data_GL8 # _chem_comp.id GL8 _chem_comp.name "GALANTHAMINE DERIVATIVE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C32 H37 N2 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(4AR,6S,8AR)-11-[8-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)OCTYL]-6-HYDROXY-3-METHOXY-5,6,9,10-TETRAHYDRO-4AH-[1]BENZOFURO[3A,3,2-EF][2]BENZAZEPIN-11-IUM" _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2004-07-25 _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 529.647 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GL8 _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 1W4L _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 GL8 C1 C1 C 0 1 N N N 2.536 67.552 63.228 -6.078 -1.818 -1.026 C1 GL8 1 GL8 C2 C2 C 0 1 N N N 2.710 68.092 62.001 -7.104 -2.601 -1.051 C2 GL8 2 GL8 C3 C3 C 0 1 N N R 4.132 68.302 61.410 -7.947 -2.862 0.169 C3 GL8 3 GL8 C4 C4 C 0 1 N N N 5.297 68.318 62.591 -7.061 -2.683 1.406 C4 GL8 4 GL8 C5 C5 C 0 1 N N S 5.044 67.066 63.510 -6.474 -1.278 1.394 C5 GL8 5 GL8 C6 C6 C 0 1 N N S 3.692 67.198 64.243 -5.572 -1.056 0.167 C6 GL8 6 GL8 C7 C7 C 0 1 Y N N 4.488 63.646 63.691 -7.523 2.029 0.337 C7 GL8 7 GL8 C8 C8 C 0 1 Y N N 3.670 62.944 64.638 -6.762 2.950 -0.380 C8 GL8 8 GL8 C9 C9 C 0 1 Y N N 2.855 63.677 65.522 -5.527 2.632 -0.894 C9 GL8 9 GL8 C10 C10 C 0 1 N N N 1.987 65.769 66.504 -3.643 1.061 -1.234 C10 GL8 10 GL8 C11 C11 C 0 1 N N N 2.239 68.248 66.149 -3.281 -1.326 -0.804 C11 GL8 11 GL8 C12 C12 C 0 1 N N N 3.625 68.230 65.432 -4.136 -1.416 0.434 C12 GL8 12 GL8 C13 C13 C 0 1 Y N N 4.406 65.035 63.668 -6.990 0.745 0.509 C13 GL8 13 GL8 C14 C14 C 0 1 Y N N 3.579 65.769 64.555 -5.769 0.407 -0.082 C14 GL8 14 GL8 C15 C15 C 0 1 Y N N 2.810 65.120 65.494 -4.984 1.341 -0.746 C15 GL8 15 GL8 C16 C16 C 0 1 N N N 5.710 61.665 63.094 -8.966 3.732 0.506 C16 GL8 16 GL8 C17 C17 C 0 1 N N N 1.043 67.113 68.107 -1.588 0.179 -1.714 C17 GL8 17 GL8 C18 C18 C 0 1 N N N 2.037 67.450 69.287 -0.600 -0.075 -0.573 C18 GL8 18 GL8 C19 C19 C 0 1 N N N 3.317 66.504 69.388 0.830 0.098 -1.088 C19 GL8 19 GL8 C20 C20 C 0 1 N N N 2.879 65.057 69.649 1.817 -0.156 0.053 C20 GL8 20 GL8 C21 C21 C 0 1 N N N 4.104 64.126 69.721 3.247 0.017 -0.462 C21 GL8 21 GL8 C22 C22 C 0 1 N N N 3.616 62.636 69.609 4.235 -0.237 0.678 C22 GL8 22 GL8 C23 C23 C 0 1 N N N 3.094 62.160 71.002 5.665 -0.063 0.163 C23 GL8 23 GL8 C24 C24 C 0 1 N N N 1.782 61.691 70.631 6.652 -0.318 1.304 C24 GL8 24 GL8 C25 C25 C 0 1 N N N -0.176 61.749 72.052 8.700 1.010 0.824 C25 GL8 25 GL8 C26 C26 C 0 1 Y N N -0.903 60.830 72.795 10.041 0.779 0.248 C26 GL8 26 GL8 C27 C27 C 0 1 Y N N -2.152 60.948 73.429 11.144 1.584 0.010 C27 GL8 27 GL8 C28 C28 C 0 1 Y N N -2.664 59.776 74.090 12.283 1.038 -0.561 C28 GL8 28 GL8 C29 C29 C 0 1 Y N N -1.912 58.571 74.089 12.325 -0.303 -0.896 C29 GL8 29 GL8 C30 C30 C 0 1 Y N N -0.641 58.490 73.442 11.229 -1.120 -0.665 C30 GL8 30 GL8 C31 C31 C 0 1 Y N N -0.178 59.654 72.799 10.084 -0.588 -0.094 C31 GL8 31 GL8 C32 C32 C 0 1 N N N 0.965 59.874 72.041 8.769 -1.142 0.291 C32 GL8 32 GL8 O1 O1 O 0 1 N N N 5.115 65.843 62.791 -7.521 -0.307 1.174 O1 GL8 33 GL8 O2 O2 O 0 1 N N N 5.473 63.058 62.869 -8.732 2.366 0.855 O2 GL8 34 GL8 O3 O3 O 0 1 N N N 4.159 67.111 60.512 -9.033 -1.934 0.212 O3 GL8 35 GL8 O25 O25 O 0 1 N N N -0.461 62.994 71.899 8.280 2.071 1.239 O25 GL8 36 GL8 O32 O32 O 0 1 N N N 1.903 59.026 71.838 8.421 -2.298 0.158 O32 GL8 37 GL8 N1 N1 N 1 1 N N N 1.757 66.985 66.827 -2.957 0.013 -1.220 N1 GL8 38 GL8 N2 N2 N 0 1 N N N 0.900 61.124 71.604 8.022 -0.152 0.811 N2 GL8 39 GL8 H1 H1 H 0 1 N N N 1.501 67.341 63.546 -5.531 -1.700 -1.950 H1 GL8 40 GL8 H2 H2 H 0 1 N N N 1.828 68.389 61.409 -7.367 -3.086 -1.980 H2 GL8 41 GL8 H3 H3 H 0 1 N N N 4.170 69.242 60.812 -8.334 -3.881 0.138 H3 GL8 42 GL8 H4C1 1H4C H 0 0 N N N 5.331 69.277 63.159 -7.659 -2.820 2.307 H4C1 GL8 43 GL8 H4C2 2H4C H 0 0 N N N 6.333 68.357 62.182 -6.254 -3.416 1.387 H4C2 GL8 44 GL8 H5 H5 H 0 1 N N N 5.846 67.049 64.284 -5.941 -1.073 2.322 H5 GL8 45 GL8 H8 H8 H 0 1 N N N 3.680 61.842 64.673 -7.154 3.943 -0.537 H8 GL8 46 GL8 H9 H9 H 0 1 N N N 2.235 63.135 66.255 -4.964 3.387 -1.422 H9 GL8 47 GL8 H10 H10 H 0 1 N N N 1.437 65.049 67.133 -3.151 1.908 -1.689 H10 GL8 48 GL8 H111 1H11 H 0 0 N N N 1.462 68.589 65.425 -3.805 -1.823 -1.620 H111 GL8 49 GL8 H112 2H11 H 0 0 N N N 2.226 69.083 66.888 -2.350 -1.864 -0.620 H112 GL8 50 GL8 H121 1H12 H 0 0 N N N 3.908 69.252 65.088 -4.093 -2.435 0.820 H121 GL8 51 GL8 H122 2H12 H 0 0 N N N 4.448 68.049 66.162 -3.736 -0.739 1.189 H122 GL8 52 GL8 H161 1H16 H 0 0 N N N 6.488 61.200 62.445 -8.177 4.355 0.928 H161 GL8 53 GL8 H162 2H16 H 0 0 N N N 4.754 61.097 63.011 -8.968 3.834 -0.580 H162 GL8 54 GL8 H163 3H16 H 0 0 N N N 5.953 61.487 64.168 -9.930 4.049 0.902 H163 GL8 55 GL8 H171 1H17 H 0 0 N N N 0.436 66.204 68.330 -1.403 -0.531 -2.519 H171 GL8 56 GL8 H172 2H17 H 0 0 N N N 0.217 67.859 68.042 -1.457 1.195 -2.088 H172 GL8 57 GL8 H181 1H18 H 0 0 N N N 1.490 67.460 70.258 -0.785 0.635 0.233 H181 GL8 58 GL8 H182 2H18 H 0 0 N N N 2.353 68.518 69.229 -0.731 -1.091 -0.199 H182 GL8 59 GL8 H191 1H19 H 0 0 N N N 4.045 66.865 70.152 1.015 -0.612 -1.894 H191 GL8 60 GL8 H192 2H19 H 0 0 N N N 3.971 66.587 68.489 0.961 1.114 -1.462 H192 GL8 61 GL8 H201 1H20 H 0 0 N N N 2.136 64.707 68.895 1.632 0.554 0.858 H201 GL8 62 GL8 H202 2H20 H 0 0 N N N 2.242 64.975 70.561 1.686 -1.172 0.427 H202 GL8 63 GL8 H211 1H21 H 0 0 N N N 4.721 64.304 70.632 3.432 -0.693 -1.268 H211 GL8 64 GL8 H212 2H21 H 0 0 N N N 4.877 64.379 68.958 3.378 1.033 -0.836 H212 GL8 65 GL8 H221 1H22 H 0 0 N N N 4.404 61.962 69.200 4.050 0.473 1.484 H221 GL8 66 GL8 H222 2H22 H 0 0 N N N 2.858 62.499 68.803 4.104 -1.253 1.052 H222 GL8 67 GL8 H231 1H23 H 0 0 N N N 3.126 62.919 71.818 5.850 -0.774 -0.642 H231 GL8 68 GL8 H232 2H23 H 0 0 N N N 3.739 61.425 71.538 5.796 0.952 -0.211 H232 GL8 69 GL8 H241 1H24 H 0 0 N N N 1.899 60.957 69.800 6.468 0.392 2.110 H241 GL8 70 GL8 H242 2H24 H 0 0 N N N 1.246 62.527 70.123 6.522 -1.333 1.678 H242 GL8 71 GL8 H27 H27 H 0 1 N N N -2.715 61.896 73.420 11.117 2.632 0.270 H27 GL8 72 GL8 H28 H28 H 0 1 N N N -3.642 59.814 74.598 13.143 1.664 -0.747 H28 GL8 73 GL8 H29 H29 H 0 1 N N N -2.317 57.680 74.598 13.217 -0.717 -1.342 H29 GL8 74 GL8 H30 H30 H 0 1 N N N -0.050 57.559 73.446 11.267 -2.166 -0.929 H30 GL8 75 GL8 HA HA H 0 1 N N N 5.028 67.239 60.151 -9.549 -2.070 -0.594 HA GL8 76 # # 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 GL8 C1 C2 DOUB N N 1 GL8 C1 C6 SING N N 2 GL8 C1 H1 SING N N 3 GL8 C2 C3 SING N N 4 GL8 C2 H2 SING N N 5 GL8 C3 C4 SING N N 6 GL8 C3 O3 SING N N 7 GL8 C3 H3 SING N N 8 GL8 C4 C5 SING N N 9 GL8 C4 H4C1 SING N N 10 GL8 C4 H4C2 SING N N 11 GL8 C5 C6 SING N N 12 GL8 C5 O1 SING N N 13 GL8 C5 H5 SING N N 14 GL8 C6 C12 SING N N 15 GL8 C6 C14 SING N N 16 GL8 C7 C8 DOUB Y N 17 GL8 C7 C13 SING Y N 18 GL8 C7 O2 SING N N 19 GL8 C8 C9 SING Y N 20 GL8 C8 H8 SING N N 21 GL8 C9 C15 DOUB Y N 22 GL8 C9 H9 SING N N 23 GL8 C10 C15 SING N N 24 GL8 C10 N1 DOUB N N 25 GL8 C10 H10 SING N N 26 GL8 C11 C12 SING N N 27 GL8 C11 N1 SING N N 28 GL8 C11 H111 SING N N 29 GL8 C11 H112 SING N N 30 GL8 C12 H121 SING N N 31 GL8 C12 H122 SING N N 32 GL8 C13 C14 DOUB Y N 33 GL8 C13 O1 SING N N 34 GL8 C14 C15 SING Y N 35 GL8 C16 O2 SING N N 36 GL8 C16 H161 SING N N 37 GL8 C16 H162 SING N N 38 GL8 C16 H163 SING N N 39 GL8 C17 C18 SING N N 40 GL8 C17 N1 SING N N 41 GL8 C17 H171 SING N N 42 GL8 C17 H172 SING N N 43 GL8 C18 C19 SING N N 44 GL8 C18 H181 SING N N 45 GL8 C18 H182 SING N N 46 GL8 C19 C20 SING N N 47 GL8 C19 H191 SING N N 48 GL8 C19 H192 SING N N 49 GL8 C20 C21 SING N N 50 GL8 C20 H201 SING N N 51 GL8 C20 H202 SING N N 52 GL8 C21 C22 SING N N 53 GL8 C21 H211 SING N N 54 GL8 C21 H212 SING N N 55 GL8 C22 C23 SING N N 56 GL8 C22 H221 SING N N 57 GL8 C22 H222 SING N N 58 GL8 C23 C24 SING N N 59 GL8 C23 H231 SING N N 60 GL8 C23 H232 SING N N 61 GL8 C24 N2 SING N N 62 GL8 C24 H241 SING N N 63 GL8 C24 H242 SING N N 64 GL8 C25 C26 SING N N 65 GL8 C25 O25 DOUB N N 66 GL8 C25 N2 SING N N 67 GL8 C26 C27 DOUB Y N 68 GL8 C26 C31 SING Y N 69 GL8 C27 C28 SING Y N 70 GL8 C27 H27 SING N N 71 GL8 C28 C29 DOUB Y N 72 GL8 C28 H28 SING N N 73 GL8 C29 C30 SING Y N 74 GL8 C29 H29 SING N N 75 GL8 C30 C31 DOUB Y N 76 GL8 C30 H30 SING N N 77 GL8 C31 C32 SING N N 78 GL8 C32 O32 DOUB N N 79 GL8 C32 N2 SING N N 80 GL8 O3 HA SING N N 81 # # 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 GL8 SMILES ACDLabs 10.04 "O=C2c1ccccc1C(=O)N2CCCCCCCC[N+]5=Cc6c3c(OC4C3(C=CC(O)C4)CC5)c(OC)cc6" GL8 SMILES_CANONICAL CACTVS 3.341 "COc1ccc2C=[N+](CCCCCCCCN3C(=O)c4ccccc4C3=O)CC[C@@]56C=C[C@H](O)C[C@@H]5Oc1c26" GL8 SMILES CACTVS 3.341 "COc1ccc2C=[N+](CCCCCCCCN3C(=O)c4ccccc4C3=O)CC[C]56C=C[CH](O)C[CH]5Oc1c26" GL8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COc1ccc2c3c1O[C@@H]4[C@@]3(CC[N+](=C2)CCCCCCCCN5C(=O)c6ccccc6C5=O)C=C[C@@H](C4)O" GL8 SMILES "OpenEye OEToolkits" 1.5.0 "COc1ccc2c3c1OC4C3(CC[N+](=C2)CCCCCCCCN5C(=O)c6ccccc6C5=O)C=CC(C4)O" GL8 InChI InChI 1.03 "InChI=1S/C32H37N2O5/c1-38-26-13-12-22-21-33(19-16-32-15-14-23(35)20-27(32)39-29(26)28(22)32)17-8-4-2-3-5-9-18-34-30(36)24-10-6-7-11-25(24)31(34)37/h6-7,10-15,21,23,27,35H,2-5,8-9,16-20H2,1H3/q+1/t23-,27-,32-/m0/s1" GL8 InChIKey InChI 1.03 VLGAHTYYCHWLNI-BHRZLAGCSA-N # _pdbx_chem_comp_identifier.comp_id GL8 _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program ACDLabs _pdbx_chem_comp_identifier.program_version 10.04 _pdbx_chem_comp_identifier.identifier "(4aS,6R,8aS)-11-[8-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)octyl]-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GL8 "Create component" 2004-07-25 EBI GL8 "Modify descriptor" 2011-06-04 RCSB GL8 "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id GL8 _pdbx_chem_comp_synonyms.name "(4AR,6S,8AR)-11-[8-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)OCTYL]-6-HYDROXY-3-METHOXY-5,6,9,10-TETRAHYDRO-4AH-[1]BENZOFURO[3A,3,2-EF][2]BENZAZEPIN-11-IUM" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##