data_NAQ # _chem_comp.id NAQ _chem_comp.name "NICOTINAMIDE ADENINE DINUCLEOTIDE 3-PENTANONE ADDUCT" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H35 N7 O15 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 747.542 _chem_comp.one_letter_code ? _chem_comp.three_letter_code NAQ _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 1B16 _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 NAQ PA PA P 0 1 N N S 7.035 -11.006 -0.564 -1.955 0.393 0.769 PA NAQ 1 NAQ O1A O1A O 0 1 N N N 6.273 -11.704 0.525 -2.434 -0.578 1.778 O1A NAQ 2 NAQ O2A O2A O 0 1 N N N 6.669 -11.381 -2.020 -1.189 1.602 1.508 O2A NAQ 3 NAQ "O5'" "O5'" O 0 1 N N N 8.595 -11.264 -0.394 -3.210 0.976 -0.053 "O5'" NAQ 4 NAQ "C5'" "C5'" C 0 1 N N N 9.162 -11.472 0.983 -4.123 1.509 0.909 "C5'" NAQ 5 NAQ "C4'" "C4'" C 0 1 N N R 10.577 -11.835 0.755 -5.345 2.082 0.189 "C4'" NAQ 6 NAQ "O4'" "O4'" O 0 1 N N N 11.178 -11.935 2.102 -6.087 1.021 -0.435 "O4'" NAQ 7 NAQ "C3'" "C3'" C 0 1 N N S 10.741 -13.270 0.138 -6.280 2.764 1.206 "C3'" NAQ 8 NAQ "O3'" "O3'" O 0 1 N N N 12.038 -13.280 -0.579 -6.446 4.148 0.895 "O3'" NAQ 9 NAQ "C2'" "C2'" C 0 1 N N R 10.791 -14.199 1.315 -7.625 2.007 1.047 "C2'" NAQ 10 NAQ "O2'" "O2'" O 0 1 N N N 11.381 -15.439 1.130 -8.729 2.913 1.097 "O2'" NAQ 11 NAQ "C1'" "C1'" C 0 1 N N R 11.602 -13.197 2.246 -7.483 1.386 -0.366 "C1'" NAQ 12 NAQ N9A N9A N 0 1 Y N N 11.531 -13.648 3.590 -8.333 0.201 -0.501 N9A NAQ 13 NAQ C8A C8A C 0 1 Y N N 10.448 -13.749 4.454 -7.974 -1.085 -0.225 C8A NAQ 14 NAQ N7A N7A N 0 1 Y N N 10.749 -14.289 5.615 -8.974 -1.885 -0.455 N7A NAQ 15 NAQ C5A C5A C 0 1 Y N N 12.090 -14.591 5.572 -10.036 -1.166 -0.893 C5A NAQ 16 NAQ C6A C6A C 0 1 Y N N 13.007 -15.215 6.584 -11.348 -1.480 -1.286 C6A NAQ 17 NAQ N6A N6A N 0 1 N N N 12.660 -15.619 7.774 -11.797 -2.789 -1.272 N6A NAQ 18 NAQ N1A N1A N 0 1 Y N N 14.327 -15.353 6.119 -12.147 -0.490 -1.670 N1A NAQ 19 NAQ C2A C2A C 0 1 Y N N 14.743 -14.981 4.910 -11.727 0.762 -1.686 C2A NAQ 20 NAQ N3A N3A N 0 1 Y N N 13.925 -14.403 3.913 -10.508 1.102 -1.326 N3A NAQ 21 NAQ C4A C4A C 0 1 Y N N 12.571 -14.212 4.324 -9.639 0.182 -0.922 C4A NAQ 22 NAQ OPP OPP O 0 1 N N N 6.990 -9.462 -0.351 -0.943 -0.342 -0.245 OPP NAQ 23 NAQ PN PN P 0 1 N N N 7.554 -8.140 -1.108 -0.033 -1.331 0.641 PN NAQ 24 NAQ O1N O1N O 0 1 N N N 6.447 -7.211 -1.278 -0.821 -2.625 0.942 O1N NAQ 25 NAQ O2N O2N O -1 1 N N N 8.383 -8.599 -2.262 0.341 -0.635 1.969 O2N NAQ 26 NAQ O5B O5* O 0 1 N N N 8.499 -7.491 -0.011 1.309 -1.696 -0.170 O5B NAQ 27 NAQ C5B C5* C 0 1 N N N 9.957 -7.434 -0.110 2.124 -2.474 0.709 C5B NAQ 28 NAQ C4B C4* C 0 1 N N R 10.545 -6.407 0.817 3.423 -2.856 -0.004 C4B NAQ 29 NAQ O4B O4* O 0 1 N N N 9.850 -5.118 0.510 4.221 -1.680 -0.259 O4B NAQ 30 NAQ C3B C3* C 0 1 N N S 10.172 -6.620 2.340 4.301 -3.739 0.910 C3B NAQ 31 NAQ O3B O3* O 0 1 N N N 11.191 -6.163 3.128 4.136 -5.120 0.581 O3B NAQ 32 NAQ C2B C2* C 0 1 N N R 8.928 -5.739 2.548 5.745 -3.277 0.603 C2B NAQ 33 NAQ O2B O2* O 0 1 N N N 8.792 -5.450 3.894 6.516 -4.360 0.078 O2B NAQ 34 NAQ C1B C1* C 0 1 N N R 9.279 -4.573 1.680 5.566 -2.168 -0.457 C1B NAQ 35 NAQ N1N N1N N 1 1 Y N N 8.196 -3.633 1.266 6.536 -1.093 -0.240 N1N NAQ 36 NAQ C2N C2N C 0 1 Y N N 7.064 -4.049 0.540 7.609 -1.036 -1.001 C2N NAQ 37 NAQ C3N C3N C 0 1 Y N N 6.249 -3.051 0.129 8.551 -0.021 -0.825 C3N NAQ 38 NAQ C7N C7N C 0 1 N N N 5.034 -3.558 -0.798 9.755 0.043 -1.679 C7N NAQ 39 NAQ O7N O7N O 0 1 N N N 4.178 -2.669 -1.029 10.509 0.993 -1.598 O7N NAQ 40 NAQ N7N N7N N 0 1 N N N 4.976 -4.849 -1.265 10.018 -0.952 -2.549 N7N NAQ 41 NAQ C4N C4N C 0 1 Y N N 6.371 -1.650 0.376 8.342 0.928 0.182 C4N NAQ 42 NAQ C5N C5N C 0 1 Y N N 7.620 -1.343 1.041 7.198 0.824 0.955 C5N NAQ 43 NAQ C6N C6N C 0 1 Y N N 8.485 -2.327 1.468 6.310 -0.209 0.714 C6N NAQ 44 NAQ C5P C5P C 0 1 N N N 2.696 -2.362 3.253 9.417 2.342 1.913 C5P NAQ 45 NAQ C4P C4P C 0 1 N N S 3.930 -3.041 2.645 9.332 2.040 0.415 C4P NAQ 46 NAQ C3P C3P C 0 1 N N N 5.036 -2.010 2.521 8.884 3.275 -0.322 C3P NAQ 47 NAQ OP OP O 0 1 N N N 5.852 -1.719 3.555 7.707 3.477 -0.502 OP NAQ 48 NAQ C2P C2P C 0 1 N N N 5.177 -1.152 1.249 9.905 4.258 -0.835 C2P NAQ 49 NAQ C1P C1P C 0 1 N N N 5.162 0.369 1.504 9.191 5.413 -1.541 C1P NAQ 50 NAQ HOA2 2HOA H 0 0 N N N 7.151 -10.939 -2.709 -0.894 2.210 0.817 HOA2 NAQ 51 NAQ "H5'1" "1H5'" H 0 0 N N N 9.021 -10.603 1.667 -4.439 0.716 1.587 "H5'1" NAQ 52 NAQ "H5'2" "2H5'" H 0 0 N N N 8.597 -12.210 1.599 -3.632 2.299 1.477 "H5'2" NAQ 53 NAQ "H4'" "H4'" H 0 1 N N N 11.032 -11.083 0.068 -5.027 2.804 -0.563 "H4'" NAQ 54 NAQ "H3'" "H3'" H 0 1 N N N 9.926 -13.561 -0.564 -5.894 2.645 2.219 "H3'" NAQ 55 NAQ "HO'3" "3HO'" H 0 0 N N N 12.137 -14.148 -0.952 -7.086 4.503 1.527 "HO'3" NAQ 56 NAQ "H2'" "H2'" H 0 1 N N N 9.809 -14.584 1.676 -7.728 1.230 1.804 "H2'" NAQ 57 NAQ "HO'2" "2HO'" H 0 0 N N N 11.412 -16.027 1.875 -8.762 3.263 1.998 "HO'2" NAQ 58 NAQ "H1'" "H1'" H 0 1 N N N 12.673 -13.190 1.935 -7.726 2.120 -1.134 "H1'" NAQ 59 NAQ H8A H8A H 0 1 N N N 9.418 -13.422 4.233 -7.003 -1.394 0.133 H8A NAQ 60 NAQ H6A1 1H6A H 0 0 N N N 13.282 -16.042 8.461 -11.204 -3.502 -0.989 H6A1 NAQ 61 NAQ H6A2 2H6A H 0 0 N N N 11.884 -16.268 7.645 -12.705 -2.992 -1.546 H6A2 NAQ 62 NAQ H2A H2A H 0 1 N N N 15.815 -15.160 4.725 -12.410 1.535 -2.006 H2A NAQ 63 NAQ H5A1 1H5* H 0 0 N N N 10.413 -8.437 0.056 1.588 -3.379 0.996 H5A1 NAQ 64 NAQ H5A2 2H5* H 0 0 N N N 10.284 -7.264 -1.162 2.357 -1.891 1.600 H5A2 NAQ 65 NAQ H4B H4* H 0 1 N N N 11.650 -6.451 0.674 3.204 -3.376 -0.937 H4B NAQ 66 NAQ H3B H3* H 0 1 N N N 9.994 -7.690 2.597 4.058 -3.565 1.958 H3B NAQ 67 NAQ HOA3 3HO* H 0 0 N N N 10.967 -6.290 4.042 4.706 -5.620 1.181 HOA3 NAQ 68 NAQ H2B H2* H 0 1 N N N 7.937 -6.174 2.278 6.216 -2.874 1.500 H2B NAQ 69 NAQ HOB2 2HO* H 0 0 N N N 8.023 -4.906 4.022 6.541 -5.043 0.763 HOB2 NAQ 70 NAQ H1B H1* H 0 1 N N N 9.942 -3.933 2.307 5.676 -2.581 -1.460 H1B NAQ 71 NAQ H2N H2N H 0 1 N N N 6.828 -5.100 0.305 7.759 -1.778 -1.771 H2N NAQ 72 NAQ H7N1 1H7N H 0 0 N N N 5.671 -5.571 -1.077 9.417 -1.711 -2.614 H7N1 NAQ 73 NAQ H7N2 2H7N H 0 0 N N N 4.206 -5.170 -1.852 10.808 -0.910 -3.110 H7N2 NAQ 74 NAQ H5N H5N H 0 1 N N N 7.929 -0.301 1.232 7.002 1.540 1.739 H5N NAQ 75 NAQ H6N H6N H 0 1 N N N 9.425 -2.064 1.980 5.417 -0.293 1.315 H6N NAQ 76 NAQ H5P1 1H5P H 0 0 N N N 1.942 -2.791 3.953 9.741 1.449 2.446 H5P1 NAQ 77 NAQ H5P2 2H5P H 0 0 N N N 3.076 -1.440 3.751 10.134 3.146 2.081 H5P2 NAQ 78 NAQ H5P3 3H5P H 0 0 N N N 2.111 -1.972 2.387 8.437 2.647 2.278 H5P3 NAQ 79 NAQ H4P H4P H 0 1 N N N 3.524 -4.058 2.856 10.313 1.734 0.050 H4P NAQ 80 NAQ H2P1 1H2P H 0 0 N N N 6.092 -1.442 0.682 10.569 3.758 -1.540 H2P1 NAQ 81 NAQ H2P2 2H2P H 0 0 N N N 4.395 -1.429 0.503 10.487 4.647 0.000 H2P2 NAQ 82 NAQ H1P1 1H1P H 0 0 N N N 5.264 0.989 0.583 9.929 6.124 -1.912 H1P1 NAQ 83 NAQ H1P2 2H1P H 0 0 N N N 4.246 0.659 2.070 8.609 5.024 -2.376 H1P2 NAQ 84 NAQ H1P3 3H1P H 0 0 N N N 5.943 0.646 2.249 8.526 5.913 -0.836 H1P3 NAQ 85 # 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 NAQ PA O1A DOUB N N 1 NAQ PA O2A SING N N 2 NAQ PA "O5'" SING N N 3 NAQ PA OPP SING N N 4 NAQ O2A HOA2 SING N N 5 NAQ "O5'" "C5'" SING N N 6 NAQ "C5'" "C4'" SING N N 7 NAQ "C5'" "H5'1" SING N N 8 NAQ "C5'" "H5'2" SING N N 9 NAQ "C4'" "O4'" SING N N 10 NAQ "C4'" "C3'" SING N N 11 NAQ "C4'" "H4'" SING N N 12 NAQ "O4'" "C1'" SING N N 13 NAQ "C3'" "O3'" SING N N 14 NAQ "C3'" "C2'" SING N N 15 NAQ "C3'" "H3'" SING N N 16 NAQ "O3'" "HO'3" SING N N 17 NAQ "C2'" "O2'" SING N N 18 NAQ "C2'" "C1'" SING N N 19 NAQ "C2'" "H2'" SING N N 20 NAQ "O2'" "HO'2" SING N N 21 NAQ "C1'" N9A SING N N 22 NAQ "C1'" "H1'" SING N N 23 NAQ N9A C8A SING Y N 24 NAQ N9A C4A SING Y N 25 NAQ C8A N7A DOUB Y N 26 NAQ C8A H8A SING N N 27 NAQ N7A C5A SING Y N 28 NAQ C5A C6A SING Y N 29 NAQ C5A C4A DOUB Y N 30 NAQ C6A N6A SING N N 31 NAQ C6A N1A DOUB Y N 32 NAQ N6A H6A1 SING N N 33 NAQ N6A H6A2 SING N N 34 NAQ N1A C2A SING Y N 35 NAQ C2A N3A DOUB Y N 36 NAQ C2A H2A SING N N 37 NAQ N3A C4A SING Y N 38 NAQ OPP PN SING N N 39 NAQ PN O1N DOUB N N 40 NAQ PN O2N SING N N 41 NAQ PN O5B SING N N 42 NAQ O5B C5B SING N N 43 NAQ C5B C4B SING N N 44 NAQ C5B H5A1 SING N N 45 NAQ C5B H5A2 SING N N 46 NAQ C4B O4B SING N N 47 NAQ C4B C3B SING N N 48 NAQ C4B H4B SING N N 49 NAQ O4B C1B SING N N 50 NAQ C3B O3B SING N N 51 NAQ C3B C2B SING N N 52 NAQ C3B H3B SING N N 53 NAQ O3B HOA3 SING N N 54 NAQ C2B O2B SING N N 55 NAQ C2B C1B SING N N 56 NAQ C2B H2B SING N N 57 NAQ O2B HOB2 SING N N 58 NAQ C1B N1N SING N N 59 NAQ C1B H1B SING N N 60 NAQ N1N C2N SING Y N 61 NAQ N1N C6N DOUB Y N 62 NAQ C2N C3N DOUB Y N 63 NAQ C2N H2N SING N N 64 NAQ C3N C7N SING N N 65 NAQ C3N C4N SING Y N 66 NAQ C7N O7N DOUB N N 67 NAQ C7N N7N SING N N 68 NAQ N7N H7N1 SING N N 69 NAQ N7N H7N2 SING N N 70 NAQ C4N C5N DOUB Y N 71 NAQ C4N C4P SING N N 72 NAQ C5N C6N SING Y N 73 NAQ C5N H5N SING N N 74 NAQ C6N H6N SING N N 75 NAQ C5P C4P SING N N 76 NAQ C5P H5P1 SING N N 77 NAQ C5P H5P2 SING N N 78 NAQ C5P H5P3 SING N N 79 NAQ C4P C3P SING N N 80 NAQ C4P H4P SING N N 81 NAQ C3P OP DOUB N N 82 NAQ C3P C2P SING N N 83 NAQ C2P C1P SING N N 84 NAQ C2P H2P1 SING N N 85 NAQ C2P H2P2 SING N N 86 NAQ C1P H1P1 SING N N 87 NAQ C1P H1P2 SING N N 88 NAQ C1P H1P3 SING N N 89 # 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 NAQ SMILES_CANONICAL CACTVS 3.341 "CCC(=O)[C@@H](C)c1cc[n+](cc1C(N)=O)[C@@H]2O[C@H](CO[P]([O-])(=O)O[P@](O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O" NAQ SMILES CACTVS 3.341 "CCC(=O)[CH](C)c1cc[n+](cc1C(N)=O)[CH]2O[CH](CO[P]([O-])(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)n4cnc5c(N)ncnc45)[CH](O)[CH]2O" NAQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CCC(=O)[C@@H](C)c1cc[n+](cc1C(=O)N)[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)O)O)O)O" NAQ SMILES "OpenEye OEToolkits" 1.5.0 "CCC(=O)C(C)c1cc[n+](cc1C(=O)N)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)n4cnc5c4ncnc5N)O)O)O)O" NAQ InChI InChI 1.03 ;InChI=1S/C26H35N7O15P2/c1-3-14(34)11(2)12-4-5-32(6-13(12)23(28)39)25-20(37)18(35)15(46-25)7-44-49(40,41)48-50(42,43)45-8-16-19(36)21(38)26(47-16)33-10-31-17-22(27)29-9-30-24(17)33/h4-6,9-11,15-16,18-21,25-26,35-38H,3,7-8H2,1-2H3,(H5-,27,28,29,30,39,40,41,42,43)/t11-,15+,16+,18+,19+,20+,21+,25+,26+/m0/s1 ; NAQ InChIKey InChI 1.03 BZJFKYRGSZWSLT-YLIVDTKOSA-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 NAQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-[3-aminocarbonyl-4-[(2S)-3-oxopentan-2-yl]pyridin-1-ium-1-yl]-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-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 NAQ "Create component" 1999-07-08 RCSB NAQ "Modify descriptor" 2011-06-04 RCSB #