data_8AX # _chem_comp.id 8AX _chem_comp.name "6-{[(3R,4R)-4-(2-{[2-(3-chlorophenyl)-2,2-difluoroethyl]amino}ethoxy)pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H27 Cl F2 N4 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-11-29 _chem_comp.pdbx_modified_date 2011-10-28 _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 424.915 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 8AX _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 3PNE _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 8AX N01 N01 N 0 1 Y N N 5.256 5.992 26.656 5.637 0.474 1.037 N01 8AX 1 8AX C02 C02 C 0 1 Y N N 4.884 7.185 27.206 6.711 1.248 1.006 C02 8AX 2 8AX N02 N02 N 0 1 N N N 5.705 8.277 27.181 7.816 0.924 1.786 N02 8AX 3 8AX C03 C03 C 0 1 Y N N 3.620 7.292 27.779 6.744 2.381 0.201 C03 8AX 4 8AX C04 C04 C 0 1 Y N N 2.756 6.196 27.806 5.638 2.691 -0.570 C04 8AX 5 8AX C05 C05 C 0 1 Y N N 3.159 4.975 27.236 4.532 1.854 -0.509 C05 8AX 6 8AX C06 C06 C 0 1 Y N N 4.439 4.890 26.665 4.568 0.745 0.312 C06 8AX 7 8AX C07 C07 C 0 1 N N N 1.393 6.365 28.458 5.633 3.910 -1.456 C07 8AX 8 8AX C08 C08 C 0 1 N N N 4.940 3.585 26.042 3.371 -0.168 0.383 C08 8AX 9 8AX O09 O09 O 0 1 N N N 6.669 1.412 25.578 1.425 -1.841 0.555 O09 8AX 10 8AX "N1'" "N1'" N 0 1 N N N 6.802 1.501 28.472 3.773 -3.038 -1.855 "N1'" 8AX 11 8AX C10 C10 C 0 1 N N N 6.646 0.728 24.330 0.492 -2.608 1.319 C10 8AX 12 8AX C11 C11 C 0 1 N N N 7.979 1.040 23.639 -0.721 -1.741 1.662 C11 8AX 13 8AX N12 N12 N 0 1 N N N 9.092 0.579 24.474 -1.432 -1.383 0.428 N12 8AX 14 8AX C13 C13 C 0 1 N N N 10.482 0.871 24.169 -2.606 -0.549 0.719 C13 8AX 15 8AX C14 C14 C 0 1 N N N 10.984 -0.053 23.054 -3.319 -0.197 -0.588 C14 8AX 16 8AX F15 F15 F 0 1 N N N 10.327 0.221 21.924 -2.443 0.506 -1.422 F15 8AX 17 8AX F16 F16 F 0 1 N N N 10.752 -1.336 23.304 -3.729 -1.372 -1.226 F16 8AX 18 8AX "C2'" "C2'" C 0 1 N N N 6.157 2.783 28.172 4.259 -1.707 -1.408 "C2'" 8AX 19 8AX C21 C21 C 0 1 Y N N 12.466 0.212 22.871 -4.522 0.659 -0.289 C21 8AX 20 8AX C22 C22 C 0 1 Y N N 12.826 1.128 21.904 -5.747 0.067 -0.044 C22 8AX 21 8AX C23 C23 C 0 1 Y N N 14.167 1.398 21.703 -6.852 0.853 0.231 C23 8AX 22 8AX CL23 CL23 CL 0 0 N N N 14.496 2.570 20.398 -8.391 0.110 0.540 CL23 8AX 23 8AX C24 C24 C 0 1 Y N N 15.176 0.787 22.455 -6.731 2.230 0.260 C24 8AX 24 8AX C25 C25 C 0 1 Y N N 14.835 -0.148 23.434 -5.505 2.821 0.014 C25 8AX 25 8AX C26 C26 C 0 1 Y N N 13.468 -0.410 23.626 -4.400 2.036 -0.254 C26 8AX 26 8AX "C3'" "C3'" C 0 1 N N R 5.133 2.448 27.072 3.802 -1.600 0.062 "C3'" 8AX 27 8AX "C4'" "C4'" C 0 1 N N R 5.627 1.107 26.503 2.601 -2.561 0.180 "C4'" 8AX 28 8AX "C5'" "C5'" C 0 1 N N N 6.277 0.390 27.687 2.432 -3.167 -1.230 "C5'" 8AX 29 8AX HN02 HN02 H 0 0 N N N 6.559 8.042 26.717 7.797 0.135 2.349 HN02 8AX 30 8AX HN0A HN0A H 0 0 N N N 5.254 9.022 26.690 8.605 1.488 1.767 HN0A 8AX 31 8AX H03 H03 H 0 1 N N N 3.305 8.232 28.207 7.621 3.011 0.178 H03 8AX 32 8AX H05 H05 H 0 1 N N N 2.498 4.121 27.237 3.653 2.068 -1.098 H05 8AX 33 8AX H07 H07 H 0 1 N N N 0.664 6.699 27.705 6.014 3.645 -2.442 H07 8AX 34 8AX H07A H07A H 0 0 N N N 1.068 5.403 28.882 4.615 4.288 -1.549 H07A 8AX 35 8AX H07B H07B H 0 0 N N N 1.461 7.115 29.260 6.267 4.681 -1.017 H07B 8AX 36 8AX H08 H08 H 0 1 N N N 4.200 3.253 25.299 2.945 -0.132 1.385 H08 8AX 37 8AX H08A H08A H 0 0 N N N 5.910 3.783 25.564 2.623 0.157 -0.341 H08A 8AX 38 8AX "HN1'" "HN1'" H 0 0 N N N 6.654 1.296 29.440 4.391 -3.772 -1.541 "HN1'" 8AX 39 8AX H10 H10 H 0 1 N N N 6.538 -0.355 24.487 0.169 -3.471 0.738 H10 8AX 40 8AX H10A H10A H 0 0 N N N 5.803 1.076 23.715 0.969 -2.947 2.239 H10A 8AX 41 8AX H11 H11 H 0 1 N N N 8.015 0.526 22.667 -1.390 -2.297 2.319 H11 8AX 42 8AX H11A H11A H 0 0 N N N 8.064 2.126 23.485 -0.388 -0.834 2.166 H11A 8AX 43 8AX HN12 HN12 H 0 0 N N N 8.930 0.984 25.374 -0.815 -0.923 -0.225 HN12 8AX 44 8AX H13 H13 H 0 1 N N N 10.569 1.917 23.839 -3.288 -1.096 1.369 H13 8AX 45 8AX H13A H13A H 0 0 N N N 11.092 0.715 25.071 -2.286 0.367 1.217 H13A 8AX 46 8AX "H2'" "H2'" H 0 1 N N N 5.663 3.198 29.063 5.345 -1.657 -1.474 "H2'" 8AX 47 8AX "H2'A" "H2'A" H 0 0 N N N 6.890 3.524 27.821 3.806 -0.917 -2.007 "H2'A" 8AX 48 8AX H22 H22 H 0 1 N N N 12.072 1.626 21.313 -5.841 -1.009 -0.067 H22 8AX 49 8AX H24 H24 H 0 1 N N N 16.212 1.037 22.279 -7.593 2.844 0.474 H24 8AX 50 8AX H25 H25 H 0 1 N N N 15.591 -0.649 24.020 -5.411 3.897 0.037 H25 8AX 51 8AX H26 H26 H 0 1 N N N 13.178 -1.120 24.387 -3.442 2.497 -0.442 H26 8AX 52 8AX "H3'" "H3'" H 0 1 N N N 4.106 2.351 27.455 4.605 -1.912 0.731 "H3'" 8AX 53 8AX "H4'" "H4'" H 0 1 N N N 4.829 0.517 26.029 2.812 -3.344 0.908 "H4'" 8AX 54 8AX "H5'" "H5'" H 0 1 N N N 7.073 -0.298 27.365 1.692 -2.605 -1.799 "H5'" 8AX 55 8AX "H5'A" "H5'A" H 0 0 N N N 5.549 -0.207 28.256 2.144 -4.216 -1.161 "H5'A" 8AX 56 # 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 8AX N01 C06 DOUB Y N 1 8AX N01 C02 SING Y N 2 8AX N02 C02 SING N N 3 8AX C02 C03 DOUB Y N 4 8AX N02 HN02 SING N N 5 8AX N02 HN0A SING N N 6 8AX C03 C04 SING Y N 7 8AX C03 H03 SING N N 8 8AX C05 C04 DOUB Y N 9 8AX C04 C07 SING N N 10 8AX C06 C05 SING Y N 11 8AX C05 H05 SING N N 12 8AX C08 C06 SING N N 13 8AX C07 H07 SING N N 14 8AX C07 H07A SING N N 15 8AX C07 H07B SING N N 16 8AX C08 "C3'" SING N N 17 8AX C08 H08 SING N N 18 8AX C08 H08A SING N N 19 8AX C10 O09 SING N N 20 8AX O09 "C4'" SING N N 21 8AX "C5'" "N1'" SING N N 22 8AX "C2'" "N1'" SING N N 23 8AX "N1'" "HN1'" SING N N 24 8AX C11 C10 SING N N 25 8AX C10 H10 SING N N 26 8AX C10 H10A SING N N 27 8AX C11 N12 SING N N 28 8AX C11 H11 SING N N 29 8AX C11 H11A SING N N 30 8AX C13 N12 SING N N 31 8AX N12 HN12 SING N N 32 8AX C14 C13 SING N N 33 8AX C13 H13 SING N N 34 8AX C13 H13A SING N N 35 8AX F15 C14 SING N N 36 8AX C21 C14 SING N N 37 8AX C14 F16 SING N N 38 8AX "C3'" "C2'" SING N N 39 8AX "C2'" "H2'" SING N N 40 8AX "C2'" "H2'A" SING N N 41 8AX C22 C21 DOUB Y N 42 8AX C21 C26 SING Y N 43 8AX C23 C22 SING Y N 44 8AX C22 H22 SING N N 45 8AX CL23 C23 SING N N 46 8AX C23 C24 DOUB Y N 47 8AX C24 C25 SING Y N 48 8AX C24 H24 SING N N 49 8AX C25 C26 DOUB Y N 50 8AX C25 H25 SING N N 51 8AX C26 H26 SING N N 52 8AX "C4'" "C3'" SING N N 53 8AX "C3'" "H3'" SING N N 54 8AX "C4'" "C5'" SING N N 55 8AX "C4'" "H4'" SING N N 56 8AX "C5'" "H5'" SING N N 57 8AX "C5'" "H5'A" SING N N 58 # 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 8AX SMILES ACDLabs 12.01 "Clc1cccc(c1)C(F)(F)CNCCOC2C(CNC2)Cc3nc(N)cc(c3)C" 8AX SMILES_CANONICAL CACTVS 3.370 "Cc1cc(N)nc(C[C@@H]2CNC[C@@H]2OCCNCC(F)(F)c3cccc(Cl)c3)c1" 8AX SMILES CACTVS 3.370 "Cc1cc(N)nc(C[CH]2CNC[CH]2OCCNCC(F)(F)c3cccc(Cl)c3)c1" 8AX SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "Cc1cc(nc(c1)N)C[C@@H]2CNC[C@@H]2OCCNCC(c3cccc(c3)Cl)(F)F" 8AX SMILES "OpenEye OEToolkits" 1.7.0 "Cc1cc(nc(c1)N)CC2CNCC2OCCNCC(c3cccc(c3)Cl)(F)F" 8AX InChI InChI 1.03 "InChI=1S/C21H27ClF2N4O/c1-14-7-18(28-20(25)8-14)9-15-11-27-12-19(15)29-6-5-26-13-21(23,24)16-3-2-4-17(22)10-16/h2-4,7-8,10,15,19,26-27H,5-6,9,11-13H2,1H3,(H2,25,28)/t15-,19+/m1/s1" 8AX InChIKey InChI 1.03 UAYPWJGHCQAPDA-BEFAXECRSA-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 8AX "SYSTEMATIC NAME" ACDLabs 12.01 "6-{[(3R,4R)-4-(2-{[2-(3-chlorophenyl)-2,2-difluoroethyl]amino}ethoxy)pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine" 8AX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "6-[[(3R,4R)-4-[2-[[2-(3-chlorophenyl)-2,2-difluoro-ethyl]amino]ethoxy]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 8AX "Create component" 2010-11-29 RCSB 8AX "Modify aromatic_flag" 2011-06-04 RCSB 8AX "Modify descriptor" 2011-06-04 RCSB #