data_KSH # _chem_comp.id KSH _chem_comp.name "2-[(3,5-dimethoxyphenyl)amino]-5-ethyl-7-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H28 N6 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-01-12 _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 440.496 _chem_comp.one_letter_code ? _chem_comp.three_letter_code KSH _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 3AC3 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # 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 KSH N1 N1 N 0 1 Y N N 5.556 1.450 -7.785 1.496 0.264 -0.208 N1 KSH 1 KSH C2 C2 C 0 1 Y N N 5.242 2.416 -6.907 2.310 -0.823 -0.366 C2 KSH 2 KSH C3 C3 C 0 1 Y N N 3.910 2.532 -6.503 3.680 -0.637 -0.366 C3 KSH 3 KSH C4 C4 C 0 1 Y N N 2.932 1.667 -7.002 4.189 0.647 -0.206 C4 KSH 4 KSH N5 N5 N 0 1 Y N N 3.281 0.709 -7.886 3.371 1.671 -0.055 N5 KSH 5 KSH C6 C6 C 0 1 Y N N 4.584 0.647 -8.236 2.048 1.504 -0.054 C6 KSH 6 KSH C7 C7 C 0 1 Y N N 5.267 -0.275 -9.163 0.979 2.412 0.086 C7 KSH 7 KSH C8 C8 C 0 1 Y N N 6.685 0.151 -9.134 -0.213 1.655 0.007 C8 KSH 8 KSH N9 N9 N 0 1 Y N N 6.861 1.204 -8.291 0.104 0.395 -0.171 N9 KSH 9 KSH C10 C10 C 0 1 N N N 4.541 -1.348 -9.899 1.082 3.857 0.275 C10 KSH 10 KSH O11 O11 O 0 1 N N N 5.168 -2.137 -10.581 1.107 4.598 -0.691 O11 KSH 11 KSH N12 N12 N 0 1 N N N 3.216 -1.415 -9.791 1.151 4.370 1.520 N12 KSH 12 KSH N16 N16 N 0 1 N N N 7.669 -0.442 -9.851 -1.507 2.163 0.097 N16 KSH 13 KSH C17 C17 C 0 1 Y N N 8.961 -0.050 -9.754 -2.600 1.292 0.118 C17 KSH 14 KSH C18 C18 C 0 1 Y N N 9.378 0.768 -8.706 -2.461 0.016 0.648 C18 KSH 15 KSH C19 C19 C 0 1 Y N N 10.710 1.167 -8.612 -3.546 -0.847 0.668 C19 KSH 16 KSH C20 C20 C 0 1 Y N N 11.628 0.748 -9.570 -4.769 -0.436 0.158 C20 KSH 17 KSH C21 C21 C 0 1 Y N N 11.219 -0.070 -10.618 -4.908 0.838 -0.371 C21 KSH 18 KSH C22 C22 C 0 1 Y N N 9.886 -0.469 -10.709 -3.826 1.705 -0.386 C22 KSH 19 KSH O26 O26 O 0 1 N N N 12.132 -0.478 -11.558 -6.107 1.239 -0.871 O26 KSH 20 KSH C27 C27 C 0 1 N N N 13.297 -1.203 -11.163 -7.180 0.297 -0.818 C27 KSH 21 KSH O31 O31 O 0 1 N N N 11.119 1.972 -7.578 -3.411 -2.096 1.186 O31 KSH 22 KSH C32 C32 C 0 1 N N N 12.181 1.560 -6.716 -4.570 -2.932 1.174 C32 KSH 23 KSH C37 C37 C 0 1 N N N 1.491 1.804 -6.561 5.679 0.870 -0.202 C37 KSH 24 KSH C38 C38 C 0 1 N N N 0.818 0.447 -6.519 5.972 2.360 -0.011 C38 KSH 25 KSH N42 N42 N 0 1 N N N 6.206 3.295 -6.381 1.774 -2.082 -0.522 N42 KSH 26 KSH C43 C43 C 0 1 N N N 6.154 3.760 -4.998 0.336 -2.407 -0.539 C43 KSH 27 KSH C44 C44 C 0 1 N N N 7.518 4.396 -4.762 0.240 -3.735 -1.331 C44 KSH 28 KSH C45 C45 C 0 1 N N N 8.278 4.366 -6.078 1.523 -4.472 -0.862 C45 KSH 29 KSH C46 C46 C 0 1 N N R 7.337 3.818 -7.145 2.541 -3.323 -0.706 C46 KSH 30 KSH C53 C53 C 0 1 N N N 6.777 4.972 -7.972 3.423 -3.575 0.518 C53 KSH 31 KSH O55 O55 O 0 1 N N N 7.545 6.162 -7.744 2.597 -3.812 1.660 O55 KSH 32 KSH H3 H3 H 0 1 N N N 3.632 3.300 -5.796 4.346 -1.478 -0.489 H3 KSH 33 KSH HN12 HN12 H 0 0 N N N 2.710 -2.127 -10.278 1.131 3.780 2.289 HN12 KSH 34 KSH HN1A HN1A H 0 0 N N N 2.727 -0.753 -9.223 1.219 5.330 1.646 HN1A KSH 35 KSH HN16 HN16 H 0 0 N N N 7.434 -1.191 -10.470 -1.649 3.121 0.146 HN16 KSH 36 KSH H18 H18 H 0 1 N N N 8.666 1.094 -7.963 -1.509 -0.304 1.044 H18 KSH 37 KSH H20 H20 H 0 1 N N N 12.660 1.058 -9.500 -5.614 -1.109 0.174 H20 KSH 38 KSH H22 H22 H 0 1 N N N 9.569 -1.105 -11.522 -3.936 2.699 -0.794 H22 KSH 39 KSH H27 H27 H 0 1 N N N 13.901 -1.439 -12.051 -7.371 0.023 0.220 H27 KSH 40 KSH H27A H27A H 0 0 N N N 13.891 -0.592 -10.468 -8.076 0.743 -1.248 H27A KSH 41 KSH H27B H27B H 0 0 N N N 12.996 -2.137 -10.666 -6.909 -0.594 -1.385 H27B KSH 42 KSH H32 H32 H 0 1 N N N 12.359 2.335 -5.956 -5.364 -2.460 1.751 H32 KSH 43 KSH H32A H32A H 0 0 N N N 11.906 0.617 -6.220 -4.904 -3.076 0.146 H32A KSH 44 KSH H32B H32B H 0 0 N N N 13.096 1.410 -7.308 -4.325 -3.898 1.615 H32B KSH 45 KSH H37 H37 H 0 1 N N N 1.462 2.252 -5.557 6.129 0.304 0.613 H37 KSH 46 KSH H37A H37A H 0 0 N N N 0.956 2.450 -7.273 6.098 0.537 -1.152 H37A KSH 47 KSH H38 H38 H 0 1 N N N -0.227 0.565 -6.197 5.522 2.926 -0.826 H38 KSH 48 KSH H38A H38A H 0 0 N N N 0.844 -0.006 -7.521 5.553 2.693 0.938 H38A KSH 49 KSH H38B H38B H 0 0 N N N 1.349 -0.204 -5.809 7.050 2.521 -0.009 H38B KSH 50 KSH H43 H43 H 0 1 N N N 5.344 4.490 -4.854 -0.034 -2.544 0.477 H43 KSH 51 KSH H43A H43A H 0 0 N N N 5.979 2.925 -4.304 -0.224 -1.622 -1.046 H43A KSH 52 KSH H44 H44 H 0 1 N N N 7.396 5.435 -4.421 -0.655 -4.292 -1.053 H44 KSH 53 KSH H44A H44A H 0 0 N N N 8.069 3.832 -3.995 0.266 -3.553 -2.405 H44A KSH 54 KSH H45 H45 H 0 1 N N N 8.605 5.381 -6.348 1.352 -4.973 0.091 H45 KSH 55 KSH H45A H45A H 0 0 N N N 9.163 3.719 -5.988 1.858 -5.182 -1.618 H45A KSH 56 KSH H46 H46 H 0 1 N N N 7.840 3.090 -7.799 3.158 -3.248 -1.602 H46 KSH 57 KSH H53 H53 H 0 1 N N N 6.824 4.709 -9.039 4.053 -4.446 0.338 H53 KSH 58 KSH H53A H53A H 0 0 N N N 5.732 5.153 -7.680 4.052 -2.704 0.699 H53A KSH 59 KSH HO55 HO55 H 0 0 N N N 7.189 6.874 -8.263 3.091 -3.980 2.474 HO55 KSH 60 # 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 KSH N1 C2 SING Y N 1 KSH N1 C6 SING Y N 2 KSH N1 N9 SING Y N 3 KSH C2 C3 DOUB Y N 4 KSH C2 N42 SING N N 5 KSH C3 C4 SING Y N 6 KSH C4 N5 DOUB Y N 7 KSH C4 C37 SING N N 8 KSH N5 C6 SING Y N 9 KSH C6 C7 DOUB Y N 10 KSH C7 C8 SING Y N 11 KSH C7 C10 SING N N 12 KSH C8 N9 DOUB Y N 13 KSH C8 N16 SING N N 14 KSH C10 O11 DOUB N N 15 KSH C10 N12 SING N N 16 KSH N16 C17 SING N N 17 KSH C17 C18 DOUB Y N 18 KSH C17 C22 SING Y N 19 KSH C18 C19 SING Y N 20 KSH C19 C20 DOUB Y N 21 KSH C19 O31 SING N N 22 KSH C20 C21 SING Y N 23 KSH C21 C22 DOUB Y N 24 KSH C21 O26 SING N N 25 KSH O26 C27 SING N N 26 KSH O31 C32 SING N N 27 KSH C37 C38 SING N N 28 KSH N42 C43 SING N N 29 KSH N42 C46 SING N N 30 KSH C43 C44 SING N N 31 KSH C44 C45 SING N N 32 KSH C45 C46 SING N N 33 KSH C46 C53 SING N N 34 KSH C53 O55 SING N N 35 KSH C3 H3 SING N N 36 KSH N12 HN12 SING N N 37 KSH N12 HN1A SING N N 38 KSH N16 HN16 SING N N 39 KSH C18 H18 SING N N 40 KSH C20 H20 SING N N 41 KSH C22 H22 SING N N 42 KSH C27 H27 SING N N 43 KSH C27 H27A SING N N 44 KSH C27 H27B SING N N 45 KSH C32 H32 SING N N 46 KSH C32 H32A SING N N 47 KSH C32 H32B SING N N 48 KSH C37 H37 SING N N 49 KSH C37 H37A SING N N 50 KSH C38 H38 SING N N 51 KSH C38 H38A SING N N 52 KSH C38 H38B SING N N 53 KSH C43 H43 SING N N 54 KSH C43 H43A SING N N 55 KSH C44 H44 SING N N 56 KSH C44 H44A SING N N 57 KSH C45 H45 SING N N 58 KSH C45 H45A SING N N 59 KSH C46 H46 SING N N 60 KSH C53 H53 SING N N 61 KSH C53 H53A SING N N 62 KSH O55 HO55 SING N N 63 # 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 KSH SMILES_CANONICAL CACTVS 3.352 "CCc1cc(N2CCC[C@@H]2CO)n3nc(Nc4cc(OC)cc(OC)c4)c(C(N)=O)c3n1" KSH SMILES CACTVS 3.352 "CCc1cc(N2CCC[CH]2CO)n3nc(Nc4cc(OC)cc(OC)c4)c(C(N)=O)c3n1" KSH SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CCc1cc(n2c(n1)c(c(n2)Nc3cc(cc(c3)OC)OC)C(=O)N)N4CCC[C@@H]4CO" KSH SMILES "OpenEye OEToolkits" 1.7.0 "CCc1cc(n2c(n1)c(c(n2)Nc3cc(cc(c3)OC)OC)C(=O)N)N4CCCC4CO" KSH InChI InChI 1.03 "InChI=1S/C22H28N6O4/c1-4-13-10-18(27-7-5-6-15(27)12-29)28-22(25-13)19(20(23)30)21(26-28)24-14-8-16(31-2)11-17(9-14)32-3/h8-11,15,29H,4-7,12H2,1-3H3,(H2,23,30)(H,24,26)/t15-/m1/s1" KSH InChIKey InChI 1.03 ITADTXCJWWSRJO-OAHLLOKOSA-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 KSH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "2-[(3,5-dimethoxyphenyl)amino]-5-ethyl-7-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site KSH "Create component" 2010-01-12 PDBJ KSH "Modify aromatic_flag" 2011-06-04 RCSB KSH "Modify descriptor" 2011-06-04 RCSB #