data_66A # _chem_comp.id 66A _chem_comp.name "7-[cis-3-(azetidin-1-ylmethyl)cyclobutyl]-5-[3-(benzyloxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H29 N5 O" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-02-03 _chem_comp.pdbx_modified_date 2016-04-01 _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 439.552 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 66A _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 5HZN _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 66A C10 C1 C 0 1 Y N N 19.525 1.484 11.974 -0.843 -1.547 -0.748 C10 66A 1 66A C11 C2 C 0 1 Y N N 20.023 2.776 12.123 -1.730 -0.632 -0.185 C11 66A 2 66A C12 C3 C 0 1 Y N N 19.896 3.657 11.051 -3.016 -0.521 -0.687 C12 66A 3 66A C13 C4 C 0 1 Y N N 19.323 3.252 9.856 -3.419 -1.321 -1.748 C13 66A 4 66A C14 C5 C 0 1 Y N N 18.893 1.944 9.694 -2.539 -2.230 -2.307 C14 66A 5 66A C15 C6 C 0 1 Y N N 19.030 1.056 10.750 -1.253 -2.342 -1.817 C15 66A 6 66A C19 C7 C 0 1 Y N N 18.712 7.914 11.799 -6.013 2.777 -0.415 C19 66A 7 66A C20 C8 C 0 1 Y N N 18.899 9.215 12.249 -6.761 3.728 0.254 C20 66A 8 66A C21 C9 C 0 1 Y N N 20.023 9.918 11.820 -7.503 3.368 1.363 C21 66A 9 66A C22 C10 C 0 1 Y N N 20.949 9.337 10.949 -7.497 2.057 1.803 C22 66A 10 66A C27 C11 C 0 1 N N N 23.800 -1.132 15.940 4.551 1.587 0.689 C27 66A 11 66A C31 C12 C 0 1 N N N 26.277 -2.055 14.197 5.089 4.727 -1.318 C31 66A 12 66A C32 C13 C 0 1 N N N 27.677 -1.454 14.033 6.400 5.341 -0.804 C32 66A 13 66A C33 C14 C 0 1 N N N 27.462 -0.533 15.237 6.195 4.369 0.366 C33 66A 14 66A N24 N1 N 0 1 N N N 16.667 -0.501 12.151 -0.366 -4.692 -0.246 N24 66A 15 66A C29 C15 C 0 1 N N N 24.961 -0.253 15.463 4.230 2.969 0.116 C29 66A 16 66A C26 C16 C 0 1 N N N 22.510 -0.432 16.366 3.405 0.981 1.515 C26 66A 17 66A C28 C17 C 0 1 N N N 23.017 -1.967 14.919 4.335 0.438 -0.310 C28 66A 18 66A C25 C18 C 0 1 N N N 21.718 -1.358 15.441 3.754 -0.368 0.864 C25 66A 19 66A N30 N2 N 0 1 N N N 26.131 -1.137 15.341 5.421 3.512 -0.551 N30 66A 20 66A C06 C19 C 0 1 Y N N 17.508 -1.076 13.043 0.880 -4.269 0.181 C06 66A 21 66A N05 N3 N 0 1 Y N N 17.070 -2.189 13.645 1.787 -5.144 0.607 N05 66A 22 66A C04 C20 C 0 1 Y N N 17.794 -2.870 14.544 2.978 -4.744 1.014 C04 66A 23 66A C07 C21 C 0 1 Y N N 18.786 -0.688 13.381 1.220 -2.910 0.170 C07 66A 24 66A C02 C22 C 0 1 Y N N 19.532 -1.303 14.257 2.499 -2.530 0.613 C02 66A 25 66A N03 N4 N 0 1 Y N N 19.021 -2.486 14.892 3.338 -3.479 1.026 N03 66A 26 66A N01 N5 N 0 1 Y N N 20.745 -0.775 14.474 2.581 -1.168 0.504 N01 66A 27 66A C08 C23 C 0 1 Y N N 19.675 0.446 12.996 0.535 -1.670 -0.216 C08 66A 28 66A C09 C24 C 0 1 Y N N 20.880 0.326 13.668 1.411 -0.660 0.010 C09 66A 29 66A O16 O1 O 0 1 N N N 20.297 4.961 11.143 -3.885 0.369 -0.141 O16 66A 30 66A C17 C25 C 0 1 N N N 19.427 5.903 10.462 -5.195 0.430 -0.708 C17 66A 31 66A C18 C26 C 0 1 Y N N 19.638 7.331 10.930 -6.011 1.466 0.021 C18 66A 32 66A C23 C27 C 0 1 Y N N 20.753 8.035 10.496 -6.749 1.107 1.134 C23 66A 33 66A H1 H1 H 0 1 N N N 20.494 3.086 13.044 -1.416 -0.010 0.640 H1 66A 34 66A H2 H2 H 0 1 N N N 19.211 3.959 9.047 -4.422 -1.234 -2.138 H2 66A 35 66A H3 H3 H 0 1 N N N 18.458 1.622 8.760 -2.857 -2.850 -3.132 H3 66A 36 66A H4 H4 H 0 1 N N N 18.749 0.022 10.619 -0.568 -3.052 -2.256 H4 66A 37 66A H5 H5 H 0 1 N N N 17.848 7.352 12.122 -5.433 3.059 -1.282 H5 66A 38 66A H6 H6 H 0 1 N N N 18.186 9.673 12.919 -6.766 4.752 -0.090 H6 66A 39 66A H7 H7 H 0 1 N N N 20.181 10.929 12.166 -8.088 4.110 1.886 H7 66A 40 66A H8 H8 H 0 1 N N N 21.815 9.897 10.628 -8.077 1.776 2.670 H8 66A 41 66A H9 H9 H 0 1 N N N 24.148 -1.785 16.754 5.518 1.552 1.192 H9 66A 42 66A H10 H10 H 0 1 N N N 25.589 -1.867 13.359 4.199 5.240 -0.955 H10 66A 43 66A H11 H11 H 0 1 N N N 26.258 -3.124 14.454 5.076 4.570 -2.396 H11 66A 44 66A H12 H12 H 0 1 N N N 28.491 -2.181 14.170 7.269 5.119 -1.423 H12 66A 45 66A H13 H13 H 0 1 N N N 27.821 -0.917 13.084 6.322 6.393 -0.529 H13 66A 46 66A H14 H14 H 0 1 N N N 28.126 -0.726 16.092 7.120 3.908 0.715 H14 66A 47 66A H15 H15 H 0 1 N N N 27.466 0.542 15.005 5.599 4.786 1.178 H15 66A 48 66A H16 H16 H 0 1 N N N 15.823 -1.035 12.095 -1.017 -4.044 -0.558 H16 66A 49 66A H17 H17 H 0 1 N N N 16.453 0.430 12.447 -0.589 -5.635 -0.233 H17 66A 50 66A H18 H18 H 0 1 N N N 25.161 0.543 16.195 3.417 2.882 -0.606 H18 66A 51 66A H19 H19 H 0 1 N N N 24.721 0.197 14.488 3.929 3.636 0.923 H19 66A 52 66A H20 H20 H 0 1 N N N 22.461 0.631 16.089 3.580 1.006 2.590 H20 66A 53 66A H21 H21 H 0 1 N N N 22.267 -0.545 17.433 2.420 1.358 1.238 H21 66A 54 66A H22 H22 H 0 1 N N N 23.098 -3.054 15.068 3.605 0.666 -1.086 H22 66A 55 66A H23 H23 H 0 1 N N N 23.240 -1.723 13.870 5.262 0.025 -0.707 H23 66A 56 66A H24 H24 H 0 1 N N N 21.203 -2.109 16.058 4.503 -0.937 1.415 H24 66A 57 66A H26 H26 H 0 1 N N N 17.371 -3.754 14.998 3.686 -5.487 1.353 H26 66A 58 66A H27 H27 H 0 1 N N N 21.745 0.966 13.576 1.214 0.387 -0.171 H27 66A 59 66A H28 H28 H 0 1 N N N 18.381 5.620 10.654 -5.123 0.700 -1.762 H28 66A 60 66A H29 H29 H 0 1 N N N 19.629 5.852 9.382 -5.677 -0.544 -0.615 H29 66A 61 66A H30 H30 H 0 1 N N N 21.458 7.579 9.817 -6.741 0.084 1.480 H30 66A 62 # 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 66A C14 C13 DOUB Y N 1 66A C14 C15 SING Y N 2 66A C13 C12 SING Y N 3 66A C17 C18 SING N N 4 66A C17 O16 SING N N 5 66A C23 C18 DOUB Y N 6 66A C23 C22 SING Y N 7 66A C15 C10 DOUB Y N 8 66A C18 C19 SING Y N 9 66A C22 C21 DOUB Y N 10 66A C12 O16 SING N N 11 66A C12 C11 DOUB Y N 12 66A C19 C20 DOUB Y N 13 66A C21 C20 SING Y N 14 66A C10 C11 SING Y N 15 66A C10 C08 SING N N 16 66A N24 C06 SING N N 17 66A C08 C07 SING Y N 18 66A C08 C09 DOUB Y N 19 66A C06 C07 DOUB Y N 20 66A C06 N05 SING Y N 21 66A C07 C02 SING Y N 22 66A N05 C04 DOUB Y N 23 66A C09 N01 SING Y N 24 66A C32 C31 SING N N 25 66A C32 C33 SING N N 26 66A C31 N30 SING N N 27 66A C02 N01 SING Y N 28 66A C02 N03 DOUB Y N 29 66A N01 C25 SING N N 30 66A C04 N03 SING Y N 31 66A C28 C25 SING N N 32 66A C28 C27 SING N N 33 66A C33 N30 SING N N 34 66A N30 C29 SING N N 35 66A C25 C26 SING N N 36 66A C29 C27 SING N N 37 66A C27 C26 SING N N 38 66A C11 H1 SING N N 39 66A C13 H2 SING N N 40 66A C14 H3 SING N N 41 66A C15 H4 SING N N 42 66A C19 H5 SING N N 43 66A C20 H6 SING N N 44 66A C21 H7 SING N N 45 66A C22 H8 SING N N 46 66A C27 H9 SING N N 47 66A C31 H10 SING N N 48 66A C31 H11 SING N N 49 66A C32 H12 SING N N 50 66A C32 H13 SING N N 51 66A C33 H14 SING N N 52 66A C33 H15 SING N N 53 66A N24 H16 SING N N 54 66A N24 H17 SING N N 55 66A C29 H18 SING N N 56 66A C29 H19 SING N N 57 66A C26 H20 SING N N 58 66A C26 H21 SING N N 59 66A C28 H22 SING N N 60 66A C28 H23 SING N N 61 66A C25 H24 SING N N 62 66A C04 H26 SING N N 63 66A C09 H27 SING N N 64 66A C17 H28 SING N N 65 66A C17 H29 SING N N 66 66A C23 H30 SING N N 67 # 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 66A SMILES ACDLabs 12.01 "c2(cc(OCc1ccccc1)ccc2)c6c3c(N)ncnc3n(C5CC(CN4CCC4)C5)c6" 66A InChI InChI 1.03 "InChI=1S/C27H29N5O/c28-26-25-24(21-8-4-9-23(14-21)33-17-19-6-2-1-3-7-19)16-32(27(25)30-18-29-26)22-12-20(13-22)15-31-10-5-11-31/h1-4,6-9,14,16,18,20,22H,5,10-13,15,17H2,(H2,28,29,30)/t20-,22+" 66A InChIKey InChI 1.03 AECDBHGVIIRMOI-GRGXKFILSA-N 66A SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n(cc(c3cccc(OCc4ccccc4)c3)c12)[C@@H]5C[C@@H](C5)CN6CCC6" 66A SMILES CACTVS 3.385 "Nc1ncnc2n(cc(c3cccc(OCc4ccccc4)c3)c12)[CH]5C[CH](C5)CN6CCC6" 66A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1ccc(cc1)COc2cccc(c2)c3cn(c4c3c(ncn4)N)C5CC(C5)CN6CCC6" 66A SMILES "OpenEye OEToolkits" 2.0.4 "c1ccc(cc1)COc2cccc(c2)c3cn(c4c3c(ncn4)N)C5CC(C5)CN6CCC6" # 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 66A "SYSTEMATIC NAME" ACDLabs 12.01 "7-[cis-3-(azetidin-1-ylmethyl)cyclobutyl]-5-[3-(benzyloxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine" 66A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "7-[3-(azetidin-1-ylmethyl)cyclobutyl]-5-(3-phenylmethoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 66A "Create component" 2016-02-03 EBI 66A "Initial release" 2016-04-06 RCSB #