data_2BU
# 
_chem_comp.id                                    2BU 
_chem_comp.name                                  
;(2S,3S)-N6-(2,3,4-TRIHYDROXYBUTYL)-2'-DEOXYADENOSINE MONO PHOSPHORIC ACID
;
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C14 H22 N5 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-02 
_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                        435.326 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     2BU 
_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        1U6O 
_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 
2BU P      P    P 0 1 N N N 2.124  9.338  14.891 -3.103 -1.229 0.243  P      2BU 1  
2BU OP1    O1P  O 0 1 N N N 1.828  10.785 14.785 -3.970 -1.331 -0.977 OP1    2BU 2  
2BU OP2    O2P  O 0 1 N N N 3.428  8.891  15.434 -3.244 0.149  1.078  OP2    2BU 3  
2BU OP3    O3P  O 0 1 N Y N ?      ?      ?      -3.361 -2.369 1.361  OP3    2BU 4  
2BU "O5'"  O5*  O 0 1 N N N 0.958  8.644  15.754 -1.513 -1.349 -0.036 "O5'"  2BU 5  
2BU "C5'"  C5*  C 0 1 N N N -0.409 8.780  15.356 -0.625 -1.263 1.065  "C5'"  2BU 6  
2BU "C4'"  C4*  C 0 1 N N R -1.329 7.884  16.183 0.802  -1.402 0.553  "C4'"  2BU 7  
2BU "O4'"  O4*  O 0 1 N N N -0.973 6.491  16.029 1.062  -0.306 -0.349 "O4'"  2BU 8  
2BU "C1'"  C1*  C 0 1 N N R -0.728 5.904  17.320 2.101  0.516  0.211  "C1'"  2BU 9  
2BU N9     N9   N 0 1 Y N N 0.473  5.038  17.254 1.818  1.923  -0.049 N9     2BU 10 
2BU C4     C4   C 0 1 Y N N 0.540  3.655  17.158 2.730  2.913  -0.277 C4     2BU 11 
2BU N3     N3   N 0 1 Y N N -0.492 2.791  17.003 4.067  2.803  -0.310 N3     2BU 12 
2BU C2     C2   C 0 1 Y N N -0.064 1.537  16.870 4.634  4.003  -0.564 C2     2BU 13 
2BU N1     N1   N 0 1 Y N N 1.202  1.113  16.899 4.033  5.200  -0.771 N1     2BU 14 
2BU C6     C6   C 0 1 Y N N 2.213  1.986  17.045 2.669  5.255  -0.727 C6     2BU 15 
2BU N6     N6   N 0 1 N N N 3.461  1.510  17.232 1.997  6.448  -0.931 N6     2BU 16 
2BU CB1    CB1  C 0 1 N N N 4.619  2.279  16.687 2.662  7.705  -1.200 CB1    2BU 17 
2BU CB2    CB2  C 0 1 N N R 5.913  1.737  17.413 1.625  8.823  -1.340 CB2    2BU 18 
2BU OH2    OH2  O 0 1 N N N 5.796  0.695  17.598 0.914  8.909  -0.100 OH2    2BU 19 
2BU CB3    CB3  C 0 1 N N S 6.914  0.669  16.763 2.232  10.204 -1.637 CB3    2BU 20 
2BU OH3    OH3  O 0 1 N N N 6.492  0.061  15.925 1.188  11.162 -1.827 OH3    2BU 21 
2BU CB4    CB4  C 0 1 N N N 8.220  1.392  16.343 3.135  10.709 -0.516 CB4    2BU 22 
2BU OH4    OH4  O 0 1 N N N 9.309  0.450  16.320 3.676  11.971 -0.895 OH4    2BU 23 
2BU C5     C5   C 0 1 Y N N 1.880  3.335  17.179 1.979  4.062  -0.469 C5     2BU 24 
2BU N7     N7   N 0 1 Y N N 2.673  4.492  17.279 0.638  3.788  -0.362 N7     2BU 25 
2BU C8     C8   C 0 1 Y N N 1.773  5.413  17.310 0.576  2.497  -0.110 C8     2BU 26 
2BU "C2'"  C2*  C 0 1 N N N -0.563 7.029  18.319 2.196  0.158  1.687  "C2'"  2BU 27 
2BU "C3'"  C3*  C 0 1 N N S -1.215 8.225  17.664 1.839  -1.311 1.668  "C3'"  2BU 28 
2BU "O3'"  O3*  O 0 1 N N N -2.502 8.508  18.260 3.000  -2.052 1.302  "O3'"  2BU 29 
2BU HOP2   2HOP H 0 0 N N N 3.618  7.963  15.502 -4.140 0.475  1.308  HOP2   2BU 30 
2BU HOP3   3HOP H 0 0 N N N 0.190  -0.928 0.068  -4.282 -2.563 1.638  HOP3   2BU 31 
2BU "H5'"  H5*  H 0 1 N N N -0.503 8.515  14.303 -0.754 -0.297 1.555  "H5'"  2BU 32 
2BU "H5''" H5** H 0 0 N N N -0.715 9.818  15.489 -0.850 -2.064 1.771  "H5''" 2BU 33 
2BU "H4'"  H4*  H 0 1 N N N -2.358 8.033  15.847 0.894  -2.332 -0.017 "H4'"  2BU 34 
2BU "H1'"  H1*  H 0 1 N N N -1.590 5.319  17.613 3.033  0.294  -0.320 "H1'"  2BU 35 
2BU H2     H2   H 0 1 N N N -0.836 0.768  16.701 5.717  4.010  -0.609 H2     2BU 36 
2BU H6     H6   H 0 1 N N N 3.591  0.518  17.111 0.986  6.446  -0.889 H6     2BU 37 
2BU HB12   HB12 H 0 0 N N N 4.460  3.339  16.914 3.245  7.593  -2.120 HB12   2BU 38 
2BU HB11   HB11 H 0 0 N N N 4.715  2.100  15.596 3.352  7.909  -0.377 HB11   2BU 39 
2BU HB2    HB2  H 0 1 N N N 6.471  2.571  17.802 0.892  8.566  -2.114 HB2    2BU 40 
2BU HO2    HO2  H 0 1 N N N 6.166  0.501  18.452 0.378  8.105  -0.041 HO2    2BU 41 
2BU HB3    HB3  H 0 1 N N N 7.134  -0.039 17.518 2.795  10.175 -2.578 HB3    2BU 42 
2BU HO3    HO3  H 0 1 N Y N 6.221  -0.808 16.289 0.696  10.875 -2.610 HO3    2BU 43 
2BU HB41   HB41 H 0 0 N N N 8.398  2.134  17.040 3.975  10.032 -0.337 HB41   2BU 44 
2BU HB42   HB42 H 0 0 N N N 8.090  1.803  15.353 2.571  10.849 0.412  HB42   2BU 45 
2BU HO4    HO4  H 0 1 N N N 8.962  -0.442 16.475 3.428  12.111 -1.822 HO4    2BU 46 
2BU H8     H8   H 0 1 N N N 2.047  6.462  17.394 -0.332 1.927  0.037  H8     2BU 47 
2BU "H2'"  H2*  H 0 1 N N N 0.487  7.222  18.489 1.451  0.718  2.266  "H2'"  2BU 48 
2BU "H2''" H2** H 0 0 N N N -1.060 6.793  19.262 3.189  0.372  2.093  "H2''" 2BU 49 
2BU "H3'"  H3*  H 0 1 N N N -0.565 9.093  17.782 1.489  -1.690 2.631  "H3'"  2BU 50 
2BU "HO3'" H3T  H 0 0 N Y N -2.431 8.721  19.183 2.721  -2.977 1.216  "HO3'" 2BU 51 
# 
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 
2BU P     OP1    DOUB N N 1  
2BU P     OP2    SING N N 2  
2BU P     OP3    SING N N 3  
2BU P     "O5'"  SING N N 4  
2BU OP2   HOP2   SING N N 5  
2BU OP3   HOP3   SING N N 6  
2BU "O5'" "C5'"  SING N N 7  
2BU "C5'" "C4'"  SING N N 8  
2BU "C5'" "H5'"  SING N N 9  
2BU "C5'" "H5''" SING N N 10 
2BU "C4'" "O4'"  SING N N 11 
2BU "C4'" "C3'"  SING N N 12 
2BU "C4'" "H4'"  SING N N 13 
2BU "O4'" "C1'"  SING N N 14 
2BU "C1'" N9     SING N N 15 
2BU "C1'" "C2'"  SING N N 16 
2BU "C1'" "H1'"  SING N N 17 
2BU N9    C4     SING Y N 18 
2BU N9    C8     SING Y N 19 
2BU C4    N3     SING Y N 20 
2BU C4    C5     DOUB Y N 21 
2BU N3    C2     DOUB Y N 22 
2BU C2    N1     SING Y N 23 
2BU C2    H2     SING N N 24 
2BU N1    C6     DOUB Y N 25 
2BU C6    N6     SING N N 26 
2BU C6    C5     SING Y N 27 
2BU N6    CB1    SING N N 28 
2BU N6    H6     SING N N 29 
2BU CB1   CB2    SING N N 30 
2BU CB1   HB12   SING N N 31 
2BU CB1   HB11   SING N N 32 
2BU CB2   OH2    SING N N 33 
2BU CB2   CB3    SING N N 34 
2BU CB2   HB2    SING N N 35 
2BU OH2   HO2    SING N N 36 
2BU CB3   OH3    SING N N 37 
2BU CB3   CB4    SING N N 38 
2BU CB3   HB3    SING N N 39 
2BU OH3   HO3    SING N N 40 
2BU CB4   OH4    SING N N 41 
2BU CB4   HB41   SING N N 42 
2BU CB4   HB42   SING N N 43 
2BU OH4   HO4    SING N N 44 
2BU C5    N7     SING Y N 45 
2BU N7    C8     DOUB Y N 46 
2BU C8    H8     SING N N 47 
2BU "C2'" "C3'"  SING N N 48 
2BU "C2'" "H2'"  SING N N 49 
2BU "C2'" "H2''" SING N N 50 
2BU "C3'" "O3'"  SING N N 51 
2BU "C3'" "H3'"  SING N N 52 
2BU "O3'" "HO3'" SING N N 53 
# 
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 
2BU SMILES           ACDLabs              10.04 "O=P(O)(O)OCC3OC(n2cnc1c(ncnc12)NCC(O)C(O)CO)CC3O"                                                                                                                                              
2BU InChI            InChI                1.02b "InChI=1/C14H22N5O9P/c20-3-9(23)8(22)2-15-13-12-14(17-5-16-13)19(6-18-12)11-1-7(21)10(28-11)4-27-29(24,25)26/h5-11,20-23H,1-4H2,(H,15,16,17)(H2,24,25,26)/t7-,8+,9-,10+,11+/m0/s1/f/h15,24-25H" 
2BU InChIKey         InChI                1.02b AIFKZZYQDFSUSI-WSPROLTDDI                                                                                                                                                                       
2BU SMILES_CANONICAL CACTVS               3.341 "OC[C@H](O)[C@H](O)CNc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO[P](O)(O)=O)O3"                                                                                                                     
2BU SMILES           CACTVS               3.341 "OC[CH](O)[CH](O)CNc1ncnc2n(cnc12)[CH]3C[CH](O)[CH](CO[P](O)(O)=O)O3"                                                                                                                           
2BU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O)NC[C@H]([C@H](CO)O)O"                                                                                                                   
2BU SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3CC(C(O3)COP(=O)(O)O)O)NCC(C(CO)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 
2BU "SYSTEMATIC NAME" ACDLabs              10.04 
;2'-deoxy-N-[(2R,3S)-2,3,4-trihydroxybutyl]adenosine 5'-(dihydrogen phosphate)
;
2BU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-3-hydroxy-5-[6-[[(2R,3S)-2,3,4-trihydroxybutyl]amino]purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate" 
# 
