data_CM3
# 
_chem_comp.id                                    CM3 
_chem_comp.name                                  (2R,3R,4S)-5-FLUORO-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H32 F N O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-01-19 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        477.567 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CM3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1YIN 
_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 
CM3 C1   C1   C 0 1 N N R 31.621 -0.621 28.640 0.125  -1.444 2.263  C1   CM3 1  
CM3 C2   C2   C 0 1 N N R 31.833 -2.024 28.061 -0.960 -0.691 1.484  C2   CM3 2  
CM3 O3   O3   O 0 1 N N N 30.640 -2.787 28.321 -0.937 0.676  1.864  O3   CM3 3  
CM3 C4   C4   C 0 1 Y N N 29.441 -2.287 27.980 -1.170 0.806  3.193  C4   CM3 4  
CM3 C5   C5   C 0 1 Y N N 28.433 -3.221 27.731 -1.710 2.019  3.623  C5   CM3 5  
CM3 C6   C6   C 0 1 Y N N 27.151 -2.818 27.369 -1.967 2.241  4.959  C6   CM3 6  
CM3 C7   C7   C 0 1 Y N N 26.874 -1.453 27.295 -1.689 1.252  5.891  C7   CM3 7  
CM3 O8   O8   O 0 1 N N N 25.662 -0.988 26.946 -1.937 1.467  7.211  O8   CM3 8  
CM3 C9   C9   C 0 1 Y N N 27.899 -0.518 27.515 -1.158 0.043  5.468  C9   CM3 9  
CM3 F10  F10  F 0 1 N N N 27.549 0.748  27.281 -0.889 -0.923 6.372  F10  CM3 10 
CM3 C11  C11  C 0 1 Y N N 29.188 -0.895 27.940 -0.902 -0.179 4.123  C11  CM3 11 
CM3 C12  C12  C 0 1 N N S 30.316 0.096  28.199 -0.335 -1.520 3.723  C12  CM3 12 
CM3 C13  C13  C 0 1 N N N 30.089 1.272  29.137 -1.414 -2.596 3.865  C13  CM3 13 
CM3 C14  C14  C 0 1 Y N N 32.878 0.190  28.411 1.432  -0.698 2.175  C14  CM3 14 
CM3 C15  C15  C 0 1 Y N N 33.059 1.083  27.340 1.680  0.359  3.030  C15  CM3 15 
CM3 C16  C16  C 0 1 Y N N 34.262 1.771  27.222 2.879  1.042  2.956  C16  CM3 16 
CM3 C17  C17  C 0 1 Y N N 35.299 1.611  28.150 3.829  0.671  2.015  C17  CM3 17 
CM3 O18  O18  O 0 1 N N N 36.449 2.295  28.027 5.007  1.345  1.936  O18  CM3 18 
CM3 C19  C19  C 0 1 Y N N 35.109 0.734  29.216 3.575  -0.386 1.155  C19  CM3 19 
CM3 C20  C20  C 0 1 Y N N 33.916 0.037  29.333 2.377  -1.068 1.237  C20  CM3 20 
CM3 C21  C21  C 0 1 Y N N 32.158 -2.133 26.597 -0.693 -0.807 0.005  C21  CM3 21 
CM3 C22  C22  C 0 1 Y N N 33.130 -3.069 26.225 0.087  0.139  -0.631 C22  CM3 22 
CM3 C23  C23  C 0 1 Y N N 33.468 -3.265 24.880 0.338  0.031  -1.985 C23  CM3 23 
CM3 C24  C24  C 0 1 Y N N 32.917 -2.470 23.862 -0.202 -1.022 -2.708 C24  CM3 24 
CM3 C25  C25  C 0 1 Y N N 31.934 -1.542 24.231 -0.989 -1.968 -2.067 C25  CM3 25 
CM3 C26  C26  C 0 1 Y N N 31.556 -1.407 25.556 -1.233 -1.858 -0.712 C26  CM3 26 
CM3 O27  O27  O 0 1 N N N 33.265 -2.609 22.564 0.038  -1.127 -4.041 O27  CM3 27 
CM3 C28  C28  C 0 1 N N N 33.882 -3.839 22.146 0.868  -0.020 -4.400 C28  CM3 28 
CM3 C29  C29  C 0 1 N N N 34.124 -3.924 20.637 1.178  -0.079 -5.897 C29  CM3 29 
CM3 N30  N30  N 0 1 N N N 32.940 -4.226 19.805 -0.075 -0.018 -6.659 N30  CM3 30 
CM3 C31  C31  C 0 1 N N N 33.473 -4.261 18.443 -0.654 1.306  -6.414 C31  CM3 31 
CM3 C32  C32  C 0 1 N N N 32.358 -4.745 17.542 -1.967 1.448  -7.186 C32  CM3 32 
CM3 C33  C33  C 0 1 N N N 31.439 -3.532 17.363 -1.687 1.316  -8.686 C33  CM3 33 
CM3 C34  C34  C 0 1 N N N 30.877 -3.191 18.765 -0.970 -0.013 -8.942 C34  CM3 34 
CM3 C35  C35  C 0 1 N N N 31.944 -3.151 19.885 0.291  -0.079 -8.078 C35  CM3 35 
CM3 H1   H1   H 0 1 N N N 31.448 -0.732 29.736 0.243  -2.450 1.858  H1   CM3 36 
CM3 H2   H2   H 0 1 N N N 32.750 -2.406 28.568 -1.936 -1.117 1.714  H2   CM3 37 
CM3 H5   H5   H 0 1 N N N 28.654 -4.298 27.822 -1.928 2.793  2.902  H5   CM3 38 
CM3 H6   H6   H 0 1 N N N 26.371 -3.565 27.145 -2.384 3.184  5.280  H6   CM3 39 
CM3 HO8  HO8  H 0 1 N N N 25.473 -0.058 26.896 -2.843 1.172  7.377  HO8  CM3 40 
CM3 H12  H12  H 0 1 N N N 30.384 0.565  27.190 0.512  -1.767 4.362  H12  CM3 41 
CM3 H131 1H13 H 0 0 N N N 30.965 1.961  29.187 -1.741 -2.648 4.904  H131 CM3 42 
CM3 H132 2H13 H 0 0 N N N 29.152 1.787  28.820 -2.263 -2.344 3.229  H132 CM3 43 
CM3 H133 3H13 H 0 0 N N N 30.075 0.972  30.211 -1.007 -3.561 3.563  H133 CM3 44 
CM3 H15  H15  H 0 1 N N N 32.261 1.243  26.596 0.940  0.647  3.762  H15  CM3 45 
CM3 H16  H16  H 0 1 N N N 34.397 2.460  26.372 3.075  1.865  3.627  H16  CM3 46 
CM3 H18  H18  H 0 1 N N N 37.152 2.187  28.656 4.874  2.069  1.310  H18  CM3 47 
CM3 H19  H19  H 0 1 N N N 35.904 0.591  29.968 4.313  -0.676 0.422  H19  CM3 48 
CM3 H20  H20  H 0 1 N N N 33.790 -0.657 30.181 2.178  -1.892 0.567  H20  CM3 49 
CM3 H22  H22  H 0 1 N N N 33.638 -3.662 27.004 0.507  0.959  -0.068 H22  CM3 50 
CM3 H23  H23  H 0 1 N N N 34.183 -4.062 24.617 0.951  0.768  -2.482 H23  CM3 51 
CM3 H25  H25  H 0 1 N N N 31.451 -0.909 23.468 -1.411 -2.789 -2.628 H25  CM3 52 
CM3 H26  H26  H 0 1 N N N 30.746 -0.696 25.791 -1.846 -2.594 -0.213 H26  CM3 53 
CM3 H281 1H28 H 0 0 N N N 33.291 -4.716 22.500 0.349  0.910  -4.172 H281 CM3 54 
CM3 H282 2H28 H 0 0 N N N 34.830 -4.014 22.707 1.798  -0.065 -3.834 H282 CM3 55 
CM3 H291 1H29 H 0 0 N N N 34.933 -4.661 20.425 1.811  0.764  -6.170 H291 CM3 56 
CM3 H292 2H29 H 0 0 N N N 34.608 -2.986 20.279 1.697  -1.011 -6.124 H292 CM3 57 
CM3 H311 1H31 H 0 0 N N N 34.404 -4.869 18.353 -0.845 1.426  -5.348 H311 CM3 58 
CM3 H312 2H31 H 0 0 N N N 33.907 -3.287 18.118 0.045  2.074  -6.745 H312 CM3 59 
CM3 H321 1H32 H 0 0 N N N 31.836 -5.656 17.918 -2.405 2.426  -6.983 H321 CM3 60 
CM3 H322 2H32 H 0 0 N N N 32.713 -5.189 16.583 -2.659 0.666  -6.874 H322 CM3 61 
CM3 H331 1H33 H 0 0 N N N 30.645 -3.690 16.597 -1.054 2.140  -9.014 H331 CM3 62 
CM3 H332 2H33 H 0 0 N N N 31.941 -2.668 16.868 -2.627 1.335  -9.236 H332 CM3 63 
CM3 H341 1H34 H 0 0 N N N 30.054 -3.892 19.036 -0.694 -0.081 -9.994 H341 CM3 64 
CM3 H342 2H34 H 0 0 N N N 30.308 -2.233 18.734 -1.632 -0.839 -8.683 H342 CM3 65 
CM3 H351 1H35 H 0 0 N N N 32.446 -2.155 19.911 0.940  0.761  -8.321 H351 CM3 66 
CM3 H352 2H35 H 0 0 N N N 31.457 -3.144 20.888 0.817  -1.012 -8.277 H352 CM3 67 
# 
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 
CM3 C1  C2   SING N N 1  
CM3 C1  C12  SING N N 2  
CM3 C1  C14  SING N N 3  
CM3 C1  H1   SING N N 4  
CM3 C2  O3   SING N N 5  
CM3 C2  C21  SING N N 6  
CM3 C2  H2   SING N N 7  
CM3 O3  C4   SING N N 8  
CM3 C4  C5   DOUB Y N 9  
CM3 C4  C11  SING Y N 10 
CM3 C5  C6   SING Y N 11 
CM3 C5  H5   SING N N 12 
CM3 C6  C7   DOUB Y N 13 
CM3 C6  H6   SING N N 14 
CM3 C7  O8   SING N N 15 
CM3 C7  C9   SING Y N 16 
CM3 O8  HO8  SING N N 17 
CM3 C9  F10  SING N N 18 
CM3 C9  C11  DOUB Y N 19 
CM3 C11 C12  SING N N 20 
CM3 C12 C13  SING N N 21 
CM3 C12 H12  SING N N 22 
CM3 C13 H131 SING N N 23 
CM3 C13 H132 SING N N 24 
CM3 C13 H133 SING N N 25 
CM3 C14 C15  DOUB Y N 26 
CM3 C14 C20  SING Y N 27 
CM3 C15 C16  SING Y N 28 
CM3 C15 H15  SING N N 29 
CM3 C16 C17  DOUB Y N 30 
CM3 C16 H16  SING N N 31 
CM3 C17 O18  SING N N 32 
CM3 C17 C19  SING Y N 33 
CM3 O18 H18  SING N N 34 
CM3 C19 C20  DOUB Y N 35 
CM3 C19 H19  SING N N 36 
CM3 C20 H20  SING N N 37 
CM3 C21 C22  DOUB Y N 38 
CM3 C21 C26  SING Y N 39 
CM3 C22 C23  SING Y N 40 
CM3 C22 H22  SING N N 41 
CM3 C23 C24  DOUB Y N 42 
CM3 C23 H23  SING N N 43 
CM3 C24 C25  SING Y N 44 
CM3 C24 O27  SING N N 45 
CM3 C25 C26  DOUB Y N 46 
CM3 C25 H25  SING N N 47 
CM3 C26 H26  SING N N 48 
CM3 O27 C28  SING N N 49 
CM3 C28 C29  SING N N 50 
CM3 C28 H281 SING N N 51 
CM3 C28 H282 SING N N 52 
CM3 C29 N30  SING N N 53 
CM3 C29 H291 SING N N 54 
CM3 C29 H292 SING N N 55 
CM3 N30 C31  SING N N 56 
CM3 N30 C35  SING N N 57 
CM3 C31 C32  SING N N 58 
CM3 C31 H311 SING N N 59 
CM3 C31 H312 SING N N 60 
CM3 C32 C33  SING N N 61 
CM3 C32 H321 SING N N 62 
CM3 C32 H322 SING N N 63 
CM3 C33 C34  SING N N 64 
CM3 C33 H331 SING N N 65 
CM3 C33 H332 SING N N 66 
CM3 C34 C35  SING N N 67 
CM3 C34 H341 SING N N 68 
CM3 C34 H342 SING N N 69 
CM3 C35 H351 SING N N 70 
CM3 C35 H352 SING N N 71 
# 
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 
CM3 SMILES           ACDLabs              10.04 Fc5c(O)ccc4OC(c2ccc(OCCN1CCCCC1)cc2)C(c3ccc(O)cc3)C(c45)C                                                                                                                                   
CM3 InChI            InChI                1.02b InChI=1/C29H32FNO4/c1-19-26(20-5-9-22(32)10-6-20)29(35-25-14-13-24(33)28(30)27(19)25)21-7-11-23(12-8-21)34-18-17-31-15-3-2-4-16-31/h5-14,19,26,29,32-33H,2-4,15-18H2,1H3/t19-,26+,29-/m0/s1 
CM3 InChIKey         InChI                1.02b KOYRLVBQHJNLQX-IFVHXUSFBS                                                                                                                                                                   
CM3 SMILES_CANONICAL CACTVS               3.341 C[C@H]1[C@@H]([C@@H](Oc2ccc(O)c(F)c12)c3ccc(OCCN4CCCCC4)cc3)c5ccc(O)cc5                                                                                                                     
CM3 SMILES           CACTVS               3.341 C[CH]1[CH]([CH](Oc2ccc(O)c(F)c12)c3ccc(OCCN4CCCCC4)cc3)c5ccc(O)cc5                                                                                                                          
CM3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]1c2c(ccc(c2F)O)O[C@H]([C@H]1c3ccc(cc3)O)c4ccc(cc4)OCCN5CCCCC5                                                                                                                        
CM3 SMILES           "OpenEye OEToolkits" 1.5.0 CC1c2c(ccc(c2F)O)OC(C1c3ccc(cc3)O)c4ccc(cc4)OCCN5CCCCC5                                                                                                                                     
# 
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 
CM3 "SYSTEMATIC NAME" ACDLabs              10.04 (2R,3R,4S)-5-fluoro-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-3,4-dihydro-2H-chromen-6-ol 
CM3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R,3R,4S)-5-fluoro-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]chroman-6-ol                 
# 
