data_5UA
# 
_chem_comp.id                                    5UA 
_chem_comp.name                                  "5'-O-CARBOXY-2'-DEOXYADENOSINE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H13 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2010-04-25 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        295.251 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5UA 
_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        2XCS 
_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 
5UA OP1    OP1    O 0 1 N N N -14.949 68.722 38.825 5.641  -2.089 -1.129 OP1    5UA 1  
5UA "O5'"  "O5'"  O 0 1 N N N -16.346 67.576 40.375 3.955  -0.562 -0.621 "O5'"  5UA 2  
5UA "C5'"  "C5'"  C 0 1 N N N -15.834 67.894 41.682 3.361  0.308  0.378  "C5'"  5UA 3  
5UA "C4'"  "C4'"  C 0 1 N N R -15.720 66.699 42.624 2.146  1.018  -0.221 "C4'"  5UA 4  
5UA "O4'"  "O4'"  O 0 1 N N N -16.995 66.080 42.828 1.096  0.070  -0.513 "O4'"  5UA 5  
5UA "C1'"  "C1'"  C 0 1 N N R -16.843 64.664 42.691 -0.133 0.812  -0.576 "C1'"  5UA 6  
5UA N9     N9     N 0 1 Y N N -18.091 64.037 42.195 -1.236 -0.009 -0.068 N9     5UA 7  
5UA C8     C8     C 0 1 Y N N -18.894 63.161 42.838 -1.129 -1.063 0.789  C8     5UA 8  
5UA N7     N7     N 0 1 Y N N -19.955 62.818 42.043 -2.306 -1.561 1.031  N7     5UA 9  
5UA C5     C5     C 0 1 Y N N -19.813 63.493 40.881 -3.242 -0.861 0.345  C5     5UA 10 
5UA C6     C6     C 0 1 Y N N -20.593 63.577 39.625 -4.639 -0.938 0.220  C6     5UA 11 
5UA N6     N6     N 0 1 N N N -21.714 62.881 39.461 -5.358 -1.906 0.899  N6     5UA 12 
5UA N1     N1     N 0 1 Y N N -20.134 64.373 38.664 -5.254 -0.060 -0.565 N1     5UA 13 
5UA C2     C2     C 0 1 Y N N -18.913 65.163 38.774 -4.576 0.868  -1.216 C2     5UA 14 
5UA N3     N3     N 0 1 Y N N -18.202 65.028 40.039 -3.267 0.978  -1.129 N3     5UA 15 
5UA C4     C4     C 0 1 Y N N -18.666 64.221 41.016 -2.567 0.147  -0.364 C4     5UA 16 
5UA "C3'"  "C3'"  C 0 1 N N S -14.792 65.623 42.087 1.498  1.965  0.820  "C3'"  5UA 17 
5UA "C2'"  "C2'"  C 0 1 N N N -15.717 64.496 41.689 0.040  2.062  0.308  "C2'"  5UA 18 
5UA "O3'"  "O3'"  O 0 1 N N N -13.984 65.193 43.159 2.129  3.247  0.806  "O3'"  5UA 19 
5UA "C6'"  "C6'"  C 0 1 N N N -15.546 67.661 39.144 5.042  -1.264 -0.251 "C6'"  5UA 20 
5UA OP3    OP3    O 0 1 N N N -15.482 66.640 38.424 5.482  -1.153 0.875  OP3    5UA 21 
5UA HP1    HP1    H 0 1 N N N -14.488 68.592 38.005 6.418  -2.572 -0.818 HP1    5UA 22 
5UA "H5'1" "H5'1" H 0 0 N N N -14.828 68.320 41.555 3.048  -0.286 1.237  "H5'1" 5UA 23 
5UA "H5'2" "H5'2" H 0 0 N N N -16.550 68.591 42.141 4.094  1.049  0.697  "H5'2" 5UA 24 
5UA "H4'"  "H4'"  H 0 1 N N N -15.318 67.105 43.564 2.428  1.567  -1.120 "H4'"  5UA 25 
5UA "H3'"  "H3'"  H 0 1 N N N -14.156 65.958 41.254 1.531  1.527  1.818  "H3'"  5UA 26 
5UA "H1'"  "H1'"  H 0 1 N N N -16.623 64.177 43.652 -0.336 1.108  -1.605 "H1'"  5UA 27 
5UA "H2'1" "H2'1" H 0 0 N N N -15.232 63.512 41.768 -0.098 2.968  -0.281 "H2'1" 5UA 28 
5UA "H2'2" "H2'2" H 0 0 N N N -16.044 64.536 40.639 -0.660 2.039  1.143  "H2'2" 5UA 29 
5UA H8     H8     H 0 1 N N N -18.724 62.785 43.836 -0.203 -1.430 1.207  H8     5UA 30 
5UA H61N   H61N   H 0 0 N N N -22.132 62.706 40.353 -4.898 -2.542 1.469  H61N   5UA 31 
5UA H62N   H62N   H 0 0 N N N -22.350 63.402 38.892 -6.323 -1.949 0.804  H62N   5UA 32 
5UA H2     H2     H 0 1 N N N -18.562 65.801 37.977 -5.115 1.562  -1.844 H2     5UA 33 
5UA "HO3'" "HO3'" H 0 0 N N N -13.087 65.096 42.861 1.759  3.875  1.441  "HO3'" 5UA 34 
# 
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 
5UA OP1   "C6'"  SING N N 1  
5UA OP3   "C6'"  DOUB N N 2  
5UA "O5'" "C5'"  SING N N 3  
5UA "O5'" "C6'"  SING N N 4  
5UA "C5'" "C4'"  SING N N 5  
5UA "C4'" "O4'"  SING N N 6  
5UA "C4'" "C3'"  SING N N 7  
5UA "O4'" "C1'"  SING N N 8  
5UA "C1'" N9     SING N N 9  
5UA "C1'" "C2'"  SING N N 10 
5UA N9    C8     SING Y N 11 
5UA N9    C4     SING Y N 12 
5UA C8    N7     DOUB Y N 13 
5UA N7    C5     SING Y N 14 
5UA C5    C6     DOUB Y N 15 
5UA C5    C4     SING Y N 16 
5UA C6    N6     SING N N 17 
5UA C6    N1     SING Y N 18 
5UA N1    C2     DOUB Y N 19 
5UA C2    N3     SING Y N 20 
5UA N3    C4     DOUB Y N 21 
5UA "C3'" "C2'"  SING N N 22 
5UA "C3'" "O3'"  SING N N 23 
5UA OP1   HP1    SING N N 24 
5UA "C5'" "H5'1" SING N N 25 
5UA "C5'" "H5'2" SING N N 26 
5UA "C4'" "H4'"  SING N N 27 
5UA "C3'" "H3'"  SING N N 28 
5UA "C1'" "H1'"  SING N N 29 
5UA "C2'" "H2'1" SING N N 30 
5UA "C2'" "H2'2" SING N N 31 
5UA C8    H8     SING N N 32 
5UA N6    H61N   SING N N 33 
5UA N6    H62N   SING N N 34 
5UA C2    H2     SING N N 35 
5UA "O3'" "HO3'" SING N N 36 
# 
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 
5UA SMILES           ACDLabs              10.04 "O=C(O)OCC3OC(n2cnc1c(ncnc12)N)CC3O"                                                                                                     
5UA SMILES_CANONICAL CACTVS               3.352 "Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](COC(O)=O)O3"                                                                                      
5UA SMILES           CACTVS               3.352 "Nc1ncnc2n(cnc12)[CH]3C[CH](O)[CH](COC(O)=O)O3"                                                                                          
5UA SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)COC(=O)O)O)N"                                                                                  
5UA SMILES           "OpenEye OEToolkits" 1.6.1 "c1nc(c2c(n1)n(cn2)C3CC(C(O3)COC(=O)O)O)N"                                                                                               
5UA InChI            InChI                1.03  "InChI=1S/C11H13N5O5/c12-9-8-10(14-3-13-9)16(4-15-8)7-1-5(17)6(21-7)2-20-11(18)19/h3-7,17H,1-2H2,(H,18,19)(H2,12,13,14)/t5-,6+,7+/m0/s1" 
5UA InChIKey         InChI                1.03  YSFXGKUPZLTGKR-RRKCRQDMSA-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 
5UA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-carboxy-2'-deoxyadenosine"                                                    
5UA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methyl hydrogen carbonate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
5UA "Create component"     2010-04-25 EBI  
5UA "Modify aromatic_flag" 2011-06-04 RCSB 
5UA "Modify descriptor"    2011-06-04 RCSB 
# 
