data_12D
# 
_chem_comp.id                                    12D 
_chem_comp.name                                  
;2',3'-O-[(1R,6R)-2,4,6-trinitrocyclohexa-2,4-diene-1,1-diyl]adenosine 5'-(trihydrogen diphosphate)
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H16 N8 O16 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-01 
_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                        638.290 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     12D 
_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        3B5J 
_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 
12D P1  P1  P 0  1 N N N 23.561 1.027  29.143 -7.402 -0.436 -0.490 P1  12D 1  
12D O1  O1  O 0  1 N N N 22.340 1.387  29.952 -7.882 0.480  -1.724 O1  12D 2  
12D O2  O2  O 0  1 N N N 23.428 1.344  27.672 -7.745 0.234  0.784  O2  12D 3  
12D O3  O3  O 0  1 N N N 24.018 -0.383 29.425 -8.143 -1.864 -0.562 O3  12D 4  
12D P2  P2  P 0  1 N N S 25.410 3.250  29.056 -4.699 -1.181 0.469  P2  12D 5  
12D O4  O4  O 0  1 N N N 26.471 2.885  28.037 -4.987 -0.640 1.816  O4  12D 6  
12D O5  O5  O 0  1 N N N 24.328 4.210  28.658 -4.731 -2.790 0.519  O5  12D 7  
12D O6  O6  O 0  1 N N N 24.771 1.918  29.705 -5.809 -0.654 -0.570 O6  12D 8  
12D O7  O7  O 0  1 N N N 26.150 3.894  30.331 -3.241 -0.688 -0.006 O7  12D 9  
12D C1  C1  C 0  1 N N N 27.376 3.377  30.851 -2.057 -0.906 0.763  C1  12D 10 
12D C2  C2  C 0  1 N N R 27.906 4.331  31.914 -0.854 -0.314 0.025  C2  12D 11 
12D O8  O8  O 0  1 N N N 28.436 5.514  31.301 -0.925 1.128  0.025  O8  12D 12 
12D C3  C3  C 0  1 N N R 26.736 4.762  32.778 0.453  -0.647 0.776  C3  12D 13 
12D O9  O9  O 0  1 N N N 27.049 4.755  34.167 1.159  -1.669 0.043  O9  12D 14 
12D C4  C4  C 0  1 N N R 26.447 6.201  32.413 1.319  0.632  0.604  C4  12D 15 
12D O10 O10 O 0  1 N N N 26.255 6.872  33.647 2.433  0.214  -0.211 O10 12D 16 
12D C5  C5  C 0  1 N N R 27.714 6.685  31.725 0.424  1.575  -0.229 C5  12D 17 
12D N1  N1  N 0  1 Y N N 27.474 7.653  30.619 0.593  2.961  0.213  N1  12D 18 
12D C6  C6  C 0  1 Y N N 26.670 7.502  29.552 -0.152 3.604  1.157  C6  12D 19 
12D N2  N2  N 0  1 Y N N 26.740 8.614  28.787 0.272  4.826  1.303  N2  12D 20 
12D C7  C7  C 0  1 Y N N 27.589 9.467  29.385 1.313  5.045  0.464  C7  12D 21 
12D C8  C8  C 0  1 Y N N 28.044 10.740 29.067 2.146  6.142  0.189  C8  12D 22 
12D N3  N3  N 0  1 N N N 27.609 11.361 27.939 1.978  7.343  0.855  N3  12D 23 
12D N4  N4  N 0  1 Y N N 28.926 11.341 29.901 3.099  6.000  -0.727 N4  12D 24 
12D C9  C9  C 0  1 Y N N 29.360 10.745 31.025 3.266  4.858  -1.368 C9  12D 25 
12D N5  N5  N 0  1 Y N N 28.939 9.508  31.342 2.510  3.804  -1.143 N5  12D 26 
12D C10 C10 C 0  1 Y N N 28.054 8.856  30.540 1.535  3.850  -0.241 C10 12D 27 
12D C11 C11 C 0  1 N N R 26.554 5.978  34.733 2.521  -1.208 -0.012 C11 12D 28 
12D C12 C12 C 0  1 N N R 25.247 5.787  35.492 3.233  -1.513 1.301  C12 12D 29 
12D C13 C13 C 0  1 N N N 25.120 6.226  36.804 3.541  -2.985 1.392  C13 12D 30 
12D C14 C14 C 0  1 N N N 26.156 6.815  37.506 3.838  -3.676 0.299  C14 12D 31 
12D C15 C15 C 0  1 N N N 27.390 7.006  36.904 3.842  -3.017 -1.016 C15 12D 32 
12D C16 C16 C 0  1 N N N 27.639 6.616  35.594 3.234  -1.846 -1.170 C16 12D 33 
12D N6  N6  N 1  1 N N N 24.115 5.234  34.957 4.482  -0.750 1.365  N6  12D 34 
12D N7  N7  N 1  1 N N N 25.967 7.218  38.787 4.167  -5.115 0.403  N7  12D 35 
12D N8  N8  N 1  1 N N N 28.898 6.863  35.133 3.259  -1.168 -2.486 N8  12D 36 
12D O11 O11 O 0  1 N N N 24.031 4.737  33.658 5.341  -0.915 0.517  O11 12D 37 
12D O12 O12 O -1 1 N N N 22.971 5.140  35.750 4.661  0.051  2.265  O12 12D 38 
12D O13 O13 O 0  1 N N N 27.014 7.817  39.480 4.440  -5.752 -0.599 O13 12D 39 
12D O14 O14 O -1 1 N N N 24.738 7.038  39.418 4.165  -5.663 1.491  O14 12D 40 
12D O15 O15 O -1 1 N N N 29.848 7.472  35.946 3.837  -1.684 -3.426 O15 12D 41 
12D O16 O16 O 0  1 N N N 29.296 6.529  33.850 2.702  -0.095 -2.629 O16 12D 42 
12D H1  H1  H 0  1 N N N 27.200 2.387  31.298 -2.161 -0.424 1.735  H1  12D 43 
12D H2  H2  H 0  1 N N N 28.112 3.280  30.039 -1.906 -1.977 0.902  H2  12D 44 
12D H3  H3  H 0  1 N N N 28.691 3.825  32.496 -0.812 -0.693 -0.996 H3  12D 45 
12D H4  H4  H 0  1 N N N 25.899 4.069  32.606 0.283  -0.918 1.818  H4  12D 46 
12D H5  H5  H 0  1 N N N 25.573 6.358  31.764 1.631  1.064  1.555  H5  12D 47 
12D H6  H6  H 0  1 N N N 28.314 7.271  32.437 0.660  1.484  -1.289 H6  12D 48 
12D H7  H7  H 0  1 N N N 26.066 6.632  29.340 -0.973 3.163  1.704  H7  12D 49 
12D H8  H8  H 0  1 N N N 27.502 12.339 28.117 1.279  7.435  1.522  H8  12D 50 
12D H9  H9  H 0  1 N N N 28.276 11.226 27.206 2.559  8.094  0.656  H9  12D 51 
12D H10 H10 H 0  1 N N N 30.050 11.262 31.676 4.053  4.785  -2.104 H10 12D 52 
12D H11 H11 H 0  1 N N N 25.986 5.331  34.817 2.592  -1.225 2.134  H11 12D 53 
12D H12 H12 H 0  1 N N N 24.168 6.102  37.299 3.521  -3.480 2.352  H12 12D 54 
12D H13 H13 H 0  1 N N N 28.182 7.472  37.471 4.339  -3.484 -1.854 H13 12D 55 
12D H14 H14 H 0  1 N N N 22.578 1.463  30.869 -8.833 0.653  -1.739 H14 12D 56 
12D H15 H15 H 0  1 N N N 24.114 -0.855 28.606 -7.964 -2.360 -1.372 H15 12D 57 
12D H16 H16 H 0  1 N N N 23.790 4.413  29.414 -4.549 -3.213 -0.331 H16 12D 58 
# 
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 
12D P1  O3  SING N N 1  
12D P1  O6  SING N N 2  
12D P1  O1  SING N N 3  
12D O1  H14 SING N N 4  
12D O2  P1  DOUB N N 5  
12D O3  H15 SING N N 6  
12D P2  O6  SING N N 7  
12D P2  O7  SING N N 8  
12D O4  P2  DOUB N N 9  
12D O5  P2  SING N N 10 
12D O5  H16 SING N N 11 
12D O7  C1  SING N N 12 
12D C1  C2  SING N N 13 
12D C1  H1  SING N N 14 
12D C1  H2  SING N N 15 
12D C2  C3  SING N N 16 
12D C2  H3  SING N N 17 
12D O8  C5  SING N N 18 
12D O8  C2  SING N N 19 
12D C3  O9  SING N N 20 
12D C3  H4  SING N N 21 
12D O9  C11 SING N N 22 
12D C4  C3  SING N N 23 
12D C4  O10 SING N N 24 
12D C4  H5  SING N N 25 
12D O10 C11 SING N N 26 
12D C5  C4  SING N N 27 
12D C5  H6  SING N N 28 
12D N1  C5  SING N N 29 
12D C6  N1  SING Y N 30 
12D C6  H7  SING N N 31 
12D N2  C7  SING Y N 32 
12D N2  C6  DOUB Y N 33 
12D C7  C10 SING Y N 34 
12D C8  C7  DOUB Y N 35 
12D C8  N4  SING Y N 36 
12D N3  C8  SING N N 37 
12D N3  H8  SING N N 38 
12D N3  H9  SING N N 39 
12D N4  C9  DOUB Y N 40 
12D C9  N5  SING Y N 41 
12D C9  H10 SING N N 42 
12D C10 N1  SING Y N 43 
12D C10 N5  DOUB Y N 44 
12D C11 C12 SING N N 45 
12D C11 C16 SING N N 46 
12D C12 C13 SING N N 47 
12D C12 H11 SING N N 48 
12D C13 C14 DOUB N N 49 
12D C13 H12 SING N N 50 
12D C14 N7  SING N N 51 
12D C15 C14 SING N N 52 
12D C15 H13 SING N N 53 
12D C16 C15 DOUB N N 54 
12D N6  C12 SING N N 55 
12D N6  O12 SING N N 56 
12D N7  O14 SING N N 57 
12D N7  O13 DOUB N N 58 
12D N8  C16 SING N N 59 
12D N8  O15 SING N N 60 
12D O11 N6  DOUB N N 61 
12D O16 N8  DOUB N N 62 
# 
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 
12D SMILES           ACDLabs              10.04 [O-][N+](=O)C5=CC([N+]([O-])=O)=CC([N+]([O-])=O)C35OC4C(OC(n1c2ncnc(N)c2nc1)C4O3)COP(=O)(O)OP(=O)(O)O 
12D InChI            InChI                1.02b 
;InChI=1/C16H16N8O16P2/c17-13-10-14(19-4-18-13)21(5-20-10)15-12-11(7(37-15)3-36-42(34,35)40-41(31,32)33)38-16(39-12)8(23(27)28)1-6(22(25)26)2-9(16)24(29)30/h1-2,4-5,7-8,11-12,15H,3H2,(H,34,35)(H2,17,18,19)(H2,31,32,33)/t7-,8-,11-,12-,15-,16-/m1/s1/f/h31-32,34H,17H2
;
12D InChIKey         InChI                1.02b WYOHYTDXVJMKHS-XLENOZFPDD 
12D SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P](O)(O)=O)[C@H]4O[C@@]5(O[C@@H]34)[C@@H](C=C(C=C5[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 
12D SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(O)=O)[CH]4O[C]5(O[CH]34)[CH](C=C(C=C5[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 
12D SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@H]4[C@@H]([C@H](O3)CO[P@](=O)(O)OP(=O)(O)O)O[C@@]5(O4)[C@@H](C=C(C=C5[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])N 
12D SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C4C(C(O3)COP(=O)(O)OP(=O)(O)O)OC5(O4)C(C=C(C=C5[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[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 
12D "SYSTEMATIC NAME" ACDLabs              10.04 
;2',3'-O-[(1R,6R)-2,4,6-trinitrocyclohexa-2,4-diene-1,1-diyl]adenosine 5'-(trihydrogen diphosphate)
;
12D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
;[(2R,3aR,4R,5'R,6R,6aR)-4-(6-aminopurin-9-yl)-1',3',5'-trinitro-spiro[3a,4,6,6a-tetrahydrofuro[4,3-d][1,3]dioxole-2,6'-cyclohexa-1,3-diene]-6-yl]methyl phosphono hydrogen phosphate
;
# 
