data_C8D # _chem_comp.id C8D _chem_comp.name "N-[(CYCLOPENTYLOXY)CARBONYL]-3-METHYL-L-VALYL-(4R)-N-{(1R)-3-HYDROXY-1-[HYDROXY(OXIDO)BORANYL]PROPYL}-4-(ISOQUINOLIN-1-YLOXY)-L-PROLINAMIDE" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H40 B N4 O8" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge -1 _chem_comp.pdbx_initial_date 2010-04-23 _chem_comp.pdbx_modified_date 2011-06-04 _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 583.461 _chem_comp.one_letter_code ? _chem_comp.three_letter_code C8D _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2XCN _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 C8D O1 O1 O 0 1 N N N 59.446 24.222 8.569 4.604 -0.462 0.488 O1 C8D 1 C8D C6 C6 C 0 1 N N N 58.875 24.277 9.620 4.585 0.680 0.073 C6 C8D 2 C8D O2 O2 O 0 1 N N N 58.371 25.429 10.061 5.734 1.287 -0.279 O2 C8D 3 C8D C7 C7 C 0 1 N N N 58.221 26.562 9.178 6.957 0.518 -0.137 C7 C8D 4 C8D C8 C8 C 0 1 N N N 57.498 27.707 9.889 8.150 1.450 0.162 C8 C8D 5 C8D C9 C9 C 0 1 N N N 56.643 28.421 8.830 9.357 0.876 -0.600 C9 C8D 6 C8D C10 C10 C 0 1 N N N 56.677 27.574 7.551 8.857 -0.385 -1.334 C10 C8D 7 C8D C11 C11 C 0 1 N N N 57.383 26.261 7.922 7.331 -0.160 -1.478 C11 C8D 8 C8D N1 N1 N 0 1 N N N 58.671 23.213 10.446 3.414 1.336 -0.041 N1 C8D 9 C8D C5 C5 C 0 1 N N S 59.146 21.872 10.062 2.163 0.673 0.336 C5 C8D 10 C8D C2 C2 C 0 1 N N N 59.850 21.041 11.203 1.937 0.829 1.842 C2 C8D 11 C8D C1 C1 C 0 1 N N N 60.201 19.600 10.772 1.961 2.313 2.210 C1 C8D 12 C8D C3 C3 C 0 1 N N N 61.150 21.732 11.668 0.579 0.232 2.218 C3 C8D 13 C8D C4 C4 C 0 1 N N N 58.996 20.898 12.469 3.044 0.096 2.602 C4 C8D 14 C8D C12 C12 C 0 1 N N N 57.855 21.132 9.582 1.016 1.301 -0.412 C12 C8D 15 C8D O3 O3 O 0 1 N N N 56.873 21.120 10.325 1.041 2.484 -0.679 O3 C8D 16 C8D N2 N2 N 0 1 N N N 57.849 20.505 8.358 -0.038 0.549 -0.784 N2 C8D 17 C8D C16 C16 C 0 1 N N S 56.669 19.793 7.826 -1.258 1.046 -1.437 C16 C8D 18 C8D C17 C17 C 0 1 N N N 56.384 18.472 8.566 -1.933 2.064 -0.554 C17 C8D 19 C8D N3 N3 N 0 1 N N N 55.061 18.119 8.610 -3.076 2.654 -0.957 N3 C8D 20 C8D C18 C18 C 0 1 N N R 54.636 16.884 9.294 -3.732 3.644 -0.099 C18 C8D 21 C8D C19 C19 C 0 1 N N N 53.916 17.195 10.643 -4.155 4.849 -0.941 C19 C8D 22 C8D C20 C20 C 0 1 N N N 54.707 18.234 11.470 -4.840 5.883 -0.044 C20 C8D 23 C8D O5 O5 O 0 1 N N N 55.350 17.486 12.476 -5.235 7.008 -0.831 O5 C8D 24 C8D B B B 0 1 N N N 53.618 15.968 8.486 -4.999 3.000 0.568 B C8D 25 C8D O6 O6 O 0 1 N N N 53.881 15.411 7.309 -6.051 2.499 -0.244 O6 C8D 26 C8D O8 O8 O -1 1 N N N 53.358 14.735 9.356 -5.084 2.928 1.833 O8 C8D 27 C8D O4 O4 O 0 1 N N N 57.328 17.837 9.050 -1.448 2.352 0.520 O4 C8D 28 C8D C13 C13 C 0 1 N N N 58.952 20.472 7.401 -0.157 -0.911 -0.611 C13 C8D 29 C8D C14 C14 C 0 1 N N R 58.193 20.409 6.055 -1.681 -1.186 -0.596 C14 C8D 30 C8D C15 C15 C 0 1 N N N 57.090 19.391 6.414 -2.191 -0.165 -1.649 C15 C8D 31 C8D O7 O7 O 0 1 N N N 57.663 21.698 5.706 -1.964 -2.526 -1.005 O7 C8D 32 C8D C21 C21 C 0 1 Y N N 57.158 21.887 4.408 -2.037 -3.464 -0.030 C21 C8D 33 C8D N4 N4 N 0 1 Y N N 57.301 20.936 3.440 -1.852 -3.125 1.230 N4 C8D 34 C8D C22 C22 C 0 1 Y N N 56.852 21.114 2.166 -1.914 -4.001 2.224 C22 C8D 35 C8D C23 C23 C 0 1 Y N N 56.208 22.286 1.749 -2.174 -5.319 2.007 C23 C8D 36 C8D C24 C24 C 0 1 Y N N 56.028 23.295 2.713 -2.383 -5.761 0.687 C24 C8D 37 C8D C29 C29 C 0 1 Y N N 56.503 23.099 4.052 -2.319 -4.806 -0.359 C29 C8D 38 C8D C25 C25 C 0 1 Y N N 55.376 24.496 2.326 -2.656 -7.103 0.384 C25 C8D 39 C8D C26 C26 C 0 1 Y N N 55.195 25.520 3.281 -2.850 -7.470 -0.914 C26 C8D 40 C8D C27 C27 C 0 1 Y N N 55.663 25.337 4.613 -2.781 -6.533 -1.943 C27 C8D 41 C8D C28 C28 C 0 1 Y N N 56.311 24.137 5.003 -2.529 -5.220 -1.682 C28 C8D 42 C8D H1 H1 H 0 1 N N N 58.197 23.343 11.317 3.398 2.247 -0.372 H1 C8D 43 C8D H7 H7 H 0 1 N N N 59.249 26.822 8.885 6.849 -0.227 0.652 H7 C8D 44 C8D H81C H81C H 0 0 N N N 56.860 27.315 10.695 7.932 2.459 -0.189 H81C C8D 45 C8D H82C H82C H 0 0 N N N 58.218 28.402 10.346 8.355 1.463 1.232 H82C C8D 46 C8D H111 H111 H 0 0 N N N 58.029 25.924 7.098 6.809 -1.110 -1.589 H111 C8D 47 C8D H112 H112 H 0 0 N N N 56.656 25.457 8.111 7.116 0.501 -2.318 H112 C8D 48 C8D H91C H91C H 0 0 N N N 55.608 28.522 9.187 9.726 1.607 -1.320 H91C C8D 49 C8D H92C H92C H 0 0 N N N 57.038 29.428 8.633 10.149 0.611 0.101 H92C C8D 50 C8D H101 H101 H 0 0 N N N 55.656 27.375 7.192 9.325 -0.466 -2.315 H101 C8D 51 C8D H102 H102 H 0 0 N N N 57.207 28.096 6.741 9.057 -1.276 -0.740 H102 C8D 52 C8D H5 H5 H 0 1 N N N 59.934 21.973 9.302 2.224 -0.387 0.086 H5 C8D 53 C8D H11C H11C H 0 0 N N N 60.284 19.555 9.676 1.173 2.835 1.668 H11C C8D 54 C8D H12C H12C H 0 0 N N N 61.159 19.305 11.225 1.800 2.425 3.282 H12C C8D 55 C8D H13C H13C H 0 0 N N N 59.409 18.914 11.108 2.929 2.738 1.942 H13C C8D 56 C8D H31C H31C H 0 0 N N N 61.808 21.896 10.802 0.590 -0.842 2.034 H31C C8D 57 C8D H32C H32C H 0 0 N N N 60.905 22.699 12.131 0.380 0.419 3.273 H32C C8D 58 C8D H33C H33C H 0 0 N N N 61.662 21.093 12.402 -0.201 0.696 1.614 H33C C8D 59 C8D H41C H41C H 0 0 N N N 59.651 20.864 13.352 4.011 0.521 2.335 H41C C8D 60 C8D H42C H42C H 0 0 N N N 58.315 21.758 12.551 2.883 0.207 3.675 H42C C8D 61 C8D H43C H43C H 0 0 N N N 58.409 19.969 12.412 3.026 -0.962 2.340 H43C C8D 62 C8D H16 H16 H 0 1 N N N 55.778 20.433 7.910 -1.008 1.497 -2.397 H16 C8D 63 C8D H131 H131 H 0 0 N N N 59.593 21.363 7.475 0.315 -1.431 -1.445 H131 C8D 64 C8D H132 H132 H 0 0 N N N 59.651 19.637 7.557 0.294 -1.218 0.333 H132 C8D 65 C8D H151 H151 H 0 0 N N N 57.471 18.360 6.387 -3.228 0.108 -1.454 H151 C8D 66 C8D H152 H152 H 0 0 N N N 56.252 19.407 5.702 -2.080 -0.566 -2.656 H152 C8D 67 C8D H3 H3 H 0 1 N N N 54.377 18.704 8.174 -3.464 2.424 -1.816 H3 C8D 68 C8D H18 H18 H 0 1 N N N 55.587 16.345 9.420 -3.038 3.968 0.677 H18 C8D 69 C8D H191 H191 H 0 0 N N N 52.915 17.597 10.429 -3.275 5.296 -1.404 H191 C8D 70 C8D H192 H192 H 0 0 N N N 53.846 16.264 11.225 -4.848 4.525 -1.717 H192 C8D 71 C8D H201 H201 H 0 0 N N N 55.440 18.762 10.842 -5.720 5.436 0.418 H201 C8D 72 C8D H202 H202 H 0 0 N N N 54.051 19.010 11.891 -4.146 6.207 0.732 H202 C8D 73 C8D HA HA H 0 1 N N N 55.495 16.599 12.168 -5.677 7.705 -0.327 HA C8D 74 C8D H6 H6 H 0 1 N N N 53.944 16.087 6.645 -6.811 2.112 0.212 H6 C8D 75 C8D H14 H14 H 0 1 N N N 58.796 20.126 5.180 -2.105 -0.982 0.387 H14 C8D 76 C8D H22 H22 H 0 1 N N N 56.998 20.320 1.449 -1.752 -3.658 3.235 H22 C8D 77 C8D H23 H23 H 0 1 N N N 55.865 22.410 0.732 -2.218 -6.013 2.833 H23 C8D 78 C8D H25 H25 H 0 1 N N N 55.023 24.624 1.313 -2.711 -7.839 1.172 H25 C8D 79 C8D H28 H28 H 0 1 N N N 56.657 24.013 6.019 -2.479 -4.505 -2.490 H28 C8D 80 C8D H26 H26 H 0 1 N N N 54.703 26.440 3.002 -3.060 -8.503 -1.149 H26 C8D 81 C8D H27 H27 H 0 1 N N N 55.522 26.125 5.338 -2.938 -6.852 -2.963 H27 C8D 82 # 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 C8D O1 C6 DOUB N N 1 C8D C6 O2 SING N N 2 C8D C6 N1 SING N N 3 C8D O2 C7 SING N N 4 C8D C7 C8 SING N N 5 C8D C7 C11 SING N N 6 C8D C8 C9 SING N N 7 C8D C9 C10 SING N N 8 C8D C10 C11 SING N N 9 C8D N1 C5 SING N N 10 C8D C5 C2 SING N N 11 C8D C5 C12 SING N N 12 C8D C2 C1 SING N N 13 C8D C2 C3 SING N N 14 C8D C2 C4 SING N N 15 C8D C12 O3 DOUB N N 16 C8D C12 N2 SING N N 17 C8D N2 C16 SING N N 18 C8D N2 C13 SING N N 19 C8D C16 C17 SING N N 20 C8D C16 C15 SING N N 21 C8D C17 N3 SING N N 22 C8D C17 O4 DOUB N N 23 C8D N3 C18 SING N N 24 C8D C18 C19 SING N N 25 C8D C18 B SING N N 26 C8D C19 C20 SING N N 27 C8D C20 O5 SING N N 28 C8D B O6 SING N N 29 C8D B O8 SING N N 30 C8D C13 C14 SING N N 31 C8D C14 C15 SING N N 32 C8D C14 O7 SING N N 33 C8D O7 C21 SING N N 34 C8D C21 N4 SING Y N 35 C8D C21 C29 DOUB Y N 36 C8D N4 C22 DOUB Y N 37 C8D C22 C23 SING Y N 38 C8D C23 C24 DOUB Y N 39 C8D C24 C29 SING Y N 40 C8D C24 C25 SING Y N 41 C8D C29 C28 SING Y N 42 C8D C25 C26 DOUB Y N 43 C8D C26 C27 SING Y N 44 C8D C27 C28 DOUB Y N 45 C8D N1 H1 SING N N 46 C8D C7 H7 SING N N 47 C8D C8 H81C SING N N 48 C8D C8 H82C SING N N 49 C8D C11 H111 SING N N 50 C8D C11 H112 SING N N 51 C8D C9 H91C SING N N 52 C8D C9 H92C SING N N 53 C8D C10 H101 SING N N 54 C8D C10 H102 SING N N 55 C8D C5 H5 SING N N 56 C8D C1 H11C SING N N 57 C8D C1 H12C SING N N 58 C8D C1 H13C SING N N 59 C8D C3 H31C SING N N 60 C8D C3 H32C SING N N 61 C8D C3 H33C SING N N 62 C8D C4 H41C SING N N 63 C8D C4 H42C SING N N 64 C8D C4 H43C SING N N 65 C8D C16 H16 SING N N 66 C8D C13 H131 SING N N 67 C8D C13 H132 SING N N 68 C8D C15 H151 SING N N 69 C8D C15 H152 SING N N 70 C8D N3 H3 SING N N 71 C8D C18 H18 SING N N 72 C8D C19 H191 SING N N 73 C8D C19 H192 SING N N 74 C8D C20 H201 SING N N 75 C8D C20 H202 SING N N 76 C8D O5 HA SING N N 77 C8D O6 H6 SING N N 78 C8D C14 H14 SING N N 79 C8D C22 H22 SING N N 80 C8D C23 H23 SING N N 81 C8D C25 H25 SING N N 82 C8D C28 H28 SING N N 83 C8D C26 H26 SING N N 84 C8D C27 H27 SING N N 85 # 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 C8D SMILES ACDLabs 10.04 "O=C(N3C(C(=O)NC(B([O-])O)CCO)CC(Oc1nccc2c1cccc2)C3)C(NC(=O)OC4CCCC4)C(C)(C)C" C8D SMILES_CANONICAL CACTVS 3.352 "CC(C)(C)[C@H](NC(=O)OC1CCCC1)C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@@H](CCO)B(O)[O-])Oc3nccc4ccccc34" C8D SMILES CACTVS 3.352 "CC(C)(C)[CH](NC(=O)OC1CCCC1)C(=O)N2C[CH](C[CH]2C(=O)N[CH](CCO)B(O)[O-])Oc3nccc4ccccc34" C8D SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "B([C@H](CCO)NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](C(C)(C)C)NC(=O)OC2CCCC2)Oc3c4ccccc4ccn3)(O)[O-]" C8D SMILES "OpenEye OEToolkits" 1.6.1 "B(C(CCO)NC(=O)C1CC(CN1C(=O)C(C(C)(C)C)NC(=O)OC2CCCC2)Oc3c4ccccc4ccn3)(O)[O-]" C8D InChI InChI 1.03 ;InChI=1S/C29H40BN4O8/c1-29(2,3)24(33-28(38)42-19-9-5-6-10-19)27(37)34-17-20(16-22(34)25(36)32-23(13-15-35)30(39)40)41-26-21-11-7-4-8-18(21)12-14-31-26/h4,7-8,11-12,14,19-20,22-24,35,39H,5-6,9-10,13,15-17H2,1-3H3,(H,32,36)(H,33,38)/q-1/t20-,22+,23+,24-/m1/s1 ; C8D InChIKey InChI 1.03 COHYIEQRPXQCHT-AYVPJYCDSA-N # 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 C8D "SYSTEMATIC NAME" ACDLabs 10.04 "N-[(cyclopentyloxy)carbonyl]-3-methyl-L-valyl-(4R)-N-{(1R)-3-hydroxy-1-[hydroxy(oxido)boranyl]propyl}-4-(isoquinolin-1-yloxy)-L-prolinamide" C8D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(1R)-1-[[(2S,4R)-1-[(2S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethyl-butanoyl]-4-isoquinolin-1-yloxy-pyrrolidin-2-yl]carbonylamino]-3-hydroxy-propyl]-hydroxy-borinate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site C8D "Create component" 2010-04-23 EBI C8D "Modify aromatic_flag" 2011-06-04 RCSB C8D "Modify descriptor" 2011-06-04 RCSB #