data_TLC
# 
_chem_comp.id                                    TLC 
_chem_comp.name                                  "2-O,3-ETHDIYL-ARABINOFURANOSYL-THYMINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C12 H17 N2 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               DT 
_chem_comp.pdbx_synonyms                         "[3.3.0]BICYCLO-ARABINO-THYMINE-5'-PHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-02-25 
_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                        364.245 
_chem_comp.one_letter_code                       T 
_chem_comp.three_letter_code                     TLC 
_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        1EI4 
_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 
TLC P      P    P 0 1 N N N 20.230 -0.828 24.389 1.173  -0.144 -4.250 P      TLC 1  
TLC OP1    O1P  O 0 1 N N N 21.056 0.212  23.751 1.758  1.149  -3.833 OP1    TLC 2  
TLC OP2    O2P  O 0 1 N N N 20.847 -2.087 24.828 2.315  -1.056 -4.926 OP2    TLC 3  
TLC OP3    O3P  O 0 1 N Y N 19.088 -0.980 23.270 -0.004 0.117  -5.316 OP3    TLC 4  
TLC "O5'"  O5*  O 0 1 N N N 19.490 -0.218 25.658 0.573  -0.902 -2.963 "O5'"  TLC 5  
TLC "C5'"  C5*  C 0 1 N N N 19.144 1.167  25.706 -0.429 -0.047 -2.410 "C5'"  TLC 6  
TLC "C4'"  C4*  C 0 1 N N R 18.267 1.446  26.898 -1.043 -0.711 -1.177 "C4'"  TLC 7  
TLC "O4'"  O4*  O 0 1 N N N 17.036 0.694  26.832 -0.065 -0.805 -0.119 "O4'"  TLC 8  
TLC "C1'"  C1*  C 0 1 N N R 16.436 0.843  28.084 -0.832 -0.957 1.094  "C1'"  TLC 9  
TLC N1     N1   N 0 1 N N N 15.338 -0.126 28.188 -0.021 -0.596 2.260  N1     TLC 10 
TLC C6     C6   C 0 1 N N N 15.518 -1.462 27.870 1.036  0.259  2.110  C6     TLC 11 
TLC C2     C2   C 0 1 N N N 14.107 0.365  28.581 -0.322 -1.109 3.466  C2     TLC 12 
TLC O2     O2   O 0 1 N N N 13.941 1.527  28.882 -1.266 -1.868 3.576  O2     TLC 13 
TLC N3     N3   N 0 1 N N N 13.086 -0.561 28.597 0.406  -0.795 4.553  N3     TLC 14 
TLC C4     C4   C 0 1 N N N 13.190 -1.906 28.260 1.458  0.040  4.447  C4     TLC 15 
TLC O4     O4   O 0 1 N N N 12.194 -2.620 28.281 2.118  0.325  5.430  O4     TLC 16 
TLC C5     C5   C 0 1 N N N 14.525 -2.357 27.881 1.783  0.591  3.184  C5     TLC 17 
TLC C5M    C5M  C 0 1 N N N 14.730 -3.800 27.523 2.952  1.532  3.039  C5M    TLC 18 
TLC "C2'"  C2*  C 0 1 N N S 17.569 0.721  29.110 -2.017 0.022  0.939  "C2'"  TLC 19 
TLC O2L    O2L  O 0 1 N N N 17.885 -0.670 29.403 -1.601 1.331  1.420  O2L    TLC 20 
TLC C3L    C3L  C 0 1 N N N 19.903 0.145  28.507 -1.859 1.649  -0.893 C3L    TLC 21 
TLC C2L    C2L  C 0 1 N N N 18.997 -1.020 28.530 -2.098 2.311  0.486  C2L    TLC 22 
TLC "C3'"  C3*  C 0 1 N N R 18.791 1.255  28.325 -2.175 0.164  -0.601 "C3'"  TLC 23 
TLC "O3'"  O3*  O 0 1 N N N 19.312 2.548  28.714 -3.468 -0.227 -1.065 "O3'"  TLC 24 
TLC HOP2   2HOP H 0 0 N N N 20.314 -2.757 25.239 2.647  -0.567 -5.691 HOP2   TLC 25 
TLC HOP3   3HOP H 0 0 N N N 18.555 -1.650 23.681 -0.357 -0.748 -5.561 HOP3   TLC 26 
TLC "H5'"  1H5* H 0 1 N N N 20.046 1.821  25.691 -1.207 0.128  -3.154 "H5'"  TLC 27 
TLC "H5''" 2H5* H 0 0 N N N 18.674 1.511  24.755 0.020  0.903  -2.125 "H5''" TLC 28 
TLC "H4'"  H4*  H 0 1 N N N 18.171 2.549  26.772 -1.423 -1.701 -1.430 "H4'"  TLC 29 
TLC "H1'"  H1*  H 0 1 N N N 15.946 1.828  28.266 -1.196 -1.981 1.188  "H1'"  TLC 30 
TLC H6     H6   H 0 1 N N N 16.516 -1.837 27.589 1.271  0.666  1.138  H6     TLC 31 
TLC HN3    HN3  H 0 1 N N N 12.169 -0.219 28.884 0.175  -1.174 5.416  HN3    TLC 32 
TLC H71    1H5M H 0 1 N N N 13.901 -4.546 27.532 3.425  1.675  4.010  H71    TLC 33 
TLC H72    2H5M H 0 1 N N N 15.198 -3.831 26.511 3.675  1.108  2.342  H72    TLC 34 
TLC H73    3H5M H 0 1 N N N 15.544 -4.194 28.174 2.601  2.492  2.661  H73    TLC 35 
TLC "H2'"  H2*  H 0 1 N N N 17.307 1.239  30.062 -2.925 -0.325 1.432  "H2'"  TLC 36 
TLC H3L1   1H3L H 0 0 N N N 20.598 0.262  29.370 -0.823 1.771  -1.208 H3L1   TLC 37 
TLC H3L2   2H3L H 0 0 N N N 20.729 0.128  27.758 -2.544 2.051  -1.641 H3L2   TLC 38 
TLC H2L1   1H2L H 0 0 N N N 19.506 -1.967 28.824 -1.534 3.241  0.568  H2L1   TLC 39 
TLC H2L2   2H2L H 0 0 N N N 18.672 -1.345 27.513 -3.161 2.491  0.647  H2L2   TLC 40 
TLC "HO3'" H3T  H 0 0 N Y N 19.636 2.429  29.598 -3.462 -0.126 -2.027 "HO3'" TLC 41 
# 
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 
TLC P     OP1    DOUB N N 1  
TLC P     OP2    SING N N 2  
TLC P     OP3    SING N N 3  
TLC P     "O5'"  SING N N 4  
TLC OP2   HOP2   SING N N 5  
TLC OP3   HOP3   SING N N 6  
TLC "O5'" "C5'"  SING N N 7  
TLC "C5'" "C4'"  SING N N 8  
TLC "C5'" "H5'"  SING N N 9  
TLC "C5'" "H5''" SING N N 10 
TLC "C4'" "O4'"  SING N N 11 
TLC "C4'" "C3'"  SING N N 12 
TLC "C4'" "H4'"  SING N N 13 
TLC "O4'" "C1'"  SING N N 14 
TLC "C1'" N1     SING N N 15 
TLC "C1'" "C2'"  SING N N 16 
TLC "C1'" "H1'"  SING N N 17 
TLC N1    C6     SING N N 18 
TLC N1    C2     SING N N 19 
TLC C6    C5     DOUB N N 20 
TLC C6    H6     SING N N 21 
TLC C2    O2     DOUB N N 22 
TLC C2    N3     SING N N 23 
TLC N3    C4     SING N N 24 
TLC N3    HN3    SING N N 25 
TLC C4    O4     DOUB N N 26 
TLC C4    C5     SING N N 27 
TLC C5    C5M    SING N N 28 
TLC C5M   H71    SING N N 29 
TLC C5M   H72    SING N N 30 
TLC C5M   H73    SING N N 31 
TLC "C2'" O2L    SING N N 32 
TLC "C2'" "C3'"  SING N N 33 
TLC "C2'" "H2'"  SING N N 34 
TLC O2L   C2L    SING N N 35 
TLC C3L   C2L    SING N N 36 
TLC C3L   "C3'"  SING N N 37 
TLC C3L   H3L1   SING N N 38 
TLC C3L   H3L2   SING N N 39 
TLC C2L   H2L1   SING N N 40 
TLC C2L   H2L2   SING N N 41 
TLC "C3'" "O3'"  SING N N 42 
TLC "O3'" "HO3'" SING N N 43 
# 
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 
TLC SMILES           ACDLabs              10.04 "O=C1C(=CN(C(=O)N1)C3OC(C2(O)CCOC23)COP(=O)(O)O)C"                                                                                                                                 
TLC InChI            InChI                1.02b "InChI=1/C12H17N2O9P/c1-6-4-14(11(16)13-9(6)15)10-8-12(17,2-3-21-8)7(23-10)5-22-24(18,19)20/h4,7-8,10,17H,2-3,5H2,1H3,(H,13,15,16)(H2,18,19,20)/t7-,8-,10-,12-/m1/s1/f/h13,18-19H" 
TLC InChIKey         InChI                1.02b GYCSZLSGLYHOGR-MAIFTAKPDW                                                                                                                                                          
TLC SMILES_CANONICAL CACTVS               3.341 "CC1=CN([C@@H]2O[C@H](CO[P](O)(O)=O)[C@]3(O)CCO[C@H]23)C(=O)NC1=O"                                                                                                                 
TLC SMILES           CACTVS               3.341 "CC1=CN([CH]2O[CH](CO[P](O)(O)=O)[C]3(O)CCO[CH]23)C(=O)NC1=O"                                                                                                                      
TLC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]3[C@@](CCO3)([C@H](O2)COP(=O)(O)O)O"                                                                                                                
TLC SMILES           "OpenEye OEToolkits" 1.5.0 "CC1=CN(C(=O)NC1=O)C2C3C(CCO3)(C(O2)COP(=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 
TLC "SYSTEMATIC NAME" ACDLabs              10.04 "[(3aR,4R,6R,6aS)-3a-hydroxy-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydrofuro[3,4-b]furan-4-yl]methyl dihydrogen phosphate" 
TLC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3aR,4R,6R,6aS)-3a-hydroxy-6-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-3,4,6,6a-tetrahydro-2H-furo[4,3-b]furan-4-yl]methyl dihydrogen phosphate" 
# 
