data_O44 # _chem_comp.id O44 _chem_comp.name "4-[(4-{4-[(3-cyclopropyl-1H-pyrazol-5-yl)amino]-6-[(prop-2-yn-1-yl)carbamoyl]pyrimidin-2-yl}piperazin-1-yl)methyl]benzene-1-sulfonyl fluoride" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H27 F N8 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-06-01 _chem_comp.pdbx_modified_date 2017-01-20 _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 538.597 _chem_comp.one_letter_code ? _chem_comp.three_letter_code O44 _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 5K9I _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 O44 OBJ O1 O 0 1 N N N -2.850 -9.850 -8.550 -8.338 1.259 -1.093 OBJ O44 1 O44 SBH S1 S 0 1 N N N -2.211 -11.054 -9.014 -7.564 0.393 -0.274 SBH O44 2 O44 OBI O2 O 0 1 N N N -3.112 -12.168 -8.898 -7.368 -0.984 -0.567 OBI O44 3 O44 CBE C1 C 0 1 Y N N -0.870 -11.340 -8.177 -5.959 1.112 -0.167 CBE O44 4 O44 CBD C2 C 0 1 Y N N -0.605 -10.747 -6.939 -5.361 1.639 -1.296 CBD O44 5 O44 CBC C3 C 0 1 Y N N 0.571 -11.042 -6.235 -4.101 2.203 -1.212 CBC O44 6 O44 CBF C4 C 0 1 Y N N 0.050 -12.229 -8.702 -5.301 1.154 1.048 CBF O44 7 O44 CBG C5 C 0 1 Y N N 1.215 -12.514 -8.008 -4.042 1.718 1.132 CBG O44 8 O44 CBB C6 C 0 1 Y N N 1.494 -11.922 -6.786 -3.441 2.240 0.002 CBB O44 9 O44 CBA C7 C 0 1 N N N 2.779 -12.351 -6.110 -2.068 2.855 0.094 CBA O44 10 O44 NAX N1 N 0 1 N N N 3.772 -11.348 -5.732 -1.051 1.821 -0.142 NAX O44 11 O44 CAY C8 C 0 1 N N N 5.001 -12.116 -5.466 0.282 2.419 -0.296 CAY O44 12 O44 CAZ C9 C 0 1 N N N 6.105 -11.205 -4.941 1.297 1.320 -0.618 CAZ O44 13 O44 CAW C10 C 0 1 N N N 4.039 -10.402 -6.826 -1.056 0.822 0.936 CAW O44 14 O44 CAV C11 C 0 1 N N N 5.040 -9.354 -6.340 -0.041 -0.277 0.613 CAV O44 15 O44 NAA N2 N 0 1 N N N 6.217 -10.058 -5.838 1.292 0.321 0.459 NAA O44 16 O44 C2 C12 C 0 1 Y N N 7.495 -9.601 -6.171 2.250 -0.654 0.237 C2 O44 17 O44 N3 N3 N 0 1 Y N N 7.619 -8.514 -6.966 3.515 -0.290 0.080 N3 O44 18 O44 N1 N4 N 0 1 Y N N 8.584 -10.255 -5.686 1.879 -1.922 0.192 N1 O44 19 O44 C6 C13 C 0 1 Y N N 9.836 -9.825 -5.988 2.772 -2.889 -0.020 C6 O44 20 O44 CAQ C14 C 0 1 N N N 11.065 -10.526 -5.454 2.345 -4.310 -0.070 CAQ O44 21 O44 NAR N5 N 0 1 N N N 10.931 -11.606 -4.675 1.047 -4.630 0.100 NAR O44 22 O44 CAS C15 C 0 1 N N N 11.919 -12.021 -3.691 0.626 -6.032 0.051 CAS O44 23 O44 CAT C16 C 0 1 N N N 12.863 -10.935 -3.369 -0.828 -6.116 0.264 CAT O44 24 O44 CBL C17 C 0 1 N N N 13.693 -9.994 -3.102 -1.988 -6.183 0.433 CBL O44 25 O44 OAU O3 O 0 1 N N N 12.150 -10.062 -5.788 3.166 -5.184 -0.264 OAU O44 26 O44 C5 C18 C 0 1 Y N N 9.977 -8.695 -6.796 4.108 -2.548 -0.195 C5 O44 27 O44 C4 C19 C 0 1 Y N N 8.845 -8.046 -7.287 4.462 -1.195 -0.135 C4 O44 28 O44 NAH N6 N 0 1 N N N 9.010 -6.961 -8.083 5.782 -0.806 -0.298 NAH O44 29 O44 CAI C20 C 0 1 Y N N 8.024 -6.298 -8.735 6.109 0.547 -0.342 CAI O44 30 O44 CAJ C21 C 0 1 Y N N 6.689 -6.525 -9.099 5.261 1.588 -0.115 CAJ O44 31 O44 NAP N7 N 0 1 Y N N 8.458 -5.102 -9.158 7.333 1.069 -0.612 NAP O44 32 O44 NAO N8 N 0 1 Y N N 7.372 -4.503 -9.810 7.226 2.465 -0.554 NAO O44 33 O44 CAK C22 C 0 1 Y N N 6.327 -5.356 -9.776 5.989 2.773 -0.258 CAK O44 34 O44 CAL C23 C 0 1 N N N 4.945 -5.184 -10.341 5.443 4.168 -0.097 CAL O44 35 O44 CAN C24 C 0 1 N N N 3.852 -5.560 -9.347 5.387 4.747 1.318 CAN O44 36 O44 CAM C25 C 0 1 N N N 4.180 -6.498 -10.505 4.097 4.322 0.614 CAM O44 37 O44 H3 H3 H 0 1 N N N -1.317 -10.052 -6.519 -5.877 1.609 -2.244 H3 O44 38 O44 H4 H4 H 0 1 N N N 0.758 -10.589 -5.273 -3.634 2.614 -2.094 H4 O44 39 O44 H5 H5 H 0 1 N N N -0.140 -12.702 -9.654 -5.770 0.747 1.931 H5 O44 40 O44 H6 H6 H 0 1 N N N 1.922 -13.214 -8.429 -3.527 1.752 2.082 H6 O44 41 O44 H7 H7 H 0 1 N N N 2.493 -12.879 -5.188 -1.970 3.639 -0.657 H7 O44 42 O44 H8 H8 H 0 1 N N N 3.279 -13.052 -6.794 -1.927 3.283 1.087 H8 O44 43 O44 H10 H10 H 0 1 N N N 4.786 -12.892 -4.716 0.263 3.146 -1.107 H10 O44 44 O44 H11 H11 H 0 1 N N N 5.339 -12.591 -6.399 0.567 2.916 0.632 H11 O44 45 O44 H12 H12 H 0 1 N N N 7.059 -11.752 -4.916 1.028 0.841 -1.559 H12 O44 46 O44 H13 H13 H 0 1 N N N 5.853 -10.861 -3.927 2.292 1.757 -0.704 H13 O44 47 O44 H14 H14 H 0 1 N N N 3.102 -9.908 -7.124 -0.787 1.301 1.877 H14 O44 48 O44 H15 H15 H 0 1 N N N 4.459 -10.942 -7.687 -2.051 0.384 1.021 H15 O44 49 O44 H16 H16 H 0 1 N N N 5.326 -8.695 -7.173 -0.023 -1.005 1.425 H16 O44 50 O44 H17 H17 H 0 1 N N N 4.592 -8.754 -5.535 -0.326 -0.775 -0.314 H17 O44 51 O44 H18 H18 H 0 1 N N N 10.104 -12.160 -4.775 0.392 -3.932 0.255 H18 O44 52 O44 H19 H19 H 0 1 N N N 11.399 -12.325 -2.771 0.876 -6.453 -0.923 H19 O44 53 O44 H20 H20 H 0 1 N N N 12.483 -12.876 -4.092 1.140 -6.594 0.832 H20 O44 54 O44 H21 H21 H 0 1 N N N 14.379 -9.216 -2.881 -3.025 -6.242 0.585 H21 O44 55 O44 H22 H22 H 0 1 N N N 10.962 -8.324 -7.040 4.855 -3.308 -0.369 H22 O44 56 O44 H23 H23 H 0 1 N N N 9.943 -6.619 -8.199 6.478 -1.477 -0.382 H23 O44 57 O44 H24 H24 H 0 1 N N N 6.083 -7.397 -8.903 4.212 1.513 0.131 H24 O44 58 O44 H25 H25 H 0 1 N N N 9.372 -4.716 -9.033 8.138 0.566 -0.810 H25 O44 59 O44 H26 H26 H 0 1 N N N 4.754 -4.369 -11.055 5.662 4.855 -0.914 H26 O44 60 O44 H27 H27 H 0 1 N N N 2.901 -5.007 -9.340 5.746 4.118 2.133 H27 O44 61 O44 H28 H28 H 0 1 N N N 4.119 -5.843 -8.318 5.570 5.815 1.432 H28 O44 62 O44 H29 H29 H 0 1 N N N 3.467 -6.620 -11.334 3.431 5.111 0.265 H29 O44 63 O44 H30 H30 H 0 1 N N N 4.684 -7.456 -10.311 3.607 3.414 0.966 H30 O44 64 O44 F1 F1 F 0 1 N N N -1.866 -10.877 -10.573 -8.215 0.457 1.197 F1 O44 65 # 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 O44 CAM CAL SING N N 1 O44 CAM CAN SING N N 2 O44 CAL CAK SING N N 3 O44 CAL CAN SING N N 4 O44 NAO CAK DOUB Y N 5 O44 NAO NAP SING Y N 6 O44 CAK CAJ SING Y N 7 O44 NAP CAI SING Y N 8 O44 CAJ CAI DOUB Y N 9 O44 SBH OBI DOUB N N 10 O44 SBH OBJ DOUB N N 11 O44 SBH CBE SING N N 12 O44 CAI NAH SING N N 13 O44 CBF CBE DOUB Y N 14 O44 CBF CBG SING Y N 15 O44 CBE CBD SING Y N 16 O44 NAH C4 SING N N 17 O44 CBG CBB DOUB Y N 18 O44 C4 N3 DOUB Y N 19 O44 C4 C5 SING Y N 20 O44 N3 C2 SING Y N 21 O44 CBD CBC DOUB Y N 22 O44 CAW CAV SING N N 23 O44 CAW NAX SING N N 24 O44 C5 C6 DOUB Y N 25 O44 CBB CBC SING Y N 26 O44 CBB CBA SING N N 27 O44 CAV NAA SING N N 28 O44 C2 NAA SING N N 29 O44 C2 N1 DOUB Y N 30 O44 CBA NAX SING N N 31 O44 C6 N1 SING Y N 32 O44 C6 CAQ SING N N 33 O44 NAA CAZ SING N N 34 O44 OAU CAQ DOUB N N 35 O44 NAX CAY SING N N 36 O44 CAY CAZ SING N N 37 O44 CAQ NAR SING N N 38 O44 NAR CAS SING N N 39 O44 CAS CAT SING N N 40 O44 CAT CBL TRIP N N 41 O44 CBD H3 SING N N 42 O44 CBC H4 SING N N 43 O44 CBF H5 SING N N 44 O44 CBG H6 SING N N 45 O44 CBA H7 SING N N 46 O44 CBA H8 SING N N 47 O44 CAY H10 SING N N 48 O44 CAY H11 SING N N 49 O44 CAZ H12 SING N N 50 O44 CAZ H13 SING N N 51 O44 CAW H14 SING N N 52 O44 CAW H15 SING N N 53 O44 CAV H16 SING N N 54 O44 CAV H17 SING N N 55 O44 NAR H18 SING N N 56 O44 CAS H19 SING N N 57 O44 CAS H20 SING N N 58 O44 CBL H21 SING N N 59 O44 C5 H22 SING N N 60 O44 NAH H23 SING N N 61 O44 CAJ H24 SING N N 62 O44 NAP H25 SING N N 63 O44 CAL H26 SING N N 64 O44 CAN H27 SING N N 65 O44 CAN H28 SING N N 66 O44 CAM H29 SING N N 67 O44 CAM H30 SING N N 68 O44 SBH F1 SING N N 69 # 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 O44 SMILES ACDLabs 12.01 "O=S(=O)(c1ccc(cc1)CN2CCN(CC2)c3nc(C(NCC#C)=O)cc(n3)Nc4cc(nn4)C5CC5)F" O44 InChI InChI 1.03 "InChI=1S/C25H27FN8O3S/c1-2-9-27-24(35)21-15-22(29-23-14-20(31-32-23)18-5-6-18)30-25(28-21)34-12-10-33(11-13-34)16-17-3-7-19(8-4-17)38(26,36)37/h1,3-4,7-8,14-15,18H,5-6,9-13,16H2,(H,27,35)(H2,28,29,30,31,32)" O44 InChIKey InChI 1.03 ZBSPMOBILDLOCV-UHFFFAOYSA-N O44 SMILES_CANONICAL CACTVS 3.385 "F[S](=O)(=O)c1ccc(CN2CCN(CC2)c3nc(Nc4[nH]nc(c4)C5CC5)cc(n3)C(=O)NCC#C)cc1" O44 SMILES CACTVS 3.385 "F[S](=O)(=O)c1ccc(CN2CCN(CC2)c3nc(Nc4[nH]nc(c4)C5CC5)cc(n3)C(=O)NCC#C)cc1" O44 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C#CCNC(=O)c1cc(nc(n1)N2CCN(CC2)Cc3ccc(cc3)S(=O)(=O)F)Nc4cc(n[nH]4)C5CC5" O44 SMILES "OpenEye OEToolkits" 2.0.6 "C#CCNC(=O)c1cc(nc(n1)N2CCN(CC2)Cc3ccc(cc3)S(=O)(=O)F)Nc4cc(n[nH]4)C5CC5" # 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 O44 "SYSTEMATIC NAME" ACDLabs 12.01 "4-[(4-{4-[(3-cyclopropyl-1H-pyrazol-5-yl)amino]-6-[(prop-2-yn-1-yl)carbamoyl]pyrimidin-2-yl}piperazin-1-yl)methyl]benzene-1-sulfonyl fluoride" O44 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "4-[[4-[4-[(3-cyclopropyl-1~{H}-pyrazol-5-yl)amino]-6-(prop-2-ynylcarbamoyl)pyrimidin-2-yl]piperazin-1-yl]methyl]benzenesulfonyl fluoride" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site O44 "Create component" 2016-06-01 RCSB O44 "Modify formula" 2016-12-16 RCSB O44 "Initial release" 2017-01-25 RCSB #