data_AP1
# 
_chem_comp.id                                    AP1 
_chem_comp.name                                  "{3-[3-(3,4-DIMETHOXY-PHENYL)-1-(1-{1-[2-(3,4,5-TRIMETHOXY-PHENYL)-BUTYRYL]-PIPERIDIN-2YL}-VINYLOXY)-PROPYL]-PHENOXY}-ACETIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C38 H47 N O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        693.780 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AP1 
_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        1BL4 
_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 
AP1 C1   C1   C 0 1 N N N 12.948 13.427 20.197 2.742  0.190  -1.545  C1   AP1 1  
AP1 C2   C2   C 0 1 N N S 14.444 13.695 19.985 4.035  -0.345 -0.984  C2   AP1 2  
AP1 C3   C3   C 0 1 N N N 15.403 12.479 20.070 4.211  -1.803 -1.405  C3   AP1 3  
AP1 C4   C4   C 0 1 N N N 15.430 11.938 21.524 5.453  -2.382 -0.724  C4   AP1 4  
AP1 C5   C5   C 0 1 N N N 16.065 13.011 22.443 5.272  -2.335 0.794   C5   AP1 5  
AP1 C6   C6   C 0 1 N N N 15.270 14.347 22.364 5.111  -0.879 1.240   C6   AP1 6  
AP1 C8   C8   C 0 1 N N N 14.980 16.054 20.589 2.989  0.337  1.121   C8   AP1 7  
AP1 C9   C9   C 0 1 N N S 15.403 17.110 21.595 3.036  0.513  2.617   C9   AP1 8  
AP1 C10  C10  C 0 1 Y N N 14.200 17.514 22.483 1.643  0.757  3.137   C10  AP1 9  
AP1 C11  C11  C 0 1 Y N N 13.051 18.078 21.899 1.088  -0.111 4.058   C11  AP1 10 
AP1 C12  C12  C 0 1 Y N N 11.887 18.267 22.658 -0.192 0.108  4.539   C12  AP1 11 
AP1 C13  C13  C 0 1 Y N N 11.914 17.963 24.037 -0.920 1.206  4.095   C13  AP1 12 
AP1 C14  C14  C 0 1 Y N N 13.067 17.475 24.649 -0.359 2.079  3.170   C14  AP1 13 
AP1 O15  O15  O 0 1 N N N 13.030 17.212 26.023 -1.066 3.155  2.732   O15  AP1 14 
AP1 C16  C16  C 0 1 N N N 17.471 18.082 20.399 4.102  1.792  4.480   C16  AP1 15 
AP1 O17  O17  O 0 1 N N N 10.706 18.753 22.075 -0.737 -0.747 5.444   O17  AP1 16 
AP1 C18  C18  C 0 1 N N N 14.098 16.486 26.672 -0.231 3.847  1.802   C18  AP1 17 
AP1 C19  C19  C 0 1 N N N 10.695 19.469 25.400 -2.046 2.246  5.728   C19  AP1 18 
AP1 C20  C20  C 0 1 N N N 10.659 19.075 20.674 0.241  -1.757 5.698   C20  AP1 19 
AP1 C21  C21  C 0 1 N N N 7.684  10.934 15.739 -4.592 -3.656 3.591   C21  AP1 20 
AP1 C22  C22  C 0 1 Y N N 11.219 14.480 23.939 0.840  -1.603 -3.920  C22  AP1 21 
AP1 C23  C23  C 0 1 Y N N 11.218 14.076 25.274 0.732  -1.967 -5.249  C23  AP1 22 
AP1 C24  C24  C 0 1 Y N N 10.924 12.758 25.593 0.043  -1.160 -6.134  C24  AP1 23 
AP1 C25  C25  C 0 1 Y N N 10.924 13.580 22.906 0.260  -0.430 -3.472  C25  AP1 24 
AP1 C26  C26  C 0 1 N N R 10.944 13.972 21.428 0.380  -0.035 -2.023  C26  AP1 25 
AP1 C27  C27  C 0 1 N N N 10.111 15.255 21.113 -0.795 -0.617 -1.237  C27  AP1 26 
AP1 C28  C28  C 0 1 N N N 8.604  14.979 20.963 -0.673 -0.217 0.234   C28  AP1 27 
AP1 C29  C29  C 0 1 Y N N 8.239  13.884 19.969 -1.833 -0.789 1.008   C29  AP1 28 
AP1 C30  C30  C 0 1 Y N N 8.060  14.237 18.628 -2.996 -0.057 1.150   C30  AP1 29 
AP1 C31  C31  C 0 1 Y N N 7.717  13.282 17.664 -4.065 -0.584 1.857   C31  AP1 30 
AP1 C32  C32  C 0 1 Y N N 7.551  11.920 18.051 -3.959 -1.847 2.432   C32  AP1 31 
AP1 C33  C33  C 0 1 Y N N 7.736  11.585 19.400 -2.788 -2.574 2.291   C33  AP1 32 
AP1 C34  C34  C 0 1 Y N N 8.076  12.558 20.337 -1.728 -2.044 1.580   C34  AP1 33 
AP1 C35  C35  C 0 1 Y N N 10.627 11.838 24.575 -0.539 0.016  -5.687  C35  AP1 34 
AP1 O36  O36  O 0 1 N N N 10.339 10.499 24.828 -1.218 0.811  -6.556  O36  AP1 35 
AP1 C37  C37  C 0 1 N N N 10.574 9.895  26.115 -1.154 0.175  -7.834  C37  AP1 36 
AP1 C38  C38  C 0 1 N N N 9.507  10.422 27.030 -1.892 1.011  -8.848  C38  AP1 37 
AP1 O39  O39  O 0 1 N N N 9.801  10.747 28.211 -2.418 2.046  -8.511  O39  AP1 38 
AP1 O40  O40  O 0 1 N N N 8.355  10.532 26.552 -1.965 0.607  -10.126 O40  AP1 39 
AP1 C41  C41  C 0 1 Y N N 10.629 12.262 23.245 -0.433 0.377  -4.352  C41  AP1 40 
AP1 C42  C42  C 0 1 N N N 8.170  14.842 15.808 -5.012 1.367  1.303   C42  AP1 41 
AP1 N7   N7   N 0 1 N N N 14.908 14.751 20.952 4.008  -0.271 0.482   N7   AP1 42 
AP1 O43  O43  O 0 1 N N N 12.356 14.171 21.151 1.625  -0.551 -1.483  O43  AP1 43 
AP1 O44  O44  O 0 1 N N N 12.380 12.578 19.531 2.712  1.287  -2.050  O44  AP1 44 
AP1 O45  O45  O 0 1 N N N 14.707 16.411 19.463 2.035  0.743  0.492   O45  AP1 45 
AP1 C46  C46  C 0 1 N N N 16.015 18.339 20.866 3.926  1.709  2.962   C46  AP1 46 
AP1 C47  C47  C 0 1 Y N N 14.213 17.263 23.872 0.925  1.854  2.697   C47  AP1 47 
AP1 O48  O48  O 0 1 N N N 10.785 18.150 24.818 -2.178 1.427  4.565   O48  AP1 48 
AP1 O49  O49  O 0 1 N N N 7.539  13.656 16.320 -5.212 0.132  1.994   O49  AP1 49 
AP1 O50  O50  O 0 1 N N N 7.197  10.929 17.100 -5.003 -2.367 3.132   O50  AP1 50 
AP1 H2   H2   H 0 1 N N N 14.505 14.022 18.920 4.869  0.246  -1.359  H2   AP1 51 
AP1 H31  1H3  H 0 1 N N N 15.142 11.685 19.330 4.330  -1.858 -2.487  H31  AP1 52 
AP1 H32  2H3  H 0 1 N N N 16.423 12.721 19.692 3.332  -2.374 -1.106  H32  AP1 53 
AP1 H41A 1H4  H 0 0 N N N 14.422 11.615 21.877 6.328  -1.795 -1.004  H41A AP1 54 
AP1 H42  2H4  H 0 1 N N N 15.943 10.951 21.602 5.592  -3.415 -1.041  H42  AP1 55 
AP1 H51  1H5  H 0 1 N N N 16.161 12.649 23.493 6.147  -2.769 1.278   H51  AP1 56 
AP1 H52  2H5  H 0 1 N N N 17.146 13.160 22.216 4.383  -2.901 1.072   H52  AP1 57 
AP1 H61  1H6  H 0 1 N N N 14.360 14.303 23.007 6.033  -0.332 1.045   H61  AP1 58 
AP1 H62  2H6  H 0 1 N N N 15.823 15.166 22.879 4.883  -0.846 2.306   H62  AP1 59 
AP1 H9   H9   H 0 1 N N N 16.191 16.685 22.259 3.443  -0.386 3.077   H9   AP1 60 
AP1 H11  H11  H 0 1 N N N 13.062 18.374 20.836 1.654  -0.964 4.402   H11  AP1 61 
AP1 H161 1H16 H 0 0 N N N 17.910 18.963 19.876 4.736  2.644  4.726   H161 AP1 62 
AP1 H162 2H16 H 0 0 N N N 18.114 17.756 21.249 3.128  1.916  4.952   H162 AP1 63 
AP1 H163 3H16 H 0 0 N N N 17.535 17.165 19.766 4.568  0.876  4.842   H163 AP1 64 
AP1 H181 1H18 H 0 0 N N N 14.068 16.276 27.766 -0.759 4.722  1.422   H181 AP1 65 
AP1 H182 2H18 H 0 0 N N N 14.231 15.516 26.137 0.683  4.164  2.301   H182 AP1 66 
AP1 H183 3H18 H 0 0 N N N 15.057 17.006 26.445 0.016  3.185  0.973   H183 AP1 67 
AP1 H191 1H19 H 0 0 N N N 9.786  19.619 26.028 -3.034 2.451  6.142   H191 AP1 68 
AP1 H192 2H19 H 0 0 N N N 11.617 19.708 25.978 -1.441 1.728  6.471   H192 AP1 69 
AP1 H193 3H19 H 0 0 N N N 10.761 20.253 24.610 -1.564 3.186  5.458   H193 AP1 70 
AP1 H201 1H20 H 0 0 N N N 9.721  19.461 20.211 -0.152 -2.470 6.422   H201 AP1 71 
AP1 H202 2H20 H 0 0 N N N 11.479 19.798 20.454 0.477  -2.275 4.768   H202 AP1 72 
AP1 H203 3H20 H 0 0 N N N 10.988 18.178 20.099 1.144  -1.296 6.096   H203 AP1 73 
AP1 H211 1H21 H 0 0 N N N 7.405  10.155 14.991 -5.401 -4.114 4.160   H211 AP1 74 
AP1 H212 2H21 H 0 0 N N N 7.429  11.925 15.297 -4.349 -4.285 2.735   H212 AP1 75 
AP1 H213 3H21 H 0 0 N N N 8.797  10.970 15.783 -3.713 -3.552 4.227   H213 AP1 76 
AP1 H22  H22  H 0 1 N N N 11.457 15.529 23.696 1.380  -2.235 -3.230  H22  AP1 77 
AP1 H23  H23  H 0 1 N N N 11.449 14.797 26.075 1.186  -2.883 -5.596  H23  AP1 78 
AP1 H24  H24  H 0 1 N N N 10.926 12.443 26.650 -0.040 -1.445 -7.172  H24  AP1 79 
AP1 H26  H26  H 0 1 N N N 10.470 13.190 20.789 0.371  1.050  -1.940  H26  AP1 80 
AP1 H271 1H27 H 0 0 N N N 10.295 16.045 21.878 -1.730 -0.230 -1.642  H271 AP1 81 
AP1 H272 2H27 H 0 0 N N N 10.510 15.775 20.211 -0.786 -1.704 -1.320  H272 AP1 82 
AP1 H281 1H28 H 0 0 N N N 8.154  14.757 21.958 0.260  -0.604 0.639   H281 AP1 83 
AP1 H282 2H28 H 0 0 N N N 8.065  15.921 20.709 -0.683 0.869  0.317   H282 AP1 84 
AP1 H30  H30  H 0 1 N N N 8.191  15.289 18.324 -3.076 0.922  0.703   H30  AP1 85 
AP1 H33  H33  H 0 1 N N N 7.612  10.539 19.729 -2.704 -3.554 2.736   H33  AP1 86 
AP1 H34  H34  H 0 1 N N N 8.219  12.272 21.392 -0.815 -2.611 1.470   H34  AP1 87 
AP1 H371 1H37 H 0 0 N N N 10.616 8.781  26.080 -0.113 0.072  -8.137  H371 AP1 88 
AP1 H372 2H37 H 0 0 N N N 11.607 10.060 26.499 -1.615 -0.810 -7.772  H372 AP1 89 
AP1 H40  H40  H 0 1 N N N 7.679  10.865 27.131 -2.438 1.144  -10.776 H40  AP1 90 
AP1 H41  H41  H 0 1 N N N 10.392 11.540 22.445 -0.887 1.292  -4.002  H41  AP1 91 
AP1 H421 1H42 H 0 0 N N N 8.028  15.138 14.742 -5.911 1.979  1.384   H421 AP1 92 
AP1 H422 2H42 H 0 0 N N N 7.876  15.702 16.453 -4.169 1.898  1.744   H422 AP1 93 
AP1 H423 3H42 H 0 0 N N N 9.264  14.772 16.010 -4.804 1.165  0.252   H423 AP1 94 
AP1 H461 1H46 H 0 0 N N N 15.371 18.664 20.015 3.460  2.625  2.600   H461 AP1 95 
AP1 H462 2H46 H 0 0 N N N 15.951 19.255 21.498 4.900  1.585  2.489   H462 AP1 96 
AP1 H47  H47  H 0 1 N N N 15.132 16.895 24.357 1.362  2.531  1.979   H47  AP1 97 
# 
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 
AP1 C1  C2   SING N N 1   
AP1 C1  O43  SING N N 2   
AP1 C1  O44  DOUB N N 3   
AP1 C2  C3   SING N N 4   
AP1 C2  N7   SING N N 5   
AP1 C2  H2   SING N N 6   
AP1 C3  C4   SING N N 7   
AP1 C3  H31  SING N N 8   
AP1 C3  H32  SING N N 9   
AP1 C4  C5   SING N N 10  
AP1 C4  H41A SING N N 11  
AP1 C4  H42  SING N N 12  
AP1 C5  C6   SING N N 13  
AP1 C5  H51  SING N N 14  
AP1 C5  H52  SING N N 15  
AP1 C6  N7   SING N N 16  
AP1 C6  H61  SING N N 17  
AP1 C6  H62  SING N N 18  
AP1 C8  C9   SING N N 19  
AP1 C8  N7   SING N N 20  
AP1 C8  O45  DOUB N N 21  
AP1 C9  C10  SING N N 22  
AP1 C9  C46  SING N N 23  
AP1 C9  H9   SING N N 24  
AP1 C10 C11  DOUB Y N 25  
AP1 C10 C47  SING Y N 26  
AP1 C11 C12  SING Y N 27  
AP1 C11 H11  SING N N 28  
AP1 C12 C13  DOUB Y N 29  
AP1 C12 O17  SING N N 30  
AP1 C13 C14  SING Y N 31  
AP1 C13 O48  SING N N 32  
AP1 C14 O15  SING N N 33  
AP1 C14 C47  DOUB Y N 34  
AP1 O15 C18  SING N N 35  
AP1 C16 C46  SING N N 36  
AP1 C16 H161 SING N N 37  
AP1 C16 H162 SING N N 38  
AP1 C16 H163 SING N N 39  
AP1 O17 C20  SING N N 40  
AP1 C18 H181 SING N N 41  
AP1 C18 H182 SING N N 42  
AP1 C18 H183 SING N N 43  
AP1 C19 O48  SING N N 44  
AP1 C19 H191 SING N N 45  
AP1 C19 H192 SING N N 46  
AP1 C19 H193 SING N N 47  
AP1 C20 H201 SING N N 48  
AP1 C20 H202 SING N N 49  
AP1 C20 H203 SING N N 50  
AP1 C21 O50  SING N N 51  
AP1 C21 H211 SING N N 52  
AP1 C21 H212 SING N N 53  
AP1 C21 H213 SING N N 54  
AP1 C22 C23  DOUB Y N 55  
AP1 C22 C25  SING Y N 56  
AP1 C22 H22  SING N N 57  
AP1 C23 C24  SING Y N 58  
AP1 C23 H23  SING N N 59  
AP1 C24 C35  DOUB Y N 60  
AP1 C24 H24  SING N N 61  
AP1 C25 C26  SING N N 62  
AP1 C25 C41  DOUB Y N 63  
AP1 C26 C27  SING N N 64  
AP1 C26 O43  SING N N 65  
AP1 C26 H26  SING N N 66  
AP1 C27 C28  SING N N 67  
AP1 C27 H271 SING N N 68  
AP1 C27 H272 SING N N 69  
AP1 C28 C29  SING N N 70  
AP1 C28 H281 SING N N 71  
AP1 C28 H282 SING N N 72  
AP1 C29 C30  DOUB Y N 73  
AP1 C29 C34  SING Y N 74  
AP1 C30 C31  SING Y N 75  
AP1 C30 H30  SING N N 76  
AP1 C31 C32  DOUB Y N 77  
AP1 C31 O49  SING N N 78  
AP1 C32 C33  SING Y N 79  
AP1 C32 O50  SING N N 80  
AP1 C33 C34  DOUB Y N 81  
AP1 C33 H33  SING N N 82  
AP1 C34 H34  SING N N 83  
AP1 C35 O36  SING N N 84  
AP1 C35 C41  SING Y N 85  
AP1 O36 C37  SING N N 86  
AP1 C37 C38  SING N N 87  
AP1 C37 H371 SING N N 88  
AP1 C37 H372 SING N N 89  
AP1 C38 O39  DOUB N N 90  
AP1 C38 O40  SING N N 91  
AP1 O40 H40  SING N N 92  
AP1 C41 H41  SING N N 93  
AP1 C42 O49  SING N N 94  
AP1 C42 H421 SING N N 95  
AP1 C42 H422 SING N N 96  
AP1 C42 H423 SING N N 97  
AP1 C46 H461 SING N N 98  
AP1 C46 H462 SING N N 99  
AP1 C47 H47  SING N N 100 
# 
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 
AP1 SMILES           ACDLabs              10.04 O=C(N3C(C(=O)OC(c1cccc(OCC(=O)O)c1)CCc2ccc(OC)c(OC)c2)CCCC3)C(c4cc(OC)c(OC)c(OC)c4)CC 
AP1 InChI            InChI                1.02b 
;InChI=1/C38H47NO11/c1-7-28(26-21-33(46-4)36(48-6)34(22-26)47-5)37(42)39-18-9-8-13-29(39)38(43)50-30(25-11-10-12-27(20-25)49-23-35(40)41)16-14-24-15-17-31(44-2)32(19-24)45-3/h10-12,15,17,19-22,28-30H,7-9,13-14,16,18,23H2,1-6H3,(H,40,41)/t28-,29-,30+/m0/s1/f/h40H
;
AP1 InChIKey         InChI                1.02b XCCRAOPQCACRFC-VWSDKQDPDH 
AP1 SMILES_CANONICAL CACTVS               3.341 CC[C@H](C(=O)N1CCCC[C@H]1C(=O)O[C@H](CCc2ccc(OC)c(OC)c2)c3cccc(OCC(O)=O)c3)c4cc(OC)c(OC)c(OC)c4 
AP1 SMILES           CACTVS               3.341 CC[CH](C(=O)N1CCCC[CH]1C(=O)O[CH](CCc2ccc(OC)c(OC)c2)c3cccc(OCC(O)=O)c3)c4cc(OC)c(OC)c(OC)c4 
AP1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H](c1cc(c(c(c1)OC)OC)OC)C(=O)N2CCCC[C@H]2C(=O)O[C@H](CCc3ccc(c(c3)OC)OC)c4cccc(c4)OCC(=O)O 
AP1 SMILES           "OpenEye OEToolkits" 1.5.0 CCC(c1cc(c(c(c1)OC)OC)OC)C(=O)N2CCCCC2C(=O)OC(CCc3ccc(c(c3)OC)OC)c4cccc(c4)OCC(=O)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 
AP1 "SYSTEMATIC NAME" ACDLabs              10.04 "(3-{(1R)-3-(3,4-dimethoxyphenyl)-1-[({(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidin-2-yl}carbonyl)oxy]propyl}phenoxy)acetic acid"  
AP1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[3-[(1R)-3-(3,4-dimethoxyphenyl)-1-[(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidin-2-yl]carbonyloxy-propyl]phenoxy]ethanoic acid" 
# 
