data_REN # _chem_comp.id REN _chem_comp.name "(S)-reticuline" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H23 N O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-06-04 _chem_comp.pdbx_modified_date 2020-06-17 _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 329.390 _chem_comp.one_letter_code ? _chem_comp.three_letter_code REN _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 3D2D _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # 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 REN C2 C2 C 0 1 Y N N 30.260 33.384 20.691 -2.157 -1.270 0.091 C2 REN 1 REN C3 C3 C 0 1 Y N N 31.051 32.455 20.026 -3.507 -1.536 0.230 C3 REN 2 REN C5 C5 C 0 1 Y N N 30.682 32.009 18.764 -4.434 -0.513 0.051 C5 REN 3 REN C8 C8 C 0 1 Y N N 29.525 32.491 18.166 -3.996 0.761 -0.261 C8 REN 4 REN C9 C9 C 0 1 Y N N 28.730 33.419 18.826 -2.641 1.023 -0.398 C9 REN 5 REN C10 C10 C 0 1 N N N 27.342 33.720 18.267 -2.213 2.429 -0.733 C10 REN 6 REN C11 C11 C 0 1 N N N 26.573 34.708 19.133 -0.773 2.429 -1.245 C11 REN 7 REN N12 N12 N 0 1 N N N 27.526 35.588 19.793 0.061 1.678 -0.294 N12 REN 8 REN C14 C14 C 0 1 N N S 28.261 34.847 20.810 -0.242 0.245 -0.374 C14 REN 9 REN C16 C16 C 0 1 N N N 27.333 34.082 21.747 0.502 -0.491 0.742 C16 REN 10 REN C17 C17 C 0 1 Y N N 26.919 34.904 22.963 1.986 -0.407 0.496 C17 REN 11 REN C25 C25 C 0 1 Y N N 27.795 35.079 24.029 2.736 0.565 1.131 C25 REN 12 REN C24 C24 C 0 1 Y N N 27.406 35.829 25.134 4.098 0.647 0.909 C24 REN 13 REN C21 C21 C 0 1 Y N N 26.140 36.405 25.175 4.715 -0.248 0.049 C21 REN 14 REN O22 O22 O 0 1 N N N 25.751 37.145 26.263 6.055 -0.170 -0.170 O22 REN 15 REN C23 C23 C 0 1 N N N 26.721 37.588 27.209 6.766 0.861 0.520 C23 REN 16 REN C19 C19 C 0 1 Y N N 25.265 36.228 24.109 3.960 -1.228 -0.589 C19 REN 17 REN O20 O20 O 0 1 N N N 24.017 36.791 24.141 4.561 -2.109 -1.434 O20 REN 18 REN C18 C18 C 0 1 Y N N 25.654 35.478 23.007 2.596 -1.307 -0.358 C18 REN 19 REN C1 C1 C 0 1 Y N N 29.101 33.866 20.092 -1.722 0.010 -0.225 C1 REN 20 REN C13 C13 C 0 1 N N N 26.884 36.793 20.303 -0.122 2.178 1.075 C13 REN 21 REN O6 O6 O 0 1 N N N 31.455 31.095 18.102 -5.764 -0.766 0.183 O6 REN 22 REN C7 C7 C 0 1 N N N 31.408 31.028 16.678 -6.656 0.333 -0.015 C7 REN 23 REN O4 O4 O 0 1 N N N 32.193 31.979 20.613 -3.927 -2.792 0.538 O4 REN 24 REN H2 H2 H 0 1 N N N 30.545 33.732 21.673 -1.436 -2.061 0.234 H2 REN 25 REN H8 H8 H 0 1 N N N 29.242 32.143 17.184 -4.714 1.556 -0.399 H8 REN 26 REN H10 H10 H 0 1 N N N 27.456 34.151 17.261 -2.871 2.834 -1.503 H10 REN 27 REN H10A H10A H 0 0 N N N 26.775 32.778 18.244 -2.280 3.051 0.160 H10A REN 28 REN H11 H11 H 0 1 N N N 25.892 35.301 18.505 -0.732 1.951 -2.224 H11 REN 29 REN H11A H11A H 0 0 N N N 25.980 34.166 19.885 -0.410 3.454 -1.320 H11A REN 30 REN H14 H14 H 0 1 N N N 28.845 35.552 21.420 0.087 -0.138 -1.340 H14 REN 31 REN H16 H16 H 0 1 N N N 26.426 33.805 21.189 0.265 -0.031 1.701 H16 REN 32 REN H16A H16A H 0 0 N N N 27.878 33.198 22.110 0.194 -1.537 0.754 H16A REN 33 REN H25 H25 H 0 1 N N N 28.778 34.632 23.999 2.257 1.263 1.801 H25 REN 34 REN H24 H24 H 0 1 N N N 28.087 35.964 25.961 4.682 1.408 1.405 H24 REN 35 REN H23 H23 H 0 1 N N N 27.695 37.702 26.710 7.822 0.812 0.256 H23 REN 36 REN H23A H23A H 0 0 N N N 26.408 38.556 27.629 6.365 1.833 0.233 H23A REN 37 REN H23B H23B H 0 0 N N N 26.808 36.848 28.018 6.652 0.723 1.595 H23B REN 38 REN HO20 HO20 H 0 0 N N N 23.751 36.921 25.044 4.877 -2.914 -1.002 HO20 REN 39 REN H18 H18 H 0 1 N N N 24.971 35.340 22.181 2.009 -2.069 -0.849 H18 REN 40 REN H13 H13 H 0 1 N N N 26.722 36.692 21.386 -1.136 1.961 1.410 H13 REN 41 REN H13A H13A H 0 0 N N N 27.529 37.662 20.108 0.592 1.691 1.739 H13A REN 42 REN H13B H13B H 0 0 N N N 25.916 36.934 19.800 0.043 3.256 1.093 H13B REN 43 REN H7 H7 H 0 1 N N N 31.396 32.047 16.263 -6.530 0.726 -1.024 H7 REN 44 REN H7A H7A H 0 1 N N N 32.294 30.491 16.307 -7.683 -0.004 0.119 H7A REN 45 REN H7B H7B H 0 1 N N N 30.498 30.494 16.366 -6.433 1.116 0.710 H7B REN 46 REN HO4 HO4 H 0 1 N N N 32.867 31.869 19.952 -3.999 -2.961 1.488 HO4 REN 47 # # 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 REN C2 C3 DOUB Y N 1 REN C2 C1 SING Y N 2 REN C3 C5 SING Y N 3 REN C3 O4 SING N N 4 REN C5 C8 DOUB Y N 5 REN C5 O6 SING N N 6 REN C8 C9 SING Y N 7 REN C9 C10 SING N N 8 REN C9 C1 DOUB Y N 9 REN C10 C11 SING N N 10 REN C11 N12 SING N N 11 REN N12 C14 SING N N 12 REN N12 C13 SING N N 13 REN C14 C16 SING N N 14 REN C14 C1 SING N N 15 REN C16 C17 SING N N 16 REN C17 C25 DOUB Y N 17 REN C17 C18 SING Y N 18 REN C25 C24 SING Y N 19 REN C24 C21 DOUB Y N 20 REN C21 O22 SING N N 21 REN C21 C19 SING Y N 22 REN O22 C23 SING N N 23 REN C19 O20 SING N N 24 REN C19 C18 DOUB Y N 25 REN O6 C7 SING N N 26 REN C2 H2 SING N N 27 REN C8 H8 SING N N 28 REN C10 H10 SING N N 29 REN C10 H10A SING N N 30 REN C11 H11 SING N N 31 REN C11 H11A SING N N 32 REN C14 H14 SING N N 33 REN C16 H16 SING N N 34 REN C16 H16A SING N N 35 REN C25 H25 SING N N 36 REN C24 H24 SING N N 37 REN C23 H23 SING N N 38 REN C23 H23A SING N N 39 REN C23 H23B SING N N 40 REN O20 HO20 SING N N 41 REN C18 H18 SING N N 42 REN C13 H13 SING N N 43 REN C13 H13A SING N N 44 REN C13 H13B SING N N 45 REN C7 H7 SING N N 46 REN C7 H7A SING N N 47 REN C7 H7B SING N N 48 REN O4 HO4 SING N N 49 # # 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 REN SMILES ACDLabs 10.04 "O(c1ccc(cc1O)CC3c2c(cc(OC)c(O)c2)CCN3C)C" REN SMILES_CANONICAL CACTVS 3.341 "COc1ccc(C[C@@H]2N(C)CCc3cc(OC)c(O)cc23)cc1O" REN SMILES CACTVS 3.341 "COc1ccc(C[CH]2N(C)CCc3cc(OC)c(O)cc23)cc1O" REN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[N@@]1CCc2cc(c(cc2[C@@H]1Cc3ccc(c(c3)O)OC)O)OC" REN SMILES "OpenEye OEToolkits" 1.5.0 "CN1CCc2cc(c(cc2C1Cc3ccc(c(c3)O)OC)O)OC" REN InChI InChI 1.03 "InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1" REN InChIKey InChI 1.03 BHLYRWXGMIUIHG-HNNXBMFYSA-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 REN "SYSTEMATIC NAME" ACDLabs 10.04 "(1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol" REN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1S,2R)-1-[(3-hydroxy-4-methoxy-phenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site REN "Create component" 2008-06-04 RCSB REN "Modify aromatic_flag" 2011-06-04 RCSB REN "Modify descriptor" 2011-06-04 RCSB REN "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id REN _pdbx_chem_comp_synonyms.name "(1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##