data_GSG
# 
_chem_comp.id                                    GSG 
_chem_comp.name                                  "1S,3AS,8AS-TRIMETHYL-1-OXIDO-1,2,3,3A,8,8A-HEXAHYDROPYRROLO[2,3-B]INDOL-5-YL 2-ETHYLPHENYLCARBAMATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H27 N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;GANSTIGMINE; (-)-(3AS,8AS,1S)-1,2,3,3A,8A-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO[2,3-B]INDOL-5-OL-2'-ETHYLPHENYLCARBAMATE N-OXIDE HYDROCHLORIDE
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-10-27 
_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                        381.468 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GSG 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
GSG C1   C1   C 0  1 Y N N 62.865 4.500 64.551 1.173  -1.514 5.039  C1   GSG 1  
GSG C2   C2   C 0  1 Y N N 62.884 3.997 65.918 1.500  -0.855 6.215  C2   GSG 2  
GSG C3   C3   C 0  1 Y N N 63.852 2.967 66.206 1.064  -1.373 7.434  C3   GSG 3  
GSG C4   C4   C 0  1 Y N N 64.730 2.475 65.223 0.308  -2.545 7.464  C4   GSG 4  
GSG C5   C5   C 0  1 Y N N 64.679 2.986 63.923 -0.014 -3.198 6.275  C5   GSG 5  
GSG C6   C6   C 0  1 Y N N 63.751 3.996 63.577 0.421  -2.680 5.055  C6   GSG 6  
GSG N1   N1   N 0  1 N N N 61.886 5.473 64.157 1.605  -1.005 3.793  N1   GSG 7  
GSG C7   C7   C 0  1 N N N 60.618 5.204 63.837 1.374  -1.528 2.535  C7   GSG 8  
GSG O1   O1   O 0  1 N N N 60.098 4.116 63.773 0.746  -2.540 2.248  O1   GSG 9  
GSG C8   C8   C 0  1 N N N 61.954 4.520 67.017 2.308  0.401  6.213  C8   GSG 10 
GSG C9   C9   C 0  1 N N N 61.682 3.540 68.158 3.805  0.125  6.310  C9   GSG 11 
GSG O2   O2   O 0  1 N N N ?      ?     ?      1.983  -0.708 1.560  O2   GSG 12 
GSG C10  C10  C 0  1 Y N N ?      ?     ?      1.824  -1.122 0.271  C10  GSG 13 
GSG C11  C11  C 0  1 Y N N ?      ?     ?      0.716  -0.671 -0.469 C11  GSG 14 
GSG C12  C12  C 0  1 Y N N ?      ?     ?      0.517  -1.072 -1.795 C12  GSG 15 
GSG C13  C13  C 0  1 Y N N ?      ?     ?      1.439  -1.934 -2.363 C13  GSG 16 
GSG N2   N2   N 0  1 N N N ?      ?     ?      1.434  -2.517 -3.665 N2   GSG 17 
GSG C14  C14  C 0  1 N N N ?      ?     ?      0.224  -2.559 -4.448 C14  GSG 18 
GSG C15  C15  C 0  1 N N S ?      ?     ?      2.265  -3.682 -3.407 C15  GSG 19 
GSG C16  C16  C 0  1 N N R ?      ?     ?      3.429  -3.178 -2.521 C16  GSG 20 
GSG C17  C17  C 0  1 Y N N ?      ?     ?      2.566  -2.367 -1.608 C17  GSG 21 
GSG C18  C18  C 0  1 Y N N ?      ?     ?      2.768  -1.976 -0.300 C18  GSG 22 
GSG C19  C19  C 0  1 N N N ?      ?     ?      4.447  -2.214 -3.174 C19  GSG 23 
GSG C20  C20  C 0  1 N N N ?      ?     ?      4.075  -4.520 -2.235 C20  GSG 24 
GSG C21  C21  C 0  1 N N N ?      ?     ?      4.052  -5.200 -3.629 C21  GSG 25 
GSG N3   N3   N 1  1 N N S ?      ?     ?      2.919  -4.533 -4.444 N3   GSG 26 
GSG O3   O3   O -1 1 N N N ?      ?     ?      3.401  -3.787 -5.477 O3   GSG 27 
GSG C22  C22  C 0  1 N N N ?      ?     ?      1.993  -5.578 -4.993 C22  GSG 28 
GSG H3   H3   H 0  1 N N N 63.904 2.562 67.206 1.310  -0.872 8.367  H3   GSG 29 
GSG H4   H4   H 0  1 N N N 65.443 1.703 65.473 -0.030 -2.949 8.414  H4   GSG 30 
GSG H5   H5   H 0  1 N N N 65.357 2.605 63.173 -0.602 -4.111 6.298  H5   GSG 31 
GSG H6   H6   H 0  1 N N N 63.721 4.380 62.568 0.165  -3.198 4.135  H6   GSG 32 
GSG HN1  HN1  H 0  1 N N N 62.177 6.429 64.119 2.153  -0.149 3.827  HN1  GSG 33 
GSG H81  1H8  H 0  1 N N N 62.422 5.415 67.452 2.107  0.983  5.300  H81  GSG 34 
GSG H82  2H8  H 0  1 N N N 60.984 4.711 66.536 2.005  1.051  7.048  H82  GSG 35 
GSG H91  1H9  H 0  1 N N N 61.617 2.518 67.756 4.047  -0.413 7.233  H91  GSG 36 
GSG H92  2H9  H 0  1 N N N 62.501 3.594 68.891 4.372  1.061  6.306  H92  GSG 37 
GSG H93  3H9  H 0  1 N N N 60.733 3.803 68.648 4.149  -0.484 5.467  H93  GSG 38 
GSG H11  H11  H 0  1 N N N ?      ?     ?      -0.004 0.000  -0.005 H11  GSG 39 
GSG H12  H12  H 0  1 N N N ?      ?     ?      -0.350 -0.717 -2.341 H12  GSG 40 
GSG H141 1H14 H 0  0 N N N ?      ?     ?      -0.575 -2.019 -3.934 H141 GSG 41 
GSG H142 2H14 H 0  0 N N N ?      ?     ?      -0.093 -3.595 -4.599 H142 GSG 42 
GSG H143 3H14 H 0  0 N N N ?      ?     ?      0.389  -2.097 -5.425 H143 GSG 43 
GSG H15  H15  H 0  1 N N N ?      ?     ?      1.645  -4.407 -2.843 H15  GSG 44 
GSG H18  H18  H 0  1 N N N ?      ?     ?      3.638  -2.306 0.257  H18  GSG 45 
GSG H191 1H19 H 0  0 N N N ?      ?     ?      4.784  -1.464 -2.452 H191 GSG 46 
GSG H192 2H19 H 0  0 N N N ?      ?     ?      5.323  -2.764 -3.533 H192 GSG 47 
GSG H193 3H19 H 0  0 N N N ?      ?     ?      3.995  -1.695 -4.024 H193 GSG 48 
GSG H201 1H20 H 0  0 N N N ?      ?     ?      3.485  -5.106 -1.520 H201 GSG 49 
GSG H202 2H20 H 0  0 N N N ?      ?     ?      5.091  -4.444 -1.836 H202 GSG 50 
GSG H211 1H21 H 0  0 N N N ?      ?     ?      4.979  -5.041 -4.189 H211 GSG 51 
GSG H212 2H21 H 0  0 N N N ?      ?     ?      3.848  -6.272 -3.546 H212 GSG 52 
GSG H221 1H22 H 0  0 N N N ?      ?     ?      1.259  -5.813 -4.220 H221 GSG 53 
GSG H222 2H22 H 0  0 N N N ?      ?     ?      1.510  -5.163 -5.880 H222 GSG 54 
GSG H223 3H22 H 0  0 N N N ?      ?     ?      2.592  -6.455 -5.246 H223 GSG 55 
# 
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 
GSG C1  C2   SING Y N 1  
GSG C1  C6   DOUB Y N 2  
GSG C1  N1   SING N N 3  
GSG C2  C3   DOUB Y N 4  
GSG C2  C8   SING N N 5  
GSG C3  C4   SING Y N 6  
GSG C3  H3   SING N N 7  
GSG C4  C5   DOUB Y N 8  
GSG C4  H4   SING N N 9  
GSG C5  C6   SING Y N 10 
GSG C5  H5   SING N N 11 
GSG C6  H6   SING N N 12 
GSG N1  C7   SING N N 13 
GSG N1  HN1  SING N N 14 
GSG C7  O1   DOUB N N 15 
GSG C7  O2   SING N N 16 
GSG C8  C9   SING N N 17 
GSG C8  H81  SING N N 18 
GSG C8  H82  SING N N 19 
GSG C9  H91  SING N N 20 
GSG C9  H92  SING N N 21 
GSG C9  H93  SING N N 22 
GSG O2  C10  SING N N 23 
GSG C10 C11  DOUB Y N 24 
GSG C10 C18  SING Y N 25 
GSG C11 C12  SING Y N 26 
GSG C11 H11  SING N N 27 
GSG C12 C13  DOUB Y N 28 
GSG C12 H12  SING N N 29 
GSG C13 N2   SING N N 30 
GSG C13 C17  SING Y N 31 
GSG N2  C14  SING N N 32 
GSG N2  C15  SING N N 33 
GSG C14 H141 SING N N 34 
GSG C14 H142 SING N N 35 
GSG C14 H143 SING N N 36 
GSG C15 C16  SING N N 37 
GSG C15 N3   SING N N 38 
GSG C15 H15  SING N N 39 
GSG C16 C17  SING N N 40 
GSG C16 C19  SING N N 41 
GSG C16 C20  SING N N 42 
GSG C17 C18  DOUB Y N 43 
GSG C18 H18  SING N N 44 
GSG C19 H191 SING N N 45 
GSG C19 H192 SING N N 46 
GSG C19 H193 SING N N 47 
GSG C20 C21  SING N N 48 
GSG C20 H201 SING N N 49 
GSG C20 H202 SING N N 50 
GSG C21 N3   SING N N 51 
GSG C21 H211 SING N N 52 
GSG C21 H212 SING N N 53 
GSG N3  O3   SING N N 54 
GSG N3  C22  SING N N 55 
GSG C22 H221 SING N N 56 
GSG C22 H222 SING N N 57 
GSG C22 H223 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 
GSG SMILES           ACDLabs              10.04 O=C(Oc1cc2c(cc1)N(C3[N+]([O-])(CCC23C)C)C)Nc4ccccc4CC                                                                                                    
GSG InChI            InChI                1.02b InChI=1/C22H27N3O3/c1-5-15-8-6-7-9-18(15)23-21(26)28-16-10-11-19-17(14-16)22(2)12-13-25(4,27)20(22)24(19)3/h6-11,14,20H,5,12-13H2,1-4H3,(H,23,26)/f/h23H 
GSG InChIKey         InChI                1.02b MVHRCJQCKYPDRL-MPIMZMORCI                                                                                                                                
GSG SMILES_CANONICAL CACTVS               3.341 CCc1ccccc1NC(=O)Oc2ccc3N(C)C4C(C)(CC[N+]4(C)[O-])c3c2                                                                                                    
GSG SMILES           CACTVS               3.341 CCc1ccccc1NC(=O)Oc2ccc3N(C)C4C(C)(CC[N+]4(C)[O-])c3c2                                                                                                    
GSG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCc1ccccc1NC(=O)Oc2ccc3c(c2)[C@]4(CC[N@+]([C@@H]4[N@]3C)(C)[O-])C                                                                                        
GSG SMILES           "OpenEye OEToolkits" 1.5.0 CCc1ccccc1NC(=O)Oc2ccc3c(c2)C4(CC[N+](C4N3C)(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 
GSG "SYSTEMATIC NAME" ACDLabs              10.04 "1,3a,8-trimethyl-1-oxido-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (2-ethylphenyl)carbamate"                    
GSG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3S,3aS,4S,8bR)-3,4,8b-trimethyl-3-oxido-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-ium-7-yl] N-(2-ethylphenyl)carbamate" 
# 
