data_ENP
# 
_chem_comp.id                                    ENP 
_chem_comp.name                                  ETHENO-NADP 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C17 H24 N5 O17 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-12-06 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        663.317 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     ENP 
_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        ? 
_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 
ENP P1     P1   P 0 1 N N R 9.238  7.594  85.898 2.058   -0.268 -0.530 P1     ENP 1  
ENP O1     O1   O 0 1 N N N 8.862  6.360  85.117 1.600   0.246  -1.985 O1     ENP 2  
ENP O2     O2   O 0 1 N N N 8.457  7.536  87.182 2.579   -1.649 -0.636 O2     ENP 3  
ENP "O5'"  O5*  O 0 1 N N N 8.824  8.896  85.085 0.795   -0.246 0.469  "O5'"  ENP 4  
ENP "C5'"  C5*  C 0 1 N N N 9.312  9.054  83.698 -0.140  -1.206 -0.027 "C5'"  ENP 5  
ENP "C4'"  C4*  C 0 1 N N R 9.395  10.518 83.128 -1.371  -1.236 0.882  "C4'"  ENP 6  
ENP "O4'"  O4*  O 0 1 N N N 10.587 11.193 83.612 -2.079  0.011  0.786  "O4'"  ENP 7  
ENP "C3'"  C3*  C 0 1 N N R 9.454  10.619 81.589 -2.333  -2.349 0.424  "C3'"  ENP 8  
ENP "O3'"  O3*  O 0 1 N N N 8.550  11.474 81.111 -2.533  -3.306 1.467  "O3'"  ENP 9  
ENP "C2'"  C2*  C 0 1 N N R 10.923 11.031 81.274 -3.656  -1.600 0.115  "C2'"  ENP 10 
ENP "O2'"  O2*  O 0 1 N N N 11.048 11.837 80.036 -4.783  -2.344 0.581  "O2'"  ENP 11 
ENP "C1'"  C1*  C 0 1 N N R 11.431 11.748 82.562 -3.484  -0.290 0.926  "C1'"  ENP 12 
ENP N9     N9   N 0 1 Y N N 12.871 11.453 82.893 -4.302  0.784  0.357  N9     ENP 13 
ENP C8     C8   C 0 1 Y N N 13.742 12.364 83.533 -3.912  1.674  -0.597 C8     ENP 14 
ENP N7     N7   N 0 1 Y N N 15.045 11.898 83.764 -4.893  2.488  -0.867 N7     ENP 15 
ENP C5     C5   C 0 1 Y N N 14.881 10.683 83.229 -5.962  2.170  -0.106 C5     ENP 16 
ENP C6     C6   C 0 1 Y N N 15.946 9.690  83.175 -7.317  2.702  0.040  C6     ENP 17 
ENP N6     N6   N 0 1 Y N N 17.159 9.988  83.680 -7.980  3.689  -0.525 N6     ENP 18 
ENP N1     N1   N 0 1 Y N N 15.606 8.515  82.600 -8.147  2.089  0.949  N1     ENP 19 
ENP C2     C2   C 0 1 Y N N 14.358 8.142  82.053 -7.694  1.028  1.672  C2     ENP 20 
ENP N3     N3   N 0 1 Y N N 13.381 9.057  82.102 -6.490  0.555  1.543  N3     ENP 21 
ENP C4     C4   C 0 1 Y N N 13.660 10.316 82.690 -5.603  1.074  0.683  C4     ENP 22 
ENP O3     O3   O 0 1 N N N 10.820 7.604  86.163 3.211   0.698  0.043  O3     ENP 23 
ENP P2     P2   P 0 1 N N S 12.116 6.768  85.705 4.561   0.334  -0.755 P2     ENP 24 
ENP O4     O4   O 0 1 N N N 12.116 6.558  84.204 4.542   1.050  -2.197 O4     ENP 25 
ENP O5     O5   O 0 1 N N N 12.159 5.397  86.343 4.649   -1.132 -0.933 O5     ENP 26 
ENP "O9'"  O9*  O 0 1 N N N 13.449 7.589  86.065 5.836   0.851  0.083  "O9'"  ENP 27 
ENP "C0'"  C0*  C 0 1 N N N 14.568 7.020  86.858 6.999   0.397  -0.613 "C0'"  ENP 28 
ENP "C9'"  C9*  C 0 1 N N R 15.984 7.407  86.288 8.252   0.856  0.135  "C9'"  ENP 29 
ENP "O8'"  O8*  O 0 1 N N N 16.159 8.837  86.127 8.341   0.198  1.418  "O8'"  ENP 30 
ENP "C8'"  C8*  C 0 1 N N S 17.261 6.951  87.086 9.524   0.418  -0.623 "C8'"  ENP 31 
ENP "O7'"  O7*  O 0 1 N N N 18.175 6.491  86.218 10.035  1.497  -1.409 "O7'"  ENP 32 
ENP "C7'"  C7*  C 0 1 N N R 17.672 8.280  87.800 10.521  0.045  0.500  "C7'"  ENP 33 
ENP "O6'"  O6*  O 0 1 N N N 18.923 8.264  88.292 11.679  0.881  0.439  "O6'"  ENP 34 
ENP "C6'"  C6*  C 0 1 N N R 17.452 9.166  86.641 9.730   0.300  1.802  "C6'"  ENP 35 
ENP P3     P3   P 0 1 N N N 10.574 11.250 78.662 -5.792  -2.488 -0.666 P3     ENP 36 
ENP O7     O7   O 0 1 N N N 9.086  11.471 78.523 -7.029  -3.431 -0.248 O7     ENP 37 
ENP O8     O8   O 0 1 N N N 11.226 11.945 77.506 -6.343  -1.034 -1.082 O8     ENP 38 
ENP O9     O9   O 0 1 N N N 10.817 9.769  78.531 -5.077  -3.092 -1.812 O9     ENP 39 
ENP C1     C1   C 0 1 Y N N 17.703 8.753  83.356 -9.215  3.740  -0.012 C1     ENP 40 
ENP C9     C9   C 0 1 Y N N 16.782 7.868  82.714 -9.342  2.757  0.904  C9     ENP 41 
ENP O6     O6   O 0 1 N N N 17.608 10.585 86.555 10.050  -0.692 2.780  O6     ENP 42 
ENP HO1    HO1  H 0 1 N N N 9.355  6.397  84.306 1.268   1.147  -1.871 HO1    ENP 43 
ENP "H5'"  1H5* H 0 1 N N N 8.696  8.424  83.014 -0.442  -0.931 -1.038 "H5'"  ENP 44 
ENP "H5''" 2H5* H 0 0 N N N 10.306 8.560  83.596 0.324   -2.192 -0.042 "H5''" ENP 45 
ENP "H4'"  H4*  H 0 1 N N N 8.448  10.989 83.482 -1.065  -1.410 1.913  "H4'"  ENP 46 
ENP "H3'"  H3*  H 0 1 N N N 9.195  9.657  81.089 -1.952  -2.837 -0.473 "H3'"  ENP 47 
ENP HO3    HO3  H 0 1 N Y N 8.586  11.536 80.164 -1.681  -3.739 1.615  HO3    ENP 48 
ENP "H2'"  H2*  H 0 1 N N N 11.561 10.146 81.043 -3.745  -1.388 -0.950 "H2'"  ENP 49 
ENP "H1'"  H1*  H 0 1 N N N 11.377 12.855 82.440 -3.740  -0.451 1.974  "H1'"  ENP 50 
ENP H8     H8   H 0 1 N N N 13.424 13.377 83.834 -2.936  1.701  -1.059 H8     ENP 51 
ENP H2     H2   H 0 1 N N N 14.151 7.159  81.598 -8.361  0.560  2.382  H2     ENP 52 
ENP HO4    HO4  H 0 1 N N N 12.881 6.064  83.934 4.484   2.002  -2.037 HO4    ENP 53 
ENP "H0'1" 1H0* H 0 0 N N N 14.466 5.914  86.954 7.004   0.812  -1.620 "H0'1" ENP 54 
ENP "H0'2" 2H0* H 0 0 N N N 14.480 7.305  87.932 6.987   -0.692 -0.668 "H0'2" ENP 55 
ENP "H9'"  H9*  H 0 1 N N N 15.942 6.838  85.330 8.240   1.939  0.264  "H9'"  ENP 56 
ENP "H8'"  H8*  H 0 1 N N N 17.123 6.118  87.815 9.315   -0.447 -1.252 "H8'"  ENP 57 
ENP "HO'7" 7HO* H 0 0 N N N 18.946 6.216  86.700 10.825  1.166  -1.857 "HO'7" ENP 58 
ENP "H7'"  H7*  H 0 1 N N N 17.122 8.557  88.729 10.805  -1.004 0.426  "H7'"  ENP 59 
ENP "HO'6" 6HO* H 0 0 N N N 19.173 9.071  88.726 12.262  0.604  1.159  "HO'6" ENP 60 
ENP "H6'"  H6*  H 0 1 N N N 18.400 8.929  86.104 9.945   1.296  2.188  "H6'"  ENP 61 
ENP HO7    HO7  H 0 1 N N N 8.799  11.115 77.690 -7.608  -3.491 -1.021 HO7    ENP 62 
ENP HO8    HO8  H 0 1 N N N 10.939 11.589 76.673 -6.801  -0.676 -0.309 HO8    ENP 63 
ENP H1     H1   H 0 1 N N N 18.753 8.502  83.584 -9.982  4.449  -0.286 H1     ENP 64 
ENP H9     H9   H 0 1 N N N 16.954 6.838  82.359 -10.222 2.538  1.491  H9     ENP 65 
ENP HO6    HO6  H 0 1 N N N 18.467 10.804 86.897 9.511   -0.499 3.559  HO6    ENP 66 
# 
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 
ENP P1    O1     SING N N 1  
ENP P1    O2     DOUB N N 2  
ENP P1    "O5'"  SING N N 3  
ENP P1    O3     SING N N 4  
ENP O1    HO1    SING N N 5  
ENP "O5'" "C5'"  SING N N 6  
ENP "C5'" "C4'"  SING N N 7  
ENP "C5'" "H5'"  SING N N 8  
ENP "C5'" "H5''" SING N N 9  
ENP "C4'" "O4'"  SING N N 10 
ENP "C4'" "C3'"  SING N N 11 
ENP "C4'" "H4'"  SING N N 12 
ENP "O4'" "C1'"  SING N N 13 
ENP "C3'" "O3'"  SING N N 14 
ENP "C3'" "C2'"  SING N N 15 
ENP "C3'" "H3'"  SING N N 16 
ENP "O3'" HO3    SING N N 17 
ENP "C2'" "O2'"  SING N N 18 
ENP "C2'" "C1'"  SING N N 19 
ENP "C2'" "H2'"  SING N N 20 
ENP "O2'" P3     SING N N 21 
ENP "C1'" N9     SING N N 22 
ENP "C1'" "H1'"  SING N N 23 
ENP N9    C8     SING Y N 24 
ENP N9    C4     SING Y N 25 
ENP C8    N7     DOUB Y N 26 
ENP C8    H8     SING N N 27 
ENP N7    C5     SING Y N 28 
ENP C5    C6     SING Y N 29 
ENP C5    C4     DOUB Y N 30 
ENP C6    N6     DOUB Y N 31 
ENP C6    N1     SING Y N 32 
ENP N6    C1     SING Y N 33 
ENP N1    C2     SING Y N 34 
ENP N1    C9     SING Y N 35 
ENP C2    N3     DOUB Y N 36 
ENP C2    H2     SING N N 37 
ENP N3    C4     SING Y N 38 
ENP O3    P2     SING N N 39 
ENP P2    O4     SING N N 40 
ENP P2    O5     DOUB N N 41 
ENP P2    "O9'"  SING N N 42 
ENP O4    HO4    SING N N 43 
ENP "O9'" "C0'"  SING N N 44 
ENP "C0'" "C9'"  SING N N 45 
ENP "C0'" "H0'1" SING N N 46 
ENP "C0'" "H0'2" SING N N 47 
ENP "C9'" "O8'"  SING N N 48 
ENP "C9'" "C8'"  SING N N 49 
ENP "C9'" "H9'"  SING N N 50 
ENP "O8'" "C6'"  SING N N 51 
ENP "C8'" "O7'"  SING N N 52 
ENP "C8'" "C7'"  SING N N 53 
ENP "C8'" "H8'"  SING N N 54 
ENP "O7'" "HO'7" SING N N 55 
ENP "C7'" "O6'"  SING N N 56 
ENP "C7'" "C6'"  SING N N 57 
ENP "C7'" "H7'"  SING N N 58 
ENP "O6'" "HO'6" SING N N 59 
ENP "C6'" O6     SING N N 60 
ENP "C6'" "H6'"  SING N N 61 
ENP P3    O7     SING N N 62 
ENP P3    O8     SING N N 63 
ENP P3    O9     DOUB N N 64 
ENP O7    HO7    SING N N 65 
ENP O8    HO8    SING N N 66 
ENP C1    C9     DOUB Y N 67 
ENP C1    H1     SING N N 68 
ENP C9    H9     SING N N 69 
ENP O6    HO6    SING N N 70 
# 
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 
ENP SMILES           ACDLabs              10.04 "O=P(O)(O)OC4C(O)C(OC4n2c3ncn1ccnc1c3nc2)COP(=O)(O)OP(=O)(O)OCC5OC(O)C(O)C5O" 
ENP InChI            InChI                1.02b 
;InChI=1/C17H24N5O17P3/c23-10-7(37-17(26)12(10)25)3-34-41(30,31)39-42(32,33)35-4-8-11(24)13(38-40(27,28)29)16(36-8)22-6-19-9-14-18-1-2-21(14)5-20-15(9)22/h1-2,5-8,10-13,16-17,23-26H,3-4H2,(H,30,31)(H,32,33)(H2,27,28,29)/t7-,8-,10-,11-,12-,13-,16-,17-/m1/s1/f/h27-28,30,32H
;
ENP InChIKey         InChI                1.02b KWEQFQACRLGUSH-YTQJZBJFDC 
ENP SMILES_CANONICAL CACTVS               3.341 "O[C@@H]1O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O[P](O)(O)=O)[C@@H]2O)n3cnc4c5nccn5cnc34)[C@@H](O)[C@H]1O" 
ENP SMILES           CACTVS               3.341 "O[CH]1O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O[P](O)(O)=O)[CH]2O)n3cnc4c5nccn5cnc34)[CH](O)[CH]1O" 
ENP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cn2cnc3c(c2n1)ncn3[C@H]4[C@@H]([C@@H]([C@H](O4)CO[P@@](=O)(O)O[P@@](=O)(O)OC[C@@H]5[C@H]([C@H]([C@@H](O5)O)O)O)O)OP(=O)(O)O" 
ENP SMILES           "OpenEye OEToolkits" 1.5.0 "c1cn2cnc3c(c2n1)ncn3C4C(C(C(O4)COP(=O)(O)OP(=O)(O)OCC5C(C(C(O5)O)O)O)O)OP(=O)(O)O" 
# 
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 
ENP "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3R,4R,5R)-3-hydroxy-5-(3H-imidazo[2,1-i]purin-3-yl)-4-(phosphonooxy)tetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)" 
ENP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3R,4R,5R)-3-hydroxy-5-imidazo[2,1-f]purin-3-yl-4-phosphonooxy-oxolan-2-yl]methyl [hydroxy-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate" 
# 
