data_GS2 # _chem_comp.id GS2 _chem_comp.name "2-[(2-{[1-(N,N-dimethylglycyl)-5-methoxy-1H-indol-6-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H27 F N8 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-09-24 _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 530.553 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GS2 _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 3EKK _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 GS2 C1 C1 C 0 1 N N N -12.237 23.692 -19.726 -7.011 1.927 -2.353 C1 GS2 1 GS2 N1 N1 N 0 1 N N N -10.952 23.885 -20.352 -6.345 0.886 -1.565 N1 GS2 2 GS2 C2 C2 C 0 1 N N N -9.811 23.982 -19.591 -6.178 1.049 -0.237 C2 GS2 3 GS2 O1 O1 O 0 1 N N N -9.767 24.027 -18.366 -6.580 2.061 0.306 O1 GS2 4 GS2 C3 C3 C 0 1 Y N N -8.561 24.084 -20.376 -5.510 0.003 0.555 C3 GS2 5 GS2 C4 C4 C 0 1 Y N N -8.612 24.649 -21.634 -6.258 -1.028 1.134 C4 GS2 6 GS2 F1 F1 F 0 1 N N N -9.786 25.079 -22.134 -7.598 -1.068 0.968 F1 GS2 7 GS2 C5 C5 C 0 1 Y N N -7.469 24.780 -22.388 -5.622 -2.006 1.875 C5 GS2 8 GS2 C6 C6 C 0 1 Y N N -6.275 24.333 -21.868 -4.250 -1.971 2.048 C6 GS2 9 GS2 C7 C7 C 0 1 Y N N -6.229 23.766 -20.614 -3.499 -0.959 1.483 C7 GS2 10 GS2 C8 C8 C 0 1 Y N N -7.367 23.631 -19.845 -4.117 0.030 0.730 C8 GS2 11 GS2 N2 N2 N 0 1 N N N -7.335 23.064 -18.555 -3.360 1.046 0.156 N2 GS2 12 GS2 C9 C9 C 0 1 Y N N -6.356 22.195 -18.035 -2.018 0.841 -0.116 C9 GS2 13 GS2 N3 N3 N 0 1 Y N N -5.287 21.751 -18.714 -1.466 -0.356 0.049 N3 GS2 14 GS2 C10 C10 C 0 1 Y N N -4.401 20.925 -18.135 -0.180 -0.557 -0.210 C10 GS2 15 GS2 N4 N4 N 0 1 N N N -3.286 20.456 -18.854 0.348 -1.825 -0.023 N4 GS2 16 GS2 C11 C11 C 0 1 Y N N -2.914 20.788 -20.176 1.724 -2.038 -0.165 C11 GS2 17 GS2 C12 C12 C 0 1 Y N N -3.834 20.954 -21.200 2.606 -0.990 0.028 C12 GS2 18 GS2 C13 C13 C 0 1 Y N N -3.369 21.276 -22.459 3.972 -1.198 -0.113 C13 GS2 19 GS2 N5 N5 N 0 1 Y N N -4.085 21.503 -23.642 5.076 -0.371 0.012 N5 GS2 20 GS2 C14 C14 C 0 1 Y N N -3.156 21.815 -24.717 6.223 -1.090 -0.236 C14 GS2 21 GS2 C15 C15 C 0 1 Y N N -1.760 21.780 -24.127 5.911 -2.361 -0.520 C15 GS2 22 GS2 C16 C16 C 0 1 Y N N -2.036 21.431 -22.712 4.450 -2.476 -0.450 C16 GS2 23 GS2 C17 C17 C 0 1 Y N N -1.108 21.263 -21.713 3.553 -3.529 -0.643 C17 GS2 24 GS2 C18 C18 C 0 1 Y N N -1.565 20.937 -20.449 2.199 -3.311 -0.496 C18 GS2 25 GS2 O2 O2 O 0 1 N N N -0.683 20.746 -19.390 1.323 -4.335 -0.678 O2 GS2 26 GS2 C19 C19 C 0 1 N N N 0.651 20.689 -19.876 1.875 -5.609 -1.015 C19 GS2 27 GS2 C20 C20 C 0 1 N N N -5.459 21.372 -23.785 5.034 0.939 0.328 C20 GS2 28 GS2 O3 O3 O 0 1 N N N -6.158 20.701 -23.034 3.968 1.480 0.528 O3 GS2 29 GS2 C21 C21 C 0 1 N N N -6.036 22.031 -25.008 6.312 1.730 0.433 C21 GS2 30 GS2 N6 N6 N 0 1 N N N -7.421 21.549 -25.277 5.999 3.122 0.786 N6 GS2 31 GS2 C22 C22 C 0 1 N N N -8.448 22.188 -24.420 5.424 3.205 2.135 C22 GS2 32 GS2 C23 C23 C 0 1 N N N -7.806 21.719 -26.701 7.188 3.976 0.666 C23 GS2 33 GS2 N7 N7 N 0 1 Y N N -4.475 20.468 -16.877 0.617 0.406 -0.641 N7 GS2 34 GS2 C24 C24 C 0 1 Y N N -5.543 20.916 -16.226 0.150 1.638 -0.835 C24 GS2 35 GS2 N8 N8 N 0 1 Y N N -5.882 20.616 -14.936 0.706 2.813 -1.260 N8 GS2 36 GS2 C25 C25 C 0 1 Y N N -7.035 21.261 -14.592 -0.244 3.804 -1.277 C25 GS2 37 GS2 C26 C26 C 0 1 Y N N -7.443 21.982 -15.691 -1.424 3.309 -0.871 C26 GS2 38 GS2 C27 C27 C 0 1 Y N N -6.499 21.764 -16.729 -1.210 1.892 -0.577 C27 GS2 39 GS2 H1 H1 H 0 1 N N N -12.110 23.643 -18.634 -7.053 1.620 -3.398 H1 GS2 40 GS2 H1A H1A H 0 1 N N N -12.899 24.533 -19.980 -8.023 2.077 -1.976 H1A GS2 41 GS2 H1B H1B H 0 1 N N N -12.682 22.753 -20.086 -6.451 2.858 -2.270 H1B GS2 42 GS2 HN1 HN1 H 0 1 N N N -10.890 23.949 -21.348 -6.026 0.079 -1.998 HN1 GS2 43 GS2 H5 H5 H 0 1 N N N -7.507 25.226 -23.371 -6.200 -2.802 2.322 H5 GS2 44 GS2 H6 H6 H 0 1 N N N -5.369 24.428 -22.447 -3.762 -2.739 2.629 H6 GS2 45 GS2 H7 H7 H 0 1 N N N -5.283 23.420 -20.224 -2.428 -0.939 1.624 H7 GS2 46 GS2 HN2 HN2 H 0 1 N N N -8.088 23.305 -17.943 -3.773 1.898 -0.055 HN2 GS2 47 GS2 HN4 HN4 H 0 1 N N N -2.688 19.814 -18.374 -0.236 -2.564 0.208 HN4 GS2 48 GS2 H12 H12 H 0 1 N N N -4.891 20.834 -21.016 2.233 -0.010 0.287 H12 GS2 49 GS2 H14 H14 H 0 1 N N N -3.413 22.031 -25.744 7.226 -0.689 -0.207 H14 GS2 50 GS2 H15 H15 H 0 1 N N N -0.812 21.962 -24.611 6.605 -3.154 -0.757 H15 GS2 51 GS2 H17 H17 H 0 1 N N N -0.053 21.382 -21.909 3.919 -4.511 -0.904 H17 GS2 52 GS2 H19 H19 H 0 1 N N N 0.641 20.674 -20.976 2.546 -5.936 -0.220 H19 GS2 53 GS2 H19A H19A H 0 0 N N N 1.206 21.572 -19.526 1.071 -6.335 -1.131 H19A GS2 54 GS2 H19B H19B H 0 0 N N N 1.139 19.777 -19.502 2.431 -5.529 -1.949 H19B GS2 55 GS2 H21 H21 H 0 1 N N N -6.062 23.119 -24.848 6.947 1.294 1.203 H21 GS2 56 GS2 H21A H21A H 0 0 N N N -5.404 21.778 -25.872 6.833 1.707 -0.524 H21A GS2 57 GS2 H22 H22 H 0 1 N N N -8.038 22.346 -23.412 6.138 2.813 2.859 H22 GS2 58 GS2 H22A H22A H 0 0 N N N -8.737 23.156 -24.854 5.201 4.246 2.371 H22A GS2 59 GS2 H22B H22B H 0 0 N N N -9.331 21.535 -24.358 4.506 2.619 2.176 H22B GS2 60 GS2 H23 H23 H 0 1 N N N -8.902 21.761 -26.783 7.552 3.950 -0.361 H23 GS2 61 GS2 H23A H23A H 0 0 N N N -7.374 22.653 -27.089 6.928 5.000 0.933 H23A GS2 62 GS2 H23B H23B H 0 0 N N N -7.427 20.869 -27.287 7.966 3.612 1.337 H23B GS2 63 GS2 HN8 HN8 H 0 1 N N N -5.361 20.012 -14.332 1.636 2.930 -1.512 HN8 GS2 64 GS2 H25 H25 H 0 1 N N N -7.534 21.214 -13.635 -0.069 4.827 -1.573 H25 GS2 65 GS2 H26 H26 H 0 1 N N N -8.324 22.603 -15.753 -2.353 3.851 -0.782 H26 GS2 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 GS2 C1 N1 SING N N 1 GS2 N1 C2 SING N N 2 GS2 C2 O1 DOUB N N 3 GS2 C2 C3 SING N N 4 GS2 C3 C4 DOUB Y N 5 GS2 C3 C8 SING Y N 6 GS2 C4 F1 SING N N 7 GS2 C4 C5 SING Y N 8 GS2 C5 C6 DOUB Y N 9 GS2 C6 C7 SING Y N 10 GS2 C7 C8 DOUB Y N 11 GS2 C8 N2 SING N N 12 GS2 N2 C9 SING N N 13 GS2 C9 N3 DOUB Y N 14 GS2 C9 C27 SING Y N 15 GS2 N3 C10 SING Y N 16 GS2 C10 N4 SING N N 17 GS2 C10 N7 DOUB Y N 18 GS2 N4 C11 SING N N 19 GS2 C11 C12 DOUB Y N 20 GS2 C11 C18 SING Y N 21 GS2 C12 C13 SING Y N 22 GS2 C13 N5 SING Y N 23 GS2 C13 C16 DOUB Y N 24 GS2 N5 C14 SING Y N 25 GS2 N5 C20 SING N N 26 GS2 C14 C15 DOUB Y N 27 GS2 C15 C16 SING Y N 28 GS2 C16 C17 SING Y N 29 GS2 C17 C18 DOUB Y N 30 GS2 C18 O2 SING N N 31 GS2 O2 C19 SING N N 32 GS2 C20 O3 DOUB N N 33 GS2 C20 C21 SING N N 34 GS2 C21 N6 SING N N 35 GS2 N6 C22 SING N N 36 GS2 N6 C23 SING N N 37 GS2 N7 C24 SING Y N 38 GS2 C24 N8 SING Y N 39 GS2 C24 C27 DOUB Y N 40 GS2 N8 C25 SING Y N 41 GS2 C25 C26 DOUB Y N 42 GS2 C26 C27 SING Y N 43 GS2 C1 H1 SING N N 44 GS2 C1 H1A SING N N 45 GS2 C1 H1B SING N N 46 GS2 N1 HN1 SING N N 47 GS2 C5 H5 SING N N 48 GS2 C6 H6 SING N N 49 GS2 C7 H7 SING N N 50 GS2 N2 HN2 SING N N 51 GS2 N4 HN4 SING N N 52 GS2 C12 H12 SING N N 53 GS2 C14 H14 SING N N 54 GS2 C15 H15 SING N N 55 GS2 C17 H17 SING N N 56 GS2 C19 H19 SING N N 57 GS2 C19 H19A SING N N 58 GS2 C19 H19B SING N N 59 GS2 C21 H21 SING N N 60 GS2 C21 H21A SING N N 61 GS2 C22 H22 SING N N 62 GS2 C22 H22A SING N N 63 GS2 C22 H22B SING N N 64 GS2 C23 H23 SING N N 65 GS2 C23 H23A SING N N 66 GS2 C23 H23B SING N N 67 GS2 N8 HN8 SING N N 68 GS2 C25 H25 SING N N 69 GS2 C26 H26 SING N N 70 # 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 GS2 SMILES ACDLabs 10.04 "O=C(n2c1cc(c(OC)cc1cc2)Nc3nc5c(c(n3)Nc4cccc(F)c4C(=O)NC)ccn5)CN(C)C" GS2 SMILES_CANONICAL CACTVS 3.341 "CNC(=O)c1c(F)cccc1Nc2nc(Nc3cc4n(ccc4cc3OC)C(=O)CN(C)C)nc5[nH]ccc25" GS2 SMILES CACTVS 3.341 "CNC(=O)c1c(F)cccc1Nc2nc(Nc3cc4n(ccc4cc3OC)C(=O)CN(C)C)nc5[nH]ccc25" GS2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CNC(=O)c1c(cccc1F)Nc2c3cc[nH]c3nc(n2)Nc4cc5c(ccn5C(=O)CN(C)C)cc4OC" GS2 SMILES "OpenEye OEToolkits" 1.5.0 "CNC(=O)c1c(cccc1F)Nc2c3cc[nH]c3nc(n2)Nc4cc5c(ccn5C(=O)CN(C)C)cc4OC" GS2 InChI InChI 1.03 "InChI=1S/C27H27FN8O3/c1-29-26(38)23-17(28)6-5-7-18(23)31-25-16-8-10-30-24(16)33-27(34-25)32-19-13-20-15(12-21(19)39-4)9-11-36(20)22(37)14-35(2)3/h5-13H,14H2,1-4H3,(H,29,38)(H3,30,31,32,33,34)" GS2 InChIKey InChI 1.03 DESOLSKAHZZIGK-UHFFFAOYSA-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 GS2 "SYSTEMATIC NAME" ACDLabs 10.04 "2-[(2-{[1-(N,N-dimethylglycyl)-5-methoxy-1H-indol-6-yl]amino}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide" GS2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[2-[[1-(2-dimethylaminoethanoyl)-5-methoxy-indol-6-yl]amino]-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amino]-6-fluoro-N-methyl-benzamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GS2 "Create component" 2008-09-24 RCSB GS2 "Modify aromatic_flag" 2011-06-04 RCSB GS2 "Modify descriptor" 2011-06-04 RCSB #