data_DN4 # _chem_comp.id DN4 _chem_comp.name ;[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-oxidanyl-4-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3S,4R,5R)-5-(3-carboxypyridin-1-ium-1-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H27 N6 O18 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Nicotinic acid adenine dinucleotide phosphate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-05-24 _chem_comp.pdbx_modified_date 2020-06-17 _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 744.390 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DN4 _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 4F45 _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 DN4 PA PA P 0 1 N N N -400.918 -938.574 4.577 0.245 -3.153 -0.038 PA DN4 1 DN4 O1A O1A O 0 1 N N N -399.818 -939.601 4.626 0.173 -4.254 -1.024 O1A DN4 2 DN4 O2A O2A O 0 1 N N N -401.583 -938.053 5.786 0.777 -3.727 1.369 O2A DN4 3 DN4 O5B O5B O 0 1 N N N -399.877 -937.299 4.740 1.256 -2.019 -0.572 O5B DN4 4 DN4 C5B C5B C 0 1 N N N -400.305 -935.902 4.608 2.607 -2.295 -0.946 C5B DN4 5 DN4 C4B C4B C 0 1 N N R -400.460 -935.068 5.947 3.283 -1.002 -1.405 C4B DN4 6 DN4 O4B O4B O 0 1 N N N -401.875 -934.629 6.164 3.409 -0.096 -0.296 O4B DN4 7 DN4 C3B C3B C 0 1 N N R -399.997 -935.717 7.264 4.707 -1.306 -1.911 C3B DN4 8 DN4 O3B O3B O 0 1 N N N -399.318 -934.735 8.037 4.843 -0.921 -3.281 O3B DN4 9 DN4 C2B C2B C 0 1 N N R -401.305 -936.110 7.950 5.623 -0.442 -1.011 C2B DN4 10 DN4 O2B O2B O 0 1 N N N -401.214 -936.068 9.386 6.672 0.155 -1.775 O2B DN4 11 DN4 C1B C1B C 0 1 N N R -402.318 -935.072 7.473 4.639 0.636 -0.487 C1B DN4 12 DN4 N9A N9A N 0 1 Y N N -403.617 -935.812 7.472 5.112 1.190 0.784 N9A DN4 13 DN4 C8A C8A C 0 1 Y N N -403.907 -936.924 6.785 4.811 0.724 2.029 C8A DN4 14 DN4 N7A N7A N 0 1 Y N N -405.156 -937.310 7.056 5.401 1.453 2.932 N7A DN4 15 DN4 C5A C5A C 0 1 Y N N -405.663 -936.438 7.926 6.115 2.431 2.325 C5A DN4 16 DN4 C6A C6A C 0 1 Y N N -406.895 -936.313 8.554 6.929 3.485 2.775 C6A DN4 17 DN4 N6A N6A N 0 1 N N N -407.859 -937.196 8.319 7.140 3.689 4.127 N6A DN4 18 DN4 N1A N1A N 0 1 Y N N -407.101 -935.280 9.393 7.491 4.280 1.871 N1A DN4 19 DN4 C2A C2A C 0 1 Y N N -406.140 -934.388 9.636 7.296 4.093 0.578 C2A DN4 20 DN4 N3A N3A N 0 1 Y N N -404.949 -934.477 9.057 6.542 3.121 0.112 N3A DN4 21 DN4 C4A C4A C 0 1 Y N N -404.687 -935.486 8.196 5.943 2.271 0.940 C4A DN4 22 DN4 O3 O3 O 0 1 N N N -401.293 -937.973 3.123 -1.220 -2.515 0.162 O3 DN4 23 DN4 PN PN P 0 1 N N N -402.761 -937.283 2.790 -2.692 -3.135 0.363 PN DN4 24 DN4 O1N O1N O -1 1 N N N -403.354 -936.766 4.058 -3.209 -3.681 -0.987 O1N DN4 25 DN4 O2N O2N O 0 1 N N N -403.619 -938.119 1.891 -2.631 -4.284 1.393 O2N DN4 26 DN4 O5D O5D O 0 1 N N N -402.022 -936.149 1.836 -3.689 -1.989 0.895 O5D DN4 27 DN4 C5D C5D C 0 1 N N N -402.456 -934.831 1.711 -5.044 -2.248 1.269 C5D DN4 28 DN4 C4D C4D C 0 1 N N R -403.059 -934.486 0.336 -5.704 -0.946 1.727 C4D DN4 29 DN4 O4D O4D O 0 1 N N N -403.573 -933.168 0.612 -5.819 -0.040 0.616 O4D DN4 30 DN4 C3D C3D C 0 1 N N S -402.043 -934.252 -0.796 -7.131 -1.232 2.233 C3D DN4 31 DN4 O3D O3D O 0 1 N N N -402.656 -934.353 -2.130 -7.263 -0.843 3.602 O3D DN4 32 DN4 C2D C2D C 0 1 N N R -401.490 -932.835 -0.475 -8.037 -0.358 1.332 C2D DN4 33 DN4 O2D O2D O 0 1 N N N -401.597 -931.982 -1.615 -9.079 0.252 2.095 O2D DN4 34 DN4 C1D C1D C 0 1 N N R -402.388 -932.279 0.665 -7.041 0.706 0.806 C1D DN4 35 DN4 N1N N1N N 1 1 Y N N -401.713 -932.077 2.016 -7.506 1.265 -0.466 N1N DN4 36 DN4 C2N C2N C 0 1 Y N N -400.419 -931.481 2.121 -8.033 2.471 -0.480 C2N DN4 37 DN4 C3N C3N C 0 1 Y N N -399.761 -931.272 3.342 -8.487 3.034 -1.674 C3N DN4 38 DN4 C7N C7N C 0 1 N N N -398.337 -930.648 3.376 -9.078 4.388 -1.690 C7N DN4 39 DN4 O7N O7N O 0 1 N N N -397.773 -930.552 2.271 -9.173 5.021 -0.658 O7N DN4 40 DN4 C4N C4N C 0 1 Y N N -400.420 -931.651 4.506 -8.373 2.293 -2.857 C4N DN4 41 DN4 C5N C5N C 0 1 Y N N -401.702 -932.217 4.423 -7.811 1.030 -2.788 C5N DN4 42 DN4 C6N C6N C 0 1 Y N N -402.365 -932.426 3.210 -7.381 0.546 -1.566 C6N DN4 43 DN4 P2B P2B P 0 1 N N N -400.888 -937.413 10.229 8.233 -0.087 -1.461 P2B DN4 44 DN4 O1X O1X O 0 1 N N N -401.469 -938.646 9.652 8.512 0.265 -0.050 O1X DN4 45 DN4 O2X O2X O 0 1 N N N -399.268 -937.400 10.279 8.597 -1.635 -1.710 O2X DN4 46 DN4 O3X O3X O 0 1 N N N -401.415 -937.137 11.732 9.125 0.838 -2.431 O3X DN4 47 DN4 O8N O8N O 0 1 N N N -397.803 -930.260 4.457 -9.513 4.919 -2.849 O8N DN4 48 DN4 H1 H1 H 0 1 N N N -401.208 -938.464 6.556 0.849 -3.058 2.064 H1 DN4 49 DN4 H2 H2 H 0 1 N N N -399.564 -935.386 3.979 3.145 -2.703 -0.090 H2 DN4 50 DN4 H3 H3 H 0 1 N N N -401.281 -935.900 4.101 2.618 -3.020 -1.760 H3 DN4 51 DN4 H4 H4 H 0 1 N N N -399.855 -934.159 5.814 2.697 -0.538 -2.198 H4 DN4 52 DN4 H5 H5 H 0 1 N N N -399.375 -936.603 7.065 4.938 -2.364 -1.787 H5 DN4 53 DN4 H6 H6 H 0 1 N N N -399.026 -935.121 8.854 4.250 -1.390 -3.883 H6 DN4 54 DN4 H7 H7 H 0 1 N N N -401.613 -937.109 7.608 6.029 -1.031 -0.190 H7 DN4 55 DN4 H8 H8 H 0 1 N N N -402.356 -934.232 8.182 4.506 1.426 -1.225 H8 DN4 56 DN4 H9 H9 H 0 1 N N N -403.232 -937.432 6.113 4.177 -0.126 2.237 H9 DN4 57 DN4 H10 H10 H 0 1 N N N -408.674 -936.948 8.844 6.724 3.101 4.777 H10 DN4 58 DN4 H11 H11 H 0 1 N N N -408.079 -937.198 7.343 7.704 4.419 4.425 H11 DN4 59 DN4 H12 H12 H 0 1 N N N -406.335 -933.575 10.319 7.772 4.764 -0.122 H12 DN4 60 DN4 H14 H14 H 0 1 N N N -401.596 -934.168 1.885 -5.586 -2.650 0.414 H14 DN4 61 DN4 H15 H15 H 0 1 N N N -403.222 -934.647 2.478 -5.063 -2.971 2.085 H15 DN4 62 DN4 H16 H16 H 0 1 N N N -403.839 -935.204 0.042 -5.112 -0.488 2.519 H16 DN4 63 DN4 H17 H17 H 0 1 N N N -401.226 -934.982 -0.702 -7.375 -2.287 2.111 H17 DN4 64 DN4 H18 H18 H 0 1 N N N -402.974 -935.238 -2.267 -8.157 -0.948 3.956 H18 DN4 65 DN4 H19 H19 H 0 1 N N N -400.450 -932.913 -0.124 -8.450 -0.944 0.511 H19 DN4 66 DN4 H20 H20 H 0 1 N N N -401.255 -931.122 -1.401 -9.677 -0.379 2.520 H20 DN4 67 DN4 H21 H21 H 0 1 N N N -402.720 -931.284 0.333 -6.897 1.496 1.543 H21 DN4 68 DN4 H22 H22 H 0 1 N N N -399.921 -931.175 1.213 -8.116 3.030 0.441 H22 DN4 69 DN4 H23 H23 H 0 1 N N N -399.949 -931.511 5.468 -8.714 2.697 -3.799 H23 DN4 70 DN4 H24 H24 H 0 1 N N N -402.199 -932.504 5.338 -7.707 0.430 -3.680 H24 DN4 71 DN4 H25 H25 H 0 1 N N N -403.359 -932.848 3.191 -6.938 -0.437 -1.510 H25 DN4 72 DN4 H26 H26 H 0 1 N N N -398.933 -938.213 9.918 8.439 -1.935 -2.616 H26 DN4 73 DN4 H27 H27 H 0 1 N N N -402.017 -937.826 11.989 10.078 0.743 -2.296 H27 DN4 74 DN4 H28 H28 H 0 1 N N N -396.942 -929.903 4.275 -9.892 5.808 -2.809 H28 DN4 75 # # 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 DN4 O3D C3D SING N N 1 DN4 O2D C2D SING N N 2 DN4 C3D C2D SING N N 3 DN4 C3D C4D SING N N 4 DN4 C2D C1D SING N N 5 DN4 C4D O4D SING N N 6 DN4 C4D C5D SING N N 7 DN4 O4D C1D SING N N 8 DN4 C1D N1N SING N N 9 DN4 C5D O5D SING N N 10 DN4 O5D PN SING N N 11 DN4 O2N PN DOUB N N 12 DN4 N1N C2N DOUB Y N 13 DN4 N1N C6N SING Y N 14 DN4 C2N C3N SING Y N 15 DN4 O7N C7N DOUB N N 16 DN4 PN O3 SING N N 17 DN4 PN O1N SING N N 18 DN4 O3 PA SING N N 19 DN4 C6N C5N DOUB Y N 20 DN4 C3N C7N SING N N 21 DN4 C3N C4N DOUB Y N 22 DN4 C7N O8N SING N N 23 DN4 C5N C4N SING Y N 24 DN4 PA O1A DOUB N N 25 DN4 PA O5B SING N N 26 DN4 PA O2A SING N N 27 DN4 C5B O5B SING N N 28 DN4 C5B C4B SING N N 29 DN4 C4B O4B SING N N 30 DN4 C4B C3B SING N N 31 DN4 O4B C1B SING N N 32 DN4 C8A N7A DOUB Y N 33 DN4 C8A N9A SING Y N 34 DN4 N7A C5A SING Y N 35 DN4 C3B C2B SING N N 36 DN4 C3B O3B SING N N 37 DN4 N9A C1B SING N N 38 DN4 N9A C4A SING Y N 39 DN4 C1B C2B SING N N 40 DN4 C5A C4A DOUB Y N 41 DN4 C5A C6A SING Y N 42 DN4 C2B O2B SING N N 43 DN4 C4A N3A SING Y N 44 DN4 N6A C6A SING N N 45 DN4 C6A N1A DOUB Y N 46 DN4 N3A C2A DOUB Y N 47 DN4 O2B P2B SING N N 48 DN4 N1A C2A SING Y N 49 DN4 O1X P2B DOUB N N 50 DN4 P2B O2X SING N N 51 DN4 P2B O3X SING N N 52 DN4 O2A H1 SING N N 53 DN4 C5B H2 SING N N 54 DN4 C5B H3 SING N N 55 DN4 C4B H4 SING N N 56 DN4 C3B H5 SING N N 57 DN4 O3B H6 SING N N 58 DN4 C2B H7 SING N N 59 DN4 C1B H8 SING N N 60 DN4 C8A H9 SING N N 61 DN4 N6A H10 SING N N 62 DN4 N6A H11 SING N N 63 DN4 C2A H12 SING N N 64 DN4 C5D H14 SING N N 65 DN4 C5D H15 SING N N 66 DN4 C4D H16 SING N N 67 DN4 C3D H17 SING N N 68 DN4 O3D H18 SING N N 69 DN4 C2D H19 SING N N 70 DN4 O2D H20 SING N N 71 DN4 C1D H21 SING N N 72 DN4 C2N H22 SING N N 73 DN4 C4N H23 SING N N 74 DN4 C5N H24 SING N N 75 DN4 C6N H25 SING N N 76 DN4 O2X H26 SING N N 77 DN4 O3X H27 SING N N 78 DN4 O8N H28 SING N N 79 # # 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 DN4 InChI InChI 1.03 "InChI=1S/C21H27N6O18P3/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1" DN4 InChIKey InChI 1.03 QOTXBMGJKFVZRD-HISDBWNOSA-N DN4 SMILES_CANONICAL CACTVS 3.370 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)O[P]([O-])(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)[n+]5cccc(c5)C(O)=O)[C@@H](O)[C@H]3O[P](O)(O)=O" DN4 SMILES CACTVS 3.370 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P]([O-])(=O)OC[CH]4O[CH]([CH](O)[CH]4O)[n+]5cccc(c5)C(O)=O)[CH](O)[CH]3O[P](O)(O)=O" DN4 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=O)O" DN4 SMILES "OpenEye OEToolkits" 1.7.6 "c1cc(c[n+](c1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=O)O" # _pdbx_chem_comp_identifier.comp_id DN4 _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program "OpenEye OEToolkits" _pdbx_chem_comp_identifier.program_version 1.7.6 _pdbx_chem_comp_identifier.identifier "[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-oxidanyl-4-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3S,4R,5R)-5-(3-carboxypyridin-1-ium-1-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DN4 "Create component" 2012-05-24 PDBJ DN4 "Initial release" 2013-04-03 RCSB DN4 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id DN4 _pdbx_chem_comp_synonyms.name "Nicotinic acid adenine dinucleotide phosphate" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##