data_18G # _chem_comp.id 18G _chem_comp.name "5-[3-(2,5-dimethoxy-4-phenylphenyl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H24 N4 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "5-[(3S)-3-(2,5-dimethoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-11-01 _chem_comp.pdbx_modified_date 2021-03-13 _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 388.462 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 18G _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 4HOE _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 18G N2 N2 N 0 1 N N N -1.967 1.309 26.291 7.020 -2.375 -0.908 N2 18G 1 18G C14 C14 C 0 1 Y N N -1.318 2.002 27.234 5.927 -1.574 -0.632 C14 18G 2 18G N1 N1 N 0 1 Y N N 0.018 1.822 27.328 6.129 -0.330 -0.223 N1 18G 3 18G C13 C13 C 0 1 Y N N 0.671 2.539 28.266 5.106 0.469 0.052 C13 18G 4 18G N N N 0 1 N N N 1.997 2.383 28.328 5.321 1.767 0.478 N 18G 5 18G N3 N3 N 0 1 Y N N -2.051 2.832 28.004 4.709 -2.072 -0.789 N3 18G 6 18G C15 C15 C 0 1 Y N N -1.402 3.541 28.940 3.635 -1.343 -0.536 C15 18G 7 18G C16 C16 C 0 1 N N N -2.241 4.446 29.793 2.257 -1.924 -0.719 C16 18G 8 18G C12 C12 C 0 1 Y N N -0.008 3.441 29.130 3.795 -0.028 -0.098 C12 18G 9 18G C11 C11 C 0 1 N N N 0.747 4.151 30.117 2.659 0.797 0.186 C11 18G 10 18G C10 C10 C 0 1 N N N 1.440 4.702 30.910 1.728 1.472 0.420 C10 18G 11 18G C8 C8 C 0 1 N N S 2.274 5.386 31.890 0.560 2.319 0.712 C8 18G 12 18G C9 C9 C 0 1 N N N 3.294 4.400 32.495 0.608 2.766 2.175 C9 18G 13 18G C7 C7 C 0 1 Y N N 1.505 6.041 33.000 -0.703 1.535 0.467 C7 18G 14 18G C1 C1 C 0 1 Y N N 1.899 7.259 33.556 -1.619 1.977 -0.478 C1 18G 15 18G O O O 0 1 N N N 2.984 7.845 32.961 -1.373 3.116 -1.180 O 18G 16 18G C C C 0 1 N N N 3.598 8.946 33.627 -2.358 3.513 -2.136 C 18G 17 18G C6 C6 C 0 1 Y N N 0.393 5.403 33.545 -0.943 0.376 1.180 C6 18G 18 18G C4 C4 C 0 1 Y N N -0.288 5.944 34.618 -2.103 -0.349 0.958 C4 18G 19 18G O1 O1 O 0 1 N N N -1.391 5.361 35.181 -2.338 -1.488 1.660 O1 18G 20 18G C5 C5 C 0 1 N N N -1.850 4.134 34.621 -1.346 -1.881 2.611 C5 18G 21 18G C3 C3 C 0 1 Y N N 0.125 7.150 35.192 -3.031 0.095 0.012 C3 18G 22 18G C2 C2 C 0 1 Y N N 1.222 7.805 34.633 -2.781 1.261 -0.707 C2 18G 23 18G C17 C17 C 0 1 Y N N -0.530 7.722 36.403 -4.274 -0.677 -0.229 C17 18G 24 18G C22 C22 C 0 1 Y N N -0.928 9.057 36.440 -5.510 -0.032 -0.224 C22 18G 25 18G C21 C21 C 0 1 Y N N -1.582 9.572 37.549 -6.663 -0.756 -0.450 C21 18G 26 18G C20 C20 C 0 1 Y N N -1.844 8.766 38.637 -6.595 -2.117 -0.682 C20 18G 27 18G C19 C19 C 0 1 Y N N -1.451 7.444 38.621 -5.371 -2.762 -0.688 C19 18G 28 18G C18 C18 C 0 1 Y N N -0.796 6.924 37.515 -4.211 -2.048 -0.469 C18 18G 29 18G H1 H1 H 0 1 N N N -1.316 0.742 25.786 7.918 -2.024 -0.802 H1 18G 30 18G H2 H2 H 0 1 N N N -2.655 0.724 26.721 6.889 -3.290 -1.204 H2 18G 31 18G H3 H3 H 0 1 N N N 2.289 1.727 27.632 6.227 2.101 0.577 H3 18G 32 18G H4 H4 H 0 1 N N N 2.444 3.263 28.166 4.567 2.344 0.676 H4 18G 33 18G H5 H5 H 0 1 N N N -3.295 4.366 29.487 1.932 -2.389 0.211 H5 18G 34 18G H6 H6 H 0 1 N N N -2.142 4.151 30.848 1.561 -1.130 -0.990 H6 18G 35 18G H7 H7 H 0 1 N N N -1.901 5.485 29.670 2.280 -2.672 -1.511 H7 18G 36 18G H8 H8 H 0 1 N N N 2.846 6.169 31.370 0.576 3.196 0.064 H8 18G 37 18G H9 H9 H 0 1 N N N 3.919 4.925 33.233 1.522 3.333 2.352 H9 18G 38 18G H10 H10 H 0 1 N N N 2.759 3.575 32.988 -0.257 3.393 2.391 H10 18G 39 18G H11 H11 H 0 1 N N N 3.932 3.996 31.695 0.592 1.890 2.823 H11 18G 40 18G H12 H12 H 0 1 N N N 4.449 9.307 33.031 -2.476 2.728 -2.883 H12 18G 41 18G H13 H13 H 0 1 N N N 2.865 9.757 33.747 -3.309 3.680 -1.631 H13 18G 42 18G H14 H14 H 0 1 N N N 3.954 8.624 34.617 -2.040 4.434 -2.625 H14 18G 43 18G H15 H15 H 0 1 N N N 0.057 4.468 33.121 -0.225 0.034 1.910 H15 18G 44 18G H16 H16 H 0 1 N N N -2.737 3.788 35.172 -1.656 -2.804 3.100 H16 18G 45 18G H17 H17 H 0 1 N N N -2.113 4.289 33.564 -0.396 -2.042 2.100 H17 18G 46 18G H18 H18 H 0 1 N N N -1.055 3.378 34.694 -1.227 -1.096 3.358 H18 18G 47 18G H19 H19 H 0 1 N N N 1.547 8.749 35.045 -3.493 1.606 -1.443 H19 18G 48 18G H20 H20 H 0 1 N N N -0.725 9.698 35.595 -5.565 1.031 -0.042 H20 18G 49 18G H21 H21 H 0 1 N N N -1.887 10.608 37.561 -7.622 -0.257 -0.445 H21 18G 50 18G H22 H22 H 0 1 N N N -2.355 9.169 39.499 -7.500 -2.679 -0.858 H22 18G 51 18G H23 H23 H 0 1 N N N -1.654 6.812 39.473 -5.324 -3.826 -0.870 H23 18G 52 18G H24 H24 H 0 1 N N N -0.488 5.889 37.515 -3.255 -2.552 -0.479 H24 18G 53 # # 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 18G N2 C14 SING N N 1 18G C14 N1 DOUB Y N 2 18G C14 N3 SING Y N 3 18G N1 C13 SING Y N 4 18G N3 C15 DOUB Y N 5 18G C13 N SING N N 6 18G C13 C12 DOUB Y N 7 18G C15 C12 SING Y N 8 18G C15 C16 SING N N 9 18G C12 C11 SING N N 10 18G C11 C10 TRIP N N 11 18G C10 C8 SING N N 12 18G C8 C9 SING N N 13 18G C8 C7 SING N N 14 18G O C1 SING N N 15 18G O C SING N N 16 18G C7 C6 DOUB Y N 17 18G C7 C1 SING Y N 18 18G C6 C4 SING Y N 19 18G C1 C2 DOUB Y N 20 18G C4 O1 SING N N 21 18G C4 C3 DOUB Y N 22 18G C5 O1 SING N N 23 18G C2 C3 SING Y N 24 18G C3 C17 SING N N 25 18G C17 C22 DOUB Y N 26 18G C17 C18 SING Y N 27 18G C22 C21 SING Y N 28 18G C18 C19 DOUB Y N 29 18G C21 C20 DOUB Y N 30 18G C19 C20 SING Y N 31 18G N2 H1 SING N N 32 18G N2 H2 SING N N 33 18G N H3 SING N N 34 18G N H4 SING N N 35 18G C16 H5 SING N N 36 18G C16 H6 SING N N 37 18G C16 H7 SING N N 38 18G C8 H8 SING N N 39 18G C9 H9 SING N N 40 18G C9 H10 SING N N 41 18G C9 H11 SING N N 42 18G C H12 SING N N 43 18G C H13 SING N N 44 18G C H14 SING N N 45 18G C6 H15 SING N N 46 18G C5 H16 SING N N 47 18G C5 H17 SING N N 48 18G C5 H18 SING N N 49 18G C2 H19 SING N N 50 18G C22 H20 SING N N 51 18G C21 H21 SING N N 52 18G C20 H22 SING N N 53 18G C19 H23 SING N N 54 18G C18 H24 SING N N 55 # # 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 18G SMILES ACDLabs 12.01 "C(#CC(c2cc(OC)c(c1ccccc1)cc2OC)C)c3c(nc(nc3C)N)N" 18G InChI InChI 1.03 "InChI=1S/C23H24N4O2/c1-14(10-11-17-15(2)26-23(25)27-22(17)24)18-12-21(29-4)19(13-20(18)28-3)16-8-6-5-7-9-16/h5-9,12-14H,1-4H3,(H4,24,25,26,27)/t14-/m0/s1" 18G InChIKey InChI 1.03 TWSMBNBBXDQFQK-AWEZNQCLSA-N 18G SMILES_CANONICAL CACTVS 3.370 "COc1cc(c(OC)cc1[C@@H](C)C#Cc2c(C)nc(N)nc2N)c3ccccc3" 18G SMILES CACTVS 3.370 "COc1cc(c(OC)cc1[CH](C)C#Cc2c(C)nc(N)nc2N)c3ccccc3" 18G SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1c(c(nc(n1)N)N)C#C[C@H](C)c2cc(c(cc2OC)c3ccccc3)OC" 18G SMILES "OpenEye OEToolkits" 1.7.6 "Cc1c(c(nc(n1)N)N)C#CC(C)c2cc(c(cc2OC)c3ccccc3)OC" # # 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 18G "SYSTEMATIC NAME" ACDLabs 12.01 "5-[(3S)-3-(2,5-dimethoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine" 18G "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "5-[(3S)-3-(2,5-dimethoxy-4-phenyl-phenyl)but-1-ynyl]-6-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 18G "Create component" 2012-11-01 RCSB 18G "Initial release" 2014-03-19 RCSB 18G "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 18G _pdbx_chem_comp_synonyms.name "5-[(3S)-3-(2,5-dimethoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##