data_9KD # _chem_comp.id 9KD _chem_comp.name "N-(6-cyano-3-{2-[2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]phenoxy}-4-methylnaphthalen-1-yl)prop-2-enamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H22 N4 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-05-17 _chem_comp.pdbx_modified_date 2017-08-18 _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 482.487 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 9KD _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 5VQS _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 9KD C1 C1 C 0 1 Y N N 460.294 3.270 117.777 2.227 1.759 -2.771 C1 9KD 1 9KD C2 C2 C 0 1 Y N N 460.551 2.723 119.058 1.850 1.321 -1.512 C2 9KD 2 9KD C4 C3 C 0 1 Y N N 462.831 3.608 118.949 -0.356 0.850 -2.343 C4 9KD 3 9KD O5 O1 O 0 1 N N N 458.456 5.222 124.535 -3.198 3.296 0.465 O5 9KD 4 9KD C7 C4 C 0 1 N N N 458.478 1.547 119.080 4.059 1.817 -0.783 C7 9KD 5 9KD C9 C5 C 0 1 N N N 458.795 -1.502 120.055 6.144 -0.338 0.412 C9 9KD 6 9KD C11 C6 C 0 1 N N N 459.611 -1.035 122.716 4.368 -1.503 2.115 C11 9KD 7 9KD C13 C7 C 0 1 Y N N 461.968 3.118 122.020 -1.122 0.087 0.124 C13 9KD 8 9KD C14 C8 C 0 1 Y N N 462.691 2.710 123.160 -1.559 -1.158 -0.272 C14 9KD 9 9KD C15 C9 C 0 1 Y N N 462.591 3.435 124.368 -2.905 -1.518 -0.085 C15 9KD 10 9KD C16 C10 C 0 1 Y N N 461.752 4.582 124.437 -3.801 -0.594 0.510 C16 9KD 11 9KD C17 C11 C 0 1 Y N N 461.025 4.996 123.289 -3.326 0.675 0.906 C17 9KD 12 9KD C19 C12 C 0 1 Y N N 463.322 3.025 125.508 -3.376 -2.780 -0.480 C19 9KD 13 9KD C21 C13 C 0 1 Y N N 462.400 4.874 126.784 -5.587 -2.175 0.308 C21 9KD 14 9KD C22 C14 C 0 1 Y N N 461.668 5.294 125.658 -5.147 -0.950 0.696 C22 9KD 15 9KD C23 C15 C 0 1 N N N 463.983 3.311 127.879 -5.196 -4.388 -0.683 C23 9KD 16 9KD C24 C16 C 0 1 N N N 463.585 1.483 123.067 -0.597 -2.131 -0.903 C24 9KD 17 9KD C25 C17 C 0 1 N N N 458.981 6.188 123.985 -4.032 2.915 1.265 C25 9KD 18 9KD C26 C18 C 0 1 N N N 458.368 7.500 123.912 -4.863 3.893 1.982 C26 9KD 19 9KD C27 C19 C 0 1 N N N 457.162 7.677 124.478 -4.703 5.194 1.757 C27 9KD 20 9KD C3 C20 C 0 1 Y N N 461.825 2.905 119.640 0.553 0.864 -1.297 C3 9KD 21 9KD C5 C21 C 0 1 Y N N 462.568 4.150 117.677 0.023 1.300 -3.594 C5 9KD 22 9KD C6 C22 C 0 1 Y N N 461.298 3.980 117.093 1.313 1.747 -3.809 C6 9KD 23 9KD O1 O2 O 0 1 N N N 462.100 2.375 120.873 0.178 0.432 -0.063 O1 9KD 24 9KD O2 O3 O 0 1 N N N 459.618 2.019 119.784 2.746 1.336 -0.489 O2 9KD 25 9KD C8 C23 C 0 1 N N N 457.656 0.666 120.028 4.918 1.760 0.481 C8 9KD 26 9KD N1 N1 N 0 1 N N N 458.450 -0.311 120.735 5.099 0.363 0.886 N1 9KD 27 9KD N2 N2 N 0 1 N N N 459.554 -2.427 120.758 6.334 -1.622 0.767 N2 9KD 28 9KD C10 C24 C 0 1 N N N 460.000 -2.282 122.068 5.473 -2.229 1.609 C10 9KD 29 9KD C12 C25 C 0 1 N N N 458.870 -0.124 122.042 4.202 -0.216 1.742 C12 9KD 30 9KD C18 C26 C 0 1 Y N N 461.135 4.254 122.090 -2.002 1.000 0.710 C18 9KD 31 9KD C20 C27 C 0 1 Y N N 463.228 3.740 126.713 -4.709 -3.102 -0.282 C20 9KD 32 9KD O3 O4 O 0 1 N N N 458.460 -1.741 118.897 6.926 0.194 -0.352 O3 9KD 33 9KD O4 O5 O 0 1 N N N 460.667 -3.171 122.589 5.644 -3.391 1.931 O4 9KD 34 9KD N3 N3 N 0 1 N N N 460.181 6.142 123.380 -4.194 1.596 1.492 N3 9KD 35 9KD N4 N4 N 0 1 N N N 464.582 2.970 128.806 -5.583 -5.407 -1.000 N4 9KD 36 9KD H1 H1 H 0 1 N N N 459.323 3.141 117.323 3.233 2.114 -2.941 H1 9KD 37 9KD H2 H2 H 0 1 N N N 463.806 3.731 119.396 -1.363 0.496 -2.179 H2 9KD 38 9KD H3 H3 H 0 1 N N N 457.870 2.399 118.744 4.509 1.195 -1.557 H3 9KD 39 9KD H4 H4 H 0 1 N N N 458.797 0.958 118.208 3.998 2.847 -1.135 H4 9KD 40 9KD H5 H5 H 0 1 N N N 459.914 -0.838 123.734 3.668 -1.972 2.790 H5 9KD 41 9KD H6 H6 H 0 1 N N N 463.958 2.154 125.451 -2.705 -3.493 -0.935 H6 9KD 42 9KD H7 H7 H 0 1 N N N 462.325 5.426 127.709 -6.623 -2.441 0.455 H7 9KD 43 9KD H8 H8 H 0 1 N N N 461.036 6.167 125.726 -5.833 -0.250 1.149 H8 9KD 44 9KD H9 H9 H 0 1 N N N 464.594 1.787 122.753 -0.136 -2.741 -0.127 H9 9KD 45 9KD H10 H10 H 0 1 N N N 463.639 0.993 124.051 -1.135 -2.774 -1.599 H10 9KD 46 9KD H11 H11 H 0 1 N N N 463.168 0.781 122.330 0.176 -1.581 -1.440 H11 9KD 47 9KD H12 H12 H 0 1 N N N 458.869 8.317 123.414 -5.604 3.555 2.692 H12 9KD 48 9KD H13 H13 H 0 1 N N N 456.683 8.644 124.438 -5.313 5.912 2.284 H13 9KD 49 9KD H14 H14 H 0 1 N N N 456.671 6.852 124.973 -3.962 5.532 1.048 H14 9KD 50 9KD H15 H15 H 0 1 N N N 463.338 4.695 117.151 -0.686 1.288 -4.409 H15 9KD 51 9KD H16 H16 H 0 1 N N N 461.094 4.396 116.117 1.606 2.098 -4.788 H16 9KD 52 9KD H17 H17 H 0 1 N N N 457.162 1.315 120.767 5.891 2.208 0.280 H17 9KD 53 9KD H18 H18 H 0 1 N N N 456.894 0.135 119.438 4.423 2.309 1.282 H18 9KD 54 9KD H19 H19 H 0 1 N N N 459.802 -3.271 120.282 7.094 -2.113 0.416 H19 9KD 55 9KD H20 H20 H 0 1 N N N 458.594 0.790 122.546 3.365 0.354 2.118 H20 9KD 56 9KD H21 H21 H 0 1 N N N 460.575 4.561 121.219 -1.639 1.970 1.014 H21 9KD 57 9KD H22 H22 H 0 1 N N N 460.511 6.986 122.957 -4.915 1.288 2.064 H22 9KD 58 # 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 9KD C6 C5 DOUB Y N 1 9KD C6 C1 SING Y N 2 9KD C5 C4 SING Y N 3 9KD C1 C2 DOUB Y N 4 9KD O3 C9 DOUB N N 5 9KD C4 C3 DOUB Y N 6 9KD C2 C3 SING Y N 7 9KD C2 O2 SING N N 8 9KD C7 O2 SING N N 9 9KD C7 C8 SING N N 10 9KD C3 O1 SING N N 11 9KD C8 N1 SING N N 12 9KD C9 N1 SING N N 13 9KD C9 N2 SING N N 14 9KD N1 C12 SING N N 15 9KD N2 C10 SING N N 16 9KD O1 C13 SING N N 17 9KD C13 C18 DOUB Y N 18 9KD C13 C14 SING Y N 19 9KD C12 C11 DOUB N N 20 9KD C10 O4 DOUB N N 21 9KD C10 C11 SING N N 22 9KD C18 C17 SING Y N 23 9KD C24 C14 SING N N 24 9KD C14 C15 DOUB Y N 25 9KD C17 N3 SING N N 26 9KD C17 C16 DOUB Y N 27 9KD N3 C25 SING N N 28 9KD C26 C25 SING N N 29 9KD C26 C27 DOUB N N 30 9KD C25 O5 DOUB N N 31 9KD C15 C16 SING Y N 32 9KD C15 C19 SING Y N 33 9KD C16 C22 SING Y N 34 9KD C19 C20 DOUB Y N 35 9KD C22 C21 DOUB Y N 36 9KD C20 C21 SING Y N 37 9KD C20 C23 SING N N 38 9KD C23 N4 TRIP N N 39 9KD C1 H1 SING N N 40 9KD C4 H2 SING N N 41 9KD C7 H3 SING N N 42 9KD C7 H4 SING N N 43 9KD C11 H5 SING N N 44 9KD C19 H6 SING N N 45 9KD C21 H7 SING N N 46 9KD C22 H8 SING N N 47 9KD C24 H9 SING N N 48 9KD C24 H10 SING N N 49 9KD C24 H11 SING N N 50 9KD C26 H12 SING N N 51 9KD C27 H13 SING N N 52 9KD C27 H14 SING N N 53 9KD C5 H15 SING N N 54 9KD C6 H16 SING N N 55 9KD C8 H17 SING N N 56 9KD C8 H18 SING N N 57 9KD N2 H19 SING N N 58 9KD C12 H20 SING N N 59 9KD C18 H21 SING N N 60 9KD N3 H22 SING N N 61 # 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 9KD SMILES ACDLabs 12.01 "c1c(c(ccc1)Oc2cc(c3c(c2C)cc(cc3)C#N)NC(=O)\C=C)OCCN4C(NC(C=C4)=O)=O" 9KD InChI InChI 1.03 "InChI=1S/C27H22N4O5/c1-3-25(32)29-21-15-24(17(2)20-14-18(16-28)8-9-19(20)21)36-23-7-5-4-6-22(23)35-13-12-31-11-10-26(33)30-27(31)34/h3-11,14-15H,1,12-13H2,2H3,(H,29,32)(H,30,33,34)" 9KD InChIKey InChI 1.03 FFULUQDOKSUESE-UHFFFAOYSA-N 9KD SMILES_CANONICAL CACTVS 3.385 "Cc1c(Oc2ccccc2OCCN3C=CC(=O)NC3=O)cc(NC(=O)C=C)c4ccc(cc14)C#N" 9KD SMILES CACTVS 3.385 "Cc1c(Oc2ccccc2OCCN3C=CC(=O)NC3=O)cc(NC(=O)C=C)c4ccc(cc14)C#N" 9KD SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "Cc1c2cc(ccc2c(cc1Oc3ccccc3OCCN4C=CC(=O)NC4=O)NC(=O)C=C)C#N" 9KD SMILES "OpenEye OEToolkits" 2.0.6 "Cc1c2cc(ccc2c(cc1Oc3ccccc3OCCN4C=CC(=O)NC4=O)NC(=O)C=C)C#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 9KD "SYSTEMATIC NAME" ACDLabs 12.01 "N-(6-cyano-3-{2-[2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]phenoxy}-4-methylnaphthalen-1-yl)prop-2-enamide" 9KD "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "~{N}-[3-[2-[2-[2,4-bis(oxidanylidene)pyrimidin-1-yl]ethoxy]phenoxy]-6-cyano-4-methyl-naphthalen-1-yl]prop-2-enamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 9KD "Create component" 2017-05-17 RCSB 9KD "Initial release" 2017-08-23 RCSB #