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                    2008-10-14 
_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 N 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 InChI            InChI                1.02b InChI=1/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                1.02b GOBIXGZJSMAOFV-QRWLVFNGBZ                                                                                                                                                    
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                                                                                                                   
# 
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   
# 
