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 2011-06-04 _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 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" 348 InChI InChI 1.03 "InChI=1S/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" 348 InChIKey InChI 1.03 XETNTDPUFDNJKX-BDUWWWMKSA-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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 348 "Create component" 2006-02-17 EBI 348 "Modify descriptor" 2011-06-04 RCSB #