data_GRA # _chem_comp.id GRA _chem_comp.name "glutaryl-coenzyme A" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H42 N7 O19 P3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-03-19 _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 881.633 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GRA _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 3GMA _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # 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 GRA O9A O9A O 0 1 N N N -81.559 90.185 -52.985 10.756 -0.088 1.821 O9A GRA 1 GRA P3X P3X P 0 1 N N N -82.360 89.588 -51.841 9.752 -1.090 1.059 P3X GRA 2 GRA O7A O7A O 0 1 N N N -82.229 88.081 -51.719 10.599 -2.095 0.130 O7A GRA 3 GRA O8A O8A O 0 1 N N N -83.784 90.099 -51.752 8.982 -1.868 2.054 O8A GRA 4 GRA O3X O3X O 0 1 N N N -81.678 90.178 -50.496 8.738 -0.239 0.142 O3X GRA 5 GRA C3X C3X C 0 1 N N S -80.421 89.649 -50.078 7.774 0.667 0.683 C3X GRA 6 GRA C2X C2X C 0 1 N N R -79.283 90.648 -50.129 7.998 2.091 0.127 C2X GRA 7 GRA O2X O2X O 0 1 N N N -79.691 91.949 -49.687 9.107 2.109 -0.774 O2X GRA 8 GRA C4X C4X C 0 1 N N R -80.405 89.129 -48.650 6.353 0.296 0.202 C4X GRA 9 GRA O4X O4X O 0 1 N N N -79.052 89.276 -48.211 5.692 1.562 -0.009 O4X GRA 10 GRA C1X C1X C 0 1 N N R -78.284 90.023 -49.168 6.686 2.412 -0.623 C1X GRA 11 GRA N9A N9A N 0 1 Y N N -77.397 89.141 -49.984 6.330 3.822 -0.448 N9A GRA 12 GRA C4A C4A C 0 1 Y N N -76.324 89.548 -50.678 6.790 4.875 -1.198 C4A GRA 13 GRA N3A N3A N 0 1 Y N N -75.728 90.761 -50.839 7.620 5.002 -2.227 N3A GRA 14 GRA C2A C2A C 0 1 Y N N -74.633 90.881 -51.604 7.870 6.185 -2.746 C2A GRA 15 GRA C8A C8A C 0 1 Y N N -77.540 87.817 -50.182 5.476 4.328 0.486 C8A GRA 16 GRA N7A N7A N 0 1 Y N N -76.557 87.371 -50.994 5.390 5.620 0.357 N7A GRA 17 GRA C5A C5A C 0 1 Y N N -75.791 88.433 -51.311 6.179 6.024 -0.668 C5A GRA 18 GRA C6A C6A C 0 1 Y N N -74.656 88.588 -52.096 6.477 7.265 -1.256 C6A GRA 19 GRA N6A N6A N 0 1 N N N -74.116 87.515 -52.722 5.906 8.431 -0.777 N6A GRA 20 GRA N1A N1A N 0 1 Y N N -74.102 89.816 -52.225 7.321 7.293 -2.283 N1A GRA 21 GRA C5X C5X C 0 1 N N N -80.795 87.661 -48.650 5.622 -0.513 1.276 C5X GRA 22 GRA O5X O5X O 0 1 N N N -80.506 87.071 -47.388 4.358 -0.945 0.768 O5X GRA 23 GRA P1A P1A P 0 1 N N R -81.611 86.151 -46.647 3.321 -1.824 1.632 P1A GRA 24 GRA O1A O1A O 0 1 N N N -82.969 86.753 -46.946 2.800 -0.959 2.886 O1A GRA 25 GRA O2A O2A O 0 1 N N N -81.174 85.961 -45.210 3.997 -3.046 2.121 O2A GRA 26 GRA O3A O3A O 0 1 N N N -81.509 84.702 -47.365 2.069 -2.236 0.707 O3A GRA 27 GRA P2A P2A P 0 1 N N S -82.520 84.181 -48.516 0.885 -3.319 0.846 P2A GRA 28 GRA O4A O4A O 0 1 N N N -82.929 85.346 -49.397 -0.259 -2.741 1.820 O4A GRA 29 GRA O5A O5A O 0 1 N N N -83.582 83.327 -47.872 1.428 -4.574 1.413 O5A GRA 30 GRA O6A O6A O 0 1 N N N -81.586 83.197 -49.387 0.256 -3.615 -0.606 O6A GRA 31 GRA C13 C13 C 0 1 N N N -80.203 83.479 -49.607 -0.745 -4.609 -0.832 C13 GRA 32 GRA C12 C12 C 0 1 N N N -79.808 83.279 -51.065 -1.119 -4.629 -2.316 C12 GRA 33 GRA C15 C15 C 0 1 N N N -80.471 82.015 -51.612 -1.661 -3.257 -2.723 C15 GRA 34 GRA C16 C16 C 0 1 N N N -78.292 83.074 -51.063 0.122 -4.955 -3.150 C16 GRA 35 GRA C14 C14 C 0 1 N N R -80.217 84.499 -51.908 -2.191 -5.693 -2.558 C14 GRA 36 GRA O1 O1 O 0 1 N N N -80.054 85.721 -51.168 -1.642 -6.988 -2.305 O1 GRA 37 GRA C1 C1 C 0 1 N N N -79.445 84.573 -53.203 -3.356 -5.452 -1.633 C1 GRA 38 GRA O2 O2 O 0 1 N N N -79.693 83.797 -54.112 -3.594 -6.236 -0.740 O2 GRA 39 GRA N1 N1 N 0 1 N N N -78.494 85.505 -53.288 -4.135 -4.365 -1.800 N1 GRA 40 GRA C2 C2 C 0 1 N N N -77.607 85.787 -54.409 -5.207 -4.078 -0.845 C2 GRA 41 GRA C3 C3 C 0 1 N N N -76.431 84.830 -54.250 -5.933 -2.797 -1.261 C3 GRA 42 GRA C4 C4 C 0 1 N N N -75.514 84.913 -55.449 -7.036 -2.503 -0.278 C4 GRA 43 GRA O3 O3 O 0 1 N N N -75.928 85.287 -56.538 -7.224 -3.244 0.663 O3 GRA 44 GRA N2 N2 N 0 1 N N N -74.252 84.548 -55.230 -7.815 -1.415 -0.445 N2 GRA 45 GRA C5 C5 C 0 1 N N N -73.146 84.507 -56.174 -8.888 -1.129 0.511 C5 GRA 46 GRA C6 C6 C 0 1 N N N -72.190 85.602 -55.723 -9.613 0.152 0.094 C6 GRA 47 GRA S1 S1 S 0 1 N N N -70.910 85.746 -56.929 -10.939 0.506 1.275 S1 GRA 48 GRA C7 C7 C 0 1 N N N -69.596 84.794 -56.509 -11.568 1.945 0.593 C7 GRA 49 GRA O4 O4 O 0 1 N N N -69.430 84.429 -55.353 -11.078 2.402 -0.418 O4 GRA 50 GRA C8 C8 C 0 1 N N N -68.624 84.376 -57.541 -12.731 2.644 1.249 C8 GRA 51 GRA C9 C9 C 0 1 N N N -67.360 84.090 -57.222 -13.094 3.894 0.445 C9 GRA 52 GRA C10 C10 C 0 1 N N N -66.409 83.651 -58.302 -14.275 4.603 1.111 C10 GRA 53 GRA C11 C11 C 0 1 N N N -67.023 82.438 -58.964 -14.632 5.835 0.319 C11 GRA 54 GRA O5 O5 O 0 1 N N N -66.870 81.322 -58.423 -14.007 6.116 -0.675 O5 GRA 55 GRA O6 O6 O 0 1 N N N -67.671 82.596 -60.021 -15.646 6.619 0.720 O6 GRA 56 GRA HO9A HO9A H 0 0 N N N -82.125 90.310 -53.737 11.294 0.455 1.229 HO9A GRA 57 GRA HO7A HO7A H 0 0 N N N -82.202 87.694 -52.586 11.232 -2.641 0.616 HO7A GRA 58 GRA H3X H3X H 0 1 N N N -80.279 88.834 -50.804 7.822 0.670 1.772 H3X GRA 59 GRA H2X H2X H 0 1 N N N -78.889 90.817 -51.142 8.157 2.798 0.941 H2X GRA 60 GRA HO2X HO2X H 0 0 N N N -79.781 91.949 -48.741 9.292 2.979 -1.153 HO2X GRA 61 GRA H4X H4X H 0 1 N N N -81.107 89.668 -47.996 6.403 -0.267 -0.730 H4X GRA 62 GRA H1X H1X H 0 1 N N N -77.660 90.754 -48.633 6.787 2.174 -1.682 H1X GRA 63 GRA H2A H2A H 0 1 N N N -74.171 91.850 -51.722 8.551 6.253 -3.582 H2A GRA 64 GRA H8A H8A H 0 1 N N N -78.321 87.205 -49.757 4.948 3.743 1.225 H8A GRA 65 GRA HN6A HN6A H 0 0 N N N -73.983 87.726 -53.690 5.293 8.398 -0.026 HN6A GRA 66 GRA HN6B HN6B H 0 0 N N N -73.234 87.295 -52.305 6.120 9.281 -1.191 HN6B GRA 67 GRA H5X H5X H 0 1 N N N -81.873 87.574 -48.851 6.222 -1.383 1.546 H5X GRA 68 GRA H5XA H5XA H 0 0 N N N -80.220 87.139 -49.429 5.467 0.109 2.157 H5XA GRA 69 GRA HO1A HO1A H 0 0 N N N -83.446 86.879 -46.134 2.346 -0.142 2.639 HO1A GRA 70 GRA HO4A HO4A H 0 0 N N N -83.015 86.130 -48.867 -0.661 -1.918 1.509 HO4A GRA 71 GRA H13 H13 H 0 1 N N N -80.008 84.525 -49.330 -0.359 -5.587 -0.542 H13 GRA 72 GRA H13A H13A H 0 0 N N N -79.610 82.785 -48.993 -1.629 -4.377 -0.238 H13A GRA 73 GRA H15 H15 H 0 1 N N N -80.630 82.123 -52.695 -0.863 -2.517 -2.659 H15 GRA 74 GRA H15A H15A H 0 0 N N N -79.821 81.148 -51.422 -2.032 -3.303 -3.747 H15A GRA 75 GRA H15B H15B H 0 0 N N N -81.439 81.864 -51.113 -2.473 -2.974 -2.054 H15B GRA 76 GRA H16 H16 H 0 1 N N N -77.927 83.025 -52.099 0.472 -5.957 -2.902 H16 GRA 77 GRA H16A H16A H 0 0 N N N -77.809 83.915 -50.544 -0.130 -4.909 -4.209 H16A GRA 78 GRA H16B H16B H 0 0 N N N -78.050 82.135 -50.544 0.907 -4.231 -2.931 H16B GRA 79 GRA H14 H14 H 0 1 N N N -81.282 84.372 -52.153 -2.530 -5.639 -3.592 H14 GRA 80 GRA HO1 HO1 H 0 1 N N N -80.018 85.527 -50.239 -1.319 -7.109 -1.401 HO1 GRA 81 GRA HN1 HN1 H 0 1 N N N -78.375 86.083 -52.481 -3.984 -3.771 -2.553 HN1 GRA 82 GRA H2 H2 H 0 1 N N N -78.122 85.618 -55.366 -5.914 -4.908 -0.832 H2 GRA 83 GRA H2B H2B H 0 1 N N N -77.278 86.837 -54.413 -4.782 -3.948 0.151 H2B GRA 84 GRA H3 H3 H 0 1 N N N -75.867 85.100 -53.345 -5.227 -1.967 -1.274 H3 GRA 85 GRA H3A H3A H 0 1 N N N -76.816 83.803 -54.167 -6.358 -2.928 -2.256 H3A GRA 86 GRA HN2 HN2 H 0 1 N N N -74.037 84.265 -54.295 -7.665 -0.822 -1.197 HN2 GRA 87 GRA H5 H5 H 0 1 N N N -72.652 83.524 -56.156 -9.594 -1.959 0.524 H5 GRA 88 GRA H5A H5A H 0 1 N N N -73.487 84.664 -57.208 -8.463 -0.998 1.506 H5A GRA 89 GRA H6 H6 H 0 1 N N N -72.729 86.557 -55.633 -8.907 0.982 0.082 H6 GRA 90 GRA H6A H6A H 0 1 N N N -71.761 85.351 -54.742 -10.038 0.022 -0.901 H6A GRA 91 GRA H8 H8 H 0 1 N N N -69.035 83.457 -57.984 -13.588 1.971 1.282 H8 GRA 92 GRA H8B H8B H 0 1 N N N -68.525 85.275 -58.167 -12.456 2.931 2.264 H8B GRA 93 GRA H9 H9 H 0 1 N N N -66.935 85.008 -56.790 -12.237 4.567 0.413 H9 GRA 94 GRA H9A H9A H 0 1 N N N -67.443 83.211 -56.566 -13.369 3.606 -0.570 H9A GRA 95 GRA H10 H10 H 0 1 N N N -66.268 84.457 -59.037 -15.132 3.931 1.144 H10 GRA 96 GRA H10A H10A H 0 0 N N N -65.422 83.410 -57.881 -14.000 4.891 2.126 H10A GRA 97 GRA HO6 HO6 H 0 1 N N N -68.005 81.757 -60.317 -15.838 7.398 0.179 HO6 GRA 98 # 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 GRA O9A P3X SING N N 1 GRA P3X O7A SING N N 2 GRA P3X O8A DOUB N N 3 GRA P3X O3X SING N N 4 GRA O3X C3X SING N N 5 GRA C3X C2X SING N N 6 GRA C3X C4X SING N N 7 GRA C2X O2X SING N N 8 GRA C2X C1X SING N N 9 GRA C4X O4X SING N N 10 GRA C4X C5X SING N N 11 GRA O4X C1X SING N N 12 GRA C1X N9A SING N N 13 GRA N9A C4A SING Y N 14 GRA N9A C8A SING Y N 15 GRA C4A N3A DOUB Y N 16 GRA C4A C5A SING Y N 17 GRA N3A C2A SING Y N 18 GRA C2A N1A DOUB Y N 19 GRA C8A N7A DOUB Y N 20 GRA N7A C5A SING Y N 21 GRA C5A C6A DOUB Y N 22 GRA C6A N6A SING N N 23 GRA C6A N1A SING Y N 24 GRA C5X O5X SING N N 25 GRA O5X P1A SING N N 26 GRA P1A O1A SING N N 27 GRA P1A O2A DOUB N N 28 GRA P1A O3A SING N N 29 GRA O3A P2A SING N N 30 GRA P2A O4A SING N N 31 GRA P2A O5A DOUB N N 32 GRA P2A O6A SING N N 33 GRA O6A C13 SING N N 34 GRA C13 C12 SING N N 35 GRA C12 C15 SING N N 36 GRA C12 C16 SING N N 37 GRA C12 C14 SING N N 38 GRA C14 O1 SING N N 39 GRA C14 C1 SING N N 40 GRA C1 O2 DOUB N N 41 GRA C1 N1 SING N N 42 GRA N1 C2 SING N N 43 GRA C2 C3 SING N N 44 GRA C3 C4 SING N N 45 GRA C4 O3 DOUB N N 46 GRA C4 N2 SING N N 47 GRA N2 C5 SING N N 48 GRA C5 C6 SING N N 49 GRA C6 S1 SING N N 50 GRA S1 C7 SING N N 51 GRA C7 O4 DOUB N N 52 GRA C7 C8 SING N N 53 GRA C8 C9 SING N N 54 GRA C9 C10 SING N N 55 GRA C10 C11 SING N N 56 GRA C11 O5 DOUB N N 57 GRA C11 O6 SING N N 58 GRA O9A HO9A SING N N 59 GRA O7A HO7A SING N N 60 GRA C3X H3X SING N N 61 GRA C2X H2X SING N N 62 GRA O2X HO2X SING N N 63 GRA C4X H4X SING N N 64 GRA C1X H1X SING N N 65 GRA C2A H2A SING N N 66 GRA C8A H8A SING N N 67 GRA N6A HN6A SING N N 68 GRA N6A HN6B SING N N 69 GRA C5X H5X SING N N 70 GRA C5X H5XA SING N N 71 GRA O1A HO1A SING N N 72 GRA O4A HO4A SING N N 73 GRA C13 H13 SING N N 74 GRA C13 H13A SING N N 75 GRA C15 H15 SING N N 76 GRA C15 H15A SING N N 77 GRA C15 H15B SING N N 78 GRA C16 H16 SING N N 79 GRA C16 H16A SING N N 80 GRA C16 H16B SING N N 81 GRA C14 H14 SING N N 82 GRA O1 HO1 SING N N 83 GRA N1 HN1 SING N N 84 GRA C2 H2 SING N N 85 GRA C2 H2B SING N N 86 GRA C3 H3 SING N N 87 GRA C3 H3A SING N N 88 GRA N2 HN2 SING N N 89 GRA C5 H5 SING N N 90 GRA C5 H5A SING N N 91 GRA C6 H6 SING N N 92 GRA C6 H6A SING N N 93 GRA C8 H8 SING N N 94 GRA C8 H8B SING N N 95 GRA C9 H9 SING N N 96 GRA C9 H9A SING N N 97 GRA C10 H10 SING N N 98 GRA C10 H10A SING N N 99 GRA O6 HO6 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 GRA SMILES ACDLabs 10.04 "O=C(O)CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O" GRA SMILES_CANONICAL CACTVS 3.341 "CC(C)(CO[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O" GRA SMILES CACTVS 3.341 "CC(C)(CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[CH](O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O" GRA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(C)(CO[P@](=O)(O)O[P@](=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSC(=O)CCCC(=O)O)O" GRA SMILES "OpenEye OEToolkits" 1.5.0 "CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)CCCC(=O)O)O" GRA InChI InChI 1.03 ;InChI=1S/C26H42N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h12-14,19-21,25,38-39H,3-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,19-,20-,21+,25-/m1/s1 ; GRA InChIKey InChI 1.03 SYKWLIJQEHRDNH-CKRMAKSASA-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 GRA "SYSTEMATIC NAME" ACDLabs 10.04 "(3R,5S,9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide (non-preferred name)" GRA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethylsulfanyl]-5-oxo-pentanoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GRA "Create component" 2009-03-19 PDBJ GRA "Modify aromatic_flag" 2011-06-04 RCSB GRA "Modify descriptor" 2011-06-04 RCSB #