data_SHY
# 
_chem_comp.id                                    SHY 
_chem_comp.name                                  4-[(3AS,4R,7R,8AS,8BR)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-7-HYDROXY-1,3-DIOXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZENECARBOXIMIDAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H24 N4 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-05-24 
_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                        448.471 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SHY 
_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        1VZQ 
_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 
SHY N1   N1   N 0 1 N N N 11.273 -9.891  24.423 4.789  0.720  4.704  N1   SHY 1  
SHY C3   C3   C 0 1 N N N 11.531 -10.991 23.661 4.124  -0.248 4.142  C3   SHY 2  
SHY N2   N2   N 0 1 N N N 10.738 -12.087 23.882 4.693  -1.498 4.027  N2   SHY 3  
SHY C4   C4   C 0 1 Y N N 12.628 -11.042 22.728 2.757  -0.007 3.626  C4   SHY 4  
SHY C9   C9   C 0 1 Y N N 13.369 -9.897  22.475 2.179  1.256  3.740  C9   SHY 5  
SHY C8   C8   C 0 1 Y N N 14.452 -9.945  21.594 0.905  1.475  3.258  C8   SHY 6  
SHY C7   C7   C 0 1 Y N N 14.808 -11.152 20.947 0.201  0.444  2.662  C7   SHY 7  
SHY C6   C6   C 0 1 Y N N 14.021 -12.279 21.182 0.770  -0.811 2.546  C6   SHY 8  
SHY C5   C5   C 0 1 Y N N 12.952 -12.238 22.050 2.046  -1.041 3.019  C5   SHY 9  
SHY C10  C10  C 0 1 N N R 16.033 -11.126 20.047 -1.189 0.689  2.137  C10  SHY 10 
SHY N11  N11  N 0 1 N N N 15.984 -12.242 19.063 -1.984 -0.558 2.184  N11  SHY 11 
SHY C12  C12  C 0 1 N N N 15.107 -11.871 17.905 -2.699 -0.512 3.503  C12  SHY 12 
SHY C13  C13  C 0 1 N N R 15.991 -11.714 16.651 -3.817 0.538  3.354  C13  SHY 13 
SHY C14  C14  C 0 1 N N N 17.347 -11.369 17.285 -4.077 0.639  1.839  C14  SHY 14 
SHY C15  C15  C 0 1 N N S 17.370 -12.257 18.504 -3.077 -0.332 1.181  C15  SHY 15 
SHY C16  C16  C 0 1 N N R 18.357 -11.698 19.554 -2.381 0.395  0.013  C16  SHY 16 
SHY C17  C17  C 0 1 N N N 19.154 -12.791 20.156 -1.778 -0.618 -0.933 C17  SHY 17 
SHY N19  N19  N 0 1 N N N 18.586 -13.278 21.327 -0.444 -0.547 -0.869 N19  SHY 18 
SHY C20  C20  C 0 1 N N N 17.467 -12.479 21.672 0.032  0.383  -0.011 C20  SHY 19 
SHY O21  O21  O 0 1 N N N 16.747 -12.734 22.627 1.205  0.609  0.196  O21  SHY 20 
SHY C22  C22  C 0 1 N N S 17.399 -11.287 20.736 -1.139 1.077  0.645  C22  SHY 21 
SHY C23  C23  C 0 1 N N N 18.993 -14.432 22.140 0.433  -1.403 -1.670 C23  SHY 22 
SHY C24  C24  C 0 1 Y N N 20.069 -14.149 23.127 0.733  -0.727 -2.983 C24  SHY 23 
SHY C32  C32  C 0 1 Y N N 19.681 -13.853 24.426 1.829  0.107  -3.095 C32  SHY 24 
SHY C31  C31  C 0 1 Y N N 20.578 -13.515 25.419 2.108  0.729  -4.298 C31  SHY 25 
SHY C30  C30  C 0 1 Y N N 21.921 -13.469 25.029 1.290  0.516  -5.395 C30  SHY 26 
SHY O29  O29  O 0 1 N N N 22.969 -13.185 25.814 1.342  0.999  -6.670 O29  SHY 27 
SHY C28  C28  C 0 1 N N N 24.132 -13.292 24.951 0.032  0.769  -7.223 C28  SHY 28 
SHY O20  O20  O 0 1 N N N 16.157 -12.951 15.945 -4.998 0.108  4.033  O20  SHY 29 
SHY O27  O27  O 0 1 N N N 23.686 -13.738 23.627 -0.453 -0.368 -6.488 O27  SHY 30 
SHY C26  C26  C 0 1 Y N N 22.327 -13.749 23.740 0.185  -0.324 -5.282 C26  SHY 31 
SHY C25  C25  C 0 1 Y N N 21.417 -14.101 22.756 -0.085 -0.948 -4.075 C25  SHY 32 
SHY O24  O24  O 0 1 N N N 20.156 -13.329 19.707 -2.407 -1.375 -1.641 O24  SHY 33 
SHY H1N  H1N  H 0 1 N N N 11.890 -9.312  23.853 4.388  1.600  4.785  H1N  SHY 34 
SHY H2N1 1H2N H 0 0 N N N 10.931 -12.910 23.312 5.589  -1.656 4.365  H2N1 SHY 35 
SHY H2N2 2H2N H 0 0 N N N 9.962  -12.051 24.542 4.197  -2.220 3.613  H2N2 SHY 36 
SHY H9   H9   H 0 1 N N N 13.103 -8.948  22.970 2.727  2.062  4.206  H9   SHY 37 
SHY H8   H8   H 0 1 N N N 15.037 -9.030  21.400 0.456  2.453  3.346  H8   SHY 38 
SHY H6   H6   H 0 1 N N N 14.259 -13.222 20.662 0.216  -1.613 2.080  H6   SHY 39 
SHY H5   H5   H 0 1 N N N 12.346 -13.144 22.216 2.488  -2.021 2.927  H5   SHY 40 
SHY H10  H10  H 0 1 N N N 16.035 -10.163 19.485 -1.679 1.473  2.716  H10  SHY 41 
SHY H121 1H12 H 0 0 N N N 14.490 -10.965 18.109 -2.010 -0.221 4.296  H121 SHY 42 
SHY H122 2H12 H 0 0 N N N 14.272 -12.594 17.752 -3.127 -1.492 3.715  H122 SHY 43 
SHY H13  H13  H 0 1 N N N 15.625 -10.900 15.983 -3.486 1.500  3.745  H13  SHY 44 
SHY H141 1H14 H 0 0 N N N 18.225 -11.481 16.606 -3.897 1.656  1.492  H141 SHY 45 
SHY H142 2H14 H 0 0 N N N 17.507 -10.285 17.491 -5.100 0.338  1.611  H142 SHY 46 
SHY H15  H15  H 0 1 N N N 17.659 -13.295 18.219 -3.547 -1.265 0.870  H15  SHY 47 
SHY H16  H16  H 0 1 N N N 18.978 -10.854 19.173 -3.039 1.102  -0.491 H16  SHY 48 
SHY H22  H22  H 0 1 N N N 17.729 -10.346 21.234 -1.126 2.156  0.493  H22  SHY 49 
SHY H231 1H23 H 0 0 N N N 19.285 -15.284 21.483 1.364  -1.576 -1.130 H231 SHY 50 
SHY H232 2H23 H 0 0 N N N 18.107 -14.877 22.650 -0.060 -2.357 -1.857 H232 SHY 51 
SHY H32  H32  H 0 1 N N N 18.607 -13.889 24.676 2.469  0.274  -2.241 H32  SHY 52 
SHY H31  H31  H 0 1 N N N 20.257 -13.296 26.451 2.965  1.381  -4.382 H31  SHY 53 
SHY H281 1H28 H 0 0 N N N 24.925 -13.948 25.380 -0.609 1.635  -7.058 H281 SHY 54 
SHY H282 2H28 H 0 0 N N N 24.723 -12.347 24.909 0.100  0.539  -8.286 H282 SHY 55 
SHY H20  H20  H 0 1 N N N 16.701 -12.854 15.173 -4.780 0.063  4.973  H20  SHY 56 
SHY H25  H25  H 0 1 N N N 21.741 -14.333 21.727 -0.937 -1.605 -3.987 H25  SHY 57 
# 
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 
SHY N1  C3   DOUB N E 1  
SHY N1  H1N  SING N N 2  
SHY C3  N2   SING N N 3  
SHY C3  C4   SING N N 4  
SHY N2  H2N1 SING N N 5  
SHY N2  H2N2 SING N N 6  
SHY C4  C9   DOUB Y N 7  
SHY C4  C5   SING Y N 8  
SHY C9  C8   SING Y N 9  
SHY C9  H9   SING N N 10 
SHY C8  C7   DOUB Y N 11 
SHY C8  H8   SING N N 12 
SHY C7  C6   SING Y N 13 
SHY C7  C10  SING N N 14 
SHY C6  C5   DOUB Y N 15 
SHY C6  H6   SING N N 16 
SHY C5  H5   SING N N 17 
SHY C10 N11  SING N N 18 
SHY C10 C22  SING N N 19 
SHY C10 H10  SING N N 20 
SHY N11 C12  SING N N 21 
SHY N11 C15  SING N N 22 
SHY C12 C13  SING N N 23 
SHY C12 H121 SING N N 24 
SHY C12 H122 SING N N 25 
SHY C13 C14  SING N N 26 
SHY C13 O20  SING N N 27 
SHY C13 H13  SING N N 28 
SHY C14 C15  SING N N 29 
SHY C14 H141 SING N N 30 
SHY C14 H142 SING N N 31 
SHY C15 C16  SING N N 32 
SHY C15 H15  SING N N 33 
SHY C16 C17  SING N N 34 
SHY C16 C22  SING N N 35 
SHY C16 H16  SING N N 36 
SHY C17 N19  SING N N 37 
SHY C17 O24  DOUB N N 38 
SHY N19 C20  SING N N 39 
SHY N19 C23  SING N N 40 
SHY C20 O21  DOUB N N 41 
SHY C20 C22  SING N N 42 
SHY C22 H22  SING N N 43 
SHY C23 C24  SING N N 44 
SHY C23 H231 SING N N 45 
SHY C23 H232 SING N N 46 
SHY C24 C32  DOUB Y N 47 
SHY C24 C25  SING Y N 48 
SHY C32 C31  SING Y N 49 
SHY C32 H32  SING N N 50 
SHY C31 C30  DOUB Y N 51 
SHY C31 H31  SING N N 52 
SHY C30 O29  SING N N 53 
SHY C30 C26  SING Y N 54 
SHY O29 C28  SING N N 55 
SHY C28 O27  SING N N 56 
SHY C28 H281 SING N N 57 
SHY C28 H282 SING N N 58 
SHY O20 H20  SING N N 59 
SHY O27 C26  SING N N 60 
SHY C26 C25  DOUB Y N 61 
SHY C25 H25  SING N N 62 
# 
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 
SHY SMILES           ACDLabs              10.04 O=C1N(C(=O)C4C1C(c2ccc(C(=[N@H])N)cc2)N3CC(O)CC34)Cc5ccc6OCOc6c5 
SHY InChI            InChI                1.02b 
InChI=1/C24H24N4O5/c25-22(26)14-4-2-13(3-5-14)21-20-19(16-8-15(29)10-27(16)21)23(30)28(24(20)31)9-12-1-6-17-18(7-12)33-11-32-17/h1-7,15-16,19-21,29H,8-11H2,(H3,25,26)/t15-,16+,19+,20+,21+/m1/s1/f/h25H,26H2/b25-22+ 
SHY InChIKey         InChI                1.02b CETLUACQMGBMFH-OTKGBNPHDK 
SHY SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@@H]4C[C@@H](O)CN24)C(=O)N(Cc5ccc6OCOc6c5)C3=O 
SHY SMILES           CACTVS               3.341 NC(=N)c1ccc(cc1)[CH]2[CH]3[CH]([CH]4C[CH](O)CN24)C(=O)N(Cc5ccc6OCOc6c5)C3=O 
SHY SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@H]4[N@@]2C[C@@H](C4)O)C(=O)N(C3=O)Cc5ccc6c(c5)OCO6)/N 
SHY SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)C2C3C(C4N2CC(C4)O)C(=O)N(C3=O)Cc5ccc6c(c5)OCO6)N 
# 
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 
SHY "SYSTEMATIC NAME" ACDLabs              10.04 4-[(3aS,4R,7R,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-7-hydroxy-1,3-dioxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                        
SHY "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(3aS,4R,5S,7R,8aS,8bR)-2-(1,3-benzodioxol-5-ylmethyl)-7-hydroxy-1,3-dioxo-4,6,7,8,8a,8b-hexahydro-3aH-pyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
