data_CM4
# 
_chem_comp.id                                    CM4 
_chem_comp.name                                  (2R,3R,4S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]CHROMAN-6-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H31 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                        445.550 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CM4 
_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        1YIM 
_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 
CM4 C1   C1   C 0 1 N N R 31.346 -0.610 28.401 0.193  1.462  2.084  C1   CM4 1  
CM4 C2   C2   C 0 1 N N R 31.534 -2.030 27.862 1.138  0.445  1.430  C2   CM4 2  
CM4 O3   O3   O 0 1 N N N 30.301 -2.737 28.114 0.879  -0.840 1.972  O3   CM4 3  
CM4 C4   C4   C 0 1 Y N N 29.100 -2.234 27.760 1.080  -0.843 3.312  C4   CM4 4  
CM4 C5   C5   C 0 1 Y N N 28.075 -3.154 27.558 1.401  -2.068 3.900  C5   CM4 5  
CM4 C6   C6   C 0 1 Y N N 26.804 -2.716 27.184 1.610  -2.162 5.259  C6   CM4 6  
CM4 C7   C7   C 0 1 Y N N 26.541 -1.356 27.029 1.501  -1.031 6.055  C7   CM4 7  
CM4 O8   O8   O 0 1 N N N 25.299 -0.988 26.628 1.702  -1.119 7.398  O8   CM4 8  
CM4 C9   C9   C 0 1 Y N N 27.570 -0.428 27.248 1.188  0.185  5.476  C9   CM4 9  
CM4 C10  C10  C 0 1 Y N N 28.879 -0.858 27.613 0.980  0.280  4.109  C10  CM4 10 
CM4 C11  C11  C 0 1 N N S 30.047 0.110  27.848 0.654  1.639  3.535  C11  CM4 11 
CM4 C12  C12  C 0 1 N N N 29.597 1.318  28.667 1.901  2.524  3.574  C12  CM4 12 
CM4 C13  C13  C 0 1 Y N N 32.667 0.154  28.235 -1.220 0.943  2.053  C13  CM4 13 
CM4 C14  C14  C 0 1 Y N N 32.885 1.011  27.146 -2.087 1.358  1.059  C14  CM4 14 
CM4 C15  C15  C 0 1 Y N N 34.126 1.673  27.085 -3.382 0.879  1.026  C15  CM4 15 
CM4 C16  C16  C 0 1 Y N N 35.125 1.478  28.053 -3.816 -0.010 1.997  C16  CM4 16 
CM4 O17  O17  O 0 1 N N N 36.307 2.147  27.956 -5.092 -0.478 1.970  O17  CM4 17 
CM4 C18  C18  C 0 1 Y N N 34.906 0.609  29.123 -2.947 -0.421 2.997  C18  CM4 18 
CM4 C19  C19  C 0 1 Y N N 33.644 -0.011 29.231 -1.651 0.056  3.023  C19  CM4 19 
CM4 C20  C20  C 0 1 Y N N 31.927 -2.223 26.404 0.902  0.421  -0.058 C20  CM4 20 
CM4 C21  C21  C 0 1 Y N N 32.898 -3.182 26.117 -0.025 -0.450 -0.596 C21  CM4 21 
CM4 C22  C22  C 0 1 Y N N 33.279 -3.438 24.783 -0.247 -0.470 -1.959 C22  CM4 22 
CM4 C23  C23  C 0 1 Y N N 32.769 -2.667 23.749 0.468  0.379  -2.790 C23  CM4 23 
CM4 C24  C24  C 0 1 Y N N 31.790 -1.710 23.995 1.403  1.249  -2.248 C24  CM4 24 
CM4 C25  C25  C 0 1 Y N N 31.390 -1.518 25.325 1.618  1.268  -0.884 C25  CM4 25 
CM4 O26  O26  O 0 1 N N N 33.106 -2.918 22.471 0.255  0.358  -4.132 O26  CM4 26 
CM4 C27  C27  C 0 1 N N N 33.712 -4.159 22.109 -0.749 -0.627 -4.375 C27  CM4 27 
CM4 C28  C28  C 0 1 N N N 34.020 -4.188 20.612 -1.038 -0.702 -5.876 C28  CM4 28 
CM4 N29  N29  N 0 1 N N N 32.797 -4.287 19.805 0.190  -1.068 -6.593 N29  CM4 29 
CM4 C30  C30  C 0 1 N N N 33.208 -4.332 18.391 1.150  0.035  -6.382 C30  CM4 30 
CM4 C31  C31  C 0 1 N N N 32.024 -3.801 17.581 1.832  0.234  -7.758 C31  CM4 31 
CM4 C32  C32  C 0 1 N N N 31.096 -3.158 18.621 0.650  -0.013 -8.732 C32  CM4 32 
CM4 C33  C33  C 0 1 N N N 31.920 -3.110 19.915 -0.155 -1.123 -8.025 C33  CM4 33 
CM4 H1   H1   H 0 1 N N N 31.125 -0.643 29.493 0.252  2.415  1.557  H1   CM4 34 
CM4 H2   H2   H 0 1 N N N 32.431 -2.418 28.400 2.172  0.724  1.632  H2   CM4 35 
CM4 H5   H5   H 0 1 N N N 28.270 -4.231 27.694 1.487  -2.951 3.284  H5   CM4 36 
CM4 H6   H6   H 0 1 N N N 26.000 -3.451 27.009 1.857  -3.115 5.703  H6   CM4 37 
CM4 HO8  HO8  H 0 1 N N N 25.120 -0.061 26.522 2.644  -0.963 7.550  HO8  CM4 38 
CM4 H9   H9   H 0 1 N N N 27.349 0.646  27.133 1.105  1.068  6.093  H9   CM4 39 
CM4 H11  H11  H 0 1 N N N 30.366 0.508  26.857 -0.141 2.102  4.117  H11  CM4 40 
CM4 H121 1H12 H 0 0 N N N 30.432 2.050  28.772 2.227  2.648  4.607  H121 CM4 41 
CM4 H122 2H12 H 0 0 N N N 28.683 1.825  28.278 2.697  2.056  2.995  H122 CM4 42 
CM4 H123 3H12 H 0 0 N N N 29.458 1.033  29.736 1.667  3.500  3.147  H123 CM4 43 
CM4 H14  H14  H 0 1 N N N 32.114 1.158  26.371 -1.748 2.051  0.303  H14  CM4 44 
CM4 H15  H15  H 0 1 N N N 34.322 2.368  26.251 -4.057 1.200  0.246  H15  CM4 45 
CM4 H17  H17  H 0 1 N N N 36.983 2.015  28.611 -5.626 0.134  2.492  H17  CM4 46 
CM4 H18  H18  H 0 1 N N N 35.705 0.418  29.860 -3.282 -1.114 3.754  H18  CM4 47 
CM4 H19  H19  H 0 1 N N N 33.417 -0.636 30.111 -0.973 -0.262 3.801  H19  CM4 48 
CM4 H21  H21  H 0 1 N N N 33.365 -3.739 26.946 -0.583 -1.111 0.050  H21  CM4 49 
CM4 H22  H22  H 0 1 N N N 33.985 -4.252 24.545 -0.976 -1.148 -2.378 H22  CM4 50 
CM4 H24  H24  H 0 1 N N N 31.349 -1.127 23.169 1.962  1.911  -2.893 H24  CM4 51 
CM4 H25  H25  H 0 1 N N N 30.608 -0.769 25.535 2.345  1.946  -0.461 H25  CM4 52 
CM4 H271 1H27 H 0 0 N N N 33.091 -5.030 22.421 -0.399 -1.598 -4.023 H271 CM4 53 
CM4 H272 2H27 H 0 0 N N N 34.618 -4.372 22.723 -1.661 -0.355 -3.843 H272 CM4 54 
CM4 H281 1H28 H 0 0 N N N 34.739 -5.003 20.361 -1.805 -1.454 -6.061 H281 CM4 55 
CM4 H282 2H28 H 0 0 N N N 34.637 -3.311 20.308 -1.388 0.268  -6.227 H282 CM4 56 
CM4 H301 1H30 H 0 0 N N N 33.552 -5.340 18.062 0.626  0.942  -6.083 H301 CM4 57 
CM4 H302 2H30 H 0 0 N N N 34.161 -3.789 18.190 1.889  -0.242 -5.630 H302 CM4 58 
CM4 H311 1H31 H 0 0 N N N 31.528 -4.571 16.945 2.625  -0.497 -7.911 H311 CM4 59 
CM4 H312 2H31 H 0 0 N N N 32.314 -3.118 16.749 2.215  1.250  -7.861 H312 CM4 60 
CM4 H321 1H32 H 0 0 N N N 30.114 -3.675 18.730 1.014  -0.358 -9.700 H321 CM4 61 
CM4 H322 2H32 H 0 0 N N N 30.686 -2.169 18.310 0.048  0.887  -8.845 H322 CM4 62 
CM4 H331 1H33 H 0 0 N N N 32.457 -2.148 20.086 0.114  -2.096 -8.435 H331 CM4 63 
CM4 H332 2H33 H 0 0 N N N 31.312 -3.072 20.849 -1.222 -0.946 -8.156 H332 CM4 64 
# 
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 
CM4 C1  C2   SING N N 1  
CM4 C1  C11  SING N N 2  
CM4 C1  C13  SING N N 3  
CM4 C1  H1   SING N N 4  
CM4 C2  O3   SING N N 5  
CM4 C2  C20  SING N N 6  
CM4 C2  H2   SING N N 7  
CM4 O3  C4   SING N N 8  
CM4 C4  C5   DOUB Y N 9  
CM4 C4  C10  SING Y N 10 
CM4 C5  C6   SING Y N 11 
CM4 C5  H5   SING N N 12 
CM4 C6  C7   DOUB Y N 13 
CM4 C6  H6   SING N N 14 
CM4 C7  O8   SING N N 15 
CM4 C7  C9   SING Y N 16 
CM4 O8  HO8  SING N N 17 
CM4 C9  C10  DOUB Y N 18 
CM4 C9  H9   SING N N 19 
CM4 C10 C11  SING N N 20 
CM4 C11 C12  SING N N 21 
CM4 C11 H11  SING N N 22 
CM4 C12 H121 SING N N 23 
CM4 C12 H122 SING N N 24 
CM4 C12 H123 SING N N 25 
CM4 C13 C14  DOUB Y N 26 
CM4 C13 C19  SING Y N 27 
CM4 C14 C15  SING Y N 28 
CM4 C14 H14  SING N N 29 
CM4 C15 C16  DOUB Y N 30 
CM4 C15 H15  SING N N 31 
CM4 C16 O17  SING N N 32 
CM4 C16 C18  SING Y N 33 
CM4 O17 H17  SING N N 34 
CM4 C18 C19  DOUB Y N 35 
CM4 C18 H18  SING N N 36 
CM4 C19 H19  SING N N 37 
CM4 C20 C21  DOUB Y N 38 
CM4 C20 C25  SING Y N 39 
CM4 C21 C22  SING Y N 40 
CM4 C21 H21  SING N N 41 
CM4 C22 C23  DOUB Y N 42 
CM4 C22 H22  SING N N 43 
CM4 C23 C24  SING Y N 44 
CM4 C23 O26  SING N N 45 
CM4 C24 C25  DOUB Y N 46 
CM4 C24 H24  SING N N 47 
CM4 C25 H25  SING N N 48 
CM4 O26 C27  SING N N 49 
CM4 C27 C28  SING N N 50 
CM4 C27 H271 SING N N 51 
CM4 C27 H272 SING N N 52 
CM4 C28 N29  SING N N 53 
CM4 C28 H281 SING N N 54 
CM4 C28 H282 SING N N 55 
CM4 N29 C30  SING N N 56 
CM4 N29 C33  SING N N 57 
CM4 C30 C31  SING N N 58 
CM4 C30 H301 SING N N 59 
CM4 C30 H302 SING N N 60 
CM4 C31 C32  SING N N 61 
CM4 C31 H311 SING N N 62 
CM4 C31 H312 SING N N 63 
CM4 C32 C33  SING N N 64 
CM4 C32 H321 SING N N 65 
CM4 C32 H322 SING N N 66 
CM4 C33 H331 SING N N 67 
CM4 C33 H332 SING N N 68 
# 
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 
CM4 SMILES           ACDLabs              10.04 Oc1ccc(cc1)C4C(c5c(OC4c3ccc(OCCN2CCCC2)cc3)ccc(O)c5)C                                                                                                                                   
CM4 InChI            InChI                1.02b InChI=1/C28H31NO4/c1-19-25-18-23(31)10-13-26(25)33-28(27(19)20-4-8-22(30)9-5-20)21-6-11-24(12-7-21)32-17-16-29-14-2-3-15-29/h4-13,18-19,27-28,30-31H,2-3,14-17H2,1H3/t19-,27-,28+/m1/s1 
CM4 InChIKey         InChI                1.02b XPVKGTWRXBSJKO-LHXLBICKBV                                                                                                                                                               
CM4 SMILES_CANONICAL CACTVS               3.341 C[C@H]1[C@@H]([C@@H](Oc2ccc(O)cc12)c3ccc(OCCN4CCCC4)cc3)c5ccc(O)cc5                                                                                                                     
CM4 SMILES           CACTVS               3.341 C[CH]1[CH]([CH](Oc2ccc(O)cc12)c3ccc(OCCN4CCCC4)cc3)c5ccc(O)cc5                                                                                                                          
CM4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]1c2cc(ccc2O[C@H]([C@H]1c3ccc(cc3)O)c4ccc(cc4)OCCN5CCCC5)O                                                                                                                        
CM4 SMILES           "OpenEye OEToolkits" 1.5.0 CC1c2cc(ccc2OC(C1c3ccc(cc3)O)c4ccc(cc4)OCCN5CCCC5)O                                                                                                                                     
# 
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 
CM4 "SYSTEMATIC NAME" ACDLabs              10.04 (2R,3R,4S)-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydro-2H-chromen-6-ol 
CM4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R,3R,4S)-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]chroman-6-ol                 
# 
