data_HUP
# 
_chem_comp.id                                    HUP 
_chem_comp.name                                  "Huperzine A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H18 N2 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2013-10-16 
_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                        242.316 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HUP 
_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        1VOT 
_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 
HUP C1   C1   C 0 1 N N N 1.096  69.169 60.667 -3.242 -0.332 0.236  C1   HUP 1  
HUP O1   O1   O 0 1 N N N 0.591  69.547 59.581 -4.396 -0.410 0.624  O1   HUP 2  
HUP N1   N1   N 0 1 N N N 2.430  68.847 60.736 -2.230 -0.587 1.080  N1   HUP 3  
HUP C2   C2   C 0 1 N N N 0.355  69.016 61.885 -2.968 0.021  -1.096 C2   HUP 4  
HUP C3   C3   C 0 1 N N N 0.971  68.614 63.025 -1.671 0.106  -1.499 C3   HUP 5  
HUP C4   C4   C 0 1 N N N 2.368  68.333 63.088 -0.631 -0.160 -0.587 C4   HUP 6  
HUP C5   C5   C 0 1 N N N 3.088  68.437 61.898 -0.923 -0.512 0.680  C5   HUP 7  
HUP C6   C6   C 0 1 N N N 4.559  68.236 61.794 0.116  -0.853 1.717  C6   HUP 8  
HUP C7   C7   C 0 1 N N R 5.125  67.577 63.086 1.483  -0.280 1.327  C7   HUP 9  
HUP C8   C8   C 0 1 N N N 4.811  66.098 63.181 1.409  1.223  1.362  C8   HUP 10 
HUP C9   C9   C 0 1 N N N 6.478  69.819 64.722 3.529  -2.196 0.566  C9   HUP 11 
HUP C10  C10  C 0 1 N N N 5.072  69.351 64.850 2.640  -1.566 -0.475 C10  HUP 12 
HUP C11  C11  C 0 1 N N N 4.540  68.311 64.266 1.722  -0.703 -0.118 C11  HUP 13 
HUP C12  C12  C 0 1 N N R 3.081  67.971 64.435 0.783  -0.022 -1.102 C12  HUP 14 
HUP N2   N2   N 0 1 N N N 2.461  68.705 65.557 0.913  -0.613 -2.441 N2   HUP 15 
HUP C13  C13  C 0 1 N N N 2.941  66.485 64.741 1.152  1.469  -1.104 C13  HUP 16 
HUP C14  C14  C 0 1 N N N 3.819  65.604 63.929 1.263  1.966  0.314  C14  HUP 17 
HUP C15  C15  C 0 1 N N N 3.555  64.125 64.106 1.196  3.456  0.528  C15  HUP 18 
HUP HN1  HN1  H 0 1 N N N 2.968  68.911 59.895 -2.430 -0.830 1.997  HN1  HUP 19 
HUP H2   H2   H 0 1 N N N -0.705 69.223 61.895 -3.773 0.220  -1.788 H2   HUP 20 
HUP H3   H3   H 0 1 N N N 0.379  68.502 63.922 -1.439 0.377  -2.519 H3   HUP 21 
HUP H61  H61  H 0 1 N N N 4.773  67.584 60.934 -0.186 -0.435 2.678  H61  HUP 22 
HUP H62  H62  H 0 1 N N N 5.046  69.211 61.645 0.193  -1.936 1.806  H62  HUP 23 
HUP H7   H7   H 0 1 N N N 6.217  67.709 63.090 2.265  -0.649 1.990  H7   HUP 24 
HUP H8   H8   H 0 1 N N N 5.419  65.408 62.616 1.483  1.712  2.322  H8   HUP 25 
HUP H91  H91  H 0 1 N N N 6.622  70.721 65.335 4.087  -1.417 1.087  H91  HUP 26 
HUP H92  H92  H 0 1 N N N 7.160  69.028 65.067 2.917  -2.744 1.282  H92  HUP 27 
HUP H93  H93  H 0 1 N N N 6.692  70.053 63.669 4.225  -2.881 0.083  H93  HUP 28 
HUP H10  H10  H 0 1 N N N 4.425  69.931 65.492 2.761  -1.825 -1.517 H10  HUP 29 
HUP HN21 HN21 H 0 0 N N N 2.925  68.465 66.410 0.297  -0.159 -3.098 HN21 HUP 30 
HUP HN22 HN22 H 0 0 N N N 2.544  69.689 65.398 1.870  -0.580 -2.759 HN22 HUP 31 
HUP H131 H131 H 0 0 N N N 3.184  66.328 65.802 2.108  1.605  -1.610 H131 HUP 32 
HUP H132 H132 H 0 0 N N N 1.897  66.193 64.557 0.382  2.032  -1.631 H132 HUP 33 
HUP H151 H151 H 0 0 N N N 2.686  63.983 64.766 1.286  3.674  1.592  H151 HUP 34 
HUP H152 H152 H 0 0 N N N 3.349  63.670 63.126 2.010  3.938  -0.012 H152 HUP 35 
HUP H153 H153 H 0 0 N N N 4.438  63.646 64.555 0.242  3.833  0.160  H153 HUP 36 
# 
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 
HUP C1  O1   DOUB N N 1  
HUP C1  N1   SING N N 2  
HUP C1  C2   SING N N 3  
HUP N1  C5   SING N N 4  
HUP N1  HN1  SING N N 5  
HUP C2  C3   DOUB N N 6  
HUP C2  H2   SING N N 7  
HUP C3  C4   SING N N 8  
HUP C3  H3   SING N N 9  
HUP C4  C5   DOUB N N 10 
HUP C4  C12  SING N N 11 
HUP C5  C6   SING N N 12 
HUP C6  C7   SING N N 13 
HUP C6  H61  SING N N 14 
HUP C6  H62  SING N N 15 
HUP C7  C8   SING N N 16 
HUP C7  C11  SING N N 17 
HUP C7  H7   SING N N 18 
HUP C8  C14  DOUB N N 19 
HUP C8  H8   SING N N 20 
HUP C9  C10  SING N N 21 
HUP C9  H91  SING N N 22 
HUP C9  H92  SING N N 23 
HUP C9  H93  SING N N 24 
HUP C10 C11  DOUB N E 25 
HUP C10 H10  SING N N 26 
HUP C11 C12  SING N N 27 
HUP C12 N2   SING N N 28 
HUP C12 C13  SING N N 29 
HUP N2  HN21 SING N N 30 
HUP N2  HN22 SING N N 31 
HUP C13 C14  SING N N 32 
HUP C13 H131 SING N N 33 
HUP C13 H132 SING N N 34 
HUP C14 C15  SING N N 35 
HUP C15 H151 SING N N 36 
HUP C15 H152 SING N N 37 
HUP C15 H153 SING N N 38 
# 
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 
HUP SMILES           ACDLabs              12.01 "O=C1C=CC2=C(N1)CC3C=C(CC2(N)/C3=C/C)C"                                                                                             
HUP InChI            InChI                1.03  "InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1" 
HUP InChIKey         InChI                1.03  ZRJBHWIHUMBLCN-YQEJDHNASA-N                                                                                                         
HUP SMILES_CANONICAL CACTVS               3.385 "C\C=C1/[C@@H]2CC3=C(C=CC(=O)N3)[C@@]1(N)CC(=C2)C"                                                                                  
HUP SMILES           CACTVS               3.385 "CC=C1[CH]2CC3=C(C=CC(=O)N3)[C]1(N)CC(=C2)C"                                                                                        
HUP SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C/C=C/1\[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3"                                                                                  
HUP SMILES           "OpenEye OEToolkits" 1.7.6 "CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3"                                                                                             
# 
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 
HUP "SYSTEMATIC NAME" ACDLabs 12.01 "(5R,9R,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-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 
HUP "Create component"  1999-07-08 EBI  
HUP "Modify descriptor" 2011-06-04 RCSB 
HUP "Modify name"       2013-10-16 RCSB 
# 
