data_ENA
# 
_chem_comp.id                                    ENA 
_chem_comp.name                                  ETHENO-NAD 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C17 H23 N5 O14 P2" 
_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                        583.337 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     ENA 
_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   Y 
_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 
ENA C8     C8   C 0 1 Y N N 13.910 10.642 82.928 6.406   0.530  -0.353 C8     ENA 1  
ENA N9     N9   N 0 1 Y N N 13.080 11.701 83.125 5.092   0.220  -0.101 N9     ENA 2  
ENA C5     C5   C 0 1 Y N N 15.081 10.942 83.550 6.628   1.773  0.246  C5     ENA 3  
ENA N3     N3   N 0 1 Y N N 13.729 9.375  82.225 7.400   -0.078 -1.013 N3     ENA 4  
ENA "C1'"  C1*  C 0 1 N N R 11.686 11.863 82.668 4.390   -0.991 -0.532 "C1'"  ENA 5  
ENA C4     C4   C 0 1 Y N N 13.759 12.638 83.859 4.564   1.242  0.627  C4     ENA 6  
ENA C6     C6   C 0 1 Y N N 16.166 9.896  83.479 7.965   2.356  0.130  C6     ENA 7  
ENA N7     N7   N 0 1 Y N N 14.962 12.198 84.122 5.472   2.154  0.829  N7     ENA 8  
ENA C2     C2   C 0 1 Y N N 14.711 8.456  82.165 8.588   0.440  -1.116 C2     ENA 9  
ENA "O2'"  O2*  O 0 1 N N N 10.946 11.083 83.645 2.965   -0.761 -0.583 "O2'"  ENA 10 
ENA "C2'"  C2*  C 0 1 N N R 11.323 11.271 81.284 4.537   -2.116 0.524  "C2'"  ENA 11 
ENA N1     N1   N 0 1 Y N N 15.926 8.703  82.787 8.913   1.644  -0.566 N1     ENA 12 
ENA N6     N6   N 0 1 Y N N 17.375 9.863  83.962 8.519   3.471  0.558  N6     ENA 13 
ENA "C4'"  C4*  C 0 1 N N R 9.807  10.441 83.070 2.330   -2.048 -0.508 "C4'"  ENA 14 
ENA "C3'"  C3*  C 0 1 N N S 9.996  10.527 81.586 3.290   -2.994 0.239  "C3'"  ENA 15 
ENA "O4'"  O4*  O 0 1 N N N 11.094 12.331 80.369 5.740   -2.858 0.314  "O4'"  ENA 16 
ENA C10    C10  C 0 1 Y N N 17.045 7.960  82.878 10.065  2.385  -0.536 C10    ENA 17 
ENA C9     C9   C 0 1 Y N N 17.955 8.636  83.592 9.797   3.508  0.163  C9     ENA 18 
ENA "C5'"  C5*  C 0 1 N N N 9.660  8.964  83.481 1.011   -1.934 0.259  "C5'"  ENA 19 
ENA "O3'"  O3*  O 0 1 N N N 8.852  11.248 81.097 3.642   -4.111 -0.581 "O3'"  ENA 20 
ENA "O5'"  O5*  O 0 1 N N N 9.468  8.927  84.919 0.089   -1.144 -0.494 "O5'"  ENA 21 
ENA P1     P1   P 0 1 N N R 9.250  7.485  85.645 -1.269  -1.065 0.368  P1     ENA 22 
ENA O2     O2   O 0 1 N N N 7.922  7.508  86.484 -2.400  -0.297 -0.481 O2     ENA 23 
ENA O1     O1   O 0 1 N N N 9.137  6.276  84.616 -0.989  -0.265 1.737  O1     ENA 24 
ENA O3     O3   O 0 1 N N N 10.405 7.284  86.522 -1.733  -2.434 0.684  O3     ENA 25 
ENA P2     P2   P 0 1 N N R 6.669  8.338  85.840 -3.808  -0.596 0.241  P2     ENA 26 
ENA O4     O4   O 0 1 N N N 6.933  9.994  85.820 -4.919  0.435  -0.301 O4     ENA 27 
ENA O5     O5   O 0 1 N N N 5.422  8.060  86.706 -4.269  -2.103 -0.088 O5     ENA 28 
ENA O6     O6   O 0 1 N N N 6.374  7.748  84.424 -3.656  -0.435 1.704  O6     ENA 29 
ENA "C6'"  C6*  C 0 1 N N N 6.010  10.972 85.223 -6.106  0.199  0.458  "C6'"  ENA 30 
ENA "C7'"  C7*  C 0 1 N N R 5.754  10.808 83.694 -7.208  1.152  -0.009 "C7'"  ENA 31 
ENA "O6'"  O6*  O 0 1 N N N 4.488  10.214 83.267 -7.600  0.842  -1.364 "O6'"  ENA 32 
ENA "C8'"  C8*  C 0 1 N N S 5.788  12.110 82.902 -8.490  0.948  0.829  "C8'"  ENA 33 
ENA "C9'"  C9*  C 0 1 N N R 4.618  10.239 81.823 -8.913  1.422  -1.523 "C9'"  ENA 34 
ENA "C0'"  C0*  C 0 1 N N R 5.001  11.733 81.586 -9.639  1.133  -0.190 "C0'"  ENA 35 
ENA "O7'"  O7*  O 0 1 N N N 7.225  12.498 82.656 -8.574  1.931  1.863  "O7'"  ENA 36 
ENA "O8'"  O8*  O 0 1 N N N 5.871  11.859 80.431 -10.469 2.234  0.185  "O8'"  ENA 37 
ENA O7     O7   O 0 1 N Y N 3.363  9.934  81.197 -9.603  0.803  -2.610 O7     ENA 38 
ENA "H1'"  H1*  H 0 1 N N N 11.473 12.954 82.574 4.760   -1.324 -1.502 "H1'"  ENA 39 
ENA H4     H4   H 0 1 N N N 13.385 13.620 84.195 3.546   1.289  0.983  H4     ENA 40 
ENA H2     H2   H 0 1 N N N 14.524 7.518  81.616 9.347   -0.104 -1.658 H2     ENA 41 
ENA "H2'"  H2*  H 0 1 N N N 12.109 10.618 80.838 4.504   -1.708 1.534  "H2'"  ENA 42 
ENA "H4'"  H4*  H 0 1 N N N 8.881  10.947 83.429 2.142   -2.428 -1.513 "H4'"  ENA 43 
ENA "H3'"  H3*  H 0 1 N N N 10.068 9.529  81.094 2.841   -3.334 1.172  "H3'"  ENA 44 
ENA "HO'4" 4HO* H 0 0 N N N 10.871 11.968 79.520 5.772   -3.539 1.000  "HO'4" ENA 45 
ENA H10    H10  H 0 1 N N N 17.192 6.959  82.439 11.010  2.120  -0.987 H10    ENA 46 
ENA H9     H9   H 0 1 N N N 18.966 8.262  83.825 10.498  4.304  0.369  H9     ENA 47 
ENA "H5'"  1H5* H 0 1 N N N 10.513 8.331  83.140 1.192   -1.460 1.224  "H5'"  ENA 48 
ENA "H5''" 2H5* H 0 0 N N N 8.853  8.436  82.921 0.594   -2.928 0.416  "H5''" ENA 49 
ENA "HO'3" 3HO* H 0 0 N N N 8.039  10.792 81.282 4.288   -4.630 -0.084 "HO'3" ENA 50 
ENA HO3    HO3  H 0 1 N Y N 10.278 6.443  86.945 ?       ?      ?      HO3    ENA 51 
ENA HO6    HO6  H 0 1 N N N 5.646  8.230  84.050 ?       ?      ?      HO6    ENA 52 
ENA "H6'1" 1H6* H 0 0 N N N 6.358  12.008 85.443 -5.902  0.369  1.515  "H6'1" ENA 53 
ENA "H6'2" 2H6* H 0 0 N N N 5.041  10.968 85.775 -6.431  -0.831 0.312  "H6'2" ENA 54 
ENA "H7'"  H7*  H 0 1 N N N 6.603  10.117 83.483 -6.870  2.186  0.061  "H7'"  ENA 55 
ENA "H8'"  H8*  H 0 1 N N N 5.332  12.994 83.406 -8.513  -0.055 1.254  "H8'"  ENA 56 
ENA "H9'"  H9*  H 0 1 N N N 5.346  9.502  81.410 -8.836  2.497  -1.687 "H9'"  ENA 57 
ENA "H0'"  H0*  H 0 1 N N N 4.119  12.387 81.390 -10.230 0.220  -0.269 "H0'"  ENA 58 
ENA "HO'7" 7HO* H 0 0 N N N 7.246  13.309 82.162 -9.390  1.755  2.350  "HO'7" ENA 59 
ENA "HO'8" 8HO* H 0 0 N N N 5.398  11.632 79.639 -11.164 2.300  -0.484 "HO'8" ENA 60 
ENA HO7    HO7  H 0 1 N N N 3.448  9.950  80.251 -9.094  0.995  -3.410 HO7    ENA 61 
# 
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 
ENA C8    N9     SING Y N 1  
ENA C8    C5     DOUB Y N 2  
ENA C8    N3     SING Y N 3  
ENA N9    "C1'"  SING N N 4  
ENA N9    C4     SING Y N 5  
ENA C5    C6     SING Y N 6  
ENA C5    N7     SING Y N 7  
ENA N3    C2     DOUB Y N 8  
ENA "C1'" "O2'"  SING N N 9  
ENA "C1'" "C2'"  SING N N 10 
ENA "C1'" "H1'"  SING N N 11 
ENA C4    N7     DOUB Y N 12 
ENA C4    H4     SING N N 13 
ENA C6    N1     SING Y N 14 
ENA C6    N6     DOUB Y N 15 
ENA C2    N1     SING Y N 16 
ENA C2    H2     SING N N 17 
ENA "O2'" "C4'"  SING N N 18 
ENA "C2'" "C3'"  SING N N 19 
ENA "C2'" "O4'"  SING N N 20 
ENA "C2'" "H2'"  SING N N 21 
ENA N1    C10    SING Y N 22 
ENA N6    C9     SING Y N 23 
ENA "C4'" "C3'"  SING N N 24 
ENA "C4'" "C5'"  SING N N 25 
ENA "C4'" "H4'"  SING N N 26 
ENA "C3'" "O3'"  SING N N 27 
ENA "C3'" "H3'"  SING N N 28 
ENA "O4'" "HO'4" SING N N 29 
ENA C10   C9     DOUB Y N 30 
ENA C10   H10    SING N N 31 
ENA C9    H9     SING N N 32 
ENA "C5'" "O5'"  SING N N 33 
ENA "C5'" "H5'"  SING N N 34 
ENA "C5'" "H5''" SING N N 35 
ENA "O3'" "HO'3" SING N N 36 
ENA "O5'" P1     SING N N 37 
ENA P1    O2     SING N N 38 
ENA P1    O1     DOUB N N 39 
ENA P1    O3     SING N N 40 
ENA O2    P2     SING N N 41 
ENA O3    HO3    SING N N 42 
ENA P2    O4     SING N N 43 
ENA P2    O5     DOUB N N 44 
ENA P2    O6     SING N N 45 
ENA O4    "C6'"  SING N N 46 
ENA O6    HO6    SING N N 47 
ENA "C6'" "C7'"  SING N N 48 
ENA "C6'" "H6'1" SING N N 49 
ENA "C6'" "H6'2" SING N N 50 
ENA "C7'" "O6'"  SING N N 51 
ENA "C7'" "C8'"  SING N N 52 
ENA "C7'" "H7'"  SING N N 53 
ENA "O6'" "C9'"  SING N N 54 
ENA "C8'" "C0'"  SING N N 55 
ENA "C8'" "O7'"  SING N N 56 
ENA "C8'" "H8'"  SING N N 57 
ENA "C9'" "C0'"  SING N N 58 
ENA "C9'" O7     SING N N 59 
ENA "C9'" "H9'"  SING N N 60 
ENA "C0'" "O8'"  SING N N 61 
ENA "C0'" "H0'"  SING N N 62 
ENA "O7'" "HO'7" SING N N 63 
ENA "O8'" "HO'8" SING N N 64 
ENA O7    HO7    SING N N 65 
# 
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 
ENA SMILES           ACDLabs              10.04 "O=P(O)(OCC4OC(n2c3ncn1ccnc1c3nc2)C(O)C4O)OP(=O)(O)OCC5OC(O)C(O)C5O" 
ENA InChI            InChI                1.02b 
"InChI=1/C17H23N5O14P2/c23-10-7(3-32-37(28,29)36-38(30,31)33-4-8-11(24)13(26)17(27)35-8)34-16(12(10)25)22-6-19-9-14-18-1-2-21(14)5-20-15(9)22/h1-2,5-8,10-13,16-17,23-27H,3-4H2,(H,28,29)(H,30,31)/t7-,8-,10-,11-,12-,13-,16-,17-/m1/s1/f/h28,30H" 
ENA InChIKey         InChI                1.02b LWAISUABIKYXTN-AFISJVTLDO 
ENA 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)[C@@H]2O)n3cnc4c5nccn5cnc34)[C@@H](O)[C@H]1O" 
ENA SMILES           CACTVS               3.341 "O[CH]1O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)n3cnc4c5nccn5cnc34)[CH](O)[CH]1O" 
ENA 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)O" 
ENA 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)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 
ENA "SYSTEMATIC NAME" ACDLabs              10.04 "[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)" 
ENA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-3,4-dihydroxy-5-imidazo[2,1-f]purin-3-yl-oxolan-2-yl]methyl [hydroxy-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate"                         
# 
