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                    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                        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 InChI            InChI                1.02b 
InChI=1/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                1.02b VLGAHTYYCHWLNI-BHRZLAGCBC 
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 
# 
_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 
# 
