data_AB8
# 
_chem_comp.id                                    AB8 
_chem_comp.name                                  "(1S,3R,8AS)-8-(2-{(4S,6S)-3-(4-HYDROXY-3-METHOXYBENZYL)-4-[2-(METHYLAMINO)-2-OXOETHYL]-2-OXO-1,3-OXAZINAN-6-YL}ETHYL)-3,7-DIMETHYL-1,2,3,7,8,8A-HEXAHYDRONAPHTHALEN-1-YL (2R)-2-METHYLBUTANOATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C34 H48 N2 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
"LFA878; (S)-2-METHYL-BUTYRIC ACID (1S,3R,7S,8S,8AR)-8-{2-[(4R,6R)-3-(4-HYDROXY-3-METHOXY-BENZYL)-4-METHYLCARBAMOYLMETHYL-2-OXO-[1,3]OXAZINAN-6-YL]-ETHYL}-3,7-DIMETHYL-1,2,3,7,8,8A-HEXAHYDRO-NAPHTHALEN-1-YL ESTER" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-09-07 
_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                        596.754 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AB8 
_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        1XDG 
_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 
AB8 C88  C88  C 0 1 N N N 52.363 28.625 15.921 6.400  0.196  -1.825 C88  AB8 1  
AB8 O87  O87  O 0 1 N N N 52.573 27.341 15.317 6.389  1.574  -1.449 O87  AB8 2  
AB8 C79  C79  C 0 1 Y N N 51.892 26.228 15.844 5.672  1.661  -0.297 C79  AB8 3  
AB8 C80  C80  C 0 1 Y N N 52.452 24.970 15.612 5.486  2.896  0.318  C80  AB8 4  
AB8 O85  O85  O 0 1 N N N 53.639 24.887 14.894 6.022  4.018  -0.233 O85  AB8 5  
AB8 C81  C81  C 0 1 Y N N 51.846 23.814 16.097 4.754  2.979  1.491  C81  AB8 6  
AB8 C83  C83  C 0 1 Y N N 50.652 23.932 16.802 4.210  1.838  2.050  C83  AB8 7  
AB8 C77  C77  C 0 1 Y N N 50.696 26.331 16.553 5.128  0.520  0.271  C77  AB8 8  
AB8 C76  C76  C 0 1 Y N N 50.078 25.176 17.027 4.394  0.611  1.439  C76  AB8 9  
AB8 C73  C73  C 0 1 N N N 48.789 25.237 17.821 3.799  -0.631 2.052  C73  AB8 10 
AB8 N1   N1   N 0 1 N N N 49.177 24.915 19.182 2.501  -0.907 1.433  N1   AB8 11 
AB8 C2   C2   C 0 1 N N R 50.045 25.808 19.957 2.471  -1.648 0.175  C2   AB8 12 
AB8 C62  C62  C 0 1 N N N 49.410 27.239 20.094 3.527  -2.754 0.218  C62  AB8 13 
AB8 C65  C65  C 0 1 N N N 50.246 28.234 20.898 3.602  -3.430 -1.127 C65  AB8 14 
AB8 N67  N67  N 0 1 N N N 49.666 28.884 21.941 4.379  -4.519 -1.291 N67  AB8 15 
AB8 C69  C69  C 0 1 N N N 50.223 30.140 22.444 4.451  -5.176 -2.599 C69  AB8 16 
AB8 O66  O66  O 0 1 N N N 51.427 28.348 20.604 2.964  -2.993 -2.061 O66  AB8 17 
AB8 C4   C4   C 0 1 N N N 50.393 25.278 21.361 1.091  -2.274 -0.039 C4   AB8 18 
AB8 C7   C7   C 0 1 N N R 50.281 23.713 21.348 0.024  -1.194 0.191  C7   AB8 19 
AB8 O9   O9   O 0 1 N N N 48.946 23.401 20.954 0.163  -0.715 1.560  O9   AB8 20 
AB8 C10  C10  C 0 1 N N N 48.617 23.825 19.741 1.394  -0.467 2.044  C10  AB8 21 
AB8 O11  O11  O 0 1 N N N 47.769 23.162 19.146 1.504  0.177  3.069  O11  AB8 22 
AB8 C12  C12  C 0 1 N N N 50.494 23.164 22.774 -1.370 -1.791 -0.011 C12  AB8 23 
AB8 C15  C15  C 0 1 N N N 50.464 21.604 22.859 -2.421 -0.686 0.117  C15  AB8 24 
AB8 C18  C18  C 0 1 N N S 50.526 21.149 24.332 -3.815 -1.283 -0.085 C18  AB8 25 
AB8 C20  C20  C 0 1 N N R 50.413 19.613 24.271 -4.870 -0.347 0.508  C20  AB8 26 
AB8 C31  C31  C 0 1 N N N 50.375 19.071 25.663 -6.222 -0.939 0.247  C31  AB8 27 
AB8 C32  C32  C 0 1 N N N 49.722 19.865 26.727 -6.382 -2.387 0.515  C32  AB8 28 
AB8 C34  C34  C 0 1 N N N 49.236 21.069 26.489 -5.311 -3.144 0.677  C34  AB8 29 
AB8 C36  C36  C 0 1 N N S 49.355 21.745 25.144 -3.903 -2.634 0.627  C36  AB8 30 
AB8 C38  C38  C 0 1 N N N 48.008 21.593 24.396 -3.378 -2.478 2.056  C38  AB8 31 
AB8 C29  C29  C 0 1 N N N 50.906 17.881 25.945 -7.251 -0.246 -0.203 C29  AB8 32 
AB8 C27  C27  C 0 1 N N R 51.580 16.972 24.951 -7.110 1.216  -0.542 C27  AB8 33 
AB8 C42  C42  C 0 1 N N N 53.057 16.787 25.361 -8.128 1.602  -1.617 C42  AB8 34 
AB8 C24  C24  C 0 1 N N N 51.473 17.478 23.494 -5.685 1.435  -1.071 C24  AB8 35 
AB8 C22  C22  C 0 1 N N S 51.583 19.030 23.440 -4.699 1.077  0.039  C22  AB8 36 
AB8 O46  O46  O 0 1 N N N 52.805 19.497 24.022 -3.346 1.252  -0.457 O46  AB8 37 
AB8 C47  C47  C 0 1 N N N 53.887 19.422 23.259 -2.739 2.444  -0.345 C47  AB8 38 
AB8 O48  O48  O 0 1 N N N 53.859 19.091 22.077 -3.319 3.371  0.169  O48  AB8 39 
AB8 C49  C49  C 0 1 N N S 55.155 19.760 24.016 -1.334 2.626  -0.860 C49  AB8 40 
AB8 C58  C58  C 0 1 N N N 56.140 18.571 23.980 -1.300 2.334  -2.361 C58  AB8 41 
AB8 C51  C51  C 0 1 N N N 55.809 20.963 23.369 -0.882 4.066  -0.610 C51  AB8 42 
AB8 C54  C54  C 0 1 N N N 54.863 22.163 23.578 0.585  4.217  -1.018 C54  AB8 43 
AB8 H881 1H88 H 0 0 N N N 52.581 28.551 17.012 6.966  0.076  -2.749 H881 AB8 44 
AB8 H882 2H88 H 0 0 N N N 52.903 29.507 15.503 6.865  -0.393 -1.035 H882 AB8 45 
AB8 H883 3H88 H 0 0 N N N 51.270 28.844 15.934 5.377  -0.147 -1.980 H883 AB8 46 
AB8 H85  H85  H 0 1 N N N 54.020 24.031 14.736 6.906  4.120  0.146  H85  AB8 47 
AB8 H81  H81  H 0 1 N N N 52.303 22.825 15.926 4.608  3.937  1.970  H81  AB8 48 
AB8 H83  H83  H 0 1 N N N 50.154 23.027 17.188 3.640  1.904  2.964  H83  AB8 49 
AB8 H77  H77  H 0 1 N N N 50.242 27.319 16.738 5.270  -0.440 -0.204 H77  AB8 50 
AB8 H731 1H73 H 0 0 N N N 47.976 24.590 17.416 3.666  -0.479 3.123  H731 AB8 51 
AB8 H732 2H73 H 0 0 N N N 48.241 26.203 17.723 4.468  -1.475 1.885  H732 AB8 52 
AB8 H2   H2   H 0 1 N N N 50.996 25.860 19.377 2.692  -0.970 -0.649 H2   AB8 53 
AB8 H621 1H62 H 0 0 N N N 48.381 27.167 20.518 4.497  -2.321 0.462  H621 AB8 54 
AB8 H622 2H62 H 0 0 N N N 49.175 27.656 19.087 3.256  -3.487 0.978  H622 AB8 55 
AB8 H67  H67  H 0 1 N N N 48.836 28.442 22.335 4.889  -4.868 -0.544 H67  AB8 56 
AB8 H691 1H69 H 0 0 N N N 50.300 30.853 21.590 3.457  -5.514 -2.892 H691 AB8 57 
AB8 H692 2H69 H 0 0 N N N 49.747 30.673 23.300 4.828  -4.470 -3.340 H692 AB8 58 
AB8 H693 3H69 H 0 0 N N N 51.296 29.969 22.695 5.123  -6.032 -2.539 H693 AB8 59 
AB8 H41  1H4  H 0 1 N N N 49.770 25.744 22.160 0.944  -3.089 0.670  H41  AB8 60 
AB8 H42  2H4  H 0 1 N N N 51.389 25.632 21.716 1.014  -2.653 -1.058 H42  AB8 61 
AB8 H7   H7   H 0 1 N N N 51.041 23.271 20.662 0.177  -0.370 -0.506 H7   AB8 62 
AB8 H121 1H12 H 0 0 N N N 49.757 23.610 23.481 -1.552 -2.554 0.746  H121 AB8 63 
AB8 H122 2H12 H 0 0 N N N 51.438 23.563 23.212 -1.433 -2.239 -1.002 H122 AB8 64 
AB8 H151 1H15 H 0 0 N N N 51.270 21.138 22.245 -2.240 0.077  -0.640 H151 AB8 65 
AB8 H152 2H15 H 0 0 N N N 49.583 21.175 22.327 -2.358 -0.237 1.108  H152 AB8 66 
AB8 H18  H18  H 0 1 N N N 51.462 21.488 24.835 -4.005 -1.417 -1.150 H18  AB8 67 
AB8 H20  H20  H 0 1 N N N 49.469 19.311 23.760 -4.725 -0.343 1.588  H20  AB8 68 
AB8 H32  H32  H 0 1 N N N 49.588 19.536 27.771 -7.369 -2.821 0.577  H32  AB8 69 
AB8 H34  H34  H 0 1 N N N 48.748 21.495 27.382 -5.460 -4.198 0.858  H34  AB8 70 
AB8 H36  H36  H 0 1 N N N 49.577 22.829 25.281 -3.282 -3.356 0.097  H36  AB8 71 
AB8 H381 1H38 H 0 0 N N N 47.813 20.531 24.120 -3.400 -3.445 2.558  H381 AB8 72 
AB8 H382 2H38 H 0 0 N N N 47.163 22.023 24.982 -2.353 -2.107 2.028  H382 AB8 73 
AB8 H383 3H38 H 0 0 N N N 48.059 22.032 23.372 -4.006 -1.772 2.599  H383 AB8 74 
AB8 H29  H29  H 0 1 N N N 50.786 17.645 27.016 -8.207 -0.732 -0.329 H29  AB8 75 
AB8 H27  H27  H 0 1 N N N 51.048 15.992 24.971 -7.269 1.820  0.351  H27  AB8 76 
AB8 H421 1H42 H 0 0 N N N 53.164 16.424 26.410 -7.973 0.984  -2.502 H421 AB8 77 
AB8 H422 2H42 H 0 0 N N N 53.556 16.114 24.625 -9.137 1.444  -1.236 H422 AB8 78 
AB8 H423 3H42 H 0 0 N N N 53.591 17.759 25.477 -7.999 2.652  -1.880 H423 AB8 79 
AB8 H241 1H24 H 0 0 N N N 50.544 17.112 22.997 -5.555 2.479  -1.355 H241 AB8 80 
AB8 H242 2H24 H 0 0 N N N 52.223 16.988 22.830 -5.513 0.795  -1.936 H242 AB8 81 
AB8 H22  H22  H 0 1 N N N 51.553 19.351 22.373 -4.857 1.749  0.882  H22  AB8 82 
AB8 H49  H49  H 0 1 N N N 54.895 19.982 25.077 -0.665 1.939  -0.341 H49  AB8 83 
AB8 H581 1H58 H 0 0 N N N 56.355 18.243 22.936 -1.622 1.308  -2.539 H581 AB8 84 
AB8 H582 2H58 H 0 0 N N N 57.073 18.820 24.537 -1.969 3.020  -2.880 H582 AB8 85 
AB8 H583 3H58 H 0 0 N N N 55.671 17.632 24.356 -0.284 2.465  -2.734 H583 AB8 86 
AB8 H511 1H51 H 0 0 N N N 56.071 20.795 22.298 -0.991 4.302  0.449  H511 AB8 87 
AB8 H512 2H51 H 0 0 N N N 56.843 21.152 23.742 -1.495 4.747  -1.199 H512 AB8 88 
AB8 H541 1H54 H 0 0 N N N 54.601 22.331 24.649 0.907  5.243  -0.840 H541 AB8 89 
AB8 H542 2H54 H 0 0 N N N 55.345 23.049 23.102 1.199  3.536  -0.428 H542 AB8 90 
AB8 H543 3H54 H 0 0 N N N 53.829 21.975 23.205 0.694  3.981  -2.076 H543 AB8 91 
# 
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 
AB8 C88 O87  SING N N 1  
AB8 C88 H881 SING N N 2  
AB8 C88 H882 SING N N 3  
AB8 C88 H883 SING N N 4  
AB8 O87 C79  SING N N 5  
AB8 C79 C80  DOUB Y N 6  
AB8 C79 C77  SING Y N 7  
AB8 C80 O85  SING N N 8  
AB8 C80 C81  SING Y N 9  
AB8 O85 H85  SING N N 10 
AB8 C81 C83  DOUB Y N 11 
AB8 C81 H81  SING N N 12 
AB8 C83 C76  SING Y N 13 
AB8 C83 H83  SING N N 14 
AB8 C77 C76  DOUB Y N 15 
AB8 C77 H77  SING N N 16 
AB8 C76 C73  SING N N 17 
AB8 C73 N1   SING N N 18 
AB8 C73 H731 SING N N 19 
AB8 C73 H732 SING N N 20 
AB8 N1  C2   SING N N 21 
AB8 N1  C10  SING N N 22 
AB8 C2  C62  SING N N 23 
AB8 C2  C4   SING N N 24 
AB8 C2  H2   SING N N 25 
AB8 C62 C65  SING N N 26 
AB8 C62 H621 SING N N 27 
AB8 C62 H622 SING N N 28 
AB8 C65 N67  SING N N 29 
AB8 C65 O66  DOUB N N 30 
AB8 N67 C69  SING N N 31 
AB8 N67 H67  SING N N 32 
AB8 C69 H691 SING N N 33 
AB8 C69 H692 SING N N 34 
AB8 C69 H693 SING N N 35 
AB8 C4  C7   SING N N 36 
AB8 C4  H41  SING N N 37 
AB8 C4  H42  SING N N 38 
AB8 C7  O9   SING N N 39 
AB8 C7  C12  SING N N 40 
AB8 C7  H7   SING N N 41 
AB8 O9  C10  SING N N 42 
AB8 C10 O11  DOUB N N 43 
AB8 C12 C15  SING N N 44 
AB8 C12 H121 SING N N 45 
AB8 C12 H122 SING N N 46 
AB8 C15 C18  SING N N 47 
AB8 C15 H151 SING N N 48 
AB8 C15 H152 SING N N 49 
AB8 C18 C20  SING N N 50 
AB8 C18 C36  SING N N 51 
AB8 C18 H18  SING N N 52 
AB8 C20 C31  SING N N 53 
AB8 C20 C22  SING N N 54 
AB8 C20 H20  SING N N 55 
AB8 C31 C32  SING N N 56 
AB8 C31 C29  DOUB N N 57 
AB8 C32 C34  DOUB N N 58 
AB8 C32 H32  SING N N 59 
AB8 C34 C36  SING N N 60 
AB8 C34 H34  SING N N 61 
AB8 C36 C38  SING N N 62 
AB8 C36 H36  SING N N 63 
AB8 C38 H381 SING N N 64 
AB8 C38 H382 SING N N 65 
AB8 C38 H383 SING N N 66 
AB8 C29 C27  SING N N 67 
AB8 C29 H29  SING N N 68 
AB8 C27 C42  SING N N 69 
AB8 C27 C24  SING N N 70 
AB8 C27 H27  SING N N 71 
AB8 C42 H421 SING N N 72 
AB8 C42 H422 SING N N 73 
AB8 C42 H423 SING N N 74 
AB8 C24 C22  SING N N 75 
AB8 C24 H241 SING N N 76 
AB8 C24 H242 SING N N 77 
AB8 C22 O46  SING N N 78 
AB8 C22 H22  SING N N 79 
AB8 O46 C47  SING N N 80 
AB8 C47 O48  DOUB N N 81 
AB8 C47 C49  SING N N 82 
AB8 C49 C58  SING N N 83 
AB8 C49 C51  SING N N 84 
AB8 C49 H49  SING N N 85 
AB8 C58 H581 SING N N 86 
AB8 C58 H582 SING N N 87 
AB8 C58 H583 SING N N 88 
AB8 C51 C54  SING N N 89 
AB8 C51 H511 SING N N 90 
AB8 C51 H512 SING N N 91 
AB8 C54 H541 SING N N 92 
AB8 C54 H542 SING N N 93 
AB8 C54 H543 SING N N 94 
# 
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 
AB8 SMILES           ACDLabs              10.04 O=C(OC1C4C(=CC(C)C1)C=CC(C4CCC2OC(=O)N(C(C2)CC(=O)NC)Cc3ccc(O)c(OC)c3)C)C(C)CC 
AB8 InChI            InChI                1.02b 
;InChI=1/C34H48N2O7/c1-7-21(3)33(39)43-30-15-20(2)14-24-10-8-22(4)27(32(24)30)12-11-26-17-25(18-31(38)35-5)36(34(40)42-26)19-23-9-13-28(37)29(16-23)41-6/h8-10,13-14,16,20-22,25-27,30,32,37H,7,11-12,15,17-19H2,1-6H3,(H,35,38)/t20-,21-,22-,25+,26+,27-,30-,32-/m0/s1/f/h35H
;
AB8 InChIKey         InChI                1.02b XGCZRGJUCNQVCO-BSAQVKNYDX 
AB8 SMILES_CANONICAL CACTVS               3.341 CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@H](CC(=O)NC)N(Cc4ccc(O)c(OC)c4)C(=O)O3)[C@@H]12 
AB8 SMILES           CACTVS               3.341 CC[CH](C)C(=O)O[CH]1C[CH](C)C=C2C=C[CH](C)[CH](CC[CH]3C[CH](CC(=O)NC)N(Cc4ccc(O)c(OC)c4)C(=O)O3)[CH]12 
AB8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@@H](N(C(=O)O3)Cc4ccc(c(c4)OC)O)CC(=O)NC)C 
AB8 SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(N(C(=O)O3)Cc4ccc(c(c4)OC)O)CC(=O)NC)C 
# 
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 
AB8 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,3R,7S,8S,8aR)-8-(2-{(4R,6R)-3-(4-hydroxy-3-methoxybenzyl)-4-[2-(methylamino)-2-oxoethyl]-2-oxo-1,3-oxazinan-6-yl}ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate" 
AB8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"[(1S,3R,7S,8S,8aR)-8-[2-[(4R,6R)-3-[(4-hydroxy-3-methoxy-phenyl)methyl]-4-(2-methylamino-2-oxo-ethyl)-2-oxo-1,3-oxazinan-6-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate" 
# 
