data_ESH
# 
_chem_comp.id                                    ESH 
_chem_comp.name                                  "4- [(1R,3AS,4R,8AS,8BR)- 2- (4-CHLOROBENZYL)- 1- ISOPROPYL- 3- OXODECAHYDROPYRROLO[3,4- A]PYRROLIZIN- 4- YL]BENZENECARBOXIMIDAMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H31 Cl N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-17 
_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                        451.004 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ESH 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_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                  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 
ESH N1   N1   N  0 1 N N N 11.213 -9.781  24.497 -5.030 1.578  -8.118  N1   ESH 1  
ESH C3   C3   C  0 1 N N N 11.469 -10.910 23.858 -5.687 1.431  -6.986  C3   ESH 2  
ESH N2   N2   N  0 1 N N N 10.698 -11.981 24.128 -6.984 1.928  -6.925  N2   ESH 3  
ESH C4   C4   C  0 1 Y N N 12.583 -11.007 22.877 -5.009 0.761  -5.888  C4   ESH 4  
ESH C9   C9   C  0 1 Y N N 13.416 -9.942  22.597 -5.665 0.582  -4.670  C9   ESH 5  
ESH C8   C8   C  0 1 Y N N 14.429 -10.025 21.658 -5.015 -0.062 -3.616  C8   ESH 6  
ESH C7   C7   C  0 1 Y N N 14.684 -11.228 20.987 -3.709 -0.527 -3.780  C7   ESH 7  
ESH C6   C6   C  0 1 Y N N 13.831 -12.301 21.255 -3.055 -0.347 -4.999  C6   ESH 8  
ESH C5   C5   C  0 1 Y N N 12.808 -12.204 22.178 -3.704 0.296  -6.053  C5   ESH 9  
ESH C10  C10  C  0 1 N N R 15.793 -11.301 19.991 -3.004 -1.226 -2.635  C10  ESH 10 
ESH N11  N11  N  0 1 N N N 15.646 -12.372 18.970 -1.532 -1.041 -2.661  N11  ESH 11 
ESH C12  C12  C  0 1 N N N 14.603 -12.051 17.951 -1.075 0.114  -1.884  C12  ESH 12 
ESH C13  C13  C  0 1 N N N 15.328 -11.704 16.659 -0.934 -0.362 -0.444  C13  ESH 13 
ESH C14  C14  C  0 1 N N N 16.816 -11.611 16.989 -0.963 -1.883 -0.509  C14  ESH 14 
ESH C15  C15  C  0 1 N N S 16.940 -12.438 18.267 -0.938 -2.215 -1.999  C15  ESH 15 
ESH C16  C16  C  0 1 N N R 17.975 -12.019 19.300 -1.832 -3.374 -2.410  C16  ESH 16 
ESH C17  C17  C  0 1 N N R 18.940 -13.139 19.735 -1.517 -3.914 -3.815  C17  ESH 17 
ESH N19  N19  N  0 1 N N N 18.518 -13.453 21.088 -2.825 -4.128 -4.405  N19  ESH 18 
ESH C20  C20  C  0 1 N N N 17.394 -12.689 21.514 -3.843 -3.457 -3.736  C20  ESH 19 
ESH O21  O21  O  0 1 N N N 16.800 -12.924 22.522 -5.027 -3.401 -4.037  O21  ESH 20 
ESH C22  C22  C  0 1 N N S 17.201 -11.570 20.530 -3.230 -2.751 -2.543  C22  ESH 21 
ESH C23  C23  C  0 1 N N N 18.717 -14.800 21.670 -3.001 -4.814 -5.671  C23  ESH 22 
ESH C24  C24  C  0 1 Y N N 19.709 -14.587 22.808 -2.744 -3.908 -6.841  C24  ESH 23 
ESH C32  C32  C  0 1 Y N N 19.272 -14.215 24.060 -3.792 -3.175 -7.386  C32  ESH 24 
ESH C31  C31  C  0 1 Y N N 20.144 -13.981 25.115 -3.553 -2.334 -8.472  C31  ESH 25 
ESH C30  C30  C  0 1 Y N N 21.501 -14.139 24.887 -2.268 -2.231 -9.006  C30  ESH 26 
ESH C26  C26  C  0 1 Y N N 21.975 -14.513 23.641 -1.223 -2.970 -8.453  C26  ESH 27 
ESH C25  C25  C  0 1 Y N N 21.081 -14.734 22.596 -1.461 -3.812 -7.367  C25  ESH 28 
ESH C18  C18  C  0 1 N N N 20.407 -12.696 19.752 -0.650 -5.166 -3.752  C18  ESH 29 
ESH C41  C41  C  0 1 N N N 20.695 -11.525 20.691 0.692  -4.856 -3.091  C41  ESH 30 
ESH C42  C42  C  0 1 N N N 20.859 -12.413 18.341 -1.372 -6.283 -3.003  C42  ESH 31 
ESH CL30 CL30 CL 0 0 N N N 22.648 -13.883 26.223 -1.974 -1.194 -10.347 CL30 ESH 32 
ESH H20  H20  H  0 1 N N N 11.762 -8.962  24.328 -4.093 1.170  -8.028  H20  ESH 33 
ESH H12  H12  H  0 1 N N N 10.855 -12.857 23.672 -7.413 2.392  -7.719  H12  ESH 34 
ESH H11  H11  H  0 1 N N N 9.963  -11.908 24.800 -7.557 1.839  -6.094  H11  ESH 35 
ESH H5   H5   H  0 1 N N N 13.273 -8.995  23.097 -6.681 0.940  -4.529  H5   ESH 36 
ESH H6   H6   H  0 1 N N N 15.069 -9.169  21.483 -5.533 -0.197 -2.670  H6   ESH 37 
ESH H8   H8   H  0 1 N N N 13.982 -13.244 20.748 -2.038 -0.706 -5.137  H8   ESH 38 
ESH H9   H9   H  0 1 N N N 12.194 -13.075 22.353 -3.184 0.431  -6.997  H9   ESH 39 
ESH H10  H10  H  0 1 N N N 15.835 -10.336 19.468 -3.423 -0.789 -1.719  H10  ESH 40 
ESH H121 1H12 H  0 0 N N N 13.956 -12.917 17.795 -1.730 0.988  -1.975  H121 ESH 41 
ESH H122 2H12 H  0 0 N N N 13.986 -11.209 18.271 -0.091 0.419  -2.261  H122 ESH 42 
ESH H132 2H13 H  0 0 N N N 15.155 -12.478 15.908 -1.762 0.002  0.174   H132 ESH 43 
ESH H131 1H13 H  0 0 N N N 14.969 -10.754 16.268 -0.000 -0.000 0.001   H131 ESH 44 
ESH H141 1H14 H  0 0 N N N 17.422 -12.037 16.187 -0.104 -2.322 0.010   H141 ESH 45 
ESH H142 2H14 H  0 0 N N N 17.112 -10.574 17.160 -1.868 -2.258 -0.015  H142 ESH 46 
ESH H15  H15  H  0 1 N N N 17.130 -13.479 17.971 0.098  -2.360 -2.328  H15  ESH 47 
ESH H16  H16  H  0 1 N N N 18.541 -11.161 18.915 -1.835 -4.182 -1.669  H16  ESH 48 
ESH H17  H17  H  0 1 N N N 18.831 -14.014 19.082 -1.010 -3.166 -4.436  H17  ESH 49 
ESH H22  H22  H  0 1 N N N 17.640 -10.641 20.915 -3.826 -2.991 -1.654  H22  ESH 50 
ESH H231 1H23 H  0 0 N N N 17.780 -15.217 22.045 -4.024 -5.205 -5.703  H231 ESH 51 
ESH H232 2H23 H  0 0 N N N 19.134 -15.481 20.925 -2.323 -5.673 -5.683  H232 ESH 52 
ESH H29  H29  H  0 1 N N N 18.211 -14.087 24.230 -4.796 -3.249 -6.977  H29  ESH 53 
ESH H28  H28  H  0 1 N N N 19.774 -13.701 26.093 -4.378 -1.764 -8.893  H28  ESH 54 
ESH H26  H26  H  0 1 N N N 23.039 -14.638 23.481 -0.216 -2.900 -8.858  H26  ESH 55 
ESH H25  H25  H  0 1 N N N 21.453 -15.023 21.622 -0.640 -4.384 -6.942  H25  ESH 56 
ESH H18  H18  H  0 1 N N N 21.001 -13.548 20.102 -0.459 -5.505 -4.777  H18  ESH 57 
ESH H323 3H32 H  0 0 N N N 21.580 -11.738 21.229 0.558  -4.514 -2.059  H323 ESH 58 
ESH H322 2H32 H  0 0 N N N 20.825 -10.636 20.142 1.330  -5.746 -3.072  H322 ESH 59 
ESH H321 1H32 H  0 0 N N N 19.895 -11.392 21.369 1.225  -4.073 -3.641  H321 ESH 60 
ESH H333 3H33 H  0 0 N N N 21.398 -11.504 18.295 -1.591 -5.994 -1.969  H333 ESH 61 
ESH H332 2H33 H  0 0 N N N 21.490 -13.201 18.025 -0.762 -7.192 -2.978  H332 ESH 62 
ESH H331 1H33 H  0 0 N N N 20.031 -12.362 17.683 -2.320 -6.529 -3.493  H331 ESH 63 
# 
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 
ESH N1  C3   DOUB N E 1  
ESH N1  H20  SING N N 2  
ESH C3  N2   SING N N 3  
ESH C3  C4   SING N N 4  
ESH N2  H12  SING N N 5  
ESH N2  H11  SING N N 6  
ESH C4  C9   DOUB Y N 7  
ESH C4  C5   SING Y N 8  
ESH C9  C8   SING Y N 9  
ESH C9  H5   SING N N 10 
ESH C8  C7   DOUB Y N 11 
ESH C8  H6   SING N N 12 
ESH C7  C6   SING Y N 13 
ESH C7  C10  SING N N 14 
ESH C6  C5   DOUB Y N 15 
ESH C6  H8   SING N N 16 
ESH C5  H9   SING N N 17 
ESH C10 N11  SING N N 18 
ESH C10 C22  SING N N 19 
ESH C10 H10  SING N N 20 
ESH N11 C12  SING N N 21 
ESH N11 C15  SING N N 22 
ESH C12 C13  SING N N 23 
ESH C12 H121 SING N N 24 
ESH C12 H122 SING N N 25 
ESH C13 C14  SING N N 26 
ESH C13 H132 SING N N 27 
ESH C13 H131 SING N N 28 
ESH C14 C15  SING N N 29 
ESH C14 H141 SING N N 30 
ESH C14 H142 SING N N 31 
ESH C15 C16  SING N N 32 
ESH C15 H15  SING N N 33 
ESH C16 C17  SING N N 34 
ESH C16 C22  SING N N 35 
ESH C16 H16  SING N N 36 
ESH C17 N19  SING N N 37 
ESH C17 C18  SING N N 38 
ESH C17 H17  SING N N 39 
ESH N19 C20  SING N N 40 
ESH N19 C23  SING N N 41 
ESH C20 O21  DOUB N N 42 
ESH C20 C22  SING N N 43 
ESH C22 H22  SING N N 44 
ESH C23 C24  SING N N 45 
ESH C23 H231 SING N N 46 
ESH C23 H232 SING N N 47 
ESH C24 C32  DOUB Y N 48 
ESH C24 C25  SING Y N 49 
ESH C32 C31  SING Y N 50 
ESH C32 H29  SING N N 51 
ESH C31 C30  DOUB Y N 52 
ESH C31 H28  SING N N 53 
ESH C30 C26  SING Y N 54 
ESH C30 CL30 SING N N 55 
ESH C26 C25  DOUB Y N 56 
ESH C26 H26  SING N N 57 
ESH C25 H25  SING N N 58 
ESH C18 C41  SING N N 59 
ESH C18 C42  SING N N 60 
ESH C18 H18  SING N N 61 
ESH C41 H323 SING N N 62 
ESH C41 H322 SING N N 63 
ESH C41 H321 SING N N 64 
ESH C42 H333 SING N N 65 
ESH C42 H332 SING N N 66 
ESH C42 H331 SING N N 67 
# 
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 
ESH SMILES           ACDLabs              10.04 Clc1ccc(cc1)CN2C(=O)C5C(C2C(C)C)C3N(CCC3)C5c4ccc(C(=[N@H])N)cc4 
ESH InChI            InChI                1.02b 
InChI=1/C26H31ClN4O/c1-15(2)23-21-20-4-3-13-30(20)24(17-7-9-18(10-8-17)25(28)29)22(21)26(32)31(23)14-16-5-11-19(27)12-6-16/h5-12,15,20-24H,3-4,13-14H2,1-2H3,(H3,28,29)/t20-,21-,22-,23+,24-/m0/s1/f/h28H,29H2/b28-25+ 
ESH InChIKey         InChI                1.02b LVAIBFBNGXNDPW-PZMDPRTQDU 
ESH SMILES_CANONICAL CACTVS               3.341 CC(C)[C@@H]1[C@H]2[C@@H]3CCCN3[C@H]([C@H]2C(=O)N1Cc4ccc(Cl)cc4)c5ccc(cc5)C(N)=N 
ESH SMILES           CACTVS               3.341 CC(C)[CH]1[CH]2[CH]3CCCN3[CH]([CH]2C(=O)N1Cc4ccc(Cl)cc4)c5ccc(cc5)C(N)=N 
ESH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1ccc(cc1)[C@H]2[C@@H]3[C@H]([C@H]4[N@@]2CCC4)[C@H](N(C3=O)Cc5ccc(cc5)Cl)C(C)C)/N 
ESH SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)C2C3C(C4N2CCC4)C(N(C3=O)Cc5ccc(cc5)Cl)C(C)C)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 
ESH "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1R,3aS,4R,8aS,8bR)-2-(4-chlorobenzyl)-1-(1-methylethyl)-3-oxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                            
ESH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1R,3aS,4R,5S,8aS,8bR)-2-[(4-chlorophenyl)methyl]-3-oxo-1-propan-2-yl-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[4,3-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
