data_348
# 
_chem_comp.id                                    348 
_chem_comp.name                                  4-[(1R,3AS,4R,8AS,8BR)-1-ISOPROPYL-2-(4-METHOXYBENZYL)-3-OXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZENECARBOXIMIDAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H34 N4 O2" 
_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                        446.584 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     348 
_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        2CF9 
_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 
348 N1   N1   N 0 1 N N N 10.579 -12.150 24.135 -5.456 0.393  0.385  N1   348 1  
348 C3   C3   C 0 1 N N N 11.362 -11.083 23.936 -4.871 1.613  0.640  C3   348 2  
348 N2   N2   N 0 1 N N N 11.125 -9.977  24.615 -5.580 2.584  1.139  N2   348 3  
348 C4   C4   C 0 1 Y N N 12.491 -11.141 22.938 -3.434 1.821  0.347  C4   348 4  
348 C9   C9   C 0 1 Y N N 12.722 -12.324 22.223 -2.839 3.056  0.604  C9   348 5  
348 C8   C8   C 0 1 Y N N 13.775 -12.382 21.302 -1.499 3.243  0.328  C8   348 6  
348 C7   C7   C 0 1 Y N N 14.608 -11.284 21.081 -0.748 2.210  -0.201 C7   348 7  
348 C6   C6   C 0 1 Y N N 14.367 -10.102 21.795 -1.334 0.985  -0.464 C6   348 8  
348 C5   C5   C 0 1 Y N N 13.312 -10.038 22.716 -2.671 0.783  -0.188 C5   348 9  
348 C10  C10  C 0 1 N N R 15.733 -11.333 20.092 0.714  2.421  -0.500 C10  348 10 
348 N11  N11  N 0 1 N N N 15.565 -12.314 18.975 1.071  1.733  -1.750 N11  348 11 
348 C12  C12  C 0 1 N N N 14.677 -11.787 17.914 1.708  2.792  -2.616 C12  348 12 
348 C13  C13  C 0 1 N N N 15.492 -11.765 16.613 2.676  1.995  -3.525 C13  348 13 
348 C14  C14  C 0 1 N N N 16.955 -11.829 17.043 3.216  0.900  -2.577 C14  348 14 
348 C15  C15  C 0 1 N N S 16.910 -12.534 18.395 2.148  0.759  -1.480 C15  348 15 
348 C16  C16  C 0 1 N N R 17.930 -12.066 19.432 2.749  1.119  -0.114 C16  348 16 
348 C17  C17  C 0 1 N N R 18.876 -13.208 19.845 2.915  -0.170 0.719  C17  348 17 
348 N19  N19  N 0 1 N N N 18.286 -13.620 21.142 1.614  -0.398 1.359  N19  348 18 
348 C20  C20  C 0 1 N N N 17.308 -12.816 21.577 0.856  0.710  1.331  C20  348 19 
348 O21  O21  O 0 1 N N N 16.668 -13.030 22.599 -0.267 0.793  1.784  O21  348 20 
348 C22  C22  C 0 1 N N S 17.134 -11.635 20.662 1.594  1.835  0.644  C22  348 21 
348 C23  C23  C 0 1 N N N 18.765 -14.860 21.793 1.195  -1.673 1.946  C23  348 22 
348 C24  C24  C 0 1 Y N N 19.643 -14.508 22.982 0.385  -2.448 0.939  C24  348 23 
348 C32  C32  C 0 1 Y N N 21.025 -14.392 22.823 1.021  -3.270 0.027  C32  348 24 
348 C31  C31  C 0 1 Y N N 21.850 -14.039 23.898 0.280  -3.981 -0.897 C31  348 25 
348 C30  C30  C 0 1 Y N N 21.281 -13.797 25.149 -1.102 -3.870 -0.910 C30  348 26 
348 O29  O29  O 0 1 N N N 22.080 -13.451 26.211 -1.833 -4.569 -1.818 O29  348 27 
348 C28  C28  C 0 1 N N N 21.613 -12.549 27.222 -3.205 -4.248 -1.580 C28  348 28 
348 C26  C26  C 0 1 Y N N 19.899 -13.922 25.316 -1.738 -3.040 0.002  C26  348 29 
348 C25  C25  C 0 1 Y N N 19.079 -14.271 24.243 -0.993 -2.335 0.928  C25  348 30 
348 C18  C18  C 0 1 N N N 20.355 -12.735 19.934 4.000  0.020  1.781  C18  348 31 
348 C41  C41  C 0 1 N N N 21.012 -12.466 18.579 4.047  -1.212 2.688  C41  348 32 
348 C42  C42  C 0 1 N N N 20.608 -11.531 20.842 5.357  0.201  1.097  C42  348 33 
348 H1N1 1H1N H 0 0 N N N 10.762 -13.005 23.610 -4.927 -0.331 0.013  H1N1 348 34 
348 H1N2 2H1N H 0 0 N N N 9.815  -12.111 24.810 -6.397 0.256  0.577  H1N2 348 35 
348 H2N  H2N  H 0 1 N N N 11.783 -9.266  24.367 -6.521 2.448  1.332  H2N  348 36 
348 H9   H9   H 0 1 N N N 12.078 -13.205 22.385 -3.424 3.863  1.017  H9   348 37 
348 H8   H8   H 0 1 N N N 13.950 -13.314 20.740 -1.037 4.199  0.527  H8   348 38 
348 H6   H6   H 0 1 N N N 15.009 -9.220  21.632 -0.743 0.182  -0.878 H6   348 39 
348 H5   H5   H 0 1 N N N 13.130 -9.103  23.272 -3.127 -0.175 -0.389 H5   348 40 
348 H10  H10  H 0 1 N N N 15.790 -10.323 19.624 0.920  3.488  -0.595 H10  348 41 
348 H121 1H12 H 0 0 N N N 14.232 -10.797 18.168 2.258  3.509  -2.006 H121 348 42 
348 H122 2H12 H 0 0 N N N 13.721 -12.354 17.822 0.951  3.298  -3.214 H122 348 43 
348 H131 1H13 H 0 0 N N N 15.257 -10.898 15.953 3.486  2.633  -3.878 H131 348 44 
348 H132 2H13 H 0 0 N N N 15.203 -12.563 15.890 2.140  1.551  -4.363 H132 348 45 
348 H141 1H14 H 0 0 N N N 17.632 -12.308 16.298 4.167  1.209  -2.142 H141 348 46 
348 H142 2H14 H 0 0 N N N 17.473 -10.842 17.057 3.333  -0.042 -3.114 H142 348 47 
348 H15  H15  H 0 1 N N N 17.050 -13.628 18.229 1.750  -0.255 -1.465 H15  348 48 
348 H16  H16  H 0 1 N N N 18.517 -11.206 19.033 3.662  1.711  -0.184 H16  348 49 
348 H17  H17  H 0 1 N N N 18.794 -14.045 19.113 3.167  -1.008 0.069  H17  348 50 
348 H22  H22  H 0 1 N N N 17.579 -10.719 21.116 1.945  2.602  1.334  H22  348 51 
348 H231 1H23 H 0 0 N N N 19.282 -15.538 21.075 0.588  -1.482 2.831  H231 348 52 
348 H232 2H23 H 0 0 N N N 17.925 -15.537 22.077 2.075  -2.251 2.227  H232 348 53 
348 H32  H32  H 0 1 N N N 21.475 -14.582 21.834 2.097  -3.356 0.038  H32  348 54 
348 H31  H31  H 0 1 N N N 22.941 -13.953 23.757 0.778  -4.624 -1.609 H31  348 55 
348 H281 1H28 H 0 0 N N N 22.262 -12.268 28.084 -3.354 -3.175 -1.706 H281 348 56 
348 H282 2H28 H 0 0 N N N 20.653 -12.948 27.626 -3.833 -4.788 -2.289 H282 348 57 
348 H283 3H28 H 0 0 N N N 21.277 -11.611 26.721 -3.474 -4.535 -0.564 H283 348 58 
348 H26  H26  H 0 1 N N N 19.451 -13.743 26.308 -2.814 -2.951 -0.006 H26  348 59 
348 H25  H25  H 0 1 N N N 17.989 -14.360 24.387 -1.488 -1.692 1.641  H25  348 60 
348 H18  H18  H 0 1 N N N 20.921 -13.583 20.385 3.773  0.903  2.378  H18  348 61 
348 H411 1H41 H 0 0 N N N 22.072 -12.127 18.643 4.156  -2.108 2.078  H411 348 62 
348 H412 2H41 H 0 0 N N N 20.406 -11.740 17.989 4.895  -1.130 3.368  H412 348 63 
348 H413 3H41 H 0 0 N N N 20.928 -13.362 17.921 3.124  -1.274 3.264  H413 348 64 
348 H421 1H42 H 0 0 N N N 21.668 -11.192 20.906 6.130  0.337  1.853  H421 348 65 
348 H422 2H42 H 0 0 N N N 20.210 -11.733 21.864 5.583  -0.682 0.499  H422 348 66 
348 H423 3H42 H 0 0 N N N 19.953 -10.681 20.540 5.323  1.078  0.451  H423 348 67 
# 
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 
348 N1  C3   SING N N 1  
348 N1  H1N1 SING N N 2  
348 N1  H1N2 SING N N 3  
348 C3  N2   DOUB N E 4  
348 C3  C4   SING N N 5  
348 N2  H2N  SING N N 6  
348 C4  C9   DOUB Y N 7  
348 C4  C5   SING Y N 8  
348 C9  C8   SING Y N 9  
348 C9  H9   SING N N 10 
348 C8  C7   DOUB Y N 11 
348 C8  H8   SING N N 12 
348 C7  C6   SING Y N 13 
348 C7  C10  SING N N 14 
348 C6  C5   DOUB Y N 15 
348 C6  H6   SING N N 16 
348 C5  H5   SING N N 17 
348 C10 N11  SING N N 18 
348 C10 C22  SING N N 19 
348 C10 H10  SING N N 20 
348 N11 C12  SING N N 21 
348 N11 C15  SING N N 22 
348 C12 C13  SING N N 23 
348 C12 H121 SING N N 24 
348 C12 H122 SING N N 25 
348 C13 C14  SING N N 26 
348 C13 H131 SING N N 27 
348 C13 H132 SING N N 28 
348 C14 C15  SING N N 29 
348 C14 H141 SING N N 30 
348 C14 H142 SING N N 31 
348 C15 C16  SING N N 32 
348 C15 H15  SING N N 33 
348 C16 C17  SING N N 34 
348 C16 C22  SING N N 35 
348 C16 H16  SING N N 36 
348 C17 N19  SING N N 37 
348 C17 C18  SING N N 38 
348 C17 H17  SING N N 39 
348 N19 C20  SING N N 40 
348 N19 C23  SING N N 41 
348 C20 O21  DOUB N N 42 
348 C20 C22  SING N N 43 
348 C22 H22  SING N N 44 
348 C23 C24  SING N N 45 
348 C23 H231 SING N N 46 
348 C23 H232 SING N N 47 
348 C24 C32  DOUB Y N 48 
348 C24 C25  SING Y N 49 
348 C32 C31  SING Y N 50 
348 C32 H32  SING N N 51 
348 C31 C30  DOUB Y N 52 
348 C31 H31  SING N N 53 
348 C30 O29  SING N N 54 
348 C30 C26  SING Y N 55 
348 O29 C28  SING N N 56 
348 C28 H281 SING N N 57 
348 C28 H282 SING N N 58 
348 C28 H283 SING N N 59 
348 C26 C25  DOUB Y N 60 
348 C26 H26  SING N N 61 
348 C25 H25  SING N N 62 
348 C18 C41  SING N N 63 
348 C18 C42  SING N N 64 
348 C18 H18  SING N N 65 
348 C41 H411 SING N N 66 
348 C41 H412 SING N N 67 
348 C41 H413 SING N N 68 
348 C42 H421 SING N N 69 
348 C42 H422 SING N N 70 
348 C42 H423 SING N N 71 
# 
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 
348 SMILES           ACDLabs              10.04 O=C3N(C(C4C1N(CCC1)C(c2ccc(C(=[N@H])N)cc2)C34)C(C)C)Cc5ccc(OC)cc5 
348 InChI            InChI                1.02b 
InChI=1/C27H34N4O2/c1-16(2)24-22-21-5-4-14-30(21)25(18-8-10-19(11-9-18)26(28)29)23(22)27(32)31(24)15-17-6-12-20(33-3)13-7-17/h6-13,16,21-25H,4-5,14-15H2,1-3H3,(H3,28,29)/t21-,22-,23-,24+,25-/m0/s1/f/h28H,29H2/b28-26+ 
348 InChIKey         InChI                1.02b XETNTDPUFDNJKX-NTXMDTAXDX 
348 SMILES_CANONICAL CACTVS               3.341 COc1ccc(CN2[C@H](C(C)C)[C@H]3[C@@H]4CCCN4[C@H]([C@H]3C2=O)c5ccc(cc5)C(N)=N)cc1 
348 SMILES           CACTVS               3.341 COc1ccc(CN2[CH](C(C)C)[CH]3[CH]4CCCN4[CH]([CH]3C2=O)c5ccc(cc5)C(N)=N)cc1 
348 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)OC)C(C)C)/N 
348 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)C2C3C(C4N2CCC4)C(N(C3=O)Cc5ccc(cc5)OC)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 
348 "SYSTEMATIC NAME" ACDLabs              10.04 4-[(1R,3aS,4R,8aS,8bR)-2-(4-methoxybenzyl)-1-(1-methylethyl)-3-oxodecahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzenecarboximidamide                            
348 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[(1R,3aS,4R,5S,8aS,8bR)-2-[(4-methoxyphenyl)methyl]-3-oxo-1-propan-2-yl-1,3a,4,6,7,8,8a,8b-octahydropyrrolo[4,3-a]pyrrolizin-4-yl]benzenecarboximidamide 
# 
