data_NOG # _chem_comp.id NOG _chem_comp.name 13-BETA-ETHYL-17-ALPHA-ETHYNYL-17-BETA-HYDROXYGON-4-EN-3-ONE _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H28 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms NORGESTREL _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-04-29 _chem_comp.pdbx_modified_date 2021-03-01 _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 312.446 _chem_comp.one_letter_code ? _chem_comp.three_letter_code NOG _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 1LHV _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 NOG C1 C1 C 0 1 N N N 24.387 9.850 30.697 1.628 0.050 2.877 C1 NOG 1 NOG C2 C2 C 0 1 N N N 25.807 10.268 30.326 1.578 -0.243 4.376 C2 NOG 2 NOG C3 C3 C 0 1 N N N 26.139 11.720 30.561 0.302 0.371 4.917 C3 NOG 3 NOG C4 C4 C 0 1 N N N 25.314 12.488 31.520 -0.931 0.060 4.188 C4 NOG 4 NOG C5 C5 C 0 1 N N N 24.244 11.966 32.181 -0.872 -0.338 2.918 C5 NOG 5 NOG C6 C6 C 0 1 N N N 23.455 12.804 33.172 -2.179 -0.662 2.219 C6 NOG 6 NOG C7 C7 C 0 1 N N N 21.917 12.702 32.962 -2.207 0.064 0.873 C7 NOG 7 NOG C8 C8 C 0 1 N N R 21.416 11.239 32.899 -0.965 -0.323 0.067 C8 NOG 8 NOG C9 C9 C 0 1 N N S 22.182 10.484 31.782 0.285 0.198 0.789 C9 NOG 9 NOG C10 C10 C 0 1 N N R 23.746 10.501 31.974 0.393 -0.492 2.155 C10 NOG 10 NOG C11 C11 C 0 1 N N N 21.663 9.010 31.626 1.556 -0.072 -0.009 C11 NOG 11 NOG C12 C12 C 0 1 N N N 20.119 8.935 31.435 1.459 0.485 -1.438 C12 NOG 12 NOG C13 C13 C 0 1 N N S 19.366 9.641 32.595 0.245 -0.151 -2.084 C13 NOG 13 NOG C14 C14 C 0 1 N N S 19.893 11.135 32.649 -1.002 0.346 -1.307 C14 NOG 14 NOG C15 C15 C 0 1 N N N 18.898 11.808 33.614 -2.150 -0.091 -2.225 C15 NOG 15 NOG C16 C16 C 0 1 N N N 17.564 11.028 33.414 -1.609 0.243 -3.642 C16 NOG 16 NOG C17 C17 C 0 1 N N R 17.836 9.919 32.372 -0.053 0.251 -3.524 C17 NOG 17 NOG C18 C18 C 0 1 N N N 19.569 8.863 33.950 0.344 -1.674 -1.983 C18 NOG 18 NOG C19 C19 C 0 1 N N N 19.549 7.334 33.945 1.683 -2.138 -2.561 C19 NOG 19 NOG C20 C20 C 0 1 N N N 17.515 10.414 30.988 0.471 1.601 -3.784 C20 NOG 20 NOG C21 C21 C 0 1 N N N 17.236 10.776 29.914 0.890 2.678 -3.992 C21 NOG 21 NOG O3 O3 O 0 1 N N N 27.074 12.219 29.975 0.302 1.081 5.900 O3 NOG 22 NOG O17 O17 O 0 1 N N N 17.013 8.779 32.601 0.517 -0.687 -4.438 O17 NOG 23 NOG HC11 1HC1 H 0 0 N N N 24.343 8.740 30.789 1.680 1.128 2.728 HC11 NOG 24 NOG HC12 2HC1 H 0 0 N N N 23.715 10.016 29.823 2.522 -0.408 2.455 HC12 NOG 25 NOG HC21 1HC2 H 0 0 N N N 26.021 9.994 29.266 2.442 0.201 4.869 HC21 NOG 26 NOG HC22 2HC2 H 0 0 N N N 26.546 9.618 30.851 1.570 -1.320 4.542 HC22 NOG 27 NOG HC4 HC4 H 0 1 N N N 25.515 13.545 31.764 -1.888 0.155 4.680 HC4 NOG 28 NOG HC61 1HC6 H 0 0 N N N 23.791 13.867 33.151 -3.015 -0.328 2.833 HC61 NOG 29 NOG HC62 2HC6 H 0 0 N N N 23.732 12.547 34.221 -2.250 -1.738 2.055 HC62 NOG 30 NOG HC71 1HC7 H 0 0 N N N 21.599 13.272 32.058 -2.211 1.141 1.041 HC71 NOG 31 NOG HC72 2HC7 H 0 0 N N N 21.368 13.279 33.743 -3.103 -0.222 0.322 HC72 NOG 32 NOG HC8 HC8 H 0 1 N N N 21.613 10.776 33.894 -0.911 -1.407 -0.032 HC8 NOG 33 NOG HC9 HC9 H 0 1 N N N 21.969 11.043 30.841 0.184 1.272 0.942 HC9 NOG 34 NOG H10C CH10 H 0 0 N N N 24.045 9.923 32.879 0.543 -1.558 1.983 H10C NOG 35 NOG H111 1H11 H 0 0 N N N 21.992 8.377 32.483 1.722 -1.148 -0.058 H111 NOG 36 NOG H112 2H11 H 0 0 N N N 22.195 8.484 30.799 2.401 0.393 0.498 H112 NOG 37 NOG H121 1H12 H 0 0 N N N 19.775 7.882 31.307 2.357 0.227 -1.999 H121 NOG 38 NOG H122 2H12 H 0 0 N N N 19.811 9.340 30.443 1.338 1.568 -1.406 H122 NOG 39 NOG H14C CH14 H 0 0 N N N 19.885 11.696 31.685 -0.991 1.430 -1.202 H14C NOG 40 NOG H151 1H15 H 0 0 N N N 18.805 12.910 33.473 -2.336 -1.160 -2.127 H151 NOG 41 NOG H152 2H15 H 0 0 N N N 19.247 11.846 34.672 -3.053 0.480 -2.012 H152 NOG 42 NOG H161 1H16 H 0 0 N N N 16.709 11.688 33.137 -1.927 -0.518 -4.354 H161 NOG 43 NOG H162 2H16 H 0 0 N N N 17.139 10.637 34.368 -1.968 1.223 -3.958 H162 NOG 44 NOG H181 1H18 H 0 0 N N N 18.816 9.228 34.687 -0.470 -2.130 -2.545 H181 NOG 45 NOG H182 2H18 H 0 0 N N N 20.520 9.206 34.420 0.277 -1.974 -0.937 H182 NOG 46 NOG H191 1H19 H 0 0 N N N 20.302 6.969 33.208 1.807 -3.205 -2.379 H191 NOG 47 NOG H192 2H19 H 0 0 N N N 19.693 6.783 34.904 1.701 -1.947 -3.634 H192 NOG 48 NOG H193 3H19 H 0 0 N N N 18.598 6.991 33.475 2.495 -1.591 -2.081 H193 NOG 49 NOG H21C CH21 H 0 0 N N N 16.976 11.114 28.911 1.265 3.641 -4.178 H21C NOG 50 NOG H17O OH17 H 0 0 N N N 16.088 8.947 32.466 0.264 -0.401 -5.326 H17O NOG 51 # # 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 NOG C1 C2 SING N N 1 NOG C1 C10 SING N N 2 NOG C1 HC11 SING N N 3 NOG C1 HC12 SING N N 4 NOG C2 C3 SING N N 5 NOG C2 HC21 SING N N 6 NOG C2 HC22 SING N N 7 NOG C3 C4 SING N N 8 NOG C3 O3 DOUB N N 9 NOG C4 C5 DOUB N N 10 NOG C4 HC4 SING N N 11 NOG C5 C6 SING N N 12 NOG C5 C10 SING N N 13 NOG C6 C7 SING N N 14 NOG C6 HC61 SING N N 15 NOG C6 HC62 SING N N 16 NOG C7 C8 SING N N 17 NOG C7 HC71 SING N N 18 NOG C7 HC72 SING N N 19 NOG C8 C9 SING N N 20 NOG C8 C14 SING N N 21 NOG C8 HC8 SING N N 22 NOG C9 C10 SING N N 23 NOG C9 C11 SING N N 24 NOG C9 HC9 SING N N 25 NOG C10 H10C SING N N 26 NOG C11 C12 SING N N 27 NOG C11 H111 SING N N 28 NOG C11 H112 SING N N 29 NOG C12 C13 SING N N 30 NOG C12 H121 SING N N 31 NOG C12 H122 SING N N 32 NOG C13 C14 SING N N 33 NOG C13 C17 SING N N 34 NOG C13 C18 SING N N 35 NOG C14 C15 SING N N 36 NOG C14 H14C SING N N 37 NOG C15 C16 SING N N 38 NOG C15 H151 SING N N 39 NOG C15 H152 SING N N 40 NOG C16 C17 SING N N 41 NOG C16 H161 SING N N 42 NOG C16 H162 SING N N 43 NOG C17 C20 SING N N 44 NOG C17 O17 SING N N 45 NOG C18 C19 SING N N 46 NOG C18 H181 SING N N 47 NOG C18 H182 SING N N 48 NOG C19 H191 SING N N 49 NOG C19 H192 SING N N 50 NOG C19 H193 SING N N 51 NOG C20 C21 TRIP N N 52 NOG C21 H21C SING N N 53 NOG O17 H17O SING N N 54 # # 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 NOG SMILES ACDLabs 10.04 "O=C4C=C3C(C2CCC1(C(CCC1(C#C)O)C2CC3)CC)CC4" NOG SMILES_CANONICAL CACTVS 3.341 "CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C" NOG SMILES CACTVS 3.341 "CC[C]12CC[CH]3[CH](CCC4=CC(=O)CC[CH]34)[CH]1CC[C]2(O)C#C" NOG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34" NOG SMILES "OpenEye OEToolkits" 1.5.0 "CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34" NOG InChI InChI 1.03 "InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1" NOG InChIKey InChI 1.03 WWYNJERNGUHSAO-XUDSTZEESA-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 NOG "SYSTEMATIC NAME" ACDLabs 10.04 "(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (non-preferred name)" NOG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site NOG "Create component" 2002-04-29 RCSB NOG "Modify descriptor" 2011-06-04 RCSB NOG "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id NOG _pdbx_chem_comp_synonyms.name NORGESTREL _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##