data_4YN # _chem_comp.id 4YN _chem_comp.name "(2R,5R)-4-[2-(6-benzyl-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-oxoethyl]-5-(methoxymethyl)-2-methylpiperazin-1-ium" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H35 N4 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2015-06-25 _chem_comp.pdbx_modified_date 2015-08-07 _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 423.571 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 4YN _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 5C83 _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 4YN C1 C1 C 0 1 N N N -14.390 -15.634 -4.326 -3.569 0.161 -3.958 C1 4YN 1 4YN C3 C2 C 0 1 N N N -16.202 -16.332 -2.919 -2.918 1.439 -2.038 C3 4YN 2 4YN C5 C3 C 0 1 N N N -15.529 -17.775 -0.988 -4.719 2.049 -0.415 C5 4YN 3 4YN C7 C4 C 0 1 N N R -15.949 -20.224 -1.049 -4.804 0.989 1.736 C7 4YN 4 4YN C8 C5 C 0 1 N N N -15.463 -21.557 -0.498 -5.154 1.186 3.212 C8 4YN 5 4YN C11 C6 C 0 1 N N N -16.455 -18.870 -4.553 -1.600 -0.016 0.029 C11 4YN 6 4YN C12 C7 C 0 1 N N N -15.173 -19.004 -5.358 -1.487 -1.475 0.389 C12 4YN 7 4YN C15 C8 C 0 1 N N N -16.506 -18.424 -7.414 -0.059 -3.507 0.640 C15 4YN 8 4YN C16 C9 C 0 1 N N N -16.151 -18.409 -8.920 1.444 -3.732 0.402 C16 4YN 9 4YN C19 C10 C 0 1 Y N N -14.640 -18.560 -8.908 1.960 -2.388 -0.053 C19 4YN 10 4YN C22 C11 C 0 1 Y N N -11.958 -18.874 -8.525 2.447 0.173 -0.820 C22 4YN 11 4YN C23 C12 C 0 1 N N N -10.467 -19.038 -8.390 2.740 1.588 -1.248 C23 4YN 12 4YN C24 C13 C 0 1 Y N N -10.012 -20.438 -8.707 3.840 2.156 -0.389 C24 4YN 13 4YN C25 C14 C 0 1 Y N N -10.129 -21.448 -7.763 5.160 2.012 -0.773 C25 4YN 14 4YN C26 C15 C 0 1 Y N N -9.711 -22.732 -8.056 6.170 2.533 0.015 C26 4YN 15 4YN C27 C16 C 0 1 Y N N -9.175 -23.018 -9.289 5.859 3.196 1.187 C27 4YN 16 4YN C28 C17 C 0 1 Y N N -9.053 -22.026 -10.234 4.539 3.340 1.571 C28 4YN 17 4YN C31 C18 C 0 1 Y N N -14.163 -18.773 -7.625 0.897 -1.494 -0.077 C31 4YN 18 4YN O2 O1 O 0 1 N N N -15.782 -15.956 -4.236 -3.792 0.444 -2.576 O2 4YN 19 4YN C4 C19 C 0 1 N N R -15.585 -17.679 -2.513 -3.246 1.660 -0.560 C4 4YN 20 4YN N6 N1 N 1 1 N N N -15.074 -19.118 -0.537 -5.037 2.242 1.005 N6 4YN 21 4YN C9 C20 C 0 1 N N N -15.935 -20.184 -2.573 -3.332 0.591 1.609 C9 4YN 22 4YN N10 N2 N 0 1 N N N -16.286 -18.854 -3.090 -2.993 0.421 0.189 N10 4YN 23 4YN O13 O2 O 0 1 N N N -14.119 -19.298 -4.808 -2.470 -2.090 0.745 O13 4YN 24 4YN N14 N3 N 0 1 N N N -15.245 -18.784 -6.714 -0.293 -2.097 0.316 N14 4YN 25 4YN C17 C21 C 0 1 N N N -16.826 -19.557 -9.663 2.132 -4.157 1.701 C17 4YN 26 4YN C18 C22 C 0 1 N N N -16.561 -17.092 -9.562 1.660 -4.784 -0.688 C18 4YN 27 4YN C20 C23 C 0 1 Y N N -13.739 -18.513 -9.953 3.220 -1.960 -0.413 C20 4YN 28 4YN N21 N4 N 0 1 Y N N -12.425 -18.667 -9.768 3.428 -0.709 -0.782 N21 4YN 29 4YN C29 C24 C 0 1 Y N N -9.469 -20.742 -9.947 3.529 2.825 0.780 C29 4YN 30 4YN C30 C25 C 0 1 Y N N -12.805 -18.934 -7.414 1.161 -0.178 -0.474 C30 4YN 31 4YN H32 H1 H 0 1 N N N -14.143 -15.357 -5.362 -2.549 -0.199 -4.096 H32 4YN 32 4YN H33 H2 H 0 1 N N N -14.165 -14.790 -3.657 -4.272 -0.604 -4.290 H33 4YN 33 4YN H34 H3 H 0 1 N N N -13.792 -16.508 -4.028 -3.717 1.069 -4.544 H34 4YN 34 4YN H35 H4 H 0 1 N N N -15.883 -15.559 -2.204 -1.885 1.106 -2.136 H35 4YN 35 4YN H36 H5 H 0 1 N N N -17.299 -16.418 -2.901 -3.052 2.373 -2.583 H36 4YN 36 4YN H39 H6 H 0 1 N N N -14.829 -17.016 -0.609 -4.905 2.976 -0.959 H39 4YN 37 4YN H38 H7 H 0 1 N N N -16.533 -17.584 -0.582 -5.345 1.256 -0.824 H38 4YN 38 4YN H42 H8 H 0 1 N N N -16.979 -20.054 -0.702 -5.430 0.201 1.316 H42 4YN 39 4YN H44 H9 H 0 1 N N N -15.493 -21.533 0.601 -6.203 1.469 3.302 H44 4YN 40 4YN H43 H10 H 0 1 N N N -16.114 -22.364 -0.865 -4.980 0.257 3.754 H43 4YN 41 4YN H45 H11 H 0 1 N N N -14.431 -21.738 -0.833 -4.528 1.974 3.632 H45 4YN 42 4YN H48 H12 H 0 1 N N N -16.944 -17.930 -4.848 -0.957 0.571 0.684 H48 4YN 43 4YN H49 H13 H 0 1 N N N -17.107 -19.718 -4.810 -1.291 0.127 -1.007 H49 4YN 44 4YN H51 H14 H 0 1 N N N -16.856 -17.432 -7.091 -0.646 -4.149 -0.017 H51 4YN 45 4YN H50 H15 H 0 1 N N N -17.286 -19.172 -7.210 -0.312 -3.703 1.683 H50 4YN 46 4YN H60 H16 H 0 1 N N N -10.177 -18.798 -7.356 3.053 1.595 -2.292 H60 4YN 47 4YN H59 H17 H 0 1 N N N -9.971 -18.340 -9.081 1.841 2.195 -1.135 H59 4YN 48 4YN H61 H18 H 0 1 N N N -10.550 -21.229 -6.793 5.403 1.493 -1.689 H61 4YN 49 4YN H62 H19 H 0 1 N N N -9.806 -23.512 -7.315 7.201 2.420 -0.285 H62 4YN 50 4YN H63 H20 H 0 1 N N N -8.849 -24.022 -9.516 6.648 3.602 1.803 H63 4YN 51 4YN H64 H21 H 0 1 N N N -8.631 -22.252 -11.202 4.296 3.862 2.484 H64 4YN 52 4YN H37 H22 H 0 1 N N N -14.549 -17.689 -2.881 -2.618 2.459 -0.164 H37 4YN 53 4YN H41 H23 H 0 1 N N N -15.082 -19.140 0.463 -4.449 2.968 1.386 H41 4YN 54 4YN H40 H24 H 0 1 N N N -14.142 -19.268 -0.867 -6.006 2.510 1.099 H40 4YN 55 4YN H46 H25 H 0 1 N N N -16.661 -20.917 -2.955 -2.706 1.372 2.041 H46 4YN 56 4YN H47 H26 H 0 1 N N N -14.927 -20.448 -2.926 -3.161 -0.346 2.139 H47 4YN 57 4YN H54 H28 H 0 1 N N N -16.534 -20.513 -9.204 1.953 -3.406 2.470 H54 4YN 58 4YN H52 H29 H 0 1 N N N -17.918 -19.440 -9.604 1.730 -5.116 2.028 H52 4YN 59 4YN H53 H30 H 0 1 N N N -16.513 -19.546 -10.717 3.204 -4.253 1.529 H53 4YN 60 4YN H56 H31 H 0 1 N N N -16.078 -16.259 -9.031 2.727 -4.887 -0.887 H56 4YN 61 4YN H55 H32 H 0 1 N N N -16.248 -17.085 -10.617 1.259 -5.741 -0.354 H55 4YN 62 4YN H57 H33 H 0 1 N N N -17.654 -16.980 -9.503 1.149 -4.474 -1.599 H57 4YN 63 4YN H58 H34 H 0 1 N N N -14.109 -18.346 -10.954 4.046 -2.655 -0.394 H58 4YN 64 4YN H65 H35 H 0 1 N N N -9.371 -19.968 -10.693 2.498 2.937 1.080 H65 4YN 65 4YN H66 H36 H 0 1 N N N -12.412 -19.101 -6.422 0.366 0.552 -0.508 H66 4YN 66 # 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 4YN C28 C29 DOUB Y N 1 4YN C28 C27 SING Y N 2 4YN C20 N21 DOUB Y N 3 4YN C20 C19 SING Y N 4 4YN C29 C24 SING Y N 5 4YN N21 C22 SING Y N 6 4YN C17 C16 SING N N 7 4YN C18 C16 SING N N 8 4YN C27 C26 DOUB Y N 9 4YN C16 C19 SING N N 10 4YN C16 C15 SING N N 11 4YN C19 C31 DOUB Y N 12 4YN C24 C23 SING N N 13 4YN C24 C25 DOUB Y N 14 4YN C22 C23 SING N N 15 4YN C22 C30 DOUB Y N 16 4YN C26 C25 SING Y N 17 4YN C31 C30 SING Y N 18 4YN C31 N14 SING N N 19 4YN C15 N14 SING N N 20 4YN N14 C12 SING N N 21 4YN C12 O13 DOUB N N 22 4YN C12 C11 SING N N 23 4YN C11 N10 SING N N 24 4YN C1 O2 SING N N 25 4YN O2 C3 SING N N 26 4YN N10 C9 SING N N 27 4YN N10 C4 SING N N 28 4YN C3 C4 SING N N 29 4YN C9 C7 SING N N 30 4YN C4 C5 SING N N 31 4YN C7 N6 SING N N 32 4YN C7 C8 SING N N 33 4YN C5 N6 SING N N 34 4YN C1 H32 SING N N 35 4YN C1 H33 SING N N 36 4YN C1 H34 SING N N 37 4YN C3 H35 SING N N 38 4YN C3 H36 SING N N 39 4YN C5 H39 SING N N 40 4YN C5 H38 SING N N 41 4YN C7 H42 SING N N 42 4YN C8 H44 SING N N 43 4YN C8 H43 SING N N 44 4YN C8 H45 SING N N 45 4YN C11 H48 SING N N 46 4YN C11 H49 SING N N 47 4YN C15 H51 SING N N 48 4YN C15 H50 SING N N 49 4YN C23 H60 SING N N 50 4YN C23 H59 SING N N 51 4YN C25 H61 SING N N 52 4YN C26 H62 SING N N 53 4YN C27 H63 SING N N 54 4YN C28 H64 SING N N 55 4YN C4 H37 SING N N 56 4YN N6 H41 SING N N 57 4YN N6 H40 SING N N 58 4YN C9 H46 SING N N 59 4YN C9 H47 SING N N 60 4YN C17 H54 SING N N 61 4YN C17 H52 SING N N 62 4YN C17 H53 SING N N 63 4YN C18 H56 SING N N 64 4YN C18 H55 SING N N 65 4YN C18 H57 SING N N 66 4YN C20 H58 SING N N 67 4YN C29 H65 SING N N 68 4YN C30 H66 SING N N 69 # 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 4YN SMILES ACDLabs 12.01 "COCC4C[NH2+]C(C)CN4CC(=O)N3CC(c2c3cc(Cc1ccccc1)nc2)(C)C" 4YN InChI InChI 1.03 "InChI=1S/C25H34N4O2/c1-18-14-28(21(12-26-18)16-31-4)15-24(30)29-17-25(2,3)22-13-27-20(11-23(22)29)10-19-8-6-5-7-9-19/h5-9,11,13,18,21,26H,10,12,14-17H2,1-4H3/p+1/t18-,21-/m1/s1" 4YN InChIKey InChI 1.03 XOZJVPQFZSCGTE-WIYYLYMNSA-O 4YN SMILES_CANONICAL CACTVS 3.385 "COC[C@H]1C[NH2+][C@H](C)CN1CC(=O)N2CC(C)(C)c3cnc(Cc4ccccc4)cc23" 4YN SMILES CACTVS 3.385 "COC[CH]1C[NH2+][CH](C)CN1CC(=O)N2CC(C)(C)c3cnc(Cc4ccccc4)cc23" 4YN SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "C[C@@H]1CN([C@H](C[NH2+]1)COC)CC(=O)N2CC(c3c2cc(nc3)Cc4ccccc4)(C)C" 4YN SMILES "OpenEye OEToolkits" 1.9.2 "CC1CN(C(C[NH2+]1)COC)CC(=O)N2CC(c3c2cc(nc3)Cc4ccccc4)(C)C" # 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 4YN "SYSTEMATIC NAME" ACDLabs 12.01 "(2R,5R)-4-[2-(6-benzyl-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-oxoethyl]-5-(methoxymethyl)-2-methylpiperazin-1-ium" 4YN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "1-[3,3-dimethyl-6-(phenylmethyl)-2H-pyrrolo[3,2-c]pyridin-1-yl]-2-[(2R,5R)-2-(methoxymethyl)-5-methyl-piperazin-4-ium-1-yl]ethanone" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 4YN "Create component" 2015-06-25 EBI 4YN "Initial release" 2015-08-12 RCSB #