data_CNA
# 
_chem_comp.id                                    CNA 
_chem_comp.name                                  CARBA-NICOTINAMIDE-ADENINE-DINUCLEOTIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H29 N7 O13 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                        661.452 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CNA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1A26 
_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 
CNA PA     AP   P 0  1 N N R 39.554 14.633 25.937 -1.929 4.698  -0.530 PA     CNA 1  
CNA O1A    AO1  O 0  1 N N N 40.511 15.386 26.828 -2.407 4.313  -1.899 O1A    CNA 2  
CNA O2A    AO2  O 0  1 N N N 38.546 13.971 26.834 -2.771 5.897  0.156  O2A    CNA 3  
CNA O5B    AO5* O 0  1 N N N 38.791 15.662 25.030 -1.948 3.506  0.564  O5B    CNA 4  
CNA C5B    AC5* C 0  1 N N N 37.646 15.220 24.148 -1.517 3.755  1.891  C5B    CNA 5  
CNA C4B    AC4* C 0  1 N N R 37.469 16.391 23.203 -1.638 2.471  2.701  C4B    CNA 6  
CNA O4B    AO4* O 0  1 N N N 36.433 16.054 22.267 -0.769 1.476  2.111  O4B    CNA 7  
CNA C3B    AC3* C 0  1 N N S 37.215 17.781 23.693 -1.185 2.636  4.148  C3B    CNA 8  
CNA O3B    AO3* O 0  1 N N N 38.372 18.610 23.558 -1.856 1.667  4.953  O3B    CNA 9  
CNA C2B    AC2* C 0  1 N N R 36.038 18.355 22.850 0.289  2.291  4.066  C2B    CNA 10 
CNA O2B    AO2* O 0  1 N N N 36.376 19.401 21.906 0.831  1.879  5.304  O2B    CNA 11 
CNA C1B    AC1* C 0  1 N N R 35.485 17.132 22.136 0.280  1.163  3.046  C1B    CNA 12 
CNA N9A    AN9  N 0  1 Y N N 34.274 16.558 22.751 1.544  0.996  2.332  N9A    CNA 13 
CNA C8A    AC8  C 0  1 Y N N 34.177 15.481 23.608 1.926  1.667  1.199  C8A    CNA 14 
CNA N7A    AN7  N 0  1 Y N N 32.919 15.252 23.958 3.122  1.302  0.784  N7A    CNA 15 
CNA C5A    AC5  C 0  1 Y N N 32.165 16.210 23.308 3.532  0.353  1.687  C5A    CNA 16 
CNA C6A    AC6  C 0  1 Y N N 30.756 16.485 23.275 4.697  -0.402 1.789  C6A    CNA 17 
CNA N6A    AN6  N 0  1 N N N 29.842 15.784 23.955 5.730  -0.259 0.848  N6A    CNA 18 
CNA N1A    AN1  N 0  1 Y N N 30.358 17.529 22.512 4.824  -1.281 2.813  N1A    CNA 19 
CNA C2A    AC2  C 0  1 Y N N 31.268 18.259 21.810 3.794  -1.375 3.688  C2A    CNA 20 
CNA N3A    AN3  N 0  1 Y N N 32.602 18.094 21.759 2.623  -0.702 3.694  N3A    CNA 21 
CNA C4A    AC4  C 0  1 Y N N 32.982 17.033 22.543 2.565  0.148  2.657  C4A    CNA 22 
CNA O3     O3   O 0  1 N N N 40.242 13.665 24.915 -0.400 5.223  -0.468 O3     CNA 23 
CNA PN     NP   P 0  1 N N N 41.155 13.739 23.638 0.334  6.486  -1.196 PN     CNA 24 
CNA O1N    NO1  O 0  1 N N N 41.243 15.171 23.289 0.372  6.227  -2.687 O1N    CNA 25 
CNA O2N    NO2  O -1 1 N N N 42.411 13.009 23.841 -0.262 7.767  -0.652 O2N    CNA 26 
CNA O5D    NO5* O 0  1 N N N 40.263 13.092 22.466 1.848  6.299  -0.606 O5D    CNA 27 
CNA C5D    NC5* C 0  1 N N N ?      ?      ?      2.603  5.161  -0.984 C5D    CNA 28 
CNA C4D    NC4* C 0  1 N N N ?      ?      ?      3.967  5.227  -0.301 C4D    CNA 29 
CNA "C4'"  C4*  C 0  1 N N N ?      ?      ?      4.748  6.485  -0.713 "C4'"  CNA 30 
CNA C3D    NC3* C 0  1 N N N ?      ?      ?      4.891  4.081  -0.738 C3D    CNA 31 
CNA O3D    NO3* O 0  1 N N N ?      ?      ?      5.892  3.847  0.248  O3D    CNA 32 
CNA C2D    NC2* C 0  1 N N N ?      ?      ?      5.508  4.562  -2.059 C2D    CNA 33 
CNA O2D    NO2* O 0  1 N N N ?      ?      ?      6.788  4.017  -2.300 O2D    CNA 34 
CNA C1D    NC1* C 0  1 N N N ?      ?      ?      5.457  6.097  -2.016 C1D    CNA 35 
CNA N1N    NN1  N 1  1 Y N N ?      ?      ?      6.777  6.763  -2.180 N1N    CNA 36 
CNA C2N    NC2  C 0  1 Y N N ?      ?      ?      7.751  6.528  -1.281 C2N    CNA 37 
CNA C3N    NC3  C 0  1 Y N N ?      ?      ?      8.991  7.137  -1.409 C3N    CNA 38 
CNA C7N    NC7  C 0  1 N N N ?      ?      ?      10.041 6.882  -0.438 C7N    CNA 39 
CNA O7N    NO7  O 0  1 N N N ?      ?      ?      11.155 7.430  -0.527 O7N    CNA 40 
CNA N7N    NN7  N 0  1 N N N ?      ?      ?      9.757  6.014  0.613  N7N    CNA 41 
CNA C4N    NC4  C 0  1 Y N N ?      ?      ?      9.209  7.995  -2.483 C4N    CNA 42 
CNA C5N    NC5  C 0  1 Y N N ?      ?      ?      8.192  8.226  -3.403 C5N    CNA 43 
CNA C6N    NC6  C 0  1 Y N N ?      ?      ?      6.972  7.590  -3.225 C6N    CNA 44 
CNA HOA2   2HOA H 0  0 N N N 38.929 13.831 27.692 -2.982 6.694  -0.376 HOA2   CNA 45 
CNA H51A   AH51 H 0  0 N N N 37.886 14.293 23.606 -0.478 4.096  1.866  H51A   CNA 46 
CNA H52A   AH52 H 0  0 N N N 36.733 14.983 24.715 -2.143 4.541  2.323  H52A   CNA 47 
CNA H4B    AH4* H 0  1 N N N 38.490 16.494 22.808 -2.664 2.096  2.633  H4B    CNA 48 
CNA H3B    AH3* H 0  1 N N N 36.967 17.760 24.764 -1.385 3.621  4.576  H3B    CNA 49 
CNA HO3A   AHO3 H 0  0 N N N 38.525 18.794 22.639 -2.804 1.846  4.864  HO3A   CNA 50 
CNA H2B    AH2* H 0  1 N N N 35.325 18.869 23.511 0.861  3.151  3.697  H2B    CNA 51 
CNA HO2A   AHO2 H 0  0 N N N 36.450 20.230 22.364 0.084  1.732  5.911  HO2A   CNA 52 
CNA H1B    AH1* H 0  1 N N N 35.276 17.480 21.114 0.073  0.187  3.500  H1B    CNA 53 
CNA H8A    AH8  H 0  1 N N N 35.019 14.898 23.950 1.294  2.406  0.725  H8A    CNA 54 
CNA H61A   AH61 H 0  0 N N N 30.177 15.609 24.881 6.353  0.524  0.915  H61A   CNA 55 
CNA H62A   AH62 H 0  0 N N N 28.990 16.305 24.002 5.776  -0.886 0.067  H62A   CNA 56 
CNA H2A    AH2  H 0  1 N N N 30.869 19.072 21.221 3.929  -2.088 4.494  H2A    CNA 57 
CNA H51N   NH51 H 0  0 N N N ?      ?      ?      2.070  4.260  -0.675 H51N   CNA 58 
CNA H52N   NH52 H 0  0 N N N ?      ?      ?      2.725  5.157  -2.069 H52N   CNA 59 
CNA H4D    NH4* H 0  1 N N N ?      ?      ?      3.814  5.226  0.784  H4D    CNA 60 
CNA "H4'1" 1H4* H 0  0 N N N ?      ?      ?      4.105  7.362  -0.840 "H4'1" CNA 61 
CNA "H4'2" 2H4* H 0  0 N N N ?      ?      ?      5.491  6.730  0.056  "H4'2" CNA 62 
CNA H3D    NH3* H 0  1 N N N ?      ?      ?      4.352  3.138  -0.870 H3D    CNA 63 
CNA HO3N   NHO3 H 0  0 N N N ?      ?      ?      5.500  3.265  0.922  HO3N   CNA 64 
CNA H2D    NH2* H 0  1 N N N ?      ?      ?      4.857  4.233  -2.879 H2D    CNA 65 
CNA HO2N   NHO2 H 0  0 N N N ?      ?      ?      6.773  3.112  -1.953 HO2N   CNA 66 
CNA H1D    NH1* H 0  1 N N N ?      ?      ?      4.877  6.466  -2.870 H1D    CNA 67 
CNA H2N    NH2  H 0  1 N N N ?      ?      ?      7.501  5.849  -0.474 H2N    CNA 68 
CNA H71N   NH71 H 0  0 N N N ?      ?      ?      8.838  5.590  0.671  H71N   CNA 69 
CNA H72N   NH72 H 0  0 N N N ?      ?      ?      10.449 5.795  1.322  H72N   CNA 70 
CNA H4N    NH4  H 0  1 N N N ?      ?      ?      10.170 8.487  -2.612 H4N    CNA 71 
CNA H5N    NH5  H 0  1 N N N ?      ?      ?      8.349  8.892  -4.245 H5N    CNA 72 
CNA H6N    NH6  H 0  1 N N N ?      ?      ?      6.136  7.723  -3.901 H6N    CNA 73 
# 
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 
CNA PA    O1A    DOUB N N 1  
CNA PA    O2A    SING N N 2  
CNA PA    O5B    SING N N 3  
CNA PA    O3     SING N N 4  
CNA O2A   HOA2   SING N N 5  
CNA O5B   C5B    SING N N 6  
CNA C5B   C4B    SING N N 7  
CNA C5B   H51A   SING N N 8  
CNA C5B   H52A   SING N N 9  
CNA C4B   O4B    SING N N 10 
CNA C4B   C3B    SING N N 11 
CNA C4B   H4B    SING N N 12 
CNA O4B   C1B    SING N N 13 
CNA C3B   O3B    SING N N 14 
CNA C3B   C2B    SING N N 15 
CNA C3B   H3B    SING N N 16 
CNA O3B   HO3A   SING N N 17 
CNA C2B   O2B    SING N N 18 
CNA C2B   C1B    SING N N 19 
CNA C2B   H2B    SING N N 20 
CNA O2B   HO2A   SING N N 21 
CNA C1B   N9A    SING N N 22 
CNA C1B   H1B    SING N N 23 
CNA N9A   C8A    SING Y N 24 
CNA N9A   C4A    SING Y N 25 
CNA C8A   N7A    DOUB Y N 26 
CNA C8A   H8A    SING N N 27 
CNA N7A   C5A    SING Y N 28 
CNA C5A   C6A    SING Y N 29 
CNA C5A   C4A    DOUB Y N 30 
CNA C6A   N6A    SING N N 31 
CNA C6A   N1A    DOUB Y N 32 
CNA N6A   H61A   SING N N 33 
CNA N6A   H62A   SING N N 34 
CNA N1A   C2A    SING Y N 35 
CNA C2A   N3A    DOUB Y N 36 
CNA C2A   H2A    SING N N 37 
CNA N3A   C4A    SING Y N 38 
CNA O3    PN     SING N N 39 
CNA PN    O1N    DOUB N N 40 
CNA PN    O2N    SING N N 41 
CNA PN    O5D    SING N N 42 
CNA O5D   C5D    SING N N 43 
CNA C5D   C4D    SING N N 44 
CNA C5D   H51N   SING N N 45 
CNA C5D   H52N   SING N N 46 
CNA C4D   "C4'"  SING N N 47 
CNA C4D   C3D    SING N N 48 
CNA C4D   H4D    SING N N 49 
CNA "C4'" C1D    SING N N 50 
CNA "C4'" "H4'1" SING N N 51 
CNA "C4'" "H4'2" SING N N 52 
CNA C3D   O3D    SING N N 53 
CNA C3D   C2D    SING N N 54 
CNA C3D   H3D    SING N N 55 
CNA O3D   HO3N   SING N N 56 
CNA C2D   O2D    SING N N 57 
CNA C2D   C1D    SING N N 58 
CNA C2D   H2D    SING N N 59 
CNA O2D   HO2N   SING N N 60 
CNA C1D   N1N    SING N N 61 
CNA C1D   H1D    SING N N 62 
CNA N1N   C2N    SING Y N 63 
CNA N1N   C6N    DOUB Y N 64 
CNA C2N   C3N    DOUB Y N 65 
CNA C2N   H2N    SING N N 66 
CNA C3N   C7N    SING N N 67 
CNA C3N   C4N    SING Y N 68 
CNA C7N   O7N    DOUB N N 69 
CNA C7N   N7N    SING N N 70 
CNA N7N   H71N   SING N N 71 
CNA N7N   H72N   SING N N 72 
CNA C4N   C5N    DOUB Y N 73 
CNA C4N   H4N    SING N N 74 
CNA C5N   C6N    SING Y N 75 
CNA C5N   H5N    SING N N 76 
CNA C6N   H6N    SING N N 77 
# 
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 
CNA SMILES           ACDLabs              10.04 O=C(N)c1ccc[n+](c1)C2CC(C(O)C2O)COP([O-])(=O)OP(=O)(O)OCC5OC(n4cnc3c(ncnc34)N)C(O)C5O 
CNA InChI            InChI                1.02b 
;InChI=1/C22H29N7O13P2/c23-19-14-21(26-8-25-19)29(9-27-14)22-18(33)17(32)13(41-22)7-40-44(37,38)42-43(35,36)39-6-11-4-12(16(31)15(11)30)28-3-1-2-10(5-28)20(24)34/h1-3,5,8-9,11-13,15-18,22,30-33H,4,6-7H2,(H5-,23,24,25,26,34,35,36,37,38)/t11?,12?,13-,15?,16?,17-,18-,22-/m1/s1/f/h37H,23-24H2
;
CNA InChIKey         InChI                1.02b DGPLSUKWXXSBCU-ADTRFAPEDZ 
CNA SMILES_CANONICAL CACTVS               3.341 NC(=O)c1ccc[n+](c1)C2CC(CO[P]([O-])(=O)O[P@@](O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)C(O)C2O 
CNA SMILES           CACTVS               3.341 NC(=O)c1ccc[n+](c1)C2CC(CO[P]([O-])(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)n4cnc5c(N)ncnc45)C(O)C2O 
CNA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(c[n+](c1)[C@@H]2C[C@H]([C@@H]([C@@H]2O)O)CO[P@](=O)([O-])O[P@](=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)O)O)C(=O)N 
CNA SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(c[n+](c1)C2CC(C(C2O)O)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)n4cnc5c4ncnc5N)O)O)C(=O)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 
CNA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(R)-[({[4-(3-carbamoylpyridinium-1-yl)-2,3-dihydroxycyclopentyl]methoxy}phosphinato)oxy](hydroxy)phosphoryl]adenosine"                                                                 
CNA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1S,2S,3R,4R)-4-(3-aminocarbonylpyridin-1-ium-1-yl)-2,3-dihydroxy-cyclopentyl]methyl [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] phosphate" 
# 
