data_3XA # _chem_comp.id 3XA _chem_comp.name "6-{[(3S,4S)-4-(2-{[2,2-difluoro-2-(3-fluorophenyl)ethyl]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 F3 N4 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-06-25 _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 408.460 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3XA _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 3NLV _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 3XA O1 O1 O 0 1 N N N 16.169 2.942 57.417 1.326 -2.531 0.056 O1 3XA 1 3XA C2 C2 C 0 1 N N N 17.317 3.743 57.660 0.400 -3.477 -0.483 C2 3XA 2 3XA C3 C3 C 0 1 N N N 18.104 3.879 56.367 -1.013 -3.138 -0.004 C3 3XA 3 3XA N4 N4 N 0 1 N N N 17.452 4.844 55.488 -1.419 -1.839 -0.557 N4 3XA 4 3XA C5 C5 C 0 1 N N N 18.229 5.731 54.642 -2.774 -1.479 -0.117 C5 3XA 5 3XA C6 C6 C 0 1 N N N 18.729 6.888 55.491 -3.160 -0.123 -0.711 C6 3XA 6 3XA F7 F7 F 0 1 N N N 17.710 7.401 56.152 -2.255 0.851 -0.277 F7 3XA 7 3XA F8 F8 F 0 1 N N N 19.647 6.423 56.324 -3.128 -0.200 -2.108 F8 3XA 8 3XA "N1'" "N1'" N 0 1 N N N 16.088 -0.621 57.276 4.773 -3.122 0.782 "N1'" 3XA 9 3XA C11 C11 C 0 1 Y N N 19.289 8.002 54.666 -4.550 0.245 -0.260 C11 3XA 10 3XA C12 C12 C 0 1 Y N N 18.469 9.101 54.440 -4.729 0.965 0.906 C12 3XA 11 3XA C13 C13 C 0 1 Y N N 18.937 10.170 53.689 -6.006 1.304 1.321 C13 3XA 12 3XA F13 F13 F 0 1 N N N 18.117 11.213 53.483 -6.183 2.008 2.460 F13 3XA 13 3XA C14 C14 C 0 1 Y N N 20.228 10.152 53.161 -7.102 0.920 0.566 C14 3XA 14 3XA C15 C15 C 0 1 Y N N 21.051 9.049 53.392 -6.920 0.201 -0.599 C15 3XA 15 3XA C16 C16 C 0 1 Y N N 20.582 7.968 54.146 -5.644 -0.132 -1.015 C16 3XA 16 3XA N1A N1A N 0 1 Y N N 12.133 -0.125 58.525 4.473 1.159 0.626 N1A 3XA 17 3XA "C2'" "C2'" C 0 1 N N N 16.689 0.592 56.775 3.391 -3.661 0.700 "C2'" 3XA 18 3XA C2A C2A C 0 1 Y N N 12.637 1.046 58.955 3.322 1.020 -0.005 C2A 3XA 19 3XA "C3'" "C3'" C 0 1 N N S 16.389 1.622 57.891 2.682 -2.759 -0.333 "C3'" 3XA 20 3XA C3A C3A C 0 1 Y N N 12.059 1.639 60.079 2.802 2.050 -0.764 C3A 3XA 21 3XA "C4'" "C4'" C 0 1 N N S 15.186 1.094 58.676 3.473 -1.435 -0.318 "C4'" 3XA 22 3XA C4A C4A C 0 1 Y N N 10.983 1.028 60.727 3.503 3.244 -0.862 C4A 3XA 23 3XA "C5'" "C5'" C 0 1 N N N 15.366 -0.423 58.552 4.593 -1.648 0.722 "C5'" 3XA 24 3XA C5A C5A C 0 1 Y N N 10.485 -0.188 60.259 4.707 3.360 -0.190 C5A 3XA 25 3XA C6A C6A C 0 1 Y N N 11.094 -0.737 59.124 5.171 2.282 0.557 C6A 3XA 26 3XA N6A N6A N 0 1 N N N 10.697 -1.916 58.580 6.379 2.385 1.237 N6A 3XA 27 3XA C7A C7A C 0 1 N N N 13.826 1.658 58.205 2.565 -0.278 0.106 C7A 3XA 28 3XA C8A C8A C 0 1 N N N 10.385 1.691 61.931 2.966 4.388 -1.683 C8A 3XA 29 3XA H2 H2 H 0 1 N N N 17.007 4.738 58.011 0.433 -3.438 -1.572 H2 3XA 30 3XA H2A H2A H 0 1 N N N 17.945 3.267 58.427 0.667 -4.479 -0.147 H2A 3XA 31 3XA H3 H3 H 0 1 N N N 19.123 4.225 56.596 -1.706 -3.908 -0.341 H3 3XA 32 3XA H3A H3A H 0 1 N N N 18.150 2.902 55.864 -1.026 -3.089 1.085 H3A 3XA 33 3XA HN4 HN4 H 0 1 N N N 16.883 4.305 54.867 -0.756 -1.118 -0.311 HN4 3XA 34 3XA H5 H5 H 0 1 N N N 19.083 5.185 54.215 -3.479 -2.239 -0.455 H5 3XA 35 3XA H5A H5A H 0 1 N N N 17.600 6.113 53.824 -2.798 -1.419 0.971 H5A 3XA 36 3XA "HN1'" "HN1'" H 0 0 N N N 15.436 -0.954 56.594 5.218 -3.398 1.645 "HN1'" 3XA 37 3XA H12 H12 H 0 1 N N N 17.469 9.123 54.848 -3.874 1.263 1.495 H12 3XA 38 3XA H14 H14 H 0 1 N N N 20.588 10.986 52.577 -8.099 1.184 0.889 H14 3XA 39 3XA H15 H15 H 0 1 N N N 22.052 9.030 52.988 -7.775 -0.098 -1.188 H15 3XA 40 3XA H16 H16 H 0 1 N N N 21.217 7.113 54.324 -5.503 -0.694 -1.926 H16 3XA 41 3XA "H2'" "H2'" H 0 1 N N N 17.771 0.472 56.614 3.406 -4.695 0.354 "H2'" 3XA 42 3XA "H2'A" "H2'A" H 0 0 N N N 16.248 0.896 55.814 2.897 -3.591 1.669 "H2'A" 3XA 43 3XA "H3'" "H3'" H 0 1 N N N 17.276 1.718 58.534 2.720 -3.214 -1.322 "H3'" 3XA 44 3XA H3AA H3AA H 0 0 N N N 12.446 2.576 60.450 1.860 1.927 -1.277 H3AA 3XA 45 3XA "H4'" "H4'" H 0 1 N N N 15.158 1.421 59.726 3.901 -1.239 -1.301 "H4'" 3XA 46 3XA "H5'" "H5'" H 0 1 N N N 14.393 -0.935 58.537 4.288 -1.263 1.695 "H5'" 3XA 47 3XA "H5'A" "H5'A" H 0 0 N N N 15.945 -0.821 59.398 5.514 -1.167 0.393 "H5'A" 3XA 48 3XA H5AA H5AA H 0 0 N N N 9.663 -0.686 60.752 5.279 4.274 -0.245 H5AA 3XA 49 3XA HN6A HN6A H 0 0 N N N 11.275 -2.132 57.793 6.707 1.636 1.760 HN6A 3XA 50 3XA HN6B HN6B H 0 0 N N N 10.779 -2.642 59.262 6.894 3.205 1.190 HN6B 3XA 51 3XA H7A H7A H 0 1 N N N 13.711 1.437 57.134 2.246 -0.426 1.137 H7A 3XA 52 3XA H7AA H7AA H 0 0 N N N 13.823 2.744 58.377 1.691 -0.246 -0.544 H7AA 3XA 53 3XA H8A H8A H 0 1 N N N 9.575 2.365 61.615 2.341 5.023 -1.055 H8A 3XA 54 3XA H8AA H8AA H 0 0 N N N 9.981 0.925 62.608 3.796 4.973 -2.078 H8AA 3XA 55 3XA H8AB H8AB H 0 0 N N N 11.161 2.270 62.454 2.372 3.995 -2.508 H8AB 3XA 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 3XA O1 C2 SING N N 1 3XA O1 "C3'" SING N N 2 3XA C3 C2 SING N N 3 3XA C2 H2 SING N N 4 3XA C2 H2A SING N N 5 3XA N4 C3 SING N N 6 3XA C3 H3 SING N N 7 3XA C3 H3A SING N N 8 3XA C5 N4 SING N N 9 3XA N4 HN4 SING N N 10 3XA C5 C6 SING N N 11 3XA C5 H5 SING N N 12 3XA C5 H5A SING N N 13 3XA C11 C6 SING N N 14 3XA C6 F7 SING N N 15 3XA C6 F8 SING N N 16 3XA "C2'" "N1'" SING N N 17 3XA "N1'" "C5'" SING N N 18 3XA "N1'" "HN1'" SING N N 19 3XA C16 C11 DOUB Y N 20 3XA C12 C11 SING Y N 21 3XA C13 C12 DOUB Y N 22 3XA C12 H12 SING N N 23 3XA C14 C13 SING Y N 24 3XA F13 C13 SING N N 25 3XA C14 C15 DOUB Y N 26 3XA C14 H14 SING N N 27 3XA C15 C16 SING Y N 28 3XA C15 H15 SING N N 29 3XA C16 H16 SING N N 30 3XA N1A C2A DOUB Y N 31 3XA N1A C6A SING Y N 32 3XA "C2'" "C3'" SING N N 33 3XA "C2'" "H2'" SING N N 34 3XA "C2'" "H2'A" SING N N 35 3XA C7A C2A SING N N 36 3XA C2A C3A SING Y N 37 3XA "C3'" "C4'" SING N N 38 3XA "C3'" "H3'" SING N N 39 3XA C3A C4A DOUB Y N 40 3XA C3A H3AA SING N N 41 3XA C7A "C4'" SING N N 42 3XA "C5'" "C4'" SING N N 43 3XA "C4'" "H4'" SING N N 44 3XA C5A C4A SING Y N 45 3XA C4A C8A SING N N 46 3XA "C5'" "H5'" SING N N 47 3XA "C5'" "H5'A" SING N N 48 3XA C6A C5A DOUB Y N 49 3XA C5A H5AA SING N N 50 3XA N6A C6A SING N N 51 3XA N6A HN6A SING N N 52 3XA N6A HN6B SING N N 53 3XA C7A H7A SING N N 54 3XA C7A H7AA SING N N 55 3XA C8A H8A SING N N 56 3XA C8A H8AA SING N N 57 3XA C8A H8AB 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 3XA SMILES ACDLabs 12.01 "Fc1cccc(c1)C(F)(F)CNCCOC2C(CNC2)Cc3nc(N)cc(c3)C" 3XA SMILES_CANONICAL CACTVS 3.370 "Cc1cc(N)nc(C[C@H]2CNC[C@H]2OCCNCC(F)(F)c3cccc(F)c3)c1" 3XA SMILES CACTVS 3.370 "Cc1cc(N)nc(C[CH]2CNC[CH]2OCCNCC(F)(F)c3cccc(F)c3)c1" 3XA SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "Cc1cc(nc(c1)N)C[C@H]2CNC[C@H]2OCCNCC(c3cccc(c3)F)(F)F" 3XA SMILES "OpenEye OEToolkits" 1.7.0 "Cc1cc(nc(c1)N)CC2CNCC2OCCNCC(c3cccc(c3)F)(F)F" 3XA InChI InChI 1.03 "InChI=1S/C21H27F3N4O/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+/m0/s1" 3XA InChIKey InChI 1.03 IRAITVAESBBILD-HNAYVOBHSA-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 3XA "SYSTEMATIC NAME" ACDLabs 12.01 "6-{[(3S,4S)-4-(2-{[2,2-difluoro-2-(3-fluorophenyl)ethyl]amino}ethoxy)pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine" 3XA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "6-[[(3S,4S)-4-[2-[[2,2-difluoro-2-(3-fluorophenyl)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 3XA "Create component" 2010-06-25 RCSB 3XA "Modify aromatic_flag" 2011-06-04 RCSB 3XA "Modify descriptor" 2011-06-04 RCSB #