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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h42H,27-28H2
;
NAQ InChIKey         InChI                1.02b BZJFKYRGSZWSLT-ZYKZXBQZDJ 
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 
# 
_pdbx_chem_comp_identifier.comp_id           NAQ 
_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-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" 
# 
