data_XCF # _chem_comp.id XCF _chem_comp.name "5-[[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl]pyrimidine-2,4-diamine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H22 N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-01-22 _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 354.403 _chem_comp.one_letter_code ? _chem_comp.three_letter_code XCF _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 3FRF _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 XCF N4 N4 N 0 1 N N N 26.679 7.174 40.996 5.848 -1.309 -1.546 N4 XCF 1 XCF C3 C3 C 0 1 Y N N 27.210 8.415 41.019 4.744 -1.062 -0.749 C3 XCF 2 XCF N5 N5 N 0 1 Y N N 26.738 9.409 40.145 4.589 0.139 -0.214 N5 XCF 3 XCF N2 N2 N 0 1 Y N N 28.238 8.736 41.909 3.866 -2.033 -0.544 N2 XCF 4 XCF C1 C1 C 0 1 Y N N 28.821 10.021 41.921 2.797 -1.836 0.214 C1 XCF 5 XCF C8 C8 C 0 1 Y N N 28.381 10.986 41.061 2.600 -0.598 0.795 C8 XCF 6 XCF C6 C6 C 0 1 Y N N 27.310 10.686 40.167 3.540 0.407 0.557 C6 XCF 7 XCF N7 N7 N 0 1 N N N 26.772 11.566 39.298 3.380 1.665 1.115 N7 XCF 8 XCF C9 C9 C 0 1 N N N 28.997 12.364 41.003 1.396 -0.337 1.662 C9 XCF 9 XCF C10 C10 C 0 1 Y N N 30.031 12.593 42.074 0.305 0.289 0.832 C10 XCF 10 XCF C11 C11 C 0 1 Y N N 31.336 12.091 41.941 -0.603 -0.515 0.150 C11 XCF 11 XCF C27 C27 C 0 1 N N N 31.742 11.350 40.755 -0.530 -1.990 0.218 C27 XCF 12 XCF C28 C28 C 0 1 N N N 32.925 10.736 40.694 -1.595 -2.689 -0.168 C28 XCF 13 XCF C14 C14 C 0 1 N N S 33.887 10.772 41.846 -2.833 -1.976 -0.644 C14 XCF 14 XCF C24 C24 C 0 1 N N N 35.325 10.998 41.347 -3.743 -1.692 0.553 C24 XCF 15 XCF C25 C25 C 0 1 N N N 36.397 11.327 42.345 -4.347 -2.894 1.283 C25 XCF 16 XCF C26 C26 C 0 1 N N N 35.908 12.382 41.393 -5.232 -2.011 0.400 C26 XCF 17 XCF O13 O13 O 0 1 N N N 33.520 11.710 42.869 -2.490 -0.743 -1.277 O13 XCF 18 XCF C12 C12 C 0 1 Y N N 32.271 12.299 42.968 -1.618 0.067 -0.623 C12 XCF 19 XCF C15 C15 C 0 1 Y N N 31.928 13.074 44.089 -1.714 1.446 -0.705 C15 XCF 20 XCF O16 O16 O 0 1 N N N 32.773 13.368 45.150 -2.696 2.019 -1.453 O16 XCF 21 XCF C17 C17 C 0 1 N N N 34.095 13.857 44.930 -3.912 2.353 -0.781 C17 XCF 22 XCF C18 C18 C 0 1 Y N N 30.626 13.559 44.201 -0.801 2.243 -0.020 C18 XCF 23 XCF C21 C21 C 0 1 Y N N 29.680 13.319 43.204 0.199 1.663 0.748 C21 XCF 24 XCF O19 O19 O 0 1 N N N 30.311 14.306 45.315 -0.893 3.597 -0.100 O19 XCF 25 XCF C20 C20 C 0 1 N N N 29.015 14.891 45.326 0.075 4.357 0.627 C20 XCF 26 XCF HN4 HN4 H 0 1 N N N 26.548 6.885 40.048 6.497 -0.605 -1.708 HN4 XCF 27 XCF HN4A HN4A H 0 0 N N N 27.299 6.538 41.456 5.976 -2.186 -1.941 HN4A XCF 28 XCF H1 H1 H 0 1 N N N 29.619 10.242 42.614 2.087 -2.634 0.374 H1 XCF 29 XCF HN7 HN7 H 0 1 N N N 26.639 12.446 39.754 4.037 2.358 0.944 HN7 XCF 30 XCF HN7A HN7A H 0 0 N N N 27.388 11.684 38.519 2.612 1.852 1.676 HN7A XCF 31 XCF H9 H9 H 0 1 N N N 29.482 12.484 40.023 1.038 -1.278 2.081 H9 XCF 32 XCF H9A H9A H 0 1 N N N 28.190 13.094 41.162 1.670 0.340 2.471 H9A XCF 33 XCF H27 H27 H 0 1 N N N 31.073 11.296 39.909 0.363 -2.487 0.570 H27 XCF 34 XCF H28 H28 H 0 1 N N N 33.197 10.201 39.796 -1.571 -3.769 -0.141 H28 XCF 35 XCF H14 H14 H 0 1 N N N 33.839 9.785 42.328 -3.362 -2.610 -1.355 H14 XCF 36 XCF H24 H24 H 0 1 N N N 35.196 10.236 40.565 -3.473 -0.823 1.153 H24 XCF 37 XCF H25 H25 H 0 1 N N N 36.393 11.291 43.444 -4.096 -3.887 0.909 H25 XCF 38 XCF H25A H25A H 0 0 N N N 37.374 10.905 42.625 -4.474 -2.816 2.362 H25A XCF 39 XCF H26 H26 H 0 1 N N N 36.441 12.965 40.628 -5.941 -1.351 0.900 H26 XCF 40 XCF H26A H26A H 0 0 N N N 35.513 13.405 41.480 -5.563 -2.422 -0.553 H26A XCF 41 XCF H17 H17 H 0 1 N N N 34.265 13.983 43.851 -4.322 1.461 -0.307 H17 XCF 42 XCF H17A H17A H 0 0 N N N 34.216 14.826 45.436 -3.711 3.108 -0.021 H17A XCF 43 XCF H17B H17B H 0 0 N N N 34.823 13.139 45.334 -4.630 2.744 -1.501 H17B XCF 44 XCF H21 H21 H 0 1 N N N 28.674 13.698 43.311 0.900 2.290 1.279 H21 XCF 45 XCF H20 H20 H 0 1 N N N 28.689 15.042 46.366 -0.001 4.120 1.688 H20 XCF 46 XCF H20A H20A H 0 0 N N N 29.046 15.860 44.807 1.074 4.110 0.270 H20A XCF 47 XCF H20B H20B H 0 0 N N N 28.307 14.223 44.814 -0.112 5.420 0.478 H20B XCF 48 # 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 XCF N4 C3 SING N N 1 XCF C3 N5 DOUB Y N 2 XCF C3 N2 SING Y N 3 XCF N5 C6 SING Y N 4 XCF N2 C1 DOUB Y N 5 XCF C1 C8 SING Y N 6 XCF C8 C6 DOUB Y N 7 XCF C8 C9 SING N N 8 XCF C6 N7 SING N N 9 XCF C9 C10 SING N N 10 XCF C10 C11 DOUB Y N 11 XCF C10 C21 SING Y N 12 XCF C11 C27 SING N N 13 XCF C11 C12 SING Y N 14 XCF C27 C28 DOUB N N 15 XCF C28 C14 SING N N 16 XCF C14 C24 SING N N 17 XCF C14 O13 SING N N 18 XCF C24 C25 SING N N 19 XCF C24 C26 SING N N 20 XCF C25 C26 SING N N 21 XCF O13 C12 SING N N 22 XCF C12 C15 DOUB Y N 23 XCF C15 O16 SING N N 24 XCF C15 C18 SING Y N 25 XCF O16 C17 SING N N 26 XCF C18 C21 DOUB Y N 27 XCF C18 O19 SING N N 28 XCF O19 C20 SING N N 29 XCF N4 HN4 SING N N 30 XCF N4 HN4A SING N N 31 XCF C1 H1 SING N N 32 XCF N7 HN7 SING N N 33 XCF N7 HN7A SING N N 34 XCF C9 H9 SING N N 35 XCF C9 H9A SING N N 36 XCF C27 H27 SING N N 37 XCF C28 H28 SING N N 38 XCF C14 H14 SING N N 39 XCF C24 H24 SING N N 40 XCF C25 H25 SING N N 41 XCF C25 H25A SING N N 42 XCF C26 H26 SING N N 43 XCF C26 H26A SING N N 44 XCF C17 H17 SING N N 45 XCF C17 H17A SING N N 46 XCF C17 H17B SING N N 47 XCF C21 H21 SING N N 48 XCF C20 H20 SING N N 49 XCF C20 H20A SING N N 50 XCF C20 H20B SING N N 51 # 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 XCF SMILES ACDLabs 10.04 "n1cc(c(nc1N)N)Cc3cc(OC)c(OC)c2OC(C=Cc23)C4CC4" XCF SMILES_CANONICAL CACTVS 3.341 "COc1cc(Cc2cnc(N)nc2N)c3C=C[C@H](Oc3c1OC)C4CC4" XCF SMILES CACTVS 3.341 "COc1cc(Cc2cnc(N)nc2N)c3C=C[CH](Oc3c1OC)C4CC4" XCF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COc1cc(c2c(c1OC)O[C@@H](C=C2)C3CC3)Cc4cnc(nc4N)N" XCF SMILES "OpenEye OEToolkits" 1.5.0 "COc1cc(c2c(c1OC)OC(C=C2)C3CC3)Cc4cnc(nc4N)N" XCF InChI InChI 1.03 "InChI=1S/C19H22N4O3/c1-24-15-8-11(7-12-9-22-19(21)23-18(12)20)13-5-6-14(10-3-4-10)26-16(13)17(15)25-2/h5-6,8-10,14H,3-4,7H2,1-2H3,(H4,20,21,22,23)/t14-/m0/s1" XCF InChIKey InChI 1.03 HWJPWWYTGBZDEG-AWEZNQCLSA-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 XCF "SYSTEMATIC NAME" ACDLabs 10.04 "5-{[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl}pyrimidine-2,4-diamine" XCF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[[(2R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl]methyl]pyrimidine-2,4-diamine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site XCF "Create component" 2009-01-22 PDBJ XCF "Modify aromatic_flag" 2011-06-04 RCSB XCF "Modify descriptor" 2011-06-04 RCSB #