data_HUB
# 
_chem_comp.id                                    HUB 
_chem_comp.name                                  "HUPERZINE B" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H20 N2 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-11-07 
_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                        256.343 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HUB 
_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        1GPN 
_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 
HUB C1   C1   C 0 1 Y N N 1.068  68.771 61.163 0.242  -0.021 3.129  C1   HUB 1  
HUB O1   O1   O 0 1 N N N 0.440  69.208 60.196 0.422  -0.214 4.321  O1   HUB 2  
HUB N1   N1   N 0 1 Y N N 2.353  68.265 60.983 0.431  -1.018 2.249  N1   HUB 3  
HUB C2   C2   C 0 1 Y N N 0.544  68.745 62.517 -0.162 1.244  2.673  C2   HUB 4  
HUB C3   C3   C 0 1 Y N N 1.302  68.245 63.545 -0.352 1.435  1.339  C3   HUB 5  
HUB C4   C4   C 0 1 Y N N 2.635  67.728 63.356 -0.144 0.370  0.440  C4   HUB 6  
HUB C5   C5   C 0 1 Y N N 3.149  67.734 62.013 0.237  -0.834 0.910  C5   HUB 7  
HUB C6   C6   C 0 1 N N N 4.520  67.211 61.630 0.469  -2.023 0.011  C6   HUB 8  
HUB C7   C7   C 0 1 N N R 5.312  66.528 62.852 0.653  -1.570 -1.437 C7   HUB 9  
HUB C8   C8   C 0 1 N N N 4.889  65.046 63.024 1.948  -0.833 -1.579 C8   HUB 10 
HUB C9   C9   C 0 1 N N N 5.125  69.456 65.431 -3.001 -0.413 -1.444 C9   HUB 11 
HUB C10  C10  C 0 1 N N N 5.432  68.738 64.106 -1.814 -1.371 -1.338 C10  HUB 12 
HUB C11  C11  C 0 1 N N R 5.024  67.256 64.187 -0.533 -0.662 -1.797 C11  HUB 13 
HUB C12  C12  C 0 1 N N R 3.516  67.141 64.569 -0.357 0.646  -1.024 C12  HUB 14 
HUB N2   N2   N 0 1 N N N 3.239  67.879 65.858 -1.525 1.515  -1.204 N2   HUB 15 
HUB C13  C13  C 0 1 N N N 3.112  65.642 64.749 0.870  1.381  -1.575 C13  HUB 16 
HUB C14  C14  C 0 1 N N N 3.887  64.648 63.892 2.048  0.455  -1.638 C14  HUB 17 
HUB C15  C15  C 0 1 N N N 3.465  63.214 64.087 3.422  1.059  -1.770 C15  HUB 18 
HUB C90  C90  C 0 1 N N N 3.651  69.386 65.801 -2.690 0.842  -0.624 C90  HUB 19 
HUB H1   H1   H 0 1 N N N 2.743  68.281 60.041 0.710  -1.888 2.573  H1   HUB 20 
HUB H2   H2   H 0 1 N N N -0.470 69.130 62.720 -0.320 2.054  3.370  H2   HUB 21 
HUB H3   H3   H 0 1 N N N 0.873  68.238 64.561 -0.661 2.401  0.969  H3   HUB 22 
HUB H6C1 1H6C H 0 0 N N N 5.133  68.017 61.164 -0.388 -2.693 0.073  H6C1 HUB 23 
HUB H6C2 2H6C H 0 0 N N N 4.447  66.510 60.766 1.362  -2.554 0.339  H6C2 HUB 24 
HUB H7   H7   H 0 1 N N N 6.407  66.571 62.644 0.656  -2.441 -2.093 H7   HUB 25 
HUB H8   H8   H 0 1 N N N 5.409  64.276 62.429 2.857  -1.414 -1.637 H8   HUB 26 
HUB H9C1 1H9C H 0 0 N N N 5.765  69.067 66.257 -3.896 -0.894 -1.050 H9C1 HUB 27 
HUB H9C2 2H9C H 0 0 N N N 5.484  70.511 65.409 -3.159 -0.139 -2.487 H9C2 HUB 28 
HUB H101 1H10 H 0 0 N N N 6.500  68.858 63.808 -1.699 -1.694 -0.303 H101 HUB 29 
HUB H102 2H10 H 0 0 N N N 4.958  69.251 63.237 -1.992 -2.241 -1.971 H102 HUB 30 
HUB H11  H11  H 0 1 N N N 5.627  66.770 64.989 -0.563 -0.479 -2.871 H11  HUB 31 
HUB HA   HA   H 0 1 N N N 2.261  67.779 66.132 -1.361 2.340  -0.647 HA   HUB 32 
HUB H131 1H13 H 0 0 N N N 2.017  65.519 64.581 1.104  2.226  -0.928 H131 HUB 33 
HUB H132 2H13 H 0 0 N N N 3.180  65.354 65.824 0.651  1.746  -2.578 H132 HUB 34 
HUB H151 1H15 H 0 0 N N N 2.658  62.893 64.786 4.167  0.264  -1.798 H151 HUB 35 
HUB H152 2H15 H 0 0 N N N 4.380  62.636 64.355 3.477  1.640  -2.690 H152 HUB 36 
HUB H153 3H15 H 0 0 N N N 3.208  62.808 63.081 3.617  1.710  -0.917 H153 HUB 37 
HUB H901 1H90 H 0 0 N N N 3.005  69.984 65.117 -2.473 0.560  0.405  H901 HUB 38 
HUB H902 2H90 H 0 0 N N N 3.416  69.933 66.744 -3.548 1.514  -0.647 H902 HUB 39 
# 
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 
HUB C1  O1   DOUB N N 1  
HUB C1  N1   SING Y N 2  
HUB C1  C2   SING Y N 3  
HUB N1  C5   SING Y N 4  
HUB N1  H1   SING N N 5  
HUB C2  C3   DOUB Y N 6  
HUB C2  H2   SING N N 7  
HUB C3  C4   SING Y N 8  
HUB C3  H3   SING N N 9  
HUB C4  C5   DOUB Y N 10 
HUB C4  C12  SING N N 11 
HUB C5  C6   SING N N 12 
HUB C6  C7   SING N N 13 
HUB C6  H6C1 SING N N 14 
HUB C6  H6C2 SING N N 15 
HUB C7  C8   SING N N 16 
HUB C7  C11  SING N N 17 
HUB C7  H7   SING N N 18 
HUB C8  C14  DOUB N N 19 
HUB C8  H8   SING N N 20 
HUB C9  C10  SING N N 21 
HUB C9  C90  SING N N 22 
HUB C9  H9C1 SING N N 23 
HUB C9  H9C2 SING N N 24 
HUB C10 C11  SING N N 25 
HUB C10 H101 SING N N 26 
HUB C10 H102 SING N N 27 
HUB C11 C12  SING N N 28 
HUB C11 H11  SING N N 29 
HUB C12 N2   SING N N 30 
HUB C12 C13  SING N N 31 
HUB N2  C90  SING N N 32 
HUB N2  HA   SING N N 33 
HUB C13 C14  SING N N 34 
HUB C13 H131 SING N N 35 
HUB C13 H132 SING N N 36 
HUB C14 C15  SING N N 37 
HUB C15 H151 SING N N 38 
HUB C15 H152 SING N N 39 
HUB C15 H153 SING N N 40 
HUB C90 H901 SING N N 41 
HUB C90 H902 SING N N 42 
# 
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 
HUB SMILES           ACDLabs              10.04 O=C1C=CC2=C(N1)CC3C=C(CC24NCCCC34)C                                                                                                                 
HUB InChI            InChI                1.02b InChI=1/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)/t11-,12+,16+/m0/s1/f/h18H 
HUB InChIKey         InChI                1.02b YYWGABLTRMRUIT-NLTFVHNHDU                                                                                                                           
HUB SMILES_CANONICAL CACTVS               3.341 CC1=C[C@H]2CC3=C(C=CC(=O)N3)[C@]4(C1)NCCC[C@H]24                                                                                                    
HUB SMILES           CACTVS               3.341 CC1=C[CH]2CC3=C(C=CC(=O)N3)[C]4(C1)NCCC[CH]24                                                                                                       
HUB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=C[C@H]2CC3=C(C=CC(=O)N3)[C@@]4(C1)[C@@H]2CCCN4                                                                                                  
HUB SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CC2CC3=C(C=CC(=O)N3)C4(C1)C2CCCN4                                                                                                               
# 
_pdbx_chem_comp_identifier.comp_id           HUB 
_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        (4aR,5R,10bR)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-prop[1]eno-1,7-phenanthrolin-8(7H)-one 
# 
