data_MA9 # _chem_comp.id MA9 _chem_comp.name "(3R,4R)-1-{6-[3-(METHYLSULFONYL)PHENYL]PYRIMIDIN-4-YL}-4-(2,4,5-TRIFLUOROPHENYL)PIPERIDIN-3-AMINE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H21 F3 N4 O2 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-02-06 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 462.488 _chem_comp.one_letter_code ? _chem_comp.three_letter_code MA9 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _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 MA9 C5 C5 C 0 1 Y N N 12.569 57.479 17.554 4.152 -6.335 -1.972 C5 MA9 1 MA9 C6 C6 C 0 1 Y N N 11.467 57.770 18.379 5.458 -5.855 -2.067 C6 MA9 2 MA9 C7 C7 C 0 1 Y N N 11.450 57.337 19.717 5.934 -4.939 -1.130 C7 MA9 3 MA9 C8 C8 C 0 1 Y N N 12.534 56.613 20.243 5.105 -4.503 -0.097 C8 MA9 4 MA9 C10 C10 C 0 1 Y N N 14.809 55.578 19.776 2.938 -4.528 1.070 C10 MA9 5 MA9 C15 C15 C 0 1 N N N 17.961 52.755 23.773 -0.864 -0.456 0.502 C15 MA9 6 MA9 C17 C17 C 0 1 Y N N 18.088 52.942 26.224 -1.618 1.785 1.357 C17 MA9 7 MA9 C21 C21 C 0 1 Y N N 18.754 51.611 28.540 -2.289 4.389 0.639 C21 MA9 8 MA9 C24 C24 C 0 1 Y N N 18.812 53.604 27.195 -2.909 2.253 1.583 C24 MA9 9 MA9 C26 C26 C 0 1 N N S 16.383 54.276 24.917 -0.107 0.284 2.790 C26 MA9 10 MA9 C28 C28 C 0 1 N N N 16.372 55.210 23.715 0.230 -1.178 3.124 C28 MA9 11 MA9 F25 F25 F 0 1 N N N 19.169 54.882 26.998 -3.834 1.463 2.144 F25 MA9 12 MA9 C23 C23 C 0 1 Y N N 19.146 52.938 28.375 -3.245 3.558 1.223 C23 MA9 13 MA9 F22 F22 F 0 1 N N N 19.053 50.954 29.660 -2.612 5.642 0.294 F22 MA9 14 MA9 C19 C19 C 0 1 Y N N 18.050 50.951 27.559 -0.997 3.915 0.415 C19 MA9 15 MA9 F F F 0 1 N N N 17.686 49.674 27.735 -0.079 4.713 -0.146 F MA9 16 MA9 C18 C18 C 0 1 Y N N 17.711 51.612 26.396 -0.660 2.610 0.774 C18 MA9 17 MA9 C16 C16 C 0 1 N N S 17.772 53.666 24.978 -1.248 0.362 1.747 C16 MA9 18 MA9 C14 C14 C 0 1 N N N 18.130 53.656 22.579 -0.517 -1.900 0.858 C14 MA9 19 MA9 N27 N27 N 0 1 N N N 16.077 54.999 26.131 -0.476 0.994 4.019 N27 MA9 20 MA9 N N N 0 1 N N N 16.949 54.515 22.549 0.517 -1.934 1.896 N MA9 21 MA9 C12 C12 C 0 1 Y N N 16.401 54.695 21.282 1.344 -3.058 2.009 C12 MA9 22 MA9 C11 C11 C 0 1 Y N N 15.253 55.469 21.083 2.137 -3.415 0.918 C11 MA9 23 MA9 N29 N29 N 0 1 Y N N 17.025 54.097 20.219 1.362 -3.778 3.168 N29 MA9 24 MA9 C30 C30 C 0 1 Y N N 16.555 54.223 18.962 2.186 -4.843 3.192 C30 MA9 25 MA9 N31 N31 N 0 1 Y N N 15.455 54.960 18.749 2.988 -5.269 2.197 N31 MA9 26 MA9 C9 C9 C 0 1 Y N N 13.619 56.344 19.403 3.796 -4.982 0.001 C9 MA9 27 MA9 C32 C32 C 0 1 Y N N 13.629 56.766 18.084 3.322 -5.899 -0.939 C32 MA9 28 MA9 S S S 0 1 N N N 12.701 57.918 16.013 3.555 -7.482 -3.145 S MA9 29 MA9 O O O 0 1 N N N 13.731 58.933 15.890 4.699 -8.189 -3.704 O MA9 30 MA9 O4 O4 O 0 1 N N N 11.423 58.419 15.551 2.459 -8.237 -2.553 O4 MA9 31 MA9 C C C 0 1 N N N 13.124 56.565 15.115 2.855 -6.474 -4.432 C MA9 32 MA9 H6 H6 H 0 1 N N N 10.631 58.328 17.983 6.113 -6.188 -2.868 H6 MA9 33 MA9 H7 H7 H 0 1 N N N 10.600 57.562 20.344 6.951 -4.565 -1.205 H7 MA9 34 MA9 H8 H8 H 0 1 N N N 12.529 56.274 21.268 5.491 -3.788 0.626 H8 MA9 35 MA9 H151 1H15 H 0 0 N N N 17.085 52.103 23.642 -0.003 0.013 0.005 H151 MA9 36 MA9 H152 2H15 H 0 0 N N N 18.836 52.101 23.903 -1.686 -0.450 -0.224 H152 MA9 37 MA9 H26 H26 H 0 1 N N N 15.617 53.493 24.818 0.787 0.772 2.379 H26 MA9 38 MA9 H281 1H28 H 0 0 N N N 16.969 56.106 23.941 1.102 -1.201 3.792 H281 MA9 39 MA9 H282 2H28 H 0 0 N N N 15.337 55.507 23.490 -0.600 -1.661 3.656 H282 MA9 40 MA9 H23 H23 H 0 1 N N N 19.701 53.445 29.151 -4.251 3.928 1.398 H23 MA9 41 MA9 H18 H18 H 0 1 N N N 17.156 51.101 25.623 0.349 2.249 0.595 H18 MA9 42 MA9 H16 H16 H 0 1 N N N 18.479 54.509 24.962 -2.158 -0.076 2.179 H16 MA9 43 MA9 H141 1H14 H 0 0 N N N 18.202 53.064 21.655 -1.409 -2.433 1.210 H141 MA9 44 MA9 H142 2H14 H 0 0 N N N 19.054 54.248 22.652 -0.164 -2.410 -0.047 H142 MA9 45 MA9 H271 1H27 H 0 0 N N N 16.006 54.356 26.894 -0.220 1.951 4.096 H271 MA9 46 MA9 H272 2H27 H 0 0 N N N 16.805 55.659 26.318 -0.778 0.450 4.795 H272 MA9 47 MA9 H11 H11 H 0 1 N N N 14.742 55.954 21.902 2.117 -2.838 0.001 H11 MA9 48 MA9 H30 H30 H 0 1 N N N 17.057 53.737 18.138 2.206 -5.419 4.109 H30 MA9 49 MA9 H32 H32 H 0 1 N N N 14.479 56.534 17.459 2.304 -6.276 -0.868 H32 MA9 50 MA9 H1 1H H 0 1 N N N 13.217 56.842 14.055 3.095 -5.431 -4.221 H1 MA9 51 MA9 H2 2H H 0 1 N N N 14.086 56.171 15.476 3.288 -6.781 -5.385 H2 MA9 52 MA9 H3 3H H 0 1 N N N 12.347 55.794 15.226 1.774 -6.624 -4.437 H3 MA9 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 MA9 C5 S SING N N 1 MA9 C5 C32 DOUB Y N 2 MA9 C5 C6 SING Y N 3 MA9 C6 C7 DOUB Y N 4 MA9 C6 H6 SING N N 5 MA9 C7 C8 SING Y N 6 MA9 C7 H7 SING N N 7 MA9 C8 C9 DOUB Y N 8 MA9 C8 H8 SING N N 9 MA9 C10 N31 SING Y N 10 MA9 C10 C9 SING Y N 11 MA9 C10 C11 DOUB Y N 12 MA9 C15 C14 SING N N 13 MA9 C15 C16 SING N N 14 MA9 C15 H151 SING N N 15 MA9 C15 H152 SING N N 16 MA9 C17 C16 SING N N 17 MA9 C17 C18 DOUB Y N 18 MA9 C17 C24 SING Y N 19 MA9 C21 C19 DOUB Y N 20 MA9 C21 C23 SING Y N 21 MA9 C21 F22 SING N N 22 MA9 C24 F25 SING N N 23 MA9 C24 C23 DOUB Y N 24 MA9 C26 C28 SING N N 25 MA9 C26 C16 SING N N 26 MA9 C26 N27 SING N N 27 MA9 C26 H26 SING N N 28 MA9 C28 N SING N N 29 MA9 C28 H281 SING N N 30 MA9 C28 H282 SING N N 31 MA9 C23 H23 SING N N 32 MA9 C19 C18 SING Y N 33 MA9 C19 F SING N N 34 MA9 C18 H18 SING N N 35 MA9 C16 H16 SING N N 36 MA9 C14 N SING N N 37 MA9 C14 H141 SING N N 38 MA9 C14 H142 SING N N 39 MA9 N27 H271 SING N N 40 MA9 N27 H272 SING N N 41 MA9 N C12 SING N N 42 MA9 C12 N29 DOUB Y N 43 MA9 C12 C11 SING Y N 44 MA9 C11 H11 SING N N 45 MA9 N29 C30 SING Y N 46 MA9 C30 N31 DOUB Y N 47 MA9 C30 H30 SING N N 48 MA9 C9 C32 SING Y N 49 MA9 C32 H32 SING N N 50 MA9 S C SING N N 51 MA9 S O4 DOUB N N 52 MA9 S O DOUB N N 53 MA9 C H1 SING N N 54 MA9 C H2 SING N N 55 MA9 C H3 SING N N 56 # 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 MA9 SMILES ACDLabs 10.04 "O=S(=O)(c1cccc(c1)c2ncnc(c2)N4CCC(c3cc(F)c(F)cc3F)C(N)C4)C" MA9 SMILES_CANONICAL CACTVS 3.341 "C[S](=O)(=O)c1cccc(c1)c2cc(ncn2)N3CC[C@@H]([C@@H](N)C3)c4cc(F)c(F)cc4F" MA9 SMILES CACTVS 3.341 "C[S](=O)(=O)c1cccc(c1)c2cc(ncn2)N3CC[CH]([CH](N)C3)c4cc(F)c(F)cc4F" MA9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)c1cccc(c1)c2cc(ncn2)N3CC[C@@H]([C@H](C3)N)c4cc(c(cc4F)F)F" MA9 SMILES "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)c1cccc(c1)c2cc(ncn2)N3CCC(C(C3)N)c4cc(c(cc4F)F)F" MA9 InChI InChI 1.03 "InChI=1S/C22H21F3N4O2S/c1-32(30,31)14-4-2-3-13(7-14)21-10-22(28-12-27-21)29-6-5-15(20(26)11-29)16-8-18(24)19(25)9-17(16)23/h2-4,7-10,12,15,20H,5-6,11,26H2,1H3/t15-,20+/m1/s1" MA9 InChIKey InChI 1.03 GOBIXGZJSMAOFV-QRWLVFNGSA-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 MA9 "SYSTEMATIC NAME" ACDLabs 10.04 "(3R,4R)-1-{6-[3-(methylsulfonyl)phenyl]pyrimidin-4-yl}-4-(2,4,5-trifluorophenyl)piperidin-3-amine" MA9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R,4R)-1-[6-(3-methylsulfonylphenyl)pyrimidin-4-yl]-4-(2,4,5-trifluorophenyl)piperidin-3-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 MA9 "Create component" 2007-02-06 EBI MA9 "Modify aromatic_flag" 2011-06-04 RCSB MA9 "Modify descriptor" 2011-06-04 RCSB #