data_COO # _chem_comp.id COO _chem_comp.name "CROTONYL COENZYME A" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H40 N7 O17 P3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-08-01 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 835.608 _chem_comp.one_letter_code ? _chem_comp.three_letter_code COO _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag Y _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2HW5 _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 COO C13 C13 C 0 1 N N S -10.317 25.669 43.313 -1.772 5.662 3.025 C13 COO 1 COO C11 C11 C 0 1 N N N -9.638 27.012 43.537 -0.368 5.064 2.711 C11 COO 2 COO C14 C14 C 0 1 N N N -8.119 26.845 43.607 -0.333 3.551 3.006 C14 COO 3 COO C12 C12 C 0 1 N N N -10.110 28.053 42.500 0.739 5.781 3.522 C12 COO 4 COO O6A O6A O 0 1 N N N -11.016 29.001 43.166 2.021 5.233 3.233 O6A COO 5 COO P2A P2A P 0 1 N N S -12.580 29.410 42.764 3.306 5.855 3.987 P2A COO 6 COO O4A O4A O 0 1 N N N -13.138 30.334 43.981 4.629 5.236 3.642 O4A COO 7 COO O5A O5A O 0 1 N N N -12.592 30.264 41.387 3.198 7.443 3.698 O5A COO 8 COO O3A O3A O 0 1 N N N -13.558 28.210 42.553 2.896 5.741 5.547 O3A COO 9 COO P1A P1A P 0 1 N N R -14.178 27.399 43.790 2.667 4.450 6.492 P1A COO 10 COO O2A O2A O 0 1 N N N -12.943 26.833 44.732 1.579 3.528 6.022 O2A COO 11 COO O1A O1A O 0 1 N N N -15.182 28.200 44.581 4.135 3.771 6.555 O1A COO 12 COO O5X O5X O 0 1 N N N -14.658 26.095 43.013 2.443 5.064 7.972 O5X COO 13 COO C5X C5X C 0 1 N N N -15.824 25.990 42.213 3.403 5.948 8.525 C5X COO 14 COO C4X C4X C 0 1 N N R -16.360 24.575 42.417 2.946 6.369 9.911 C4X COO 15 COO O4X O4X O 0 1 N N N -15.343 23.604 41.979 3.884 7.305 10.468 O4X COO 16 COO C3X C3X C 0 1 N N R -16.517 24.351 43.925 1.611 7.093 9.915 C3X COO 17 COO O3X O3X O 0 1 N N N -17.586 23.439 44.156 0.521 6.198 9.854 O3X COO 18 COO P3X P3X P 0 1 N N N -18.617 23.827 45.312 -0.970 6.805 9.967 P3X COO 19 COO O9A O9A O 0 1 N N N -19.951 22.951 45.027 -1.263 7.544 11.240 O9A COO 20 COO O7A O7A O 0 1 N N N -18.973 25.374 44.981 -1.928 5.536 9.669 O7A COO 21 COO O8A O8A O 0 1 N N N -18.054 23.591 46.661 -1.094 7.689 8.619 O8A COO 22 COO C2X C2X C 0 1 N N R -15.191 23.708 44.315 1.675 7.880 11.210 C2X COO 23 COO O2X O2X O 0 1 N N N -15.339 22.985 45.541 1.274 7.081 12.321 O2X COO 24 COO C1X C1X C 0 1 N N S -15.004 22.768 43.122 3.164 8.207 11.335 C1X COO 25 COO N9A N9A N 0 1 Y N N -13.608 22.323 42.952 3.493 9.589 10.982 N9A COO 26 COO C8A C8A C 0 1 Y N N -12.587 23.091 42.578 3.764 10.059 9.723 C8A COO 27 COO N7A N7A N 0 1 Y N N -11.477 22.355 42.528 4.027 11.349 9.718 N7A COO 28 COO C5A C5A C 0 1 Y N N -11.786 21.108 42.870 3.922 11.734 11.031 C5A COO 29 COO C4A C4A C 0 1 Y N N -13.147 21.091 43.137 3.590 10.654 11.834 C4A COO 30 COO N3A N3A N 0 1 Y N N -13.725 19.941 43.511 3.405 10.656 13.163 N3A COO 31 COO C2A C2A C 0 1 Y N N -13.004 18.832 43.619 3.587 11.898 13.662 C2A COO 32 COO N1A N1A N 0 1 Y N N -11.702 18.821 43.364 3.911 13.039 13.007 N1A COO 33 COO C6A C6A C 0 1 Y N N -11.061 19.927 42.993 4.083 12.962 11.665 C6A COO 34 COO N6A N6A N 0 1 N N N -9.759 19.873 42.747 4.419 14.111 10.928 N6A COO 35 COO O1 O1 O 0 1 N N N ? ? ? -1.786 7.052 2.710 O1 COO 36 COO C1 C1 C 0 1 N N N ? ? ? -2.189 5.546 4.490 C1 COO 37 COO O2 O2 O 0 1 N N N ? ? ? -1.878 6.390 5.329 O2 COO 38 COO N1 N1 N 0 1 N N N ? ? ? -2.958 4.422 4.742 N1 COO 39 COO C2 C2 C 0 1 N N N ? ? ? -3.492 4.110 6.047 C2 COO 40 COO C3 C3 C 0 1 N N N ? ? ? -2.497 3.256 6.821 C3 COO 41 COO C4 C4 C 0 1 N N N ? ? ? -3.005 2.879 8.201 C4 COO 42 COO O3 O3 O 0 1 N N N ? ? ? -4.098 3.231 8.634 O3 COO 43 COO N2 N2 N 0 1 N N N ? ? ? -2.084 2.102 8.889 N2 COO 44 COO C5 C5 C 0 1 N N N ? ? ? -2.318 1.609 10.226 C5 COO 45 COO C6 C6 C 0 1 N N N ? ? ? -1.831 2.565 11.307 C6 COO 46 COO S1 S1 S 0 1 N N N ? ? ? -0.037 2.849 11.216 S1 COO 47 COO C7 C7 C 0 1 N N N ? ? ? 0.181 3.894 12.613 C7 COO 48 COO O4 O4 O 0 1 N N N ? ? ? -0.677 4.659 13.031 O4 COO 49 COO C8 C8 C 0 1 N N N ? ? ? 1.524 3.739 13.226 C8 COO 50 COO C9 C9 C 0 1 N N N ? ? ? 1.853 4.466 14.303 C9 COO 51 COO C10 C10 C 0 1 N N N ? ? ? 3.181 4.373 14.982 C10 COO 52 COO C15 C15 C 0 1 N N N ? ? ? -0.081 5.249 1.202 C15 COO 53 COO HO1 HO1 H 0 1 N N N ? ? ? -1.751 7.527 3.554 HO1 COO 54 COO H13 H13 H 0 1 N N N -10.847 25.742 44.274 -2.531 5.180 2.395 H13 COO 55 COO HN1 HN1 H 0 1 N N N ? ? ? -3.188 3.793 3.978 HN1 COO 56 COO H21 1H2 H 0 1 N N N ? ? ? -3.700 5.042 6.585 H21 COO 57 COO H22 2H2 H 0 1 N N N ? ? ? -4.445 3.581 5.932 H22 COO 58 COO H31 1H3 H 0 1 N N N ? ? ? -1.549 3.796 6.937 H31 COO 59 COO H32 2H3 H 0 1 N N N ? ? ? -2.283 2.334 6.267 H32 COO 60 COO HN2 HN2 H 0 1 N N N ? ? ? -1.207 1.869 8.432 HN2 COO 61 COO H51 1H5 H 0 1 N N N ? ? ? -3.400 1.471 10.323 H51 COO 62 COO H52 2H5 H 0 1 N N N ? ? ? -1.848 0.623 10.310 H52 COO 63 COO H61 1H6 H 0 1 N N N ? ? ? -2.340 3.531 11.230 H61 COO 64 COO H62 2H6 H 0 1 N N N ? ? ? -2.050 2.143 12.293 H62 COO 65 COO H8 H8 H 0 1 N N N ? ? ? 2.229 3.037 12.794 H8 COO 66 COO H9 H9 H 0 1 N N N ? ? ? 1.147 5.169 14.734 H9 COO 67 COO H101 1H10 H 0 0 N N N ? ? ? 3.676 5.349 14.966 H101 COO 68 COO H102 2H10 H 0 0 N N N ? ? ? 3.844 3.647 14.501 H102 COO 69 COO H103 3H10 H 0 0 N N N ? ? ? 3.045 4.073 16.025 H103 COO 70 COO H151 1H15 H 0 0 N N N ? ? ? -0.874 4.800 0.594 H151 COO 71 COO H152 2H15 H 0 0 N N N ? ? ? 0.863 4.776 0.909 H152 COO 72 COO H153 3H15 H 0 0 N N N ? ? ? -0.013 6.309 0.933 H153 COO 73 COO H141 1H14 H 0 0 N N N -7.707 26.805 42.588 0.599 3.094 2.654 H141 COO 74 COO H142 2H14 H 0 0 N N N -7.681 27.698 44.146 -1.159 3.033 2.505 H142 COO 75 COO H143 3H14 H 0 0 N N N -7.877 25.912 44.137 -0.404 3.348 4.080 H143 COO 76 COO H121 1H12 H 0 0 N N N -9.242 28.592 42.092 0.570 5.672 4.598 H121 COO 77 COO H122 2H12 H 0 0 N N N -10.634 27.549 41.674 0.771 6.850 3.285 H122 COO 78 COO H5A H5A H 0 1 N N N -12.594 31.192 41.589 3.489 7.788 2.827 H5A COO 79 COO H1A H1A H 0 1 N N N -14.839 28.368 45.451 4.230 2.885 6.965 H1A COO 80 COO H5X1 1H5X H 0 0 N N N -16.572 26.734 42.523 4.366 5.433 8.579 H5X1 COO 81 COO H5X2 2H5X H 0 0 N N N -15.598 26.181 41.154 3.498 6.820 7.871 H5X2 COO 82 COO H4X H4X H 0 1 N N N -17.302 24.453 41.862 2.920 5.483 10.556 H4X COO 83 COO H1X H1X H 0 1 N N N -15.610 21.859 43.246 3.538 8.075 12.355 H1X COO 84 COO H8A H8A H 0 1 N N N -12.648 24.145 42.351 3.755 9.415 8.853 H8A COO 85 COO H2A H2A H 0 1 N N N -13.489 17.916 43.922 3.458 11.996 14.735 H2A COO 86 COO H6A1 1H6A H 0 0 N N N -9.606 19.859 41.759 5.313 14.163 10.478 H6A1 COO 87 COO H6A2 2H6A H 0 0 N N N -9.312 20.675 43.142 3.803 14.901 10.939 H6A2 COO 88 COO H2X H2X H 0 1 N N N -14.351 24.396 44.491 1.025 8.760 11.199 H2X COO 89 COO H1 H1 H 0 1 N N N -15.372 22.053 45.358 1.584 7.530 13.127 H1 COO 90 COO H3X H3X H 0 1 N N N -16.739 25.268 44.491 1.552 7.785 9.066 H3X COO 91 COO H7A H7A H 0 1 N N N -19.043 25.864 45.792 -2.899 5.647 9.745 H7A COO 92 COO H2 H2 H 0 1 N N N -17.107 23.540 46.605 -1.890 8.247 8.489 H2 COO 93 # 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 COO C13 O1 SING N N 1 COO C13 H13 SING N N 2 COO C13 C1 SING N N 3 COO C13 C11 SING N N 4 COO C11 C15 SING N N 5 COO C11 C14 SING N N 6 COO C11 C12 SING N N 7 COO C14 H141 SING N N 8 COO C14 H142 SING N N 9 COO C14 H143 SING N N 10 COO C12 H121 SING N N 11 COO C12 H122 SING N N 12 COO C12 O6A SING N N 13 COO O6A P2A SING N N 14 COO P2A O4A DOUB N N 15 COO P2A O5A SING N N 16 COO P2A O3A SING N N 17 COO O5A H5A SING N N 18 COO O3A P1A SING N N 19 COO P1A O2A DOUB N N 20 COO P1A O1A SING N N 21 COO P1A O5X SING N N 22 COO O1A H1A SING N N 23 COO O5X C5X SING N N 24 COO C5X H5X1 SING N N 25 COO C5X H5X2 SING N N 26 COO C5X C4X SING N N 27 COO C4X H4X SING N N 28 COO C4X O4X SING N N 29 COO C4X C3X SING N N 30 COO O4X C1X SING N N 31 COO C3X C2X SING N N 32 COO C3X H3X SING N N 33 COO C3X O3X SING N N 34 COO O3X P3X SING N N 35 COO P3X O9A DOUB N N 36 COO P3X O7A SING N N 37 COO P3X O8A SING N N 38 COO O7A H7A SING N N 39 COO O8A H2 SING N N 40 COO C2X C1X SING N N 41 COO C2X H2X SING N N 42 COO C2X O2X SING N N 43 COO O2X H1 SING N N 44 COO C1X H1X SING N N 45 COO C1X N9A SING N N 46 COO N9A C8A SING Y N 47 COO N9A C4A SING Y N 48 COO C8A H8A SING N N 49 COO C8A N7A DOUB Y N 50 COO N7A C5A SING Y N 51 COO C5A C6A DOUB Y N 52 COO C5A C4A SING Y N 53 COO C4A N3A DOUB Y N 54 COO N3A C2A SING Y N 55 COO C2A N1A DOUB Y N 56 COO C2A H2A SING N N 57 COO N1A C6A SING Y N 58 COO C6A N6A SING N N 59 COO N6A H6A1 SING N N 60 COO N6A H6A2 SING N N 61 COO O1 HO1 SING N N 62 COO C1 O2 DOUB N N 63 COO C1 N1 SING N N 64 COO N1 HN1 SING N N 65 COO N1 C2 SING N N 66 COO C2 H21 SING N N 67 COO C2 H22 SING N N 68 COO C2 C3 SING N N 69 COO C3 H31 SING N N 70 COO C3 H32 SING N N 71 COO C3 C4 SING N N 72 COO C4 O3 DOUB N N 73 COO C4 N2 SING N N 74 COO N2 HN2 SING N N 75 COO N2 C5 SING N N 76 COO C5 H51 SING N N 77 COO C5 H52 SING N N 78 COO C5 C6 SING N N 79 COO C6 H61 SING N N 80 COO C6 H62 SING N N 81 COO C6 S1 SING N N 82 COO S1 C7 SING N N 83 COO C7 O4 DOUB N N 84 COO C7 C8 SING N N 85 COO C8 H8 SING N N 86 COO C8 C9 DOUB N N 87 COO C9 H9 SING N N 88 COO C9 C10 SING N N 89 COO C10 H101 SING N N 90 COO C10 H102 SING N N 91 COO C10 H103 SING N N 92 COO C15 H151 SING N N 93 COO C15 H152 SING N N 94 COO C15 H153 SING N N 95 # 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 COO SMILES ACDLabs 10.04 "O=C(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)/C=C/C" COO SMILES_CANONICAL CACTVS 3.341 "CC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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" COO SMILES CACTVS 3.341 "CC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23" COO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC=CC(=O)SCCNC(=O)CCNC(=O)[C@H](C(C)(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)O" COO SMILES "OpenEye OEToolkits" 1.5.0 "CC=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O" COO InChI InChI 1.03 ;InChI=1S/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,18-,19-,20?,24-/m1/s1 ; COO InChIKey InChI 1.03 KFWWCMJSYSSPSK-XBTRWLRFSA-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 COO "SYSTEMATIC NAME" ACDLabs 10.04 ;S-{(13R,15S)-17-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-9,13,15-trihydroxy-10,10-dimethyl-13,15-dioxido-4,8-dioxo-12,14,16-trioxa-3,7-diaza-13,15-diphosphaheptadec-1-yl} but-2-enethioate (non-preferred name) ; COO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "S-[2-[3-[[(2S)-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]ethyl] but-2-enethioate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site COO "Create component" 2006-08-01 RCSB COO "Modify descriptor" 2011-06-04 RCSB #