data_99S # _chem_comp.id 99S _chem_comp.name "methyl 5-{3-[(4S)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl}thiophene-2-carboxylate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H21 N5 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2014-06-09 _chem_comp.pdbx_modified_date 2015-03-20 _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 459.520 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 99S _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 4TMR _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 99S O31 O1 O 0 1 N N N 11.928 -31.611 -24.039 6.882 -0.012 -0.091 O31 99S 1 99S C30 C1 C 0 1 N N N 12.841 -31.303 -24.776 5.795 0.531 -0.033 C30 99S 2 99S O32 O2 O 0 1 N N N 12.529 -30.873 -26.133 5.715 1.876 0.035 O32 99S 3 99S C33 C2 C 0 1 N N N 12.954 -29.591 -26.617 6.948 2.599 0.043 C33 99S 4 99S C28 C3 C 0 1 Y N N 14.258 -31.332 -24.322 4.574 -0.274 -0.045 C28 99S 5 99S C27 C4 C 0 1 Y N N 15.447 -31.449 -25.025 4.531 -1.640 -0.112 C27 99S 6 99S C26 C5 C 0 1 Y N N 16.585 -31.400 -24.217 3.271 -2.173 -0.110 C26 99S 7 99S S29 S1 S 0 1 Y N N 14.602 -31.141 -22.636 2.938 0.365 0.032 S29 99S 8 99S C25 C6 C 0 1 Y N N 16.313 -31.238 -22.866 2.262 -1.257 -0.041 C25 99S 9 99S C21 C7 C 0 1 Y N N 17.209 -31.157 -21.685 0.820 -1.579 -0.024 C21 99S 10 99S C20 C8 C 0 1 Y N N 16.892 -30.413 -20.568 0.400 -2.907 -0.080 C20 99S 11 99S C19 C9 C 0 1 Y N N 17.786 -30.378 -19.500 -0.962 -3.202 -0.064 C19 99S 12 99S C23 C10 C 0 1 N N N 17.504 -29.719 -18.449 -1.402 -4.563 -0.121 C23 99S 13 99S N24 N1 N 0 1 N N N 17.240 -29.122 -17.496 -1.751 -5.643 -0.166 N24 99S 14 99S C18 C11 C 0 1 Y N N 18.979 -31.066 -19.536 -1.897 -2.166 0.010 C18 99S 15 99S C22 C12 C 0 1 Y N N 18.413 -31.850 -21.722 -0.126 -0.554 0.055 C22 99S 16 99S C17 C13 C 0 1 Y N N 19.323 -31.806 -20.662 -1.474 -0.853 0.065 C17 99S 17 99S C4 C14 C 0 1 N N S 20.621 -32.588 -20.681 -2.488 0.259 0.150 C4 99S 18 99S C14 C15 C 0 1 N N N 21.836 -31.818 -20.118 -3.888 -0.332 0.327 C14 99S 19 99S C16 C16 C 0 1 N N N 22.199 -30.542 -20.864 -3.973 -1.046 1.677 C16 99S 20 99S C15 C17 C 0 1 N N N 23.084 -32.695 -20.014 -4.926 0.791 0.277 C15 99S 21 99S C3 C18 C 0 1 N N N 20.357 -33.762 -19.749 -2.163 1.156 1.317 C3 99S 22 99S C8 C19 C 0 1 N N N 19.997 -33.539 -18.560 -1.885 0.553 2.586 C8 99S 23 99S N9 N2 N 0 1 N N N 19.706 -33.345 -17.454 -1.664 0.074 3.592 N9 99S 24 99S C2 C20 C 0 1 N N N 20.524 -35.046 -20.091 -2.122 2.501 1.222 C2 99S 25 99S N7 N3 N 0 1 N N N 20.469 -36.005 -19.174 -1.819 3.213 2.356 N7 99S 26 99S C5 C21 C 0 1 Y N N 20.876 -33.125 -22.053 -2.441 1.088 -1.108 C5 99S 27 99S C10 C22 C 0 1 Y N N 21.097 -32.498 -23.383 -2.447 0.697 -2.392 C10 99S 28 99S C13 C23 C 0 1 N N N 21.125 -31.024 -23.707 -2.503 -0.725 -2.889 C13 99S 29 99S N11 N4 N 0 1 Y N N 21.256 -33.496 -24.278 -2.394 1.810 -3.159 N11 99S 30 99S N12 N5 N 0 1 Y N N 21.155 -34.769 -23.690 -2.353 2.925 -2.308 N12 99S 31 99S C6 C24 C 0 1 Y N N 20.939 -34.530 -22.398 -2.381 2.498 -1.079 C6 99S 32 99S O1 O3 O 0 1 N N N 20.781 -35.472 -21.440 -2.357 3.195 0.090 O1 99S 33 99S H1 H1 H 0 1 N N N 12.620 -29.462 -27.657 6.742 3.668 0.101 H1 99S 34 99S H2 H2 H 0 1 N N N 12.517 -28.799 -25.991 7.542 2.296 0.905 H2 99S 35 99S H3 H3 H 0 1 N N N 14.051 -29.528 -26.574 7.501 2.385 -0.872 H3 99S 36 99S H4 H4 H 0 1 N N N 15.489 -31.567 -26.098 5.421 -2.249 -0.163 H4 99S 37 99S H5 H5 H 0 1 N N N 17.588 -31.481 -24.609 3.089 -3.236 -0.159 H5 99S 38 99S H6 H6 H 0 1 N N N 15.963 -29.865 -20.522 1.127 -3.703 -0.137 H6 99S 39 99S H7 H7 H 0 1 N N N 19.648 -31.031 -18.689 -2.953 -2.393 0.023 H7 99S 40 99S H8 H8 H 0 1 N N N 18.652 -32.439 -22.595 0.198 0.475 0.103 H8 99S 41 99S H9 H9 H 0 1 N N N 21.571 -31.522 -19.092 -4.086 -1.045 -0.474 H9 99S 42 99S H10 H10 H 0 1 N N N 23.072 -30.073 -20.386 -3.922 -0.312 2.481 H10 99S 43 99S H11 H11 H 0 1 N N N 22.440 -30.785 -21.910 -4.916 -1.590 1.742 H11 99S 44 99S H12 H12 H 0 1 N N N 21.348 -29.846 -20.836 -3.143 -1.746 1.771 H12 99S 45 99S H13 H13 H 0 1 N N N 22.837 -33.622 -19.476 -4.854 1.310 -0.678 H13 99S 46 99S H14 H14 H 0 1 N N N 23.444 -32.941 -21.024 -5.925 0.368 0.387 H14 99S 47 99S H15 H15 H 0 1 N N N 23.869 -32.152 -19.467 -4.738 1.495 1.089 H15 99S 48 99S H16 H16 H 0 1 N N N 20.624 -36.892 -19.609 -1.643 2.747 3.188 H16 99S 49 99S H17 H17 H 0 1 N N N 21.174 -35.846 -18.482 -1.780 4.182 2.325 H17 99S 50 99S H18 H18 H 0 1 N N N 20.109 -30.684 -23.957 -3.539 -1.062 -2.909 H18 99S 51 99S H19 H19 H 0 1 N N N 21.495 -30.464 -22.836 -2.084 -0.775 -3.894 H19 99S 52 99S H20 H20 H 0 1 N N N 21.791 -30.850 -24.565 -1.925 -1.365 -2.222 H20 99S 53 99S H21 H21 H 0 1 N N N 21.427 -33.346 -25.252 -2.384 1.833 -4.129 H21 99S 54 # 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 99S C33 O32 SING N N 1 99S O32 C30 SING N N 2 99S C27 C28 DOUB Y N 3 99S C27 C26 SING Y N 4 99S C30 C28 SING N N 5 99S C30 O31 DOUB N N 6 99S C28 S29 SING Y N 7 99S N11 N12 SING Y N 8 99S N11 C10 SING Y N 9 99S C26 C25 DOUB Y N 10 99S C13 C10 SING N N 11 99S N12 C6 DOUB Y N 12 99S C10 C5 DOUB Y N 13 99S C25 S29 SING Y N 14 99S C25 C21 SING N N 15 99S C6 C5 SING Y N 16 99S C6 O1 SING N N 17 99S C5 C4 SING N N 18 99S C22 C21 DOUB Y N 19 99S C22 C17 SING Y N 20 99S C21 C20 SING Y N 21 99S O1 C2 SING N N 22 99S C16 C14 SING N N 23 99S C4 C17 SING N N 24 99S C4 C14 SING N N 25 99S C4 C3 SING N N 26 99S C17 C18 DOUB Y N 27 99S C20 C19 DOUB Y N 28 99S C14 C15 SING N N 29 99S C2 C3 DOUB N N 30 99S C2 N7 SING N N 31 99S C3 C8 SING N N 32 99S C18 C19 SING Y N 33 99S C19 C23 SING N N 34 99S C8 N9 TRIP N N 35 99S C23 N24 TRIP N N 36 99S C33 H1 SING N N 37 99S C33 H2 SING N N 38 99S C33 H3 SING N N 39 99S C27 H4 SING N N 40 99S C26 H5 SING N N 41 99S C20 H6 SING N N 42 99S C18 H7 SING N N 43 99S C22 H8 SING N N 44 99S C14 H9 SING N N 45 99S C16 H10 SING N N 46 99S C16 H11 SING N N 47 99S C16 H12 SING N N 48 99S C15 H13 SING N N 49 99S C15 H14 SING N N 50 99S C15 H15 SING N N 51 99S N7 H16 SING N N 52 99S N7 H17 SING N N 53 99S C13 H18 SING N N 54 99S C13 H19 SING N N 55 99S C13 H20 SING N N 56 99S N11 H21 SING N N 57 # 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 99S SMILES ACDLabs 12.01 "N#CC2=C(Oc1nnc(c1C2(c4cc(C#N)cc(c3sc(C(=O)OC)cc3)c4)C(C)C)C)N" 99S InChI InChI 1.03 "InChI=1S/C24H21N5O3S/c1-12(2)24(17(11-26)21(27)32-22-20(24)13(3)28-29-22)16-8-14(10-25)7-15(9-16)18-5-6-19(33-18)23(30)31-4/h5-9,12H,27H2,1-4H3,(H,28,29)/t24-/m0/s1" 99S InChIKey InChI 1.03 CTJJXDPGSNOYMV-DEOSSOPVSA-N 99S SMILES_CANONICAL CACTVS 3.385 "COC(=O)c1sc(cc1)c2cc(cc(c2)[C@@]3(C(C)C)C(=C(N)Oc4n[nH]c(C)c34)C#N)C#N" 99S SMILES CACTVS 3.385 "COC(=O)c1sc(cc1)c2cc(cc(c2)[C]3(C(C)C)C(=C(N)Oc4n[nH]c(C)c34)C#N)C#N" 99S SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "Cc1c2c(n[nH]1)OC(=C([C@@]2(c3cc(cc(c3)c4ccc(s4)C(=O)OC)C#N)C(C)C)C#N)N" 99S SMILES "OpenEye OEToolkits" 1.9.2 "Cc1c2c(n[nH]1)OC(=C(C2(c3cc(cc(c3)c4ccc(s4)C(=O)OC)C#N)C(C)C)C#N)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 99S "SYSTEMATIC NAME" ACDLabs 12.01 "methyl 5-{3-[(4S)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl}thiophene-2-carboxylate" 99S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "methyl 5-[3-[(4S)-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2H-pyrano[2,3-c]pyrazol-4-yl]-5-cyano-phenyl]thiophene-2-carboxylate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 99S "Create component" 2014-06-09 RCSB 99S "Modify descriptor" 2014-09-05 RCSB 99S "Initial release" 2015-03-25 RCSB #