data_27H # _chem_comp.id 27H _chem_comp.name ferutinine _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H30 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-09-05 _chem_comp.pdbx_modified_date 2020-06-17 _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 358.471 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 27H _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 4MG7 _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 27H CAB CAB C 0 1 N N N -14.325 -10.019 49.671 0.198 3.808 0.448 CAB 27H 1 27H CAV CAV C 0 1 N N N -13.932 -11.449 49.638 0.537 2.549 -0.352 CAV 27H 2 27H CAC CAC C 0 1 N N N -15.201 -12.209 49.877 1.200 2.947 -1.672 CAC 27H 3 27H CAZ CAZ C 0 1 N N R -13.269 -11.852 48.263 1.496 1.673 0.457 CAZ 27H 4 27H CAX CAX C 0 1 N N S -12.799 -13.353 48.320 1.868 0.419 -0.338 CAX 27H 5 27H OAG OAG O 0 1 N N N -12.276 -10.997 47.933 0.900 1.310 1.704 OAG 27H 6 27H CAO CAO C 0 1 N N N -14.235 -11.836 47.152 2.829 2.421 0.697 CAO 27H 7 27H CAN CAN C 0 1 N N N -14.189 -13.153 46.506 3.942 1.552 0.058 CAN 27H 8 27H CAY CAY C 0 1 N N R -12.903 -13.759 46.859 3.321 0.144 0.026 CAY 27H 9 27H CAD CAD C 0 1 N N N -11.835 -13.114 45.953 3.394 -0.484 1.419 CAD 27H 10 27H CAM CAM C 0 1 N N N -13.007 -15.223 46.702 3.975 -0.783 -0.986 CAM 27H 11 27H CAH CAH C 0 1 N N N -11.862 -15.920 46.950 3.691 -2.200 -0.528 CAH 27H 12 27H CAR CAR C 0 1 N N N -11.028 -15.868 48.016 2.478 -2.677 -0.577 CAR 27H 13 27H CAA CAA C 0 1 N N N -9.943 -16.706 47.970 2.217 -4.072 -0.069 CAA 27H 14 27H CAP CAP C 0 1 N N N -11.247 -15.128 49.188 1.325 -1.867 -1.132 CAP 27H 15 27H CAW CAW C 0 1 N N S -11.470 -13.640 49.026 0.950 -0.759 -0.136 CAW 27H 16 27H OAQ OAQ O 0 1 N N N -11.518 -13.077 50.326 -0.424 -0.349 -0.363 OAQ 27H 17 27H CAS CAS C 0 1 N N N -10.559 -12.331 50.768 -1.380 -1.001 0.327 CAS 27H 18 27H OAE OAE O 0 1 N N N -9.548 -12.200 50.177 -1.073 -1.889 1.098 OAE 27H 19 27H CAU CAU C 0 1 Y N N -10.800 -11.750 52.030 -2.797 -0.638 0.148 CAU 27H 20 27H CAK CAK C 0 1 Y N N -11.936 -12.070 52.751 -3.153 0.380 -0.742 CAK 27H 21 27H CAI CAI C 0 1 Y N N -12.232 -11.524 53.966 -4.478 0.715 -0.907 CAI 27H 22 27H CAT CAT C 0 1 Y N N -11.347 -10.627 54.474 -5.462 0.045 -0.189 CAT 27H 23 27H OAF OAF O 0 1 N N N -11.597 -10.084 55.615 -6.766 0.379 -0.355 OAF 27H 24 27H CAJ CAJ C 0 1 Y N N -10.214 -10.293 53.800 -5.113 -0.968 0.697 CAJ 27H 25 27H CAL CAL C 0 1 Y N N -9.930 -10.849 52.582 -3.790 -1.313 0.864 CAL 27H 26 27H H1 H1 H 0 1 N N N -14.781 -9.786 50.645 -0.486 4.431 -0.128 H1 27H 27 27H H2 H2 H 0 1 N N N -13.434 -9.391 49.523 -0.275 3.524 1.389 H2 27H 28 27H H3 H3 H 0 1 N N N -15.051 -9.820 48.869 1.112 4.365 0.654 H3 27H 29 27H H4 H4 H 0 1 N N N -13.217 -11.659 50.447 -0.377 1.992 -0.558 H4 27H 30 27H H5 H5 H 0 1 N N N -15.635 -11.905 50.841 2.171 3.399 -1.469 H5 27H 31 27H H6 H6 H 0 1 N N N -15.915 -11.993 49.069 1.335 2.060 -2.293 H6 27H 32 27H H7 H7 H 0 1 N N N -14.984 -13.287 49.897 0.567 3.663 -2.195 H7 27H 33 27H H8 H8 H 0 1 N N N -13.579 -13.905 48.866 1.851 0.680 -1.396 H8 27H 34 27H H9 H9 H 0 1 N N N -11.629 -10.979 48.628 0.644 2.064 2.252 H9 27H 35 27H H10 H10 H 0 1 N N N -13.962 -11.054 46.429 2.799 3.401 0.220 H10 27H 36 27H H11 H11 H 0 1 N N N -15.247 -11.642 47.537 3.008 2.532 1.766 H11 27H 37 27H H12 H12 H 0 1 N N N -14.267 -13.041 45.414 4.166 1.896 -0.952 H12 27H 38 27H H13 H13 H 0 1 N N N -15.015 -13.781 46.870 4.840 1.561 0.676 H13 27H 39 27H H14 H14 H 0 1 N N N -10.849 -13.542 46.186 2.867 0.150 2.131 H14 27H 40 27H H15 H15 H 0 1 N N N -12.081 -13.311 44.899 2.929 -1.470 1.398 H15 27H 41 27H H16 H16 H 0 1 N N N -11.813 -12.028 46.128 4.437 -0.580 1.720 H16 27H 42 27H H17 H17 H 0 1 N N N -13.781 -15.585 47.395 3.546 -0.618 -1.974 H17 27H 43 27H H18 H18 H 0 1 N N N -13.314 -15.432 45.667 5.050 -0.608 -1.011 H18 27H 44 27H H19 H19 H 0 1 N N N -11.576 -16.620 46.179 4.496 -2.818 -0.160 H19 27H 45 27H H20 H20 H 0 1 N N N -9.341 -16.578 48.882 3.149 -4.508 0.291 H20 27H 46 27H H21 H21 H 0 1 N N N -10.288 -17.748 47.901 1.495 -4.032 0.747 H21 27H 47 27H H22 H22 H 0 1 N N N -9.330 -16.464 47.089 1.818 -4.684 -0.878 H22 27H 48 27H H23 H23 H 0 1 N N N -12.136 -15.545 49.683 1.620 -1.418 -2.081 H23 27H 49 27H H24 H24 H 0 1 N N N -10.369 -15.264 49.836 0.466 -2.519 -1.291 H24 27H 50 27H H25 H25 H 0 1 N N N -10.646 -13.206 48.440 1.056 -1.133 0.882 H25 27H 51 27H H26 H26 H 0 1 N N N -12.624 -12.789 52.331 -2.389 0.901 -1.300 H26 27H 52 27H H27 H27 H 0 1 N N N -13.131 -11.793 54.501 -4.753 1.501 -1.595 H27 27H 53 27H H28 H28 H 0 1 N N N -12.419 -10.420 55.953 -7.214 -0.117 -1.053 H28 27H 54 27H H29 H29 H 0 1 N N N -9.529 -9.579 54.232 -5.880 -1.486 1.253 H29 27H 55 27H H30 H30 H 0 1 N N N -9.024 -10.578 52.059 -3.520 -2.103 1.549 H30 27H 56 # # 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 27H CAD CAY SING N N 1 27H CAN CAY SING N N 2 27H CAN CAO SING N N 3 27H CAM CAY SING N N 4 27H CAM CAH SING N N 5 27H CAY CAX SING N N 6 27H CAH CAR DOUB N N 7 27H CAO CAZ SING N N 8 27H OAG CAZ SING N N 9 27H CAA CAR SING N N 10 27H CAR CAP SING N N 11 27H CAZ CAX SING N N 12 27H CAZ CAV SING N N 13 27H CAX CAW SING N N 14 27H CAW CAP SING N N 15 27H CAW OAQ SING N N 16 27H CAV CAB SING N N 17 27H CAV CAC SING N N 18 27H OAE CAS DOUB N N 19 27H OAQ CAS SING N N 20 27H CAS CAU SING N N 21 27H CAU CAL DOUB Y N 22 27H CAU CAK SING Y N 23 27H CAL CAJ SING Y N 24 27H CAK CAI DOUB Y N 25 27H CAJ CAT DOUB Y N 26 27H CAI CAT SING Y N 27 27H CAT OAF SING N N 28 27H CAB H1 SING N N 29 27H CAB H2 SING N N 30 27H CAB H3 SING N N 31 27H CAV H4 SING N N 32 27H CAC H5 SING N N 33 27H CAC H6 SING N N 34 27H CAC H7 SING N N 35 27H CAX H8 SING N N 36 27H OAG H9 SING N N 37 27H CAO H10 SING N N 38 27H CAO H11 SING N N 39 27H CAN H12 SING N N 40 27H CAN H13 SING N N 41 27H CAD H14 SING N N 42 27H CAD H15 SING N N 43 27H CAD H16 SING N N 44 27H CAM H17 SING N N 45 27H CAM H18 SING N N 46 27H CAH H19 SING N N 47 27H CAA H20 SING N N 48 27H CAA H21 SING N N 49 27H CAA H22 SING N N 50 27H CAP H23 SING N N 51 27H CAP H24 SING N N 52 27H CAW H25 SING N N 53 27H CAK H26 SING N N 54 27H CAI H27 SING N N 55 27H OAF H28 SING N N 56 27H CAJ H29 SING N N 57 27H CAL H30 SING N N 58 # # 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 27H SMILES ACDLabs 12.01 "O=C(OC1C2C(CC=C(C)C1)(CCC2(O)C(C)C)C)c3ccc(O)cc3" 27H InChI InChI 1.03 "InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1" 27H InChIKey InChI 1.03 CYSHNJQMYORNJI-YUVXSKOASA-N 27H SMILES_CANONICAL CACTVS 3.385 "CC(C)[C@]1(O)CC[C@]2(C)CC=C(C)C[C@H](OC(=O)c3ccc(O)cc3)[C@@H]12" 27H SMILES CACTVS 3.385 "CC(C)[C]1(O)CC[C]2(C)CC=C(C)C[CH](OC(=O)c3ccc(O)cc3)[CH]12" 27H SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CC1=CC[C@]2(CC[C@]([C@@H]2[C@H](C1)OC(=O)c3ccc(cc3)O)(C(C)C)O)C" 27H SMILES "OpenEye OEToolkits" 1.7.6 "CC1=CCC2(CCC(C2C(C1)OC(=O)c3ccc(cc3)O)(C(C)C)O)C" # # 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 27H "SYSTEMATIC NAME" ACDLabs 12.01 "(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate" 27H "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(3R,3aS,4S,8aR)-6,8a-dimethyl-3-oxidanyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-oxidanylbenzoate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 27H "Create component" 2013-09-05 RCSB 27H "Initial release" 2014-09-03 RCSB 27H "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 27H _pdbx_chem_comp_synonyms.name "(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##