data_C2E
# 
_chem_comp.id                                    C2E 
_chem_comp.name                                  
"9,9'-[(2R,3R,3aS,5S,7aR,9R,10R,10aS,12S,14aR)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-2,9-diyl]bis(2-amino-1,9-dihydro-6H-purin-6-one)" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H24 N10 O14 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "c-di-GMP, Cyclic diguanosine monophosphate" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-10-15 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        690.411 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     C2E 
_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        2RDE 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
C2E P1   P1   P 0 1 N N S 2.904  -21.000 -7.328  0.809   2.236  0.614  P1   C2E 1  
C2E O1   O1   O 0 1 N N N 2.614  -20.463 -5.950  1.044   2.538  -0.950 O1   C2E 2  
C2E O2   O2   O 0 1 N N N 2.870  -22.498 -7.405  0.614   3.511  1.339  O2   C2E 3  
C2E O3   O3   O 0 1 N N N 1.861  -20.471 -8.398  -0.498  1.313  0.792  O3   C2E 4  
C2E C3   C3   C 0 1 N N N 1.971  -20.901 -9.750  -1.828  1.795  0.590  C3   C2E 5  
C2E C4   C4   C 0 1 N N R 0.899  -20.225 -10.577 -2.826  0.815  1.208  C4   C2E 6  
C2E O4   O4   O 0 1 N N N -0.389 -20.452 -9.994  -4.150  1.351  1.124  O4   C2E 7  
C2E C5   C5   C 0 1 N N S 1.063  -18.717 -10.636 -2.813  -0.509 0.427  C5   C2E 8  
C2E O5   O5   O 0 1 N N N 2.000  -18.334 -11.654 -2.101  -1.511 1.154  O5   C2E 9  
C2E C6   C6   C 0 1 N N R -0.350 -18.292 -10.868 -4.297  -0.899 0.287  C6   C2E 10 
C2E O6   O6   O 0 1 N N N -0.626 -18.346 -12.271 -4.578  -2.071 1.055  O6   C2E 11 
C2E C7   C7   C 0 1 N N R -1.212 -19.291 -10.119 -5.078  0.303  0.840  C7   C2E 12 
C2E N7   N7   N 0 1 Y N N -1.507 -18.784 -8.781  -6.051  0.760  -0.154 N7   C2E 13 
C2E C8   C8   C 0 1 Y N N -1.074 -19.304 -7.629  -5.865  1.758  -1.067 C8   C2E 14 
C2E N8   N8   N 0 1 Y N N -1.523 -18.591 -6.578  -6.935  1.898  -1.792 N8   C2E 15 
C2E C9   C9   C 0 1 Y N N -2.263 -17.593 -7.067  -7.870  1.002  -1.390 C9   C2E 16 
C2E C10  C10  C 0 1 N N N -3.030 -16.469 -6.501  -9.189  0.702  -1.804 C10  C2E 17 
C2E O10  O10  O 0 1 N N N -3.091 -16.295 -5.263  -9.713  1.319  -2.716 O10  C2E 18 
C2E N11  N11  N 0 1 N N N -3.665 -15.645 -7.344  -9.854  -0.285 -1.163 N11  C2E 19 
C2E C12  C12  C 0 1 N N N -3.615 -15.816 -8.681  -9.258  -0.967 -0.145 C12  C2E 20 
C2E N12  N12  N 0 1 N N N -4.278 -14.952 -9.485  -9.957  -1.964 0.488  N12  C2E 21 
C2E N13  N13  N 0 1 N N N -2.924 -16.831 -9.266  -8.033  -0.698 0.249  N13  C2E 22 
C2E C14  C14  C 0 1 Y N N -2.242 -17.727 -8.519  -7.312  0.261  -0.343 C14  C2E 23 
C2E P15  P15  P 0 1 N N S 2.786  -17.024 -11.195 -0.794  -2.253 0.577  P15  C2E 24 
C2E O15  O15  O 0 1 N N N 1.787  -15.967 -10.842 -0.927  -2.409 -1.020 O15  C2E 25 
C2E O16  O16  O 0 1 N N N 3.645  -16.587 -12.339 -0.675  -3.593 1.195  O16  C2E 26 
C2E O17  O17  O 0 1 N N N 3.695  -17.385 -9.945  0.515   -1.384 0.924  O17  C2E 27 
C2E C17  C17  C 0 1 N N N 4.726  -18.365 -10.103 1.845   -1.829 0.651  C17  C2E 28 
C2E C18  C18  C 0 1 N N R 5.447  -18.579 -8.792  2.846   -0.847 1.260  C18  C2E 29 
C2E O18  O18  O 0 1 N N N 6.015  -17.354 -8.279  4.173   -1.374 1.161  O18  C2E 30 
C2E C19  C19  C 0 1 N N S 4.537  -19.101 -7.690  2.819   0.479  0.483  C19  C2E 31 
C2E O19  O19  O 0 1 N N N 4.390  -20.532 -7.761  2.093   1.470  1.212  O19  C2E 32 
C2E C20  C20  C 0 1 N N R 5.239  -18.621 -6.460  4.299   0.887  0.347  C20  C2E 33 
C2E O20  O20  O 0 1 N N N 6.209  -19.604 -6.062  4.570   2.046  1.139  O20  C2E 34 
C2E C21  C21  C 0 1 N N R 5.915  -17.310 -6.851  5.091   -0.318 0.876  C21  C2E 35 
C2E N21  N21  N 0 1 Y N N 5.066  -16.178 -6.432  6.051   -0.760 -0.139 N21  C2E 36 
C2E C22  C22  C 0 1 Y N N 4.215  -15.478 -7.209  5.858   -1.755 -1.054 C22  C2E 37 
C2E N22  N22  N 0 1 Y N N 3.584  -14.516 -6.498  6.918   -1.880 -1.798 N22  C2E 38 
C2E C23  C23  C 0 1 Y N N 4.032  -14.594 -5.236  7.850   -0.977 -1.408 C23  C2E 39 
C2E C24  C24  C 0 1 N N N 3.784  -13.882 -3.970  9.159   -0.662 -1.842 C24  C2E 40 
C2E O24  O24  O 0 1 N N N 2.968  -12.941 -3.892  9.673   -1.268 -2.767 O24  C2E 41 
C2E N25  N25  N 0 1 N N N 4.459  -14.276 -2.885  9.825   0.327  -1.206 N25  C2E 42 
C2E C25  C25  C 0 1 N N N 5.352  -15.291 -2.919  9.241   0.998  -0.174 C25  C2E 43 
C2E N26  N26  N 0 1 N N N 6.000  -15.627 -1.778  9.942   1.997  0.453  N26  C2E 44 
C2E N27  N27  N 0 1 N N N 5.624  -15.989 -4.046  8.026   0.715  0.239  N27  C2E 45 
C2E C27  C27  C 0 1 Y N N 5.008  -15.685 -5.212  7.303   -0.248 -0.346 C27  C2E 46 
C2E H1O  H1O  H 0 1 N N N 2.553  -21.184 -5.335  0.308   2.999  -1.376 H1O  C2E 47 
C2E H31  H31  H 0 1 N N N 1.842  -21.992 -9.801  -1.936  2.771  1.064  H31  C2E 48 
C2E H32  H32  H 0 1 N N N 2.963  -20.634 -10.143 -2.023  1.886  -0.479 H32  C2E 49 
C2E H4   H4   H 0 1 N N N 0.991  -20.653 -11.586 -2.569  0.632  2.251  H4   C2E 50 
C2E H5   H5   H 0 1 N N N 1.496  -18.240 -9.745  -2.367  -0.364 -0.556 H5   C2E 51 
C2E H6   H6   H 0 1 N N N -0.543 -17.266 -10.521 -4.548  -1.064 -0.761 H6   C2E 52 
C2E H6O  H6O  H 0 1 N N N -1.566 -18.358 -12.409 -5.498  -2.364 1.004  H6O  C2E 53 
C2E H7   H7   H 0 1 N N N -2.164 -19.486 -10.634 -5.597  0.014  1.754  H7   C2E 54 
C2E H8   H8   H 0 1 N N N -0.447 -20.180 -7.551  -4.963  2.344  -1.171 H8   C2E 55 
C2E H11N H11N H 0 0 N N N -4.192 -14.881 -6.972  -10.759 -0.508 -1.429 H11N C2E 56 
C2E H121 H121 H 0 0 N N N -4.145 -15.215 -10.441 -10.862 -2.174 0.208  H121 C2E 57 
C2E H122 H122 H 0 0 N N N -4.818 -14.171 -9.171  -9.547  -2.459 1.214  H122 C2E 58 
C2E H15O H15O H 0 0 N N N 1.575  -16.027 -9.918  -0.173  -2.849 -1.436 H15O C2E 59 
C2E H171 H171 H 0 0 N N N 4.277  -19.315 -10.429 1.995   -2.817 1.086  H171 C2E 60 
C2E H172 H172 H 0 0 N N N 5.446  -18.011 -10.856 1.997   -1.880 -0.427 H172 C2E 61 
C2E H18  H18  H 0 1 N N N 6.226  -19.317 -9.034  2.600   -0.666 2.306  H18  C2E 62 
C2E H19  H19  H 0 1 N N N 3.497  -18.746 -7.743  2.378   0.332  -0.502 H19  C2E 63 
C2E H20  H20  H 0 1 N N N 4.554  -18.467 -5.613  4.546   1.077  -0.697 H20  C2E 64 
C2E H20O H20O H 0 0 N N N 6.423  -20.157 -6.804  5.487   2.348  1.092  H20O C2E 65 
C2E H21  H21  H 0 1 N N N 6.899  -17.183 -6.377  5.623   -0.038 1.785  H21  C2E 66 
C2E H22  H22  H 0 1 N N N 4.058  -15.662 -8.262  4.961   -2.348 -1.146 H22  C2E 67 
C2E H25N H25N H 0 0 N N N 4.298  -13.804 -2.018  10.724  0.561  -1.486 H25N C2E 68 
C2E H261 H261 H 0 0 N N N 6.627  -16.389 -1.941  10.839  2.218  0.159  H261 C2E 69 
C2E H262 H262 H 0 0 N N N 5.870  -15.176 -0.895  9.539   2.484  1.189  H262 C2E 70 
# 
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 
C2E O16 P15  DOUB N N 1  
C2E O6  C6   SING N N 2  
C2E O5  P15  SING N N 3  
C2E O5  C5   SING N N 4  
C2E P15 O15  SING N N 5  
C2E P15 O17  SING N N 6  
C2E C6  C5   SING N N 7  
C2E C6  C7   SING N N 8  
C2E C5  C4   SING N N 9  
C2E C4  O4   SING N N 10 
C2E C4  C3   SING N N 11 
C2E C7  O4   SING N N 12 
C2E C7  N7   SING N N 13 
C2E C17 O17  SING N N 14 
C2E C17 C18  SING N N 15 
C2E C3  O3   SING N N 16 
C2E N12 C12  SING N N 17 
C2E N13 C12  DOUB N N 18 
C2E N13 C14  SING N N 19 
C2E C18 O18  SING N N 20 
C2E C18 C19  SING N N 21 
C2E N7  C14  SING N N 22 
C2E N7  C8   SING Y N 23 
C2E C12 N11  SING Y N 24 
C2E C14 C9   DOUB Y N 25 
C2E O3  P1   SING N N 26 
C2E O18 C21  SING Y N 27 
C2E O19 C19  SING N N 28 
C2E O19 P1   SING N N 29 
C2E C19 C20  SING N N 30 
C2E C8  N8   DOUB N N 31 
C2E O2  P1   DOUB N N 32 
C2E N11 C10  SING N N 33 
C2E P1  O1   SING N N 34 
C2E C22 N22  DOUB N N 35 
C2E C22 N21  SING N N 36 
C2E C9  N8   SING N N 37 
C2E C9  C10  SING Y N 38 
C2E C21 C20  SING N N 39 
C2E C21 N21  SING N N 40 
C2E C10 O10  DOUB N N 41 
C2E N22 C23  SING N N 42 
C2E C20 O20  SING N N 43 
C2E N21 C27  SING N N 44 
C2E C23 C27  DOUB N N 45 
C2E C23 C24  SING N N 46 
C2E C27 N27  SING N N 47 
C2E N27 C25  DOUB N N 48 
C2E C24 O24  DOUB N N 49 
C2E C24 N25  SING N N 50 
C2E C25 N25  SING N N 51 
C2E C25 N26  SING N N 52 
C2E O1  H1O  SING N N 53 
C2E C3  H31  SING N N 54 
C2E C3  H32  SING N N 55 
C2E C4  H4   SING N N 56 
C2E C5  H5   SING N N 57 
C2E C6  H6   SING N N 58 
C2E O6  H6O  SING N N 59 
C2E C7  H7   SING N N 60 
C2E C8  H8   SING Y N 61 
C2E N11 H11N SING Y N 62 
C2E N12 H121 SING Y N 63 
C2E N12 H122 SING N N 64 
C2E O15 H15O SING Y N 65 
C2E C17 H171 SING Y N 66 
C2E C17 H172 SING N N 67 
C2E C18 H18  SING N N 68 
C2E C19 H19  SING N N 69 
C2E C20 H20  SING N N 70 
C2E O20 H20O SING N N 71 
C2E C21 H21  SING N N 72 
C2E C22 H22  SING N N 73 
C2E N25 H25N SING N N 74 
C2E N26 H261 SING N N 75 
C2E N26 H262 SING N N 76 
# 
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 
C2E SMILES           ACDLabs              10.04 O=C7NC(=Nc1c7ncn1C6OC5COP(=O)(O)OC4C(OC(n2c3N=C(N)NC(=O)c3nc2)C4O)COP(=O)(O)OC5C6O)N 
C2E InChI            InChI                1.02b 
;InChI=1/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1/f/h27-28,35,37H,21-22H2
;
C2E InChIKey         InChI                1.02b PKFDLKSEZWEFGL-QGCQUEQCDF 
C2E SMILES_CANONICAL CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@@H]4CO[P@@](O)(=O)O[C@H]5[C@@H](O)[C@@H](O[C@@H]5CO[P@@](O)(=O)O[C@H]4[C@H]3O)n6cnc7C(=O)NC(=Nc67)N 
C2E SMILES           CACTVS               3.341 NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH]4CO[P](O)(=O)O[CH]5[CH](O)[CH](O[CH]5CO[P](O)(=O)O[CH]4[CH]3O)n6cnc7C(=O)NC(=Nc67)N 
C2E SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(n1[C@H]3[C@@H]([C@H]4[C@H](O3)CO[P@@](=O)(O[C@@H]5[C@@H](CO[P@@](=O)(O4)O)O[C@H]([C@@H]5O)n6cnc7c6N=C(NC7=O)N)O)O)N=C(NC2=O)N 
C2E SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(n1C3C(C4C(O3)COP(=O)(OC5C(COP(=O)(O4)O)OC(C5O)n6cnc7c6N=C(NC7=O)N)O)O)N=C(NC2=O)N 
# 
_pdbx_chem_comp_identifier.comp_id           C2E 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        
"9,9'-[(2R,3R,3aS,5S,7aR,9R,10R,10aS,12S,14aR)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-2,9-diyl]bis(2-amino-1,9-dihydro-6H-purin-6-one)" 
# 
