data_4SC
# 
_chem_comp.id                                    4SC 
_chem_comp.name                                  
;4'-THIO-2'-DEOXYCYTIDINE-5'-MONOPHOSPHATE GROUP
;
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H16 N3 O5 P S" 
_chem_comp.mon_nstd_parent_comp_id               DC 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        321.290 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     4SC 
_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        6MHT 
_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 
4SC P      P    P 1  1 N N N -19.306 45.420 87.739 3.891  -1.444 -0.041 P      4SC 1  
4SC OP1    O1P  O -1 1 N N N -19.710 45.872 86.370 5.086  -1.034 -0.974 OP1    4SC 2  
4SC OP2    O2P  O 0  1 N N N -17.881 45.200 87.986 3.992  -2.741 0.837  OP2    4SC 3  
4SC "O5'"  O5*  O 0  1 N N N -20.057 43.953 87.967 2.473  -0.473 0.018  "O5'"  4SC 4  
4SC "C5'"  C5*  C 0  1 N N N -19.584 42.997 88.988 2.805  0.780  -0.584 "C5'"  4SC 5  
4SC "C4'"  C4*  C 0  1 N N R -20.227 41.613 88.748 1.580  1.696  -0.563 "C4'"  4SC 6  
4SC "S4'"  S4*  S 0  1 N N N -19.615 41.206 87.075 0.122  0.896  -1.376 "S4'"  4SC 7  
4SC "C3'"  C3*  C 0  1 N N S -19.735 40.545 89.724 1.019  1.860  0.877  "C3'"  4SC 8  
4SC "O3'"  O3*  O 0  1 N N N -20.543 40.545 91.028 1.768  2.865  1.563  "O3'"  4SC 9  
4SC "C2'"  C2*  C 0  1 N N N -20.000 39.193 88.937 -0.452 2.270  0.829  "C2'"  4SC 10 
4SC "C1'"  C1*  C 0  1 N N R -19.633 39.423 87.466 -1.203 1.722  -0.401 "C1'"  4SC 11 
4SC N1     N1   N 0  1 N N N -18.565 38.656 86.776 -2.225 0.754  0.007  N1     4SC 12 
4SC C2     C2   C 0  1 N N N -18.515 38.779 85.376 -1.888 -0.281 0.796  C2     4SC 13 
4SC O2     O2   O 0  1 N N N -19.412 39.394 84.818 -0.756 -0.350 1.236  O2     4SC 14 
4SC N3     N3   N 0  1 N N N -17.482 38.177 84.665 -2.775 -1.238 1.110  N3     4SC 15 
4SC C4     C4   C 0  1 N N N -16.486 37.441 85.286 -3.902 -1.368 0.459  C4     4SC 16 
4SC N4     N4   N 0  1 N N N -15.388 36.985 84.562 -4.785 -2.321 0.830  N4     4SC 17 
4SC C5     C5   C 0  1 N N R -16.569 37.288 86.760 -4.222 -0.460 -0.701 C5     4SC 18 
4SC C6     C6   C 0  1 N N N -17.601 37.907 87.431 -3.608 0.919  -0.449 C6     4SC 19 
4SC C5M    C5M  C 0  1 N N N -16.750 35.700 86.690 -3.641 -1.050 -1.988 C5M    4SC 20 
4SC "H5'"  1H5* H 0  1 N N N -18.471 42.941 89.026 3.119  0.616  -1.615 "H5'"  4SC 21 
4SC "H5''" 2H5* H 0  0 N N N -19.762 43.368 90.024 3.617  1.247  -0.027 "H5''" 4SC 22 
4SC "H4'"  H4*  H 0  1 N N N -21.334 41.639 88.873 1.803  2.663  -1.015 "H4'"  4SC 23 
4SC "H3'"  H3*  H 0  1 N N N -18.672 40.705 90.021 1.112  0.913  1.410  "H3'"  4SC 24 
4SC "HO3'" *HO3 H 0  0 N Y N -20.237 39.881 91.634 1.414  2.912  2.462  "HO3'" 4SC 25 
4SC "H2'"  1H2* H 0  1 N N N -19.466 38.321 89.383 -0.511 3.358  0.817  "H2'"  4SC 26 
4SC "H2''" 2H2* H 0  0 N N N -21.040 38.813 89.068 -0.946 1.906  1.730  "H2''" 4SC 27 
4SC "H1'"  H1*  H 0  1 N N N -20.480 38.885 86.980 -1.651 2.535  -0.972 "H1'"  4SC 28 
4SC HN41   1HN4 H 0  0 N N N -14.654 36.443 85.019 -4.582 -2.906 1.577  HN41   4SC 29 
4SC HN42   2HN4 H 0  0 N N N -14.954 37.785 84.101 -5.622 -2.420 0.350  HN42   4SC 30 
4SC H5     H5   H 0  1 N N N -15.729 37.746 87.332 -5.304 -0.364 -0.801 H5     4SC 31 
4SC H61    1H6  H 0  1 N N N -17.151 38.551 88.222 -3.621 1.498  -1.372 H61    4SC 32 
4SC H62    2H6  H 0  1 N N N -18.127 37.129 88.032 -4.183 1.440  0.317  H62    4SC 33 
4SC H71    1H5M H 0  1 N N N -16.812 35.585 87.797 -2.560 -1.146 -1.888 H71    4SC 34 
4SC H72    2H5M H 0  1 N N N -17.577 35.287 86.066 -4.078 -2.033 -2.166 H72    4SC 35 
4SC H73    3H5M H 0  1 N N N -15.987 35.103 86.136 -3.872 -0.393 -2.826 H73    4SC 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 
4SC P     OP1    SING N N 1  
4SC P     OP2    DOUB N N 2  
4SC P     "O5'"  SING N N 3  
4SC "O5'" "C5'"  SING N N 4  
4SC "C5'" "C4'"  SING N N 5  
4SC "C5'" "H5'"  SING N N 6  
4SC "C5'" "H5''" SING N N 7  
4SC "C4'" "S4'"  SING N N 8  
4SC "C4'" "C3'"  SING N N 9  
4SC "C4'" "H4'"  SING N N 10 
4SC "S4'" "C1'"  SING N N 11 
4SC "C3'" "O3'"  SING N N 12 
4SC "C3'" "C2'"  SING N N 13 
4SC "C3'" "H3'"  SING N N 14 
4SC "O3'" "HO3'" SING N N 15 
4SC "C2'" "C1'"  SING N N 16 
4SC "C2'" "H2'"  SING N N 17 
4SC "C2'" "H2''" SING N N 18 
4SC "C1'" N1     SING N N 19 
4SC "C1'" "H1'"  SING N N 20 
4SC N1    C2     SING N N 21 
4SC N1    C6     SING N N 22 
4SC C2    O2     DOUB N N 23 
4SC C2    N3     SING N N 24 
4SC N3    C4     DOUB N N 25 
4SC C4    N4     SING N N 26 
4SC C4    C5     SING N N 27 
4SC N4    HN41   SING N N 28 
4SC N4    HN42   SING N N 29 
4SC C5    C6     SING N N 30 
4SC C5    C5M    SING N N 31 
4SC C5    H5     SING N N 32 
4SC C6    H61    SING N N 33 
4SC C6    H62    SING N N 34 
4SC C5M   H71    SING N N 35 
4SC C5M   H72    SING N N 36 
4SC C5M   H73    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 
4SC SMILES           ACDLabs              10.04 "[O-][PH2+](=O)OCC2SC(N1C(=O)N=C(N)C(C1)C)CC2O"                                                                                            
4SC InChI            InChI                1.02b "InChI=1/C10H16N3O5PS/c1-5-3-13(10(15)12-9(5)11)8-2-6(14)7(20-8)4-18-19(16)17/h5-8,14H,2-4H2,1H3,(H2,11,12,15)/t5-,6+,7-,8-/m1/s1/f/h11H2" 
4SC InChIKey         InChI                1.02b KMWLOPTUNJILSZ-PHXQHRBLDQ                                                                                                                  
4SC SMILES_CANONICAL CACTVS               3.341 "C[C@@H]1CN([C@H]2C[C@H](O)[C@@H](CO[P+]([O-])=O)S2)C(=O)N=C1N"                                                                            
4SC SMILES           CACTVS               3.341 "C[CH]1CN([CH]2C[CH](O)[CH](CO[P+]([O-])=O)S2)C(=O)N=C1N"                                                                                  
4SC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1CN(C(=O)N=C1N)[C@H]2C[C@@H]([C@H](S2)CO[P+](=O)[O-])O"                                                                            
4SC SMILES           "OpenEye OEToolkits" 1.5.0 "CC1CN(C(=O)N=C1N)C2CC(C(S2)CO[P+](=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 
4SC "SYSTEMATIC NAME" ACDLabs              10.04 "2'-deoxy-5-methyl-5'-O-[oxido(oxo)phosphonio]-4'-thiocytidine"                                                              
4SC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-[(5R)-4-amino-5-methyl-2-oxo-5,6-dihydropyrimidin-1-yl]-3-hydroxy-thiolan-2-yl]methoxy-oxido-oxo-phosphanium" 
# 
