data_H5W # _chem_comp.id H5W _chem_comp.name "6-{[(3R,4R)-4-{[(3E)-4-(3-fluorophenyl)but-3-en-1-yl]oxy}pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H26 F N3 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-11-23 _chem_comp.pdbx_modified_date 2012-07-06 _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 355.449 _chem_comp.one_letter_code ? _chem_comp.three_letter_code H5W _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 3UFR _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 H5W F23 F23 F 0 1 N N N -0.011 3.819 27.403 8.115 1.311 0.235 F23 H5W 1 H5W C23 C23 C 0 1 Y N N 1.133 4.535 27.312 7.440 0.142 0.180 C23 H5W 2 H5W C24 C24 C 0 1 Y N N 1.099 5.944 27.359 8.103 -1.052 0.417 C24 H5W 3 H5W C25 C25 C 0 1 Y N N 2.291 6.670 27.265 7.418 -2.252 0.362 C25 H5W 4 H5W C26 C26 C 0 1 Y N N 3.510 5.984 27.125 6.069 -2.268 0.072 C26 H5W 5 H5W C22 C22 C 0 1 Y N N 2.359 3.856 27.174 6.088 0.138 -0.107 C22 H5W 6 H5W C21 C21 C 0 1 Y N N 3.556 4.581 27.075 5.395 -1.071 -0.168 C21 H5W 7 H5W C13 C13 C 0 1 N N N 4.882 3.914 26.946 3.950 -1.082 -0.479 C13 H5W 8 H5W C12 C12 C 0 1 N N N 5.021 2.586 26.674 3.311 0.057 -0.706 C12 H5W 9 H5W C11 C11 C 0 1 N N N 6.371 2.032 26.222 1.838 0.045 -1.024 C11 H5W 10 H5W C10 C10 C 0 1 N N N 6.976 2.741 24.980 1.098 0.956 -0.042 C10 H5W 11 H5W O09 O09 O 0 1 N N N 7.951 1.919 24.318 -0.299 0.945 -0.343 O09 H5W 12 H5W "C3'" "C3'" C 0 1 N N R 8.758 1.160 25.235 -1.087 1.768 0.519 "C3'" H5W 13 H5W "C2'" "C2'" C 0 1 N N N 8.270 -0.291 25.323 -1.227 3.186 -0.074 "C2'" H5W 14 H5W "N1'" "N1'" N 0 1 N N N 8.967 -0.933 24.226 -2.615 3.596 0.261 "N1'" H5W 15 H5W "C5'" "C5'" C 0 1 N N N 9.938 -0.043 23.593 -3.418 2.362 0.062 "C5'" H5W 16 H5W "C4'" "C4'" C 0 1 N N R 10.176 0.936 24.735 -2.528 1.226 0.609 "C4'" H5W 17 H5W C08 C08 C 0 1 N N N 11.050 2.159 24.463 -2.678 -0.029 -0.254 C08 H5W 18 H5W C06 C06 C 0 1 Y N N 12.341 1.716 23.788 -4.077 -0.571 -0.112 C06 H5W 19 H5W N01 N01 N 0 1 Y N N 13.134 0.689 24.237 -4.550 -0.847 1.088 N01 H5W 20 H5W C02 C02 C 0 1 Y N N 14.265 0.351 23.569 -5.773 -1.325 1.259 C02 H5W 21 H5W N02 N02 N 0 1 N N N 15.019 -0.646 24.019 -6.231 -1.602 2.542 N02 H5W 22 H5W C03 C03 C 0 1 Y N N 14.636 1.004 22.410 -6.604 -1.552 0.167 C03 H5W 23 H5W C05 C05 C 0 1 Y N N 12.689 2.371 22.620 -4.849 -0.767 -1.240 C05 H5W 24 H5W C04 C04 C 0 1 Y N N 13.837 2.028 21.930 -6.136 -1.272 -1.104 C04 H5W 25 H5W C07 C07 C 0 1 N N N 14.160 2.764 20.652 -7.004 -1.503 -2.314 C07 H5W 26 H5W H1 H1 H 0 1 N N N 0.157 6.460 27.467 9.159 -1.045 0.645 H1 H5W 27 H5W H2 H2 H 0 1 N N N 2.275 7.749 27.300 7.940 -3.179 0.547 H2 H5W 28 H5W H3 H3 H 0 1 N N N 4.429 6.547 27.055 5.536 -3.207 0.029 H3 H5W 29 H5W H4 H4 H 0 1 N N N 2.378 2.777 27.144 5.572 1.069 -0.291 H4 H5W 30 H5W H5 H5 H 0 1 N N N 5.773 4.510 27.074 3.414 -2.019 -0.522 H5 H5W 31 H5W H6 H6 H 0 1 N N N 4.175 1.923 26.778 3.847 0.994 -0.663 H6 H5W 32 H5W H7 H7 H 0 1 N N N 6.241 0.967 25.980 1.683 0.405 -2.041 H7 H5W 33 H5W H8 H8 H 0 1 N N N 7.081 2.135 27.056 1.456 -0.971 -0.935 H8 H5W 34 H5W H9 H9 H 0 1 N N N 7.458 3.675 25.303 1.253 0.596 0.975 H9 H5W 35 H5W H10 H10 H 0 1 N N N 6.166 2.972 24.273 1.480 1.973 -0.131 H10 H5W 36 H5W H11 H11 H 0 1 N N N 8.772 1.617 26.235 -0.636 1.816 1.511 H11 H5W 37 H5W H12 H12 H 0 1 N N N 7.180 -0.351 25.189 -0.509 3.864 0.387 H12 H5W 38 H5W H13 H13 H 0 1 N N N 8.546 -0.744 26.287 -1.087 3.162 -1.155 H13 H5W 39 H5W H14 H14 H 0 1 N N N 8.296 -1.218 23.541 -2.931 4.335 -0.349 H14 H5W 40 H5W H16 H16 H 0 1 N N N 10.859 -0.576 23.312 -4.350 2.420 0.625 H16 H5W 41 H5W H17 H17 H 0 1 N N N 9.518 0.456 22.707 -3.623 2.209 -0.998 H17 H5W 42 H5W H18 H18 H 0 1 N N N 10.690 0.365 25.522 -2.787 1.008 1.645 H18 H5W 43 H5W H19 H19 H 0 1 N N N 11.286 2.661 25.413 -2.490 0.223 -1.297 H19 H5W 44 H5W H20 H20 H 0 1 N N N 10.511 2.856 23.804 -1.962 -0.782 0.073 H20 H5W 45 H5W H21 H21 H 0 1 N N N 14.608 -1.028 24.847 -5.655 -1.446 3.307 H21 H5W 46 H5W H22 H22 H 0 1 N N N 15.082 -1.358 23.320 -7.126 -1.952 2.672 H22 H5W 47 H5W H23 H23 H 0 1 N N N 15.536 0.720 21.886 -7.601 -1.942 0.309 H23 H5W 48 H5W H24 H24 H 0 1 N N N 12.056 3.160 22.242 -4.453 -0.538 -2.218 H24 H5W 49 H5W H25 H25 H 0 1 N N N 13.692 2.246 19.802 -7.577 -0.601 -2.528 H25 H5W 50 H5W H26 H26 H 0 1 N N N 13.773 3.792 20.713 -6.376 -1.747 -3.171 H26 H5W 51 H5W H27 H27 H 0 1 N N N 15.250 2.791 20.510 -7.687 -2.330 -2.118 H27 H5W 52 # 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 H5W C07 C04 SING N N 1 H5W C04 C03 DOUB Y N 2 H5W C04 C05 SING Y N 3 H5W C03 C02 SING Y N 4 H5W C05 C06 DOUB Y N 5 H5W C02 N02 SING N N 6 H5W C02 N01 DOUB Y N 7 H5W "C5'" "N1'" SING N N 8 H5W "C5'" "C4'" SING N N 9 H5W C06 N01 SING Y N 10 H5W C06 C08 SING N N 11 H5W "N1'" "C2'" SING N N 12 H5W O09 C10 SING N N 13 H5W O09 "C3'" SING N N 14 H5W C08 "C4'" SING N N 15 H5W "C4'" "C3'" SING N N 16 H5W C10 C11 SING N N 17 H5W "C3'" "C2'" SING N N 18 H5W C11 C12 SING N N 19 H5W C12 C13 DOUB N E 20 H5W C13 C21 SING N N 21 H5W C21 C26 DOUB Y N 22 H5W C21 C22 SING Y N 23 H5W C26 C25 SING Y N 24 H5W C22 C23 DOUB Y N 25 H5W C25 C24 DOUB Y N 26 H5W C23 C24 SING Y N 27 H5W C23 F23 SING N N 28 H5W C24 H1 SING N N 29 H5W C25 H2 SING N N 30 H5W C26 H3 SING N N 31 H5W C22 H4 SING N N 32 H5W C13 H5 SING N N 33 H5W C12 H6 SING N N 34 H5W C11 H7 SING N N 35 H5W C11 H8 SING N N 36 H5W C10 H9 SING N N 37 H5W C10 H10 SING N N 38 H5W "C3'" H11 SING N N 39 H5W "C2'" H12 SING N N 40 H5W "C2'" H13 SING N N 41 H5W "N1'" H14 SING N N 42 H5W "C5'" H16 SING N N 43 H5W "C5'" H17 SING N N 44 H5W "C4'" H18 SING N N 45 H5W C08 H19 SING N N 46 H5W C08 H20 SING N N 47 H5W N02 H21 SING N N 48 H5W N02 H22 SING N N 49 H5W C03 H23 SING N N 50 H5W C05 H24 SING N N 51 H5W C07 H25 SING N N 52 H5W C07 H26 SING N N 53 H5W C07 H27 SING N N 54 # 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 H5W SMILES ACDLabs 12.01 "Fc1cccc(c1)/C=C/CCOC2C(CNC2)Cc3nc(N)cc(c3)C" H5W InChI InChI 1.03 "InChI=1S/C21H26FN3O/c1-15-9-19(25-21(23)10-15)12-17-13-24-14-20(17)26-8-3-2-5-16-6-4-7-18(22)11-16/h2,4-7,9-11,17,20,24H,3,8,12-14H2,1H3,(H2,23,25)/b5-2+/t17-,20+/m1/s1" H5W InChIKey InChI 1.03 GKGVFZUGOXZFKN-YUOLOVIMSA-N H5W SMILES_CANONICAL CACTVS 3.370 "Cc1cc(N)nc(C[C@@H]2CNC[C@@H]2OCC\C=C\c3cccc(F)c3)c1" H5W SMILES CACTVS 3.370 "Cc1cc(N)nc(C[CH]2CNC[CH]2OCCC=Cc3cccc(F)c3)c1" H5W SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1cc(nc(c1)N)C[C@@H]2CNC[C@@H]2OCC/C=C/c3cccc(c3)F" H5W SMILES "OpenEye OEToolkits" 1.7.6 "Cc1cc(nc(c1)N)CC2CNCC2OCCC=Cc3cccc(c3)F" # 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 H5W "SYSTEMATIC NAME" ACDLabs 12.01 "6-{[(3R,4R)-4-{[(3E)-4-(3-fluorophenyl)but-3-en-1-yl]oxy}pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine" H5W "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "6-[[(3R,4R)-4-[(E)-4-(3-fluorophenyl)but-3-enoxy]pyrrolidin-3-yl]methyl]-4-methyl-pyridin-2-amine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site H5W "Create component" 2011-11-23 RCSB #