data_NBC # _chem_comp.id NBC _chem_comp.name S-4-NITROBUTYRYL-COA _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H41 N8 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 2002-04-30 _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 882.622 _chem_comp.one_letter_code ? _chem_comp.three_letter_code NBC _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _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 NBC P31 P31 P 0 1 N N S 73.754 6.950 37.714 1.281 1.877 7.550 P31 NBC 1 NBC O33 O33 O 0 1 N N N 73.622 5.494 37.440 0.972 3.246 8.354 O33 NBC 2 NBC O34 O34 O 0 1 N N N 74.080 7.333 39.140 2.182 0.922 8.277 O34 NBC 3 NBC O23 O23 O 0 1 N N N 74.886 7.578 36.778 -0.181 1.285 7.185 O23 NBC 4 NBC C19 C19 C 0 1 N N N 75.310 8.939 36.764 -1.121 2.092 6.499 C19 NBC 5 NBC C18 C18 C 0 1 N N R 76.892 9.171 36.903 -1.484 1.422 5.186 C18 NBC 6 NBC O22 O22 O 0 1 N N N 77.041 9.562 38.284 -0.299 1.219 4.399 O22 NBC 7 NBC C15 C15 C 0 1 N N R 77.952 8.705 39.001 -0.480 0.029 3.603 C15 NBC 8 NBC N9 N9 N 0 1 Y N N 77.602 8.580 40.456 0.672 -0.857 3.781 N9 NBC 9 NBC C4 C4 C 0 1 Y N N 78.409 9.115 41.431 1.226 -1.682 2.842 C4 NBC 10 NBC N3 N3 N 0 1 Y N N 79.632 9.826 41.286 0.834 -1.853 1.571 N3 NBC 11 NBC C2 C2 C 0 1 Y N N 80.276 10.282 42.518 1.626 -2.753 0.949 C2 NBC 12 NBC N1 N1 N 0 1 Y N N 79.703 10.022 43.771 2.686 -3.437 1.444 N1 NBC 13 NBC C6 C6 C 0 1 Y N N 78.420 9.272 43.907 3.026 -3.214 2.737 C6 NBC 14 NBC N6 N6 N 0 1 N N N 77.919 9.057 45.120 4.116 -3.893 3.308 N6 NBC 15 NBC C5 C5 C 0 1 Y N N 77.724 8.785 42.670 2.283 -2.306 3.485 C5 NBC 16 NBC N7 N7 N 0 1 Y N N 76.561 8.085 42.434 2.381 -1.880 4.785 N7 NBC 17 NBC C8 C8 C 0 1 Y N N 76.524 7.983 41.134 1.402 -1.012 4.931 C8 NBC 18 NBC C16 C16 C 0 1 N N R 77.926 7.416 38.183 -1.810 -0.605 4.014 C16 NBC 19 NBC O20 O20 O 0 1 N N N 79.055 6.566 38.480 -2.811 -0.259 3.058 O20 NBC 20 NBC C17 C17 C 0 1 N N S 77.807 7.921 36.682 -2.089 0.039 5.359 C17 NBC 21 NBC O21 O21 O 0 1 N N N 79.113 8.394 36.202 -3.461 0.096 5.682 O21 NBC 22 NBC P39 P39 P 0 1 N N N 80.149 8.537 34.937 -4.278 -1.293 5.784 P39 NBC 23 NBC O40 O40 O 0 1 N N N 80.468 7.138 34.434 -4.301 -2.113 4.528 O40 NBC 24 NBC O41 O41 O 0 1 N N N 79.452 9.377 33.860 -5.727 -0.849 6.347 O41 NBC 25 NBC O42 O42 O 0 1 N N N 81.368 9.250 35.512 -3.589 -2.013 7.058 O42 NBC 26 NBC O32 O32 O 0 1 N N N 72.368 7.743 37.310 1.870 2.401 6.139 O32 NBC 27 NBC P35 P35 P 0 1 N N S 70.813 7.162 37.457 3.219 3.220 5.791 P35 NBC 28 NBC O36 O36 O 0 1 N N N 70.294 7.011 35.994 3.333 4.565 6.448 O36 NBC 29 NBC O37 O37 O 0 1 N N N 70.724 5.752 38.025 4.398 2.176 6.162 O37 NBC 30 NBC O38 O38 O 0 1 N N N 69.687 8.066 38.254 3.173 3.216 4.177 O38 NBC 31 NBC C46 C46 C 0 1 N N N 69.623 8.066 39.708 4.280 3.762 3.469 C46 NBC 32 NBC C45 C45 C 0 1 N N N 70.251 9.226 40.510 4.061 3.672 1.939 C45 NBC 33 NBC C53 C53 C 0 1 N N N 71.475 9.688 39.681 2.778 4.456 1.572 C53 NBC 34 NBC C57 C57 C 0 1 N N N 69.188 10.281 40.576 5.239 4.343 1.204 C57 NBC 35 NBC C44 C44 C 0 1 N N R 70.666 8.813 41.980 3.886 2.194 1.481 C44 NBC 36 NBC O52 O52 O 0 1 N N N 71.609 7.720 41.916 3.692 2.148 0.070 O52 NBC 37 NBC C43 C43 C 0 1 N N N 71.352 9.980 42.855 5.086 1.298 1.782 C43 NBC 38 NBC O51 O51 O 0 1 N N N 72.494 9.781 43.303 6.041 1.199 1.014 O51 NBC 39 NBC N68 N68 N 0 1 N N N 70.741 11.209 43.130 4.980 0.650 3.002 N68 NBC 40 NBC C62 C62 C 0 1 N N N 69.933 11.354 44.304 6.002 -0.231 3.518 C62 NBC 41 NBC C61 C61 C 0 1 N N N 69.403 12.779 44.352 7.000 0.566 4.346 C61 NBC 42 NBC C69 C69 C 0 1 N N N 70.489 13.860 44.574 8.113 -0.300 4.907 C69 NBC 43 NBC O72 O72 O 0 1 N N N 71.503 13.784 43.801 8.188 -1.510 4.708 O72 NBC 44 NBC N71 N71 N 0 1 N N N 70.217 14.827 45.634 9.011 0.445 5.658 N71 NBC 45 NBC C74 C74 C 0 1 N N N 71.253 15.841 45.827 10.163 -0.137 6.305 C74 NBC 46 NBC C73 C73 C 0 1 N N N 70.911 16.782 46.915 9.873 -0.614 7.722 C73 NBC 47 NBC S81 S81 S 0 1 N N N 71.773 18.431 46.952 9.356 0.747 8.813 S81 NBC 48 NBC "C1'" C1* C 0 1 N N N 71.777 19.042 48.726 9.193 -0.124 10.340 "C1'" NBC 49 NBC "O1'" O1* O 0 1 N N N 70.821 18.542 49.339 9.384 -1.329 10.442 "O1'" NBC 50 NBC "C2'" C2* C 0 1 N N N 72.779 19.997 49.342 8.758 0.772 11.484 "C2'" NBC 51 NBC "C3'" C3* C 0 1 N N N 72.598 20.356 50.789 9.196 0.253 12.854 "C3'" NBC 52 NBC "C4'" C4* C 0 1 N N N 73.870 20.500 51.584 10.710 0.207 12.991 "C4'" NBC 53 NBC "N5'" N5* N 1 1 N N N 73.728 20.836 52.953 11.026 -0.235 14.360 "N5'" NBC 54 NBC "O2'" O2* O 0 1 N N N 74.596 20.305 53.812 11.112 -1.459 14.562 "O2'" NBC 55 NBC "O3'" O3* O -1 1 N N N 72.792 21.641 53.374 11.170 0.639 15.232 "O3'" NBC 56 NBC H28 H28 H 0 1 N N N 73.417 5.253 36.544 0.728 3.194 9.303 H28 NBC 57 NBC H29 H29 H 0 1 N N N 74.769 9.515 37.550 -2.009 2.211 7.127 H29 NBC 58 NBC H30 H30 H 0 1 N N N 74.929 9.448 35.848 -0.676 3.075 6.318 H30 NBC 59 NBC H36 H36 H 0 1 N N N 77.213 9.895 36.118 -2.158 2.083 4.629 H36 NBC 60 NBC H37 H37 H 0 1 N N N 78.993 9.098 39.077 -0.460 0.316 2.546 H37 NBC 61 NBC H39 H39 H 0 1 N N N 81.227 10.841 42.502 1.383 -2.955 -0.088 H39 NBC 62 NBC H40 H40 H 0 1 N N N 77.827 9.953 45.599 4.927 -3.375 3.589 H40 NBC 63 NBC H41 H41 H 0 1 N N N 77.042 8.544 45.213 4.109 -4.895 3.342 H41 NBC 64 NBC H38 H38 H 0 1 N N N 75.679 7.453 40.663 1.172 -0.469 5.837 H38 NBC 65 NBC H34 H34 H 0 1 N N N 77.073 6.740 38.423 -1.785 -1.697 4.068 H34 NBC 66 NBC H35 H35 H 0 1 N N N 79.039 5.764 37.971 -2.380 -0.232 2.186 H35 NBC 67 NBC H31 H31 H 0 1 N N N 77.445 7.155 35.957 -1.559 -0.511 6.146 H31 NBC 68 NBC H33 H33 H 0 1 N N N 80.052 9.460 33.128 -6.430 -1.527 6.434 H33 NBC 69 NBC H32 H32 H 0 1 N N N 81.968 9.333 34.780 -3.848 -2.933 7.281 H32 NBC 70 NBC H27 H27 H 0 1 N N N 69.838 5.421 38.109 4.639 2.046 7.104 H27 NBC 71 NBC H25 H25 H 0 1 N N N 70.054 7.107 40.079 4.393 4.803 3.789 H25 NBC 72 NBC H26 H26 H 0 1 N N N 68.556 7.964 40.014 5.176 3.210 3.772 H26 NBC 73 NBC H22 H22 H 0 1 N N N 71.228 9.954 38.627 2.559 4.371 0.501 H22 NBC 74 NBC H23 H23 H 0 1 N N N 71.929 10.526 40.260 2.876 5.523 1.801 H23 NBC 75 NBC H24 H24 H 0 1 N N N 72.192 8.867 39.445 1.907 4.081 2.122 H24 NBC 76 NBC H19 H19 H 0 1 N N N 68.220 9.918 40.993 5.280 5.419 1.409 H19 NBC 77 NBC H20 H20 H 0 1 N N N 69.642 11.119 41.155 5.146 4.222 0.119 H20 NBC 78 NBC H21 H21 H 0 1 N N N 68.794 10.585 39.578 6.200 3.921 1.513 H21 NBC 79 NBC H18 H18 H 0 1 N N N 69.709 8.545 42.485 2.989 1.764 1.944 H18 NBC 80 NBC H17 H17 H 0 1 N N N 71.858 7.472 42.799 4.571 2.232 -0.333 H17 NBC 81 NBC H16 H16 H 0 1 N N N 70.882 11.987 42.485 4.164 0.814 3.585 H16 NBC 82 NBC H14 H14 H 0 1 N N N 70.476 11.068 45.235 5.533 -1.012 4.127 H14 NBC 83 NBC H15 H15 H 0 1 N N N 69.120 10.593 44.361 6.506 -0.728 2.682 H15 NBC 84 NBC H12 H12 H 0 1 N N N 68.602 12.870 45.122 6.487 1.055 5.184 H12 NBC 85 NBC H13 H13 H 0 1 N N N 68.812 13.005 43.434 7.452 1.356 3.733 H13 NBC 86 NBC H11 H11 H 0 1 N N N 69.367 14.797 46.197 8.851 1.443 5.756 H11 NBC 87 NBC H91 1H9 H 0 1 N N N 71.471 16.383 44.877 10.469 -0.991 5.691 H91 NBC 88 NBC H10 H10 H 0 1 N N N 72.251 15.373 45.996 10.973 0.599 6.279 H10 NBC 89 NBC H71 1H7 H 0 1 N N N 71.056 16.273 47.896 9.088 -1.377 7.724 H71 NBC 90 NBC H81 1H8 H 0 1 N N N 69.808 16.947 46.921 10.777 -1.057 8.152 H81 NBC 91 NBC H51 1H5 H 0 1 N N N 72.820 20.930 48.733 9.152 1.784 11.333 H51 NBC 92 NBC H61 1H6 H 0 1 N N N 73.809 19.600 49.187 7.663 0.824 11.460 H61 NBC 93 NBC H31A 1H3 H 0 0 N N N 71.920 19.622 51.283 8.767 -0.740 13.039 H31A NBC 94 NBC H41A 1H4 H 0 0 N N N 71.984 21.283 50.879 8.782 0.917 13.624 H41A NBC 95 NBC H11A 1H1 H 0 0 N N N 74.542 21.237 51.085 11.172 1.191 12.869 H11A NBC 96 NBC H21A 1H2 H 0 0 N N N 74.479 19.571 51.488 11.180 -0.514 12.319 H21A NBC 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 NBC P31 O33 SING N N 1 NBC P31 O34 DOUB N N 2 NBC P31 O23 SING N N 3 NBC P31 O32 SING N N 4 NBC O33 H28 SING N N 5 NBC O23 C19 SING N N 6 NBC C19 C18 SING N N 7 NBC C19 H29 SING N N 8 NBC C19 H30 SING N N 9 NBC C18 O22 SING N N 10 NBC C18 C17 SING N N 11 NBC C18 H36 SING N N 12 NBC O22 C15 SING N N 13 NBC C15 N9 SING N N 14 NBC C15 C16 SING N N 15 NBC C15 H37 SING N N 16 NBC N9 C4 SING Y N 17 NBC N9 C8 SING Y N 18 NBC C4 N3 DOUB Y N 19 NBC C4 C5 SING Y N 20 NBC N3 C2 SING Y N 21 NBC C2 N1 DOUB Y N 22 NBC C2 H39 SING N N 23 NBC N1 C6 SING Y N 24 NBC C6 N6 SING N N 25 NBC C6 C5 DOUB Y N 26 NBC N6 H40 SING N N 27 NBC N6 H41 SING N N 28 NBC C5 N7 SING Y N 29 NBC N7 C8 DOUB Y N 30 NBC C8 H38 SING N N 31 NBC C16 O20 SING N N 32 NBC C16 C17 SING N N 33 NBC C16 H34 SING N N 34 NBC O20 H35 SING N N 35 NBC C17 O21 SING N N 36 NBC C17 H31 SING N N 37 NBC O21 P39 SING N N 38 NBC P39 O40 DOUB N N 39 NBC P39 O41 SING N N 40 NBC P39 O42 SING N N 41 NBC O41 H33 SING N N 42 NBC O42 H32 SING N N 43 NBC O32 P35 SING N N 44 NBC P35 O36 DOUB N N 45 NBC P35 O37 SING N N 46 NBC P35 O38 SING N N 47 NBC O37 H27 SING N N 48 NBC O38 C46 SING N N 49 NBC C46 C45 SING N N 50 NBC C46 H25 SING N N 51 NBC C46 H26 SING N N 52 NBC C45 C53 SING N N 53 NBC C45 C57 SING N N 54 NBC C45 C44 SING N N 55 NBC C53 H22 SING N N 56 NBC C53 H23 SING N N 57 NBC C53 H24 SING N N 58 NBC C57 H19 SING N N 59 NBC C57 H20 SING N N 60 NBC C57 H21 SING N N 61 NBC C44 O52 SING N N 62 NBC C44 C43 SING N N 63 NBC C44 H18 SING N N 64 NBC O52 H17 SING N N 65 NBC C43 O51 DOUB N N 66 NBC C43 N68 SING N N 67 NBC N68 C62 SING N N 68 NBC N68 H16 SING N N 69 NBC C62 C61 SING N N 70 NBC C62 H14 SING N N 71 NBC C62 H15 SING N N 72 NBC C61 C69 SING N N 73 NBC C61 H12 SING N N 74 NBC C61 H13 SING N N 75 NBC C69 O72 DOUB N N 76 NBC C69 N71 SING N N 77 NBC N71 C74 SING N N 78 NBC N71 H11 SING N N 79 NBC C74 C73 SING N N 80 NBC C74 H91 SING N N 81 NBC C74 H10 SING N N 82 NBC C73 S81 SING N N 83 NBC C73 H71 SING N N 84 NBC C73 H81 SING N N 85 NBC S81 "C1'" SING N N 86 NBC "C1'" "O1'" DOUB N N 87 NBC "C1'" "C2'" SING N N 88 NBC "C2'" "C3'" SING N N 89 NBC "C2'" H51 SING N N 90 NBC "C2'" H61 SING N N 91 NBC "C3'" "C4'" SING N N 92 NBC "C3'" H31A SING N N 93 NBC "C3'" H41A SING N N 94 NBC "C4'" "N5'" SING N N 95 NBC "C4'" H11A SING N N 96 NBC "C4'" H21A SING N N 97 NBC "N5'" "O2'" DOUB N N 98 NBC "N5'" "O3'" SING N N 99 # 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 NBC SMILES ACDLabs 10.04 "[O-][N+](=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" NBC 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)CCC[N+]([O-])=O" NBC 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)CCC[N+]([O-])=O" NBC 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)CCC[N+](=O)[O-])O" NBC 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)CCC[N+](=O)[O-])O" NBC InChI InChI 1.03 ;InChI=1S/C25H41N8O19P3S/c1-25(2,20(37)23(38)28-6-5-15(34)27-7-9-56-16(35)4-3-8-33(39)40)11-49-55(46,47)52-54(44,45)48-10-14-19(51-53(41,42)43)18(36)24(50-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,36-37H,3-11H2,1-2H3,(H,27,34)(H,28,38)(H,44,45)(H,46,47)(H2,26,29,30)(H2,41,42,43)/t14-,18-,19-,20+,24-/m1/s1 ; NBC InChIKey InChI 1.03 PXNIOQHGCSEKCC-CITAKDKDSA-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 NBC "SYSTEMATIC NAME" ACDLabs 10.04 ;S-{(9R,13S,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} 4-nitrobutanethioate (non-preferred name) ; NBC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "S-[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]ethyl] 4-nitrobutanethioate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site NBC "Create component" 2002-04-30 RCSB NBC "Modify descriptor" 2011-06-04 RCSB #