442  C1   545 26 
545 O28  O28  O 0 1 N N N 32.491 11.796 85.713 -0.367 2.086  2.210  O28  545 27 
545 O32  O32  O 0 1 N N N 34.518 15.425 85.833 3.564  1.720  0.862  O32  545 28 
545 O29  O29  O 0 1 N N N 37.127 14.717 86.225 4.398  -0.772 1.783  O29  545 29 
545 C30  C30  C 0 1 N N N 36.695 12.544 87.144 2.988  -0.625 3.742  C30  545 30 
545 O31  O31  O 0 1 N N N 36.740 11.275 86.437 4.095  -0.179 4.528  O31  545 31 
545 O64  O64  O 0 1 N N N 36.966 12.713 84.200 1.849  -2.088 1.591  O64  545 32 
545 O13  O13  O 0 1 N N N 25.638 7.481  84.112 -0.585 0.942  -8.760 O13  545 33 
545 H8   H8   H 0 1 N N N 29.269 7.484  81.522 -0.512 -2.191 -5.515 H8   545 34 
545 H7   H7   H 0 1 N N N 26.870 6.842  81.904 -0.257 -1.496 -7.862 H7   545 35 
545 H11  H11  H 0 1 N N N 26.722 9.583  85.222 -1.224 2.520  -6.769 H11  545 36 
545 H10  H10  H 0 1 N N N 28.793 10.721 84.362 -1.482 1.816  -4.425 H10  545 37 
545 H141 1H14 H 0 0 N N N 31.277 9.530  83.010 -1.497 -1.694 -3.355 H141 545 38 
545 H142 2H14 H 0 0 N N N 30.729 9.419  81.378 -1.900 -0.021 -2.900 H142 545 39 
545 H15  H15  H 0 1 N N N 30.140 11.878 83.164 0.514  0.507  -2.709 H15  545 40 
545 H19  H19  H 0 1 N N N 32.368 10.845 83.658 -0.444 0.876  -0.543 H19  545 41 
545 H20  H20  H 0 1 N N N 34.097 13.196 82.964 -0.505 -1.556 1.151  H20  545 42 
545 H241 1H24 H 0 0 N N N 35.709 8.218  81.454 -4.256 0.064  2.669  H241 545 43 
545 H242 2H24 H 0 0 N N N 35.602 9.379  80.225 -3.309 1.299  3.532  H242 545 44 
545 H251 1H25 H 0 0 N N N 37.598 10.676 81.033 -2.951 -0.285 5.406  H251 545 45 
545 H252 2H25 H 0 0 N N N 37.479 10.088 82.625 -3.899 -1.520 4.542  H252 545 46 
545 H261 1H26 H 0 0 N N N 37.876 7.754  80.733 -5.875 -0.023 4.570  H261 545 47 
545 H262 2H26 H 0 0 N N N 39.059 8.930  80.419 -4.928 1.211  5.433  H262 545 48 
545 H271 1H27 H 0 0 N N N 39.900 7.348  82.250 -6.306 -0.116 7.010  H271 545 49 
545 H272 2H27 H 0 0 N N N 39.661 9.013  82.997 -5.518 -1.608 6.443  H272 545 50 
545 H273 3H27 H 0 0 N N N 38.478 7.837  83.311 -4.570 -0.373 7.307  H273 545 51 
545 H161 1H16 H 0 0 N N N 29.686 12.891 81.029 0.824  -2.331 -3.278 H161 545 52 
545 H162 2H16 H 0 0 N N N 28.676 11.549 81.228 1.168  -1.134 -4.312 H162 545 53 
545 H6   H6   H 0 1 N N N 35.004 11.296 85.118 0.568  -0.186 2.970  H6   545 54 
545 H41  1H4  H 0 1 N N N 32.852 13.836 87.396 1.709  1.612  3.655  H41  545 55 
545 H42  2H4  H 0 1 N N N 33.994 12.638 87.740 2.004  3.019  2.607  H42  545 56 
545 H3   H3   H 0 1 N N N 35.084 14.874 87.783 4.067  1.685  2.866  H3   545 57 
545 H1   H1   H 0 1 N N N 35.534 14.212 84.225 2.185  -0.437 0.394  H1   545 58 
545 H28  H28  H 0 1 N N N 31.765 12.069 86.261 -0.555 1.695  3.074  H28  545 59 
545 H32  H32  H 0 1 N N N 35.215 16.062 85.735 3.609  2.686  0.855  H32  545 60 
545 H29  H29  H 0 1 N N N 37.899 14.281 85.884 5.117  -0.446 2.342  H29  545 61 
545 H301 1H30 H 0 0 N N N 37.693 12.806 87.564 2.069  -0.183 4.126  H301 545 62 
545 H302 2H30 H 0 0 N N N 36.120 12.455 88.095 2.919  -1.712 3.795  H302 545 63 
545 H31  H31  H 0 1 N N N 37.079 10.572 86.979 3.928  -0.468 5.435  H31  545 64 
545 H64  H64  H 0 1 N N N 37.685 13.332 84.235 1.169  -2.362 0.961  H64  545 65 
545 H13  H13  H 0 1 N N N 25.198 7.819  84.883 -1.453 0.846  -9.175 H13  545 66 
# 
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 
545 C8  C7   DOUB Y N 1  
545 C8  C9   SING Y N 2  
545 C8  H8   SING N N 3  
545 C7  C12  SING Y N 4  
545 C7  H7   SING N N 5  
545 C12 C11  DOUB Y N 6  
545 C12 O13  SING N N 7  
545 C11 C10  SING Y N 8  
545 C11 H11  SING N N 9  
545 C10 C9   DOUB Y N 10 
545 C10 H10  SING N N 11 
545 C9  C14  SING N N 12 
545 C14 C15  SING N N 13 
545 C14 H141 SING N N 14 
545 C14 H142 SING N N 15 
545 C15 C17  SING N N 16 
545 C15 N16  SING N N 17 
545 C15 H15  SING N N 18 
545 C17 N19  SING N N 19 
545 C17 O18  DOUB N N 20 
545 N19 C20  SING N N 21 
545 N19 H19  SING N N 22 
545 C20 C21  SING N N 23 
545 C20 C6   SING N N 24 
545 C20 H20  SING N N 25 
545 C21 O23  SING N N 26 
545 C21 O22  DOUB N N 27 
545 O23 C24  SING N N 28 
545 C24 C25  SING N N 29 
545 C24 H241 SING N N 30 
545 C24 H242 SING N N 31 
545 C25 C26  SING N N 32 
545 C25 H251 SING N N 33 
545 C25 H252 SING N N 34 
545 C26 C27  SING N N 35 
545 C26 H261 SING N N 36 
545 C26 H262 SING N N 37 
545 C27 H271 SING N N 38 
545 C27 H272 SING N N 39 
545 C27 H273 SING N N 40 
545 N16 H161 SING N N 41 
545 N16 H162 SING N N 42 
545 C6  N5   SING N N 43 
545 C6  C1   SING N N 44 
545 C6  H6   SING N N 45 
545 N5  C4   SING N N 46 
545 N5  O28  SING N N 47 
545 C4  C3   SING N N 48 
545 C4  H41  SING N N 49 
545 C4  H42  SING N N 50 
545 C3  C2   SING N N 51 
545 C3  O32  SING N N 52 
545 C3  H3   SING N N 53 
545 C2  C1   SING N N 54 
545 C2  O29  SING N N 55 
545 C2  C30  SING N N 56 
545 C1  O64  SING N N 57 
545 C1  H1   SING N N 58 
545 O28 H28  SING N N 59 
545 O32 H32  SING N N 60 
545 O29 H29  SING N N 61 
545 C30 O31  SING N N 62 
545 C30 H301 SING N N 63 
545 C30 H302 SING N N 64 
545 O31 H31  SING N N 65 
545 O64 H64  SING N N 66 
545 O13 H13  SING N N 67 
# 
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 
545 SMILES           ACDLabs              10.04 O=C(OCCCC)C(NC(=O)C(N)Cc1ccc(O)cc1)C2N(O)CC(O)C(O)(C2O)CO                                                                                                                                                     
545 InChI            InChI                1.02b InChI=1/C21H33N3O9/c1-2-3-8-33-20(30)16(17-18(28)21(31,11-25)15(27)10-24(17)32)23-19(29)14(22)9-12-4-6-13(26)7-5-12/h4-7,14-18,25-28,31-32H,2-3,8-11,22H2,1H3,(H,23,29)/t14-,15-,16-,17-,18-,21-/m0/s1/f/h23H 
545 InChIKey         InChI                1.02b IPZUTNGJHRAITA-BVIMEGJMDH                                                                                                                                                                                     
545 SMILES_CANONICAL CACTVS               3.341 CCCCOC(=O)[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)[C@H]2[C@H](O)[C@](O)(CO)[C@@H](O)CN2O                                                                                                                           
545 SMILES           CACTVS               3.341 CCCCOC(=O)[CH](NC(=O)[CH](N)Cc1ccc(O)cc1)[CH]2[CH](O)[C](O)(CO)[CH](O)CN2O                                                                                                                                    
545 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCOC(=O)[C@H]([C@H]1[C@@H]([C@@]([C@H](C[N@@]1O)O)(CO)O)O)NC(=O)[C@H](Cc2ccc(cc2)O)N                                                                                                                        
545 SMILES           "OpenEye OEToolkits" 1.5.0 CCCCOC(=O)C(C1C(C(C(CN1O)O)(CO)O)O)NC(=O)C(Cc2ccc(cc2)O)N                                                                                                                                                     
# 
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 
545 "SYSTEMATIC NAME" ACDLabs              10.04 "butyl (2S)-[(2S,3S,4S,5S)-1,3,4,5-tetrahydroxy-4-(hydroxymethyl)piperidin-2-yl](L-tyrosylamino)ethanoate"                                           
545 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "butyl (2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-2-[(1S,2S,3S,4S,5S)-1,3,4,5-tetrahydroxy-4-(hydroxymethyl)piperidin-2-yl]ethanoate" 
# 
