data_NAP # _chem_comp.id NAP _chem_comp.name "NADP NICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H28 N7 O17 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "2'-MONOPHOSPHOADENOSINE 5'-DIPHOSPHORIBOSE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 743.405 _chem_comp.one_letter_code ? _chem_comp.three_letter_code NAP _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1D4O _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 NAP PA AP P 0 1 N N R 17.174 26.134 12.040 -0.035 -0.972 0.719 PA NAP 1 NAP O1A AO1 O 0 1 N N N 16.048 25.314 12.500 0.490 -0.256 1.903 O1A NAP 2 NAP O2A AO2 O 0 1 N N N 18.478 26.114 12.670 -0.725 -2.349 1.187 O2A NAP 3 NAP O5B AO5* O 0 1 N N N 17.317 25.889 10.437 -1.126 -0.051 -0.026 O5B NAP 4 NAP C5B AC5* C 0 1 N N N 17.813 26.990 9.495 -2.109 0.297 0.952 C5B NAP 5 NAP C4B AC4* C 0 1 N N R 17.962 26.155 8.345 -3.181 1.177 0.307 C4B NAP 6 NAP O4B AO4* O 0 1 N N N 17.859 27.351 7.294 -3.920 0.416 -0.663 O4B NAP 7 NAP C3B AC3* C 0 1 N N R 18.840 25.789 7.535 -4.181 1.655 1.377 C3B NAP 8 NAP O3B AO3* O 0 1 N N N 18.208 24.597 7.839 -4.196 3.082 1.456 O3B NAP 9 NAP C2B AC2* C 0 1 N N R 19.276 25.751 6.147 -5.550 1.124 0.876 C2B NAP 10 NAP O2B AO2* O 0 1 N N N 18.883 24.739 5.481 -6.576 2.099 1.071 O2B NAP 11 NAP C1B AC1* C 0 1 N N R 18.394 26.894 5.988 -5.279 0.901 -0.633 C1B NAP 12 NAP N9A AN9 N 0 1 Y N N 19.237 28.090 5.590 -6.196 -0.101 -1.183 N9A NAP 13 NAP C8A AC8 C 0 1 Y N N 20.466 28.637 6.011 -5.978 -1.445 -1.249 C8A NAP 14 NAP N7A AN7 N 0 1 Y N N 20.935 29.548 5.192 -7.000 -2.036 -1.795 N7A NAP 15 NAP C5A AC5 C 0 1 Y N N 20.003 29.624 4.173 -7.938 -1.111 -2.114 C5A NAP 16 NAP C6A AC6 C 0 1 Y N N 19.935 30.402 2.975 -9.210 -1.158 -2.708 C6A NAP 17 NAP N6A AN6 N 0 1 N N N 20.889 31.262 2.635 -9.759 -2.363 -3.112 N6A NAP 18 NAP N1A AN1 N 0 1 Y N N 18.841 30.230 2.153 -9.874 -0.019 -2.874 N1A NAP 19 NAP C2A AC2 C 0 1 Y N N 17.867 29.350 2.480 -9.358 1.135 -2.492 C2A NAP 20 NAP N3A AN3 N 0 1 Y N N 17.859 28.574 3.579 -8.171 1.227 -1.931 N3A NAP 21 NAP C4A AC4 C 0 1 Y N N 18.962 28.758 4.395 -7.435 0.141 -1.720 C4A NAP 22 NAP O3 O3 O 0 1 N N N 16.458 27.566 12.208 1.175 -1.294 -0.293 O3 NAP 23 NAP PN NP P 0 1 N N N 15.216 28.068 13.153 2.390 -1.858 0.599 PN NAP 24 NAP O1N NO1 O 0 1 N N N 13.983 27.417 12.642 2.142 -3.348 0.925 O1N NAP 25 NAP O2N NO2 O -1 1 N N N 15.308 29.554 13.093 2.481 -1.051 1.914 O2N NAP 26 NAP O5D NO5* O 0 1 N N N 15.487 27.658 14.685 3.770 -1.710 -0.218 O5D NAP 27 NAP C5D NC5* C 0 1 N N N 16.599 28.169 15.475 4.818 -2.114 0.665 C5D NAP 28 NAP C4D NC4* C 0 1 N N R 17.395 26.968 16.025 6.164 -1.997 -0.053 C4D NAP 29 NAP O4D NO4* O 0 1 N N N 18.653 27.366 16.614 6.466 -0.613 -0.332 O4D NAP 30 NAP C3D NC3* C 0 1 N N S 16.694 26.193 17.167 7.310 -2.474 0.866 C3D NAP 31 NAP O3D NO3* O 0 1 N N N 17.085 24.806 17.287 7.670 -3.822 0.559 O3D NAP 32 NAP C2D NC2* C 0 1 N N R 17.093 26.936 18.393 8.478 -1.513 0.540 C2D NAP 33 NAP O2D NO2* O 0 1 N N N 16.979 26.205 19.588 9.595 -2.239 0.025 O2D NAP 34 NAP C1D NC1* C 0 1 N N R 18.569 27.243 18.038 7.895 -0.568 -0.534 C1D NAP 35 NAP N1N NN1 N 1 1 Y N N 19.125 28.361 18.811 8.395 0.795 -0.341 N1N NAP 36 NAP C2N NC2 C 0 1 Y N N 18.555 29.641 18.667 9.364 1.237 -1.116 C2N NAP 37 NAP C3N NC3 C 0 1 Y N N 19.141 30.683 19.465 9.869 2.527 -0.955 C3N NAP 38 NAP C7N NC7 C 0 1 N N N 18.652 32.050 19.414 10.961 3.021 -1.820 C7N NAP 39 NAP O7N NO7 O 0 1 N N N 19.161 32.943 20.102 11.430 2.299 -2.678 O7N NAP 40 NAP N7N NN7 N 0 1 N N N 17.622 32.390 18.616 11.437 4.272 -1.658 N7N NAP 41 NAP C4N NC4 C 0 1 Y N N 20.222 30.376 20.317 9.320 3.349 0.037 C4N NAP 42 NAP C5N NC5 C 0 1 Y N N 20.746 29.139 20.435 8.300 2.840 0.821 C5N NAP 43 NAP C6N NC6 C 0 1 Y N N 20.202 28.129 19.681 7.859 1.547 0.601 C6N NAP 44 NAP P2B AP2* P 0 1 N N N 19.664 24.555 4.097 -7.765 1.370 1.875 P2B NAP 45 NAP O1X AOP1 O 0 1 N N N 21.117 24.360 4.404 -7.226 0.774 3.119 O1X NAP 46 NAP O2X AOP2 O 0 1 N N N 18.964 23.410 3.543 -8.903 2.447 2.246 O2X NAP 47 NAP O3X AOP3 O 0 1 N N N 19.391 25.798 3.381 -8.402 0.211 0.957 O3X NAP 48 NAP HOA2 2HOA H 0 0 N N N 19.207 26.645 12.372 -1.053 -2.783 0.387 HOA2 NAP 49 NAP H51A AH51 H 0 0 N N N 17.176 27.899 9.389 -2.570 -0.610 1.343 H51A NAP 50 NAP H52A AH52 H 0 0 N N N 18.702 27.579 9.819 -1.633 0.843 1.767 H52A NAP 51 NAP H4B AH4* H 0 1 N N N 17.494 25.243 8.784 -2.714 2.037 -0.175 H4B NAP 52 NAP H3B AH3* H 0 1 N N N 19.753 26.421 7.625 -3.936 1.223 2.347 H3B NAP 53 NAP HO3A AHO3 H 0 0 N N N 18.875 24.318 7.223 -3.323 3.353 1.772 HO3A NAP 54 NAP H2B AH2* H 0 1 N N N 20.353 25.734 5.862 -5.809 0.186 1.368 H2B NAP 55 NAP H1B AH1* H 0 1 N N N 17.599 26.587 5.268 -5.364 1.839 -1.182 H1B NAP 56 NAP H8A AH8 H 0 1 N N N 21.025 28.369 6.923 -5.087 -1.946 -0.899 H8A NAP 57 NAP H61A AH61 H 0 0 N N N 20.840 31.816 1.780 -9.265 -3.187 -2.985 H61A NAP 58 NAP H62A AH62 H 0 0 N N N 21.774 30.755 2.625 -10.638 -2.382 -3.521 H62A NAP 59 NAP H2A AH2 H 0 1 N N N 17.008 29.257 1.793 -9.932 2.037 -2.646 H2A NAP 60 NAP H51N NH51 H 0 0 N N N 17.238 28.882 14.904 4.658 -3.148 0.970 H51N NAP 61 NAP H52N NH52 H 0 0 N N N 16.269 28.869 16.277 4.819 -1.472 1.546 H52N NAP 62 NAP H4D NH4* H 0 1 N N N 17.508 26.330 15.117 6.152 -2.577 -0.976 H4D NAP 63 NAP H3D NH3* H 0 1 N N N 15.595 26.147 16.979 7.022 -2.385 1.913 H3D NAP 64 NAP HO3N NHO3 H 0 0 N N N 16.654 24.330 17.987 8.387 -4.064 1.162 HO3N NAP 65 NAP H2D NH2* H 0 1 N N N 16.445 27.817 18.610 8.766 -0.948 1.427 H2D NAP 66 NAP HO2N NHO2 H 0 0 N N N 17.233 26.679 20.370 9.874 -2.852 0.719 HO2N NAP 67 NAP H1D NH1* H 0 1 N N N 19.235 26.404 18.346 8.149 -0.927 -1.532 H1D NAP 68 NAP H2N NH2 H 0 1 N N N 17.710 29.814 17.978 9.778 0.591 -1.876 H2N NAP 69 NAP H71N NH71 H 0 0 N N N 17.202 31.653 18.048 12.153 4.595 -2.226 H71N NAP 70 NAP H72N NH72 H 0 0 N N N 17.278 33.349 18.580 11.060 4.849 -0.976 H72N NAP 71 NAP H4N NH4 H 0 1 N N N 20.691 31.159 20.935 9.684 4.355 0.187 H4N NAP 72 NAP H5N NH5 H 0 1 N N N 21.589 28.959 21.123 7.853 3.445 1.596 H5N NAP 73 NAP H6N NH6 H 0 1 N N N 20.635 27.119 19.775 7.063 1.146 1.211 H6N NAP 74 NAP HOP2 2HOP H 0 0 N N N 19.427 23.300 2.721 -9.594 1.970 2.725 HOP2 NAP 75 NAP HOP3 3HOP H 0 0 N N N 19.854 25.688 2.559 -8.740 0.640 0.160 HOP3 NAP 76 # # 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 NAP PA O1A DOUB N N 1 NAP PA O2A SING N N 2 NAP PA O5B SING N N 3 NAP PA O3 SING N N 4 NAP O2A HOA2 SING N N 5 NAP O5B C5B SING N N 6 NAP C5B C4B SING N N 7 NAP C5B H51A SING N N 8 NAP C5B H52A SING N N 9 NAP C4B O4B SING N N 10 NAP C4B C3B SING N N 11 NAP C4B H4B SING N N 12 NAP O4B C1B SING N N 13 NAP C3B O3B SING N N 14 NAP C3B C2B SING N N 15 NAP C3B H3B SING N N 16 NAP O3B HO3A SING N N 17 NAP C2B O2B SING N N 18 NAP C2B C1B SING N N 19 NAP C2B H2B SING N N 20 NAP O2B P2B SING N N 21 NAP C1B N9A SING N N 22 NAP C1B H1B SING N N 23 NAP N9A C8A SING Y N 24 NAP N9A C4A SING Y N 25 NAP C8A N7A DOUB Y N 26 NAP C8A H8A SING N N 27 NAP N7A C5A SING Y N 28 NAP C5A C6A SING Y N 29 NAP C5A C4A DOUB Y N 30 NAP C6A N6A SING N N 31 NAP C6A N1A DOUB Y N 32 NAP N6A H61A SING N N 33 NAP N6A H62A SING N N 34 NAP N1A C2A SING Y N 35 NAP C2A N3A DOUB Y N 36 NAP C2A H2A SING N N 37 NAP N3A C4A SING Y N 38 NAP O3 PN SING N N 39 NAP PN O1N DOUB N N 40 NAP PN O2N SING N N 41 NAP PN O5D SING N N 42 NAP O5D C5D SING N N 43 NAP C5D C4D SING N N 44 NAP C5D H51N SING N N 45 NAP C5D H52N SING N N 46 NAP C4D O4D SING N N 47 NAP C4D C3D SING N N 48 NAP C4D H4D SING N N 49 NAP O4D C1D SING N N 50 NAP C3D O3D SING N N 51 NAP C3D C2D SING N N 52 NAP C3D H3D SING N N 53 NAP O3D HO3N SING N N 54 NAP C2D O2D SING N N 55 NAP C2D C1D SING N N 56 NAP C2D H2D SING N N 57 NAP O2D HO2N SING N N 58 NAP C1D N1N SING N N 59 NAP C1D H1D SING N N 60 NAP N1N C2N SING Y N 61 NAP N1N C6N DOUB Y N 62 NAP C2N C3N DOUB Y N 63 NAP C2N H2N SING N N 64 NAP C3N C7N SING N N 65 NAP C3N C4N SING Y N 66 NAP C7N O7N DOUB N N 67 NAP C7N N7N SING N N 68 NAP N7N H71N SING N N 69 NAP N7N H72N SING N N 70 NAP C4N C5N DOUB Y N 71 NAP C4N H4N SING N N 72 NAP C5N C6N SING Y N 73 NAP C5N H5N SING N N 74 NAP C6N H6N SING N N 75 NAP P2B O1X DOUB N N 76 NAP P2B O2X SING N N 77 NAP P2B O3X SING N N 78 NAP O2X HOP2 SING N N 79 NAP O3X HOP3 SING N N 80 # # 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 NAP SMILES_CANONICAL CACTVS 3.341 "NC(=O)c1ccc[n+](c1)[C@@H]2O[C@H](CO[P]([O-])(=O)O[P@@](O)(=O)OC[C@H]3O[C@H]([C@H](O[P](O)(O)=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O" NAP SMILES CACTVS 3.341 "NC(=O)c1ccc[n+](c1)[CH]2O[CH](CO[P]([O-])(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O[P](O)(O)=O)[CH]3O)n4cnc5c(N)ncnc45)[CH](O)[CH]2O" NAP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@@](=O)([O-])O[P@](=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)OP(=O)(O)O)O)O)O)C(=O)N" NAP SMILES "OpenEye OEToolkits" 1.5.0 "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)N" NAP InChI InChI 1.03 "InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1" NAP InChIKey InChI 1.03 XJLXINKUBYWONI-NNYOXOHSSA-N # _pdbx_chem_comp_identifier.comp_id NAP _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program "OpenEye OEToolkits" _pdbx_chem_comp_identifier.program_version 1.5.0 _pdbx_chem_comp_identifier.identifier "[(2R,3S,4R,5R)-5-(3-aminocarbonylpyridin-1-ium-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] 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 NAP "Create component" 1999-07-08 RCSB NAP "Modify descriptor" 2011-06-04 RCSB NAP "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id NAP _pdbx_chem_comp_synonyms.name "2'-MONOPHOSPHOADENOSINE 5'-DIPHOSPHORIBOSE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##