data_HN3 # _chem_comp.id HN3 _chem_comp.name "1-(4-methylphenyl)-2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C17 H23 N O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-09-25 _chem_comp.pdbx_modified_date 2021-03-13 _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 305.369 _chem_comp.one_letter_code ? _chem_comp.three_letter_code HN3 _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 3EJQ _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 HN3 O10 O10 O 0 1 N N N 26.620 64.743 8.360 1.583 -1.083 -2.091 O10 HN3 1 HN3 C10 C10 C 0 1 N N N 26.993 65.767 8.929 1.587 -0.378 -1.104 C10 HN3 2 HN3 C11 C11 C 0 1 Y N N 25.987 66.623 9.677 2.860 -0.027 -0.455 C11 HN3 3 HN3 C16 C16 C 0 1 Y N N 24.630 66.266 9.676 4.068 -0.504 -0.973 C16 HN3 4 HN3 C15 C15 C 0 1 Y N N 23.684 67.041 10.369 5.257 -0.171 -0.358 C15 HN3 5 HN3 C14 C14 C 0 1 Y N N 24.085 68.192 11.051 5.256 0.634 0.768 C14 HN3 6 HN3 C17 C17 C 0 1 N N N 23.087 69.048 11.807 6.560 0.993 1.433 C17 HN3 7 HN3 C13 C13 C 0 1 Y N N 25.432 68.547 11.065 4.064 1.110 1.287 C13 HN3 8 HN3 C12 C12 C 0 1 Y N N 26.382 67.762 10.384 2.868 0.790 0.680 C12 HN3 9 HN3 C9 C9 C 0 1 N N N 28.451 66.202 8.899 0.287 0.144 -0.546 C9 HN3 10 HN3 C5 C5 C 0 1 N N R 29.407 65.171 8.264 -0.882 -0.471 -1.318 C5 HN3 11 HN3 C6 C6 C 0 1 N N N 29.192 65.048 6.748 -0.945 -1.983 -1.050 C6 HN3 12 HN3 C7 C7 C 0 1 N N N 29.685 66.306 6.017 -1.196 -2.259 0.432 C7 HN3 13 HN3 C8 C8 C 0 1 N N R 31.166 66.564 6.325 -2.445 -1.506 0.919 C8 HN3 14 HN3 O8 O8 O 0 1 N N N 31.561 67.800 5.742 -2.606 -1.694 2.326 O8 HN3 15 HN3 C8A C8A C 0 1 N N R 31.395 66.640 7.831 -2.238 -0.029 0.614 C8A HN3 16 HN3 C1 C1 C 0 1 N N S 32.847 66.687 8.316 -3.436 0.854 0.983 C1 HN3 17 HN3 O1 O1 O 0 1 N N N 33.755 65.878 7.532 -4.644 0.092 0.964 O1 HN3 18 HN3 N4 N4 N 0 1 N N N 30.860 65.426 8.482 -2.136 0.114 -0.862 N4 HN3 19 HN3 C3 C3 C 0 1 N N N 31.307 65.585 9.894 -2.306 1.558 -1.085 C3 HN3 20 HN3 C2 C2 C 0 1 N N R 32.744 66.119 9.733 -3.461 1.941 -0.122 C2 HN3 21 HN3 O2 O2 O 0 1 N N N 33.673 65.042 9.900 -4.712 1.917 -0.812 O2 HN3 22 HN3 H16 H16 H 0 1 N N N 24.309 65.387 9.137 4.070 -1.132 -1.851 H16 HN3 23 HN3 H15 H15 H 0 1 N N N 22.645 66.746 10.374 6.190 -0.538 -0.757 H15 HN3 24 HN3 H17 H17 H 0 1 N N N 23.471 69.255 12.817 6.948 1.914 0.998 H17 HN3 25 HN3 H17A H17A H 0 0 N N N 22.937 69.996 11.270 6.395 1.137 2.501 H17A HN3 26 HN3 H17B H17B H 0 0 N N N 22.129 68.513 11.883 7.279 0.188 1.281 H17B HN3 27 HN3 H13 H13 H 0 1 N N N 25.749 69.429 11.601 4.072 1.737 2.166 H13 HN3 28 HN3 H12 H12 H 0 1 N N N 27.425 68.042 10.408 1.939 1.166 1.084 H12 HN3 29 HN3 H9 H9 H 0 1 N N N 28.515 67.130 8.311 0.210 -0.126 0.507 H9 HN3 30 HN3 H9A H9A H 0 1 N N N 28.767 66.327 9.945 0.258 1.229 -0.646 H9A HN3 31 HN3 H5 H5 H 0 1 N N N 29.144 64.241 8.790 -0.756 -0.291 -2.385 H5 HN3 32 HN3 H6 H6 H 0 1 N N N 29.752 64.177 6.377 -1.753 -2.418 -1.638 H6 HN3 33 HN3 H6A H6A H 0 1 N N N 28.116 64.929 6.555 -0.000 -2.439 -1.345 H6A HN3 34 HN3 H7 H7 H 0 1 N N N 29.562 66.164 4.933 -1.342 -3.329 0.579 H7 HN3 35 HN3 H7A H7A H 0 1 N N N 29.095 67.169 6.359 -0.332 -1.931 1.010 H7A HN3 36 HN3 H8 H8 H 0 1 N N N 31.759 65.736 5.909 -3.326 -1.873 0.393 H8 HN3 37 HN3 HO8 HO8 H 0 1 N N N 31.649 68.458 6.422 -2.713 -2.618 2.590 HO8 HN3 38 HN3 H8A H8A H 0 1 N N N 30.903 67.589 8.091 -1.335 0.335 1.105 H8A HN3 39 HN3 H1 H1 H 0 1 N N N 33.258 67.705 8.244 -3.288 1.308 1.963 H1 HN3 40 HN3 HO1 HO1 H 0 1 N N N 33.369 65.701 6.682 -5.434 0.602 1.190 HO1 HN3 41 HN3 H3 H3 H 0 1 N N N 30.669 66.289 10.449 -1.395 2.097 -0.825 H3 HN3 42 HN3 H3A H3A H 0 1 N N N 31.252 64.653 10.475 -2.588 1.756 -2.120 H3A HN3 43 HN3 H2 H2 H 0 1 N N N 32.974 66.891 10.482 -3.284 2.925 0.310 H2 HN3 44 HN3 HO2 HO2 H 0 1 N N N 33.879 64.666 9.052 -4.785 2.577 -1.516 HO2 HN3 45 # # 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 HN3 O10 C10 DOUB N N 1 HN3 C10 C11 SING N N 2 HN3 C10 C9 SING N N 3 HN3 C11 C16 DOUB Y N 4 HN3 C11 C12 SING Y N 5 HN3 C16 C15 SING Y N 6 HN3 C15 C14 DOUB Y N 7 HN3 C14 C17 SING N N 8 HN3 C14 C13 SING Y N 9 HN3 C13 C12 DOUB Y N 10 HN3 C9 C5 SING N N 11 HN3 C5 C6 SING N N 12 HN3 C5 N4 SING N N 13 HN3 C6 C7 SING N N 14 HN3 C7 C8 SING N N 15 HN3 C8 O8 SING N N 16 HN3 C8 C8A SING N N 17 HN3 C8A C1 SING N N 18 HN3 C8A N4 SING N N 19 HN3 C1 O1 SING N N 20 HN3 C1 C2 SING N N 21 HN3 N4 C3 SING N N 22 HN3 C3 C2 SING N N 23 HN3 C2 O2 SING N N 24 HN3 C16 H16 SING N N 25 HN3 C15 H15 SING N N 26 HN3 C17 H17 SING N N 27 HN3 C17 H17A SING N N 28 HN3 C17 H17B SING N N 29 HN3 C13 H13 SING N N 30 HN3 C12 H12 SING N N 31 HN3 C9 H9 SING N N 32 HN3 C9 H9A SING N N 33 HN3 C5 H5 SING N N 34 HN3 C6 H6 SING N N 35 HN3 C6 H6A SING N N 36 HN3 C7 H7 SING N N 37 HN3 C7 H7A SING N N 38 HN3 C8 H8 SING N N 39 HN3 O8 HO8 SING N N 40 HN3 C8A H8A SING N N 41 HN3 C1 H1 SING N N 42 HN3 O1 HO1 SING N N 43 HN3 C3 H3 SING N N 44 HN3 C3 H3A SING N N 45 HN3 C2 H2 SING N N 46 HN3 O2 HO2 SING N N 47 # # 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 HN3 SMILES ACDLabs 10.04 "O=C(c1ccc(cc1)C)CC2N3C(C(O)CC2)C(O)C(O)C3" HN3 SMILES_CANONICAL CACTVS 3.341 "Cc1ccc(cc1)C(=O)C[C@H]2CC[C@@H](O)[C@@H]3[C@H](O)[C@H](O)CN23" HN3 SMILES CACTVS 3.341 "Cc1ccc(cc1)C(=O)C[CH]2CC[CH](O)[CH]3[CH](O)[CH](O)CN23" HN3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1ccc(cc1)C(=O)C[C@H]2CC[C@H]([C@H]3[N@]2C[C@H]([C@H]3O)O)O" HN3 SMILES "OpenEye OEToolkits" 1.5.0 "Cc1ccc(cc1)C(=O)CC2CCC(C3N2CC(C3O)O)O" HN3 InChI InChI 1.03 "InChI=1S/C17H23NO4/c1-10-2-4-11(5-3-10)14(20)8-12-6-7-13(19)16-17(22)15(21)9-18(12)16/h2-5,12-13,15-17,19,21-22H,6-9H2,1H3/t12-,13-,15-,16-,17-/m1/s1" HN3 InChIKey InChI 1.03 APAFVLSHHZZYGV-PVTMVUMOSA-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 HN3 "SYSTEMATIC NAME" ACDLabs 10.04 "1-(4-methylphenyl)-2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizin-5-yl]ethanone" HN3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[(1S,2R,4S,5R,8R,8aR)-1,2,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-5-yl]-1-(4-methylphenyl)ethanone" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site HN3 "Create component" 2008-09-25 RCSB HN3 "Modify aromatic_flag" 2011-06-04 RCSB HN3 "Modify descriptor" 2011-06-04 RCSB HN3 "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id HN3 _pdbx_chem_comp_synonyms.name "(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##