data_55W # _chem_comp.id 55W _chem_comp.name "1-[4-(7-amino-5-methylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl]-3-{[(R)-(2,4-dimethylphenyl)(methoxy)phosphoryl]amino}-1H-pyrazole-4-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H26 N7 O4 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-07-31 _chem_comp.pdbx_modified_date 2016-06-10 _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 531.503 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 55W _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 5CZB _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 55W C1 C1 C 0 1 Y N N -26.115 -23.058 16.845 -2.792 0.544 0.072 C1 55W 1 55W C2 C2 C 0 1 Y N N -26.605 -22.579 18.049 -3.768 -0.451 0.047 C2 55W 2 55W C3 C3 C 0 1 Y N N -26.962 -23.446 15.834 -1.457 0.198 0.085 C3 55W 3 55W C4 C4 C 0 1 Y N N -27.961 -22.516 18.247 -3.393 -1.793 0.042 C4 55W 4 55W C5 C5 C 0 1 Y N N -28.325 -23.374 16.052 -1.085 -1.141 0.075 C5 55W 5 55W C6 C6 C 0 1 Y N N -28.834 -22.896 17.246 -2.057 -2.134 0.061 C6 55W 6 55W C8 C7 C 0 1 Y N N -29.094 -23.685 13.715 0.758 -2.743 0.079 C8 55W 7 55W C12 C8 C 0 1 N N N -30.568 -24.168 11.701 3.086 -3.775 0.087 C12 55W 8 55W O14 O1 O 0 1 N N N -29.772 -23.943 10.835 4.282 -3.560 0.098 O14 55W 9 55W C15 C9 C 0 1 Y N N -25.724 -22.230 19.159 -5.205 -0.081 0.027 C15 55W 10 55W C16 C10 C 0 1 Y N N -24.393 -22.524 19.293 -6.278 -0.978 0.002 C16 55W 11 55W C17 C11 C 0 1 Y N N -24.067 -22.059 20.543 -7.446 -0.232 -0.010 C17 55W 12 55W C21 C12 C 0 1 Y N N -22.872 -21.522 22.482 -9.689 0.329 -0.041 C21 55W 13 55W C23 C13 C 0 1 Y N N -25.178 -21.028 22.298 -8.048 2.060 0.000 C23 55W 14 55W O28 O2 O 0 1 N N N -34.998 -25.029 15.035 3.282 1.545 -1.153 O28 55W 15 55W O29 O3 O 0 1 N N N -32.970 -25.515 16.574 3.318 1.451 1.369 O29 55W 16 55W C30 C14 C 0 1 N N N -36.104 -24.370 15.679 3.293 2.950 -1.419 C30 55W 17 55W C31 C15 C 0 1 Y N N -33.636 -20.229 16.566 8.432 1.862 0.205 C31 55W 18 55W C32 C16 C 0 1 Y N N -33.222 -21.176 17.499 7.548 2.642 0.928 C32 55W 19 55W C33 C17 C 0 1 Y N N -33.992 -20.644 15.287 7.964 0.794 -0.538 C33 55W 20 55W C34 C18 C 0 1 Y N N -33.167 -22.527 17.157 6.197 2.350 0.912 C34 55W 21 55W C35 C19 C 0 1 Y N N -33.945 -22.008 14.926 6.613 0.502 -0.553 C35 55W 22 55W C36 C20 C 0 1 Y N N -33.524 -22.970 15.872 5.730 1.278 0.175 C36 55W 23 55W C37 C21 C 0 1 N N N -34.385 -22.340 13.506 6.103 -0.663 -1.362 C37 55W 24 55W C38 C22 C 0 1 N N N -33.685 -18.758 16.935 9.905 2.180 0.223 C38 55W 25 55W P27 P1 P 0 1 N N R -33.480 -24.765 15.433 3.957 0.895 0.155 P27 55W 26 55W N26 N1 N 0 1 N N N -32.390 -24.828 14.214 3.750 -0.732 0.125 N26 55W 27 55W C10 C23 C 0 1 Y N N -31.066 -24.413 14.200 2.464 -1.271 0.107 C10 55W 28 55W C9 C24 C 0 1 Y N N -30.263 -24.103 13.144 2.137 -2.652 0.091 C9 55W 29 55W O13 O4 O 0 1 N N N -31.840 -24.381 11.373 2.630 -5.043 0.071 O13 55W 30 55W N11 N2 N 0 1 Y N N -30.429 -24.150 15.340 1.344 -0.592 0.111 N11 55W 31 55W N7 N3 N 0 1 Y N N -29.280 -23.748 15.040 0.271 -1.490 0.088 N7 55W 32 55W N19 N4 N 0 1 Y N N -26.149 -21.678 20.310 -5.684 1.150 0.036 N19 55W 33 55W N18 N5 N 0 1 Y N N -25.169 -21.583 21.082 -7.081 1.090 0.007 N18 55W 34 55W N24 N6 N 0 1 N N N -26.372 -20.529 22.776 -7.700 3.394 0.017 N24 55W 35 55W C22 C25 C 0 1 Y N N -24.026 -21.002 23.019 -9.364 1.686 -0.023 C22 55W 36 55W C25 C26 C 0 1 N N N -21.603 -21.482 23.281 -11.135 -0.094 -0.067 C25 55W 37 55W N20 N7 N 0 1 Y N N -22.870 -22.054 21.212 -8.741 -0.582 -0.034 N20 55W 38 55W H1 H1 H 0 1 N N N -25.047 -23.128 16.698 -3.080 1.584 0.075 H1 55W 39 55W H2 H2 H 0 1 N N N -26.571 -23.799 14.891 -0.700 0.968 0.104 H2 55W 40 55W H3 H3 H 0 1 N N N -28.349 -22.167 19.192 -4.148 -2.565 0.024 H3 55W 41 55W H4 H4 H 0 1 N N N -29.901 -22.821 17.394 -1.766 -3.174 0.053 H4 55W 42 55W H5 H5 H 0 1 N N N -28.199 -23.367 13.201 0.177 -3.653 0.062 H5 55W 43 55W H6 H6 H 0 1 N N N -23.747 -23.011 18.578 -6.208 -2.055 -0.006 H6 55W 44 55W H7 H7 H 0 1 N N N -37.048 -24.716 15.232 2.788 3.477 -0.609 H7 55W 45 55W H8 H8 H 0 1 N N N -36.098 -24.608 16.753 4.324 3.297 -1.491 H8 55W 46 55W H9 H9 H 0 1 N N N -36.011 -23.282 15.544 2.777 3.146 -2.358 H9 55W 47 55W H10 H10 H 0 1 N N N -32.942 -20.862 18.494 7.913 3.478 1.504 H10 55W 48 55W H11 H11 H 0 1 N N N -34.309 -19.912 14.559 8.654 0.188 -1.106 H11 55W 49 55W H12 H12 H 0 1 N N N -32.844 -23.247 17.894 5.506 2.958 1.477 H12 55W 50 55W H13 H13 H 0 1 N N N -33.515 -22.305 12.834 6.090 -1.558 -0.741 H13 55W 51 55W H14 H14 H 0 1 N N N -34.825 -23.348 13.485 5.093 -0.448 -1.711 H14 55W 52 55W H15 H15 H 0 1 N N N -35.134 -21.606 13.173 6.757 -0.824 -2.219 H15 55W 53 55W H16 H16 H 0 1 N N N -34.678 -18.514 17.339 10.383 1.642 1.041 H16 55W 54 55W H17 H17 H 0 1 N N N -32.918 -18.545 17.694 10.354 1.876 -0.723 H17 55W 55 55W H18 H18 H 0 1 N N N -33.494 -18.149 16.039 10.044 3.252 0.363 H18 55W 56 55W H19 H19 H 0 1 N N N -32.819 -24.314 13.471 4.522 -1.319 0.121 H19 55W 57 55W H20 H20 H 0 1 N N N -31.939 -24.319 10.430 3.292 -5.748 0.069 H20 55W 58 55W H21 H21 H 0 1 N N N -26.232 -20.147 23.689 -8.391 4.076 0.013 H21 55W 59 55W H22 H22 H 0 1 N N N -26.703 -19.813 22.162 -6.765 3.652 0.034 H22 55W 60 55W H23 H23 H 0 1 N N N -24.017 -20.574 24.011 -10.144 2.433 -0.029 H23 55W 61 55W H24 H24 H 0 1 N N N -20.784 -21.919 22.691 -11.468 -0.187 -1.100 H24 55W 62 55W H25 H25 H 0 1 N N N -21.359 -20.439 23.530 -11.241 -1.055 0.437 H25 55W 63 55W H26 H26 H 0 1 N N N -21.735 -22.059 24.208 -11.742 0.653 0.445 H26 55W 64 # 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 55W O14 C12 DOUB N N 1 55W O13 C12 SING N N 2 55W C12 C9 SING N N 3 55W C9 C8 DOUB Y N 4 55W C9 C10 SING Y N 5 55W C37 C35 SING N N 6 55W C8 N7 SING Y N 7 55W C10 N26 SING N N 8 55W C10 N11 DOUB Y N 9 55W N26 P27 SING N N 10 55W C35 C33 DOUB Y N 11 55W C35 C36 SING Y N 12 55W O28 P27 SING N N 13 55W O28 C30 SING N N 14 55W N7 N11 SING Y N 15 55W N7 C5 SING N N 16 55W C33 C31 SING Y N 17 55W P27 C36 SING N N 18 55W P27 O29 DOUB N N 19 55W C3 C5 DOUB Y N 20 55W C3 C1 SING Y N 21 55W C36 C34 DOUB Y N 22 55W C5 C6 SING Y N 23 55W C31 C38 SING N N 24 55W C31 C32 DOUB Y N 25 55W C1 C2 DOUB Y N 26 55W C34 C32 SING Y N 27 55W C6 C4 DOUB Y N 28 55W C2 C4 SING Y N 29 55W C2 C15 SING N N 30 55W C15 C16 SING Y N 31 55W C15 N19 DOUB Y N 32 55W C16 C17 DOUB Y N 33 55W N19 N18 SING Y N 34 55W C17 N18 SING Y N 35 55W C17 N20 SING Y N 36 55W N18 C23 SING Y N 37 55W N20 C21 DOUB Y N 38 55W C23 N24 SING N N 39 55W C23 C22 DOUB Y N 40 55W C21 C22 SING Y N 41 55W C21 C25 SING N N 42 55W C1 H1 SING N N 43 55W C3 H2 SING N N 44 55W C4 H3 SING N N 45 55W C6 H4 SING N N 46 55W C8 H5 SING N N 47 55W C16 H6 SING N N 48 55W C30 H7 SING N N 49 55W C30 H8 SING N N 50 55W C30 H9 SING N N 51 55W C32 H10 SING N N 52 55W C33 H11 SING N N 53 55W C34 H12 SING N N 54 55W C37 H13 SING N N 55 55W C37 H14 SING N N 56 55W C37 H15 SING N N 57 55W C38 H16 SING N N 58 55W C38 H17 SING N N 59 55W C38 H18 SING N N 60 55W N26 H19 SING N N 61 55W O13 H20 SING N N 62 55W N24 H21 SING N N 63 55W N24 H22 SING N N 64 55W C22 H23 SING N N 65 55W C25 H24 SING N N 66 55W C25 H25 SING N N 67 55W C25 H26 SING N N 68 # 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 55W SMILES ACDLabs 12.01 "c1c(ccc(c1)n3cc(C(=O)O)c(NP(OC)(=O)c2ccc(C)cc2C)n3)c5cc4n(c(N)cc(C)n4)n5" 55W InChI InChI 1.03 "InChI=1S/C26H26N7O4P/c1-15-5-10-22(16(2)11-15)38(36,37-4)31-25-20(26(34)35)14-32(30-25)19-8-6-18(7-9-19)21-13-24-28-17(3)12-23(27)33(24)29-21/h5-14H,27H2,1-4H3,(H,34,35)(H,30,31,36)/t38-/m1/s1" 55W InChIKey InChI 1.03 DGOTYTQLPLGHOO-KXQOOQHDSA-N 55W SMILES_CANONICAL CACTVS 3.385 "CO[P@@](=O)(Nc1nn(cc1C(O)=O)c2ccc(cc2)c3cc4nc(C)cc(N)n4n3)c5ccc(C)cc5C" 55W SMILES CACTVS 3.385 "CO[P](=O)(Nc1nn(cc1C(O)=O)c2ccc(cc2)c3cc4nc(C)cc(N)n4n3)c5ccc(C)cc5C" 55W SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "Cc1ccc(c(c1)C)[P@](=O)(Nc2c(cn(n2)c3ccc(cc3)c4cc5nc(cc(n5n4)N)C)C(=O)O)OC" 55W SMILES "OpenEye OEToolkits" 1.9.2 "Cc1ccc(c(c1)C)P(=O)(Nc2c(cn(n2)c3ccc(cc3)c4cc5nc(cc(n5n4)N)C)C(=O)O)OC" # 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 55W "SYSTEMATIC NAME" ACDLabs 12.01 "1-[4-(7-amino-5-methylpyrazolo[1,5-a]pyrimidin-2-yl)phenyl]-3-{[(R)-(2,4-dimethylphenyl)(methoxy)phosphoryl]amino}-1H-pyrazole-4-carboxylic acid" 55W "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "1-[4-(7-azanyl-5-methyl-pyrazolo[1,5-a]pyrimidin-2-yl)phenyl]-3-[[(2,4-dimethylphenyl)-methoxy-phosphoryl]amino]pyrazole-4-carboxylic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 55W "Create component" 2015-07-31 EBI 55W "Initial release" 2016-06-15 RCSB #