data_THS
# 
_chem_comp.id                                    THS 
_chem_comp.name                                  "THYMIDINE-5'-(DITHIO)PHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H15 N2 O6 P S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        354.340 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     THS 
_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        1AK0 
_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 
THS P      P    P 0 1 N N N 19.867 19.259 -3.202 0.801  0.175  -3.653 P      THS 1  
THS O1P    O1P  O 0 1 N Y N 19.705 19.283 -4.863 1.357  1.458  -3.169 O1P    THS 2  
THS S2P    S2P  S 0 1 N N N 21.262 18.004 -2.659 2.316  -0.918 -4.655 S2P    THS 3  
THS S3P    S3P  S 0 1 N N N 19.858 21.065 -2.455 -0.796 0.558  -4.993 S3P    THS 4  
THS "O5'"  O5*  O 0 1 N N N 18.486 18.544 -2.765 0.259  -0.681 -2.402 "O5'"  THS 5  
THS "C5'"  C5*  C 0 1 N N N 17.259 19.235 -2.961 -0.753 0.104  -1.772 "C5'"  THS 6  
THS "C4'"  C4*  C 0 1 N N R 16.433 19.067 -1.733 -1.313 -0.656 -0.568 "C4'"  THS 7  
THS "O4'"  O4*  O 0 1 N N N 16.228 17.696 -1.507 -0.303 -0.815 0.453  "O4'"  THS 8  
THS "C3'"  C3*  C 0 1 N N S 17.065 19.590 -0.438 -2.416 0.173  0.136  "C3'"  THS 9  
THS "O3'"  O3*  O 0 1 N N N 15.928 20.159 0.169  -3.689 -0.045 -0.473 "O3'"  THS 10 
THS "C2'"  C2*  C 0 1 N N N 17.581 18.402 0.340  -2.386 -0.401 1.573  "C2'"  THS 11 
THS "C1'"  C1*  C 0 1 N N R 16.760 17.251 -0.230 -0.994 -1.052 1.690  "C1'"  THS 12 
THS N1     N1   N 0 1 N N N 17.506 15.959 -0.396 -0.253 -0.447 2.799  N1     THS 13 
THS C2     C2   C 0 1 N N N 16.955 14.859 0.307  0.002  0.873  2.788  C2     THS 14 
THS O2     O2   O 0 1 N N N 16.003 14.950 1.103  -0.385 1.550  1.856  O2     THS 15 
THS N3     N3   N 0 1 N N N 17.559 13.644 0.072  0.681  1.455  3.794  N3     THS 16 
THS C4     C4   C 0 1 N N N 18.606 13.404 -0.775 1.114  0.718  4.837  C4     THS 17 
THS O4     O4   O 0 1 N N N 19.029 12.250 -0.898 1.728  1.244  5.748  O4     THS 18 
THS C5     C5   C 0 1 N N N 19.110 14.581 -1.456 0.856  -0.673 4.859  C5     THS 19 
THS C5M    C5M  C 0 1 N N N 20.298 14.379 -2.399 1.332  -1.520 6.011  C5M    THS 20 
THS C6     C6   C 0 1 N N N 18.569 15.807 -1.261 0.172  -1.231 3.837  C6     THS 21 
THS HSP2   2HSP H 0 0 N N N 21.354 17.990 -1.713 2.621  -0.049 -5.636 HSP2   THS 22 
THS HSP3   3HSP H 0 0 N N N 19.950 21.051 -1.509 -1.147 -0.701 -5.304 HSP3   THS 23 
THS "H5'1" 1H5* H 0 0 N N N 17.406 20.304 -3.238 -1.556 0.301  -2.482 "H5'1" THS 24 
THS "H5'2" 2H5* H 0 0 N N N 16.726 18.913 -3.886 -0.324 1.049  -1.437 "H5'2" THS 25 
THS "H4'"  H4*  H 0 1 N N N 15.508 19.655 -1.937 -1.702 -1.627 -0.876 "H4'"  THS 26 
THS "H3'"  H3*  H 0 1 N N N 17.922 20.296 -0.536 -2.165 1.234  0.136  "H3'"  THS 27 
THS "HO3'" *HO3 H 0 0 N N N 16.319 20.483 0.971  -4.342 0.422  0.064  "HO3'" THS 28 
THS "H2'1" 1H2* H 0 0 N N N 18.685 18.256 0.295  -3.169 -1.148 1.701  "H2'1" THS 29 
THS "H2'2" 2H2* H 0 0 N N N 17.529 18.510 1.448  -2.496 0.397  2.306  "H2'2" THS 30 
THS "H1'"  H1*  H 0 1 N N N 15.958 17.010 0.506  -1.100 -2.125 1.856  "H1'"  THS 31 
THS HN3    HN3  H 0 1 N N N 17.192 12.837 0.578  0.856  2.408  3.770  HN3    THS 32 
THS HM51   1HM5 H 0 0 N N N 20.685 15.283 -2.922 1.860  -0.892 6.730  HM51   THS 33 
THS HM52   2HM5 H 0 0 N N N 21.130 13.881 -1.848 0.476  -1.988 6.497  HM52   THS 34 
THS HM53   3HM5 H 0 0 N N N 20.048 13.592 -3.149 2.006  -2.292 5.640  HM53   THS 35 
THS H6     H6   H 0 1 N N N 18.989 16.672 -1.800 -0.036 -2.290 3.838  H6     THS 36 
# 
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 
THS P     O1P    DOUB N N 1  
THS P     S2P    SING N N 2  
THS P     S3P    SING N N 3  
THS P     "O5'"  SING N N 4  
THS S2P   HSP2   SING N N 5  
THS S3P   HSP3   SING N N 6  
THS "O5'" "C5'"  SING N N 7  
THS "C5'" "C4'"  SING N N 8  
THS "C5'" "H5'1" SING N N 9  
THS "C5'" "H5'2" SING N N 10 
THS "C4'" "O4'"  SING N N 11 
THS "C4'" "C3'"  SING N N 12 
THS "C4'" "H4'"  SING N N 13 
THS "O4'" "C1'"  SING N N 14 
THS "C3'" "O3'"  SING N N 15 
THS "C3'" "C2'"  SING N N 16 
THS "C3'" "H3'"  SING N N 17 
THS "O3'" "HO3'" SING N N 18 
THS "C2'" "C1'"  SING N N 19 
THS "C2'" "H2'1" SING N N 20 
THS "C2'" "H2'2" SING N N 21 
THS "C1'" N1     SING N N 22 
THS "C1'" "H1'"  SING N N 23 
THS N1    C2     SING N N 24 
THS N1    C6     SING N N 25 
THS C2    O2     DOUB N N 26 
THS C2    N3     SING N N 27 
THS N3    C4     SING N N 28 
THS N3    HN3    SING N N 29 
THS C4    O4     DOUB N N 30 
THS C4    C5     SING N N 31 
THS C5    C5M    SING N N 32 
THS C5    C6     DOUB N N 33 
THS C5M   HM51   SING N N 34 
THS C5M   HM52   SING N N 35 
THS C5M   HM53   SING N N 36 
THS C6    H6     SING N N 37 
# 
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 
THS SMILES           ACDLabs              10.04 O=P(S)(S)OCC2OC(N1C(=O)NC(=O)C(=C1)C)CC2O                                                                                                                    
THS InChI            InChI                1.02b InChI=1/C10H15N2O6PS2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(18-8)4-17-19(16,20)21/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,20,21)/t6-,7+,8+/m0/s1/f/h11,20-21H 
THS InChIKey         InChI                1.02b KMPXQZWMYQHTNT-AUIIBIFODP                                                                                                                                    
THS SMILES_CANONICAL CACTVS               3.341 CC1=CN([C@H]2C[C@H](O)[C@@H](CO[P](S)(S)=O)O2)C(=O)NC1=O                                                                                                     
THS SMILES           CACTVS               3.341 CC1=CN([CH]2C[CH](O)[CH](CO[P](S)(S)=O)O2)C(=O)NC1=O                                                                                                         
THS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)(S)S)O                                                                                                       
THS SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(S)S)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 
THS "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(dithiophosphono)]thymidine"                                                                    
THS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R,4S,5R)-5-(bis-sulfanylphosphoryloxymethyl)-4-hydroxy-oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione 
# 
