data_0JH # _chem_comp.id 0JH _chem_comp.name "tert-butyl (2S)-3-[4-amino-7-(3-hydroxypropyl)-5-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyanopropanoate" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H29 N5 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(E)-tert-butyl 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-cyanoacrylate, bound form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-01-23 _chem_comp.pdbx_modified_date 2020-06-17 _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 435.519 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 0JH _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 4D9U _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 0JH N01 N01 N 0 1 N N N -33.962 15.310 -19.882 3.939 2.646 -0.551 N01 0JH 1 0JH C02 C02 C 0 1 Y N N -33.538 14.796 -21.081 3.975 1.268 -0.671 C02 0JH 2 0JH C03 C03 C 0 1 Y N N -32.512 13.800 -21.172 2.846 0.492 -0.374 C03 0JH 3 0JH C04 C04 C 0 1 Y N N -32.216 13.443 -22.529 2.931 -0.904 -0.511 C04 0JH 4 0JH N05 N05 N 0 1 Y N N -31.201 12.462 -22.575 1.712 -1.424 -0.166 N05 0JH 5 0JH C06 C06 C 0 1 N N N -30.741 11.990 -23.928 1.379 -2.850 -0.172 C06 0JH 6 0JH C07 C07 C 0 1 N N N -29.717 12.849 -24.741 1.697 -3.454 1.198 C07 0JH 7 0JH C08 C08 C 0 1 N N N -29.221 12.008 -25.960 1.348 -4.944 1.191 C08 0JH 8 0JH O09 O09 O 0 1 N N N -28.540 10.843 -25.582 1.645 -5.508 2.470 O09 0JH 9 0JH C10 C10 C 0 1 Y N N -30.863 12.189 -21.204 0.851 -0.421 0.185 C10 0JH 10 0JH C11 C11 C 0 1 N N N -29.838 11.232 -20.598 -0.577 -0.617 0.623 C11 0JH 11 0JH C12 C12 C 0 1 N N S -28.542 11.224 -21.487 -1.509 -0.426 -0.576 C12 0JH 12 0JH C13 C13 C 0 1 N N N -27.447 10.169 -21.164 -2.942 -0.488 -0.113 C13 0JH 13 0JH O14 O14 O 0 1 N N N -27.759 8.851 -21.320 -3.940 -0.346 -0.999 O14 0JH 14 0JH C15 C15 C 0 1 N N N -26.852 7.764 -21.060 -5.295 -0.417 -0.483 C15 0JH 15 0JH C16 C16 C 0 1 N N N -25.713 7.768 -22.101 -6.289 -0.234 -1.632 C16 0JH 16 0JH C17 C17 C 0 1 N N N -27.601 6.437 -21.166 -5.520 -1.780 0.173 C17 0JH 17 0JH C18 C18 C 0 1 N N N -26.184 7.909 -19.694 -5.504 0.689 0.553 C18 0JH 18 0JH O19 O19 O 0 1 N N N -26.333 10.514 -20.779 -3.192 -0.667 1.055 O19 0JH 19 0JH C20 C20 C 0 1 N N N -27.896 12.512 -21.333 -1.265 -1.492 -1.561 C20 0JH 20 0JH N21 N21 N 0 1 N N N -27.441 13.558 -21.198 -1.076 -2.315 -2.321 N21 0JH 21 0JH C22 C22 C 0 1 Y N N -31.610 13.011 -20.349 1.479 0.776 0.081 C22 0JH 22 0JH C23 C23 C 0 1 Y N N -31.486 12.917 -18.856 0.900 2.110 0.369 C23 0JH 23 0JH C24 C24 C 0 1 Y N N -30.433 13.475 -18.113 0.682 3.017 -0.667 C24 0JH 24 0JH C25 C25 C 0 1 Y N N -30.315 13.318 -16.728 0.143 4.257 -0.393 C25 0JH 25 0JH C26 C26 C 0 1 Y N N -31.244 12.582 -16.002 -0.183 4.601 0.907 C26 0JH 26 0JH C27 C27 C 0 1 N N N -31.185 12.374 -14.520 -0.772 5.957 1.200 C27 0JH 27 0JH C28 C28 C 0 1 Y N N -32.290 12.009 -16.722 0.031 3.705 1.939 C28 0JH 28 0JH C29 C29 C 0 1 Y N N -32.401 12.163 -18.104 0.564 2.460 1.676 C29 0JH 29 0JH N30 N30 N 0 1 Y N N -32.822 13.976 -23.666 4.084 -1.434 -0.917 N30 0JH 30 0JH C31 C31 C 0 1 Y N N -33.766 14.899 -23.405 5.119 -0.668 -1.184 C31 0JH 31 0JH N32 N32 N 0 1 Y N N -34.175 15.349 -22.189 5.079 0.648 -1.075 N32 0JH 32 0JH H1 H1 H 0 1 N N N -34.666 16.001 -20.045 3.125 3.087 -0.259 H1 0JH 33 0JH H2 H2 H 0 1 N N N -34.341 14.575 -19.320 4.728 3.171 -0.756 H2 0JH 34 0JH H3 H3 H 0 1 N N N -31.640 11.889 -24.553 0.317 -2.974 -0.386 H3 0JH 35 0JH H4 H4 H 0 1 N N N -30.283 11.001 -23.782 1.965 -3.357 -0.938 H4 0JH 36 0JH H5 H5 H 0 1 N N N -28.863 13.113 -24.100 2.759 -3.330 1.411 H5 0JH 37 0JH H6 H6 H 0 1 N N N -30.205 13.768 -25.098 1.110 -2.947 1.964 H6 0JH 38 0JH H7 H7 H 0 1 N N N -28.543 12.630 -26.562 0.287 -5.068 0.978 H7 0JH 39 0JH H8 H8 H 0 1 N N N -30.093 11.723 -26.567 1.935 -5.451 0.426 H8 0JH 40 0JH H9 H9 H 0 1 N N N -28.262 10.372 -26.359 1.449 -6.452 2.539 H9 0JH 41 0JH H10 H10 H 0 1 N N N -30.262 10.218 -20.558 -0.700 -1.623 1.023 H10 0JH 42 0JH H11 H11 H 0 1 N N N -29.583 11.563 -19.581 -0.824 0.113 1.395 H11 0JH 43 0JH H12 H12 H 0 1 N N N -28.850 11.089 -22.534 -1.317 0.544 -1.034 H12 0JH 44 0JH H13 H13 H 0 1 N N N -25.025 6.935 -21.895 -6.140 -1.021 -2.371 H13 0JH 45 0JH H14 H14 H 0 1 N N N -26.137 7.653 -23.109 -7.306 -0.287 -1.245 H14 0JH 46 0JH H15 H15 H 0 1 N N N -25.165 8.720 -22.041 -6.128 0.738 -2.100 H15 0JH 47 0JH H16 H16 H 0 1 N N N -28.418 6.417 -20.430 -4.812 -1.911 0.992 H16 0JH 48 0JH H17 H17 H 0 1 N N N -28.017 6.331 -22.179 -6.537 -1.834 0.561 H17 0JH 49 0JH H18 H18 H 0 1 N N N -26.907 5.607 -20.966 -5.371 -2.568 -0.565 H18 0JH 50 0JH H19 H19 H 0 1 N N N -26.953 7.912 -18.908 -5.344 1.660 0.086 H19 0JH 51 0JH H20 H20 H 0 1 N N N -25.497 7.066 -19.531 -6.522 0.636 0.941 H20 0JH 52 0JH H21 H21 H 0 1 N N N -25.621 8.853 -19.660 -4.797 0.558 1.372 H21 0JH 53 0JH H22 H22 H 0 1 N N N -29.682 14.050 -18.634 0.936 2.750 -1.683 H22 0JH 54 0JH H23 H23 H 0 1 N N N -29.485 13.778 -16.212 -0.026 4.961 -1.195 H23 0JH 55 0JH H24 H24 H 0 1 N N N -31.738 13.179 -14.014 -1.859 5.902 1.135 H24 0JH 56 0JH H25 H25 H 0 1 N N N -31.638 11.404 -14.268 -0.484 6.269 2.203 H25 0JH 57 0JH H26 H26 H 0 1 N N N -30.136 12.386 -14.190 -0.401 6.679 0.473 H26 0JH 58 0JH H27 H27 H 0 1 N N N -33.035 11.430 -16.196 -0.225 3.979 2.952 H27 0JH 59 0JH H28 H28 H 0 1 N N N -33.223 11.684 -18.615 0.726 1.759 2.482 H28 0JH 60 0JH H29 H29 H 0 1 N N N -34.257 15.334 -24.263 6.037 -1.133 -1.511 H29 0JH 61 # # 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 0JH C08 O09 SING N N 1 0JH C08 C07 SING N N 2 0JH C07 C06 SING N N 3 0JH C06 N05 SING N N 4 0JH N30 C31 DOUB Y N 5 0JH N30 C04 SING Y N 6 0JH C31 N32 SING Y N 7 0JH N05 C04 SING Y N 8 0JH N05 C10 SING Y N 9 0JH C04 C03 DOUB Y N 10 0JH N32 C02 DOUB Y N 11 0JH C16 C15 SING N N 12 0JH C12 C20 SING N N 13 0JH C12 C13 SING N N 14 0JH C12 C11 SING N N 15 0JH C20 N21 TRIP N N 16 0JH O14 C13 SING N N 17 0JH O14 C15 SING N N 18 0JH C10 C11 SING N N 19 0JH C10 C22 DOUB Y N 20 0JH C03 C02 SING Y N 21 0JH C03 C22 SING Y N 22 0JH C17 C15 SING N N 23 0JH C13 O19 DOUB N N 24 0JH C02 N01 SING N N 25 0JH C15 C18 SING N N 26 0JH C22 C23 SING N N 27 0JH C23 C24 DOUB Y N 28 0JH C23 C29 SING Y N 29 0JH C24 C25 SING Y N 30 0JH C29 C28 DOUB Y N 31 0JH C25 C26 DOUB Y N 32 0JH C28 C26 SING Y N 33 0JH C26 C27 SING N N 34 0JH N01 H1 SING N N 35 0JH N01 H2 SING N N 36 0JH C06 H3 SING N N 37 0JH C06 H4 SING N N 38 0JH C07 H5 SING N N 39 0JH C07 H6 SING N N 40 0JH C08 H7 SING N N 41 0JH C08 H8 SING N N 42 0JH O09 H9 SING N N 43 0JH C11 H10 SING N N 44 0JH C11 H11 SING N N 45 0JH C12 H12 SING N N 46 0JH C16 H13 SING N N 47 0JH C16 H14 SING N N 48 0JH C16 H15 SING N N 49 0JH C17 H16 SING N N 50 0JH C17 H17 SING N N 51 0JH C17 H18 SING N N 52 0JH C18 H19 SING N N 53 0JH C18 H20 SING N N 54 0JH C18 H21 SING N N 55 0JH C24 H22 SING N N 56 0JH C25 H23 SING N N 57 0JH C27 H24 SING N N 58 0JH C27 H25 SING N N 59 0JH C27 H26 SING N N 60 0JH C28 H27 SING N N 61 0JH C29 H28 SING N N 62 0JH C31 H29 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 0JH SMILES ACDLabs 12.01 "O=C(OC(C)(C)C)C(C#N)Cc2c(c1c(ncnc1n2CCCO)N)c3ccc(cc3)C" 0JH InChI InChI 1.03 "InChI=1S/C24H29N5O3/c1-15-6-8-16(9-7-15)19-18(12-17(13-25)23(31)32-24(2,3)4)29(10-5-11-30)22-20(19)21(26)27-14-28-22/h6-9,14,17,30H,5,10-12H2,1-4H3,(H2,26,27,28)/t17-/m0/s1" 0JH InChIKey InChI 1.03 YQNJEMHLWSEPFO-KRWDZBQOSA-N 0JH SMILES_CANONICAL CACTVS 3.370 "Cc1ccc(cc1)c2c(C[C@@H](C#N)C(=O)OC(C)(C)C)n(CCCO)c3ncnc(N)c23" 0JH SMILES CACTVS 3.370 "Cc1ccc(cc1)c2c(C[CH](C#N)C(=O)OC(C)(C)C)n(CCCO)c3ncnc(N)c23" 0JH SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1ccc(cc1)c2c(n(c3c2c(ncn3)N)CCCO)C[C@@H](C#N)C(=O)OC(C)(C)C" 0JH SMILES "OpenEye OEToolkits" 1.7.6 "Cc1ccc(cc1)c2c(n(c3c2c(ncn3)N)CCCO)CC(C#N)C(=O)OC(C)(C)C" # # 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 0JH "SYSTEMATIC NAME" ACDLabs 12.01 "tert-butyl (2S)-3-[4-amino-7-(3-hydroxypropyl)-5-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyanopropanoate" 0JH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "tert-butyl (2S)-3-[4-azanyl-5-(4-methylphenyl)-7-(3-oxidanylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]-2-cyano-propanoate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 0JH "Create component" 2012-01-23 RCSB 0JH "Modify formula" 2012-04-02 RCSB 0JH "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 0JH _pdbx_chem_comp_synonyms.name "(E)-tert-butyl 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-cyanoacrylate, bound form" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##