data_4S2
# 
_chem_comp.id                                    4S2 
_chem_comp.name                                  "5-(1,3-benzothiazol-2-yl)-2-(cyclopropylamino)-6-{[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]amino}pyrimidin-4(3H)-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 N5 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-05-17 
_chem_comp.pdbx_modified_date                    2015-08-28 
_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                        429.493 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4S2 
_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        4ZTM 
_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 
4S2 C01 C1  C 0 1 N N N 29.350 7.739  -7.113  -0.361 0.840  0.113  C01 4S2 1  
4S2 N02 N1  N 0 1 N N N 28.697 7.284  -5.992  -1.565 1.416  0.141  N02 4S2 2  
4S2 C03 C2  C 0 1 N N N 28.707 6.043  -5.624  -1.700 2.725  0.105  C03 4S2 3  
4S2 N04 N2  N 0 1 N N N 29.403 5.077  -6.398  -0.624 3.556  0.038  N04 4S2 4  
4S2 C05 C3  C 0 1 N N N 30.106 5.405  -7.557  0.627  3.048  0.006  C05 4S2 5  
4S2 C06 C4  C 0 1 N N N 30.066 6.875  -7.933  0.789  1.644  0.044  C06 4S2 6  
4S2 N07 N3  N 0 1 N N N 29.184 9.125  -7.302  -0.247 -0.530 0.157  N07 4S2 7  
4S2 N08 N4  N 0 1 N N N 27.998 5.647  -4.498  -2.956 3.266  0.135  N08 4S2 8  
4S2 O09 O1  O 0 1 N N N 30.687 4.489  -8.203  1.596  3.786  -0.053 O09 4S2 9  
4S2 C10 C5  C 0 1 Y N N 30.790 7.354  -9.132  2.130  1.040  0.012  C10 4S2 10 
4S2 C11 C6  C 0 1 N N R 28.550 10.246 -6.587  -1.441 -1.360 0.336  C11 4S2 11 
4S2 C12 C7  C 0 1 N N S 28.673 10.180 -5.054  -2.112 -1.657 -1.029 C12 4S2 12 
4S2 C13 C8  C 0 1 N N R 28.363 11.619 -4.568  -2.908 -2.955 -0.784 C13 4S2 13 
4S2 C14 C9  C 0 1 N N R 28.696 12.501 -5.769  -2.239 -3.664 0.407  C14 4S2 14 
4S2 C15 C10 C 0 1 N N N 29.301 11.567 -6.817  -1.058 -2.772 0.843  C15 4S2 15 
4S2 O16 O2  O 0 1 N N N 27.759 9.263  -4.481  -2.991 -0.592 -1.397 O16 4S2 16 
4S2 O17 O3  O 0 1 N N N 26.996 11.877 -4.155  -4.266 -2.643 -0.467 O17 4S2 17 
4S2 C18 C11 C 0 1 N N N 29.503 13.759 -5.414  -1.725 -5.039 -0.024 C18 4S2 18 
4S2 O19 O4  O 0 1 N N N 29.152 14.789 -6.336  -1.211 -5.733 1.115  O19 4S2 19 
4S2 C20 C12 C 0 1 N N N 27.978 4.441  -3.709  -4.128 2.390  0.207  C20 4S2 20 
4S2 C21 C13 C 0 1 N N N 26.692 4.052  -2.993  -5.451 2.935  -0.335 C21 4S2 21 
4S2 C22 C14 C 0 1 N N N 27.838 4.673  -2.216  -5.247 2.784  1.174  C22 4S2 22 
4S2 S23 S1  S 0 1 Y N N 31.906 6.310  -9.972  3.639  1.939  0.082  S23 4S2 23 
4S2 C24 C15 C 0 1 Y N N 32.490 7.669  -10.917 4.555  0.437  -0.013 C24 4S2 24 
4S2 C25 C16 C 0 1 Y N N 31.718 8.821  -10.609 3.652  -0.629 -0.090 C25 4S2 25 
4S2 N26 N5  N 0 1 Y N N 30.782 8.628  -9.589  2.367  -0.230 -0.067 N26 4S2 26 
4S2 C27 C17 C 0 1 Y N N 33.574 7.747  -11.824 5.927  0.199  -0.025 C27 4S2 27 
4S2 C28 C18 C 0 1 Y N N 33.894 9.001  -12.475 6.407  -1.089 -0.113 C28 4S2 28 
4S2 C29 C19 C 0 1 Y N N 33.103 10.138 -12.225 5.522  -2.154 -0.191 C29 4S2 29 
4S2 C30 C20 C 0 1 Y N N 32.027 10.045 -11.280 4.167  -1.940 -0.174 C30 4S2 30 
4S2 H1  H1  H 0 1 N N N 29.388 4.123  -6.100  -0.756 4.516  0.013  H1  4S2 31 
4S2 H3  H3  H 0 1 N N N 27.367 6.347  -4.163  -3.071 4.228  0.110  H3  4S2 32 
4S2 H4  H4  H 0 1 N N N 27.495 10.354 -6.878  -2.145 -0.879 1.015  H4  4S2 33 
4S2 H5  H5  H 0 1 N N N 29.708 9.925  -4.784  -1.356 -1.813 -1.799 H5  4S2 34 
4S2 H6  H6  H 0 1 N N N 29.052 11.865 -3.747  -2.868 -3.590 -1.668 H6  4S2 35 
4S2 H7  H7  H 0 1 N N N 27.736 12.851 -6.177  -2.950 -3.771 1.226  H7  4S2 36 
4S2 H8  H8  H 0 1 N N N 30.382 11.440 -6.655  -0.133 -3.108 0.375  H8  4S2 37 
4S2 H9  H9  H 0 1 N N N 29.125 11.949 -7.834  -0.960 -2.773 1.929  H9  4S2 38 
4S2 H10 H10 H 0 1 N N N 27.869 9.254  -3.537  -3.438 -0.726 -2.243 H10 4S2 39 
4S2 H11 H11 H 0 1 N N N 26.782 11.331 -3.408  -4.737 -2.176 -1.170 H11 4S2 40 
4S2 H12 H12 H 0 1 N N N 30.579 13.544 -5.488  -2.543 -5.612 -0.460 H12 4S2 41 
4S2 H13 H13 H 0 1 N N N 29.262 14.079 -4.389  -0.933 -4.916 -0.763 H13 4S2 42 
4S2 H14 H14 H 0 1 N N N 29.642 15.577 -6.133  -0.867 -6.615 0.915  H14 4S2 43 
4S2 H15 H15 H 0 1 N N N 28.635 3.614  -4.016  -3.930 1.327  0.073  H15 4S2 44 
4S2 H16 H16 H 0 1 N N N 25.770 4.626  -3.167  -5.450 3.946  -0.744 H16 4S2 45 
4S2 H17 H17 H 0 1 N N N 26.441 2.991  -2.850  -6.124 2.231  -0.824 H17 4S2 46 
4S2 H18 H18 H 0 1 N N N 28.417 4.062  -1.508  -5.784 1.980  1.677  H18 4S2 47 
4S2 H19 H19 H 0 1 N N N 27.746 5.697  -1.825  -5.110 3.695  1.757  H19 4S2 48 
4S2 H20 H20 H 0 1 N N N 34.165 6.867  -12.032 6.617  1.028  0.035  H20 4S2 49 
4S2 H21 H21 H 0 1 N N N 34.736 9.063  -13.149 7.472  -1.269 -0.127 H21 4S2 50 
4S2 H22 H22 H 0 1 N N N 33.303 11.068 -12.737 5.904  -3.162 -0.260 H22 4S2 51 
4S2 H23 H23 H 0 1 N N N 31.435 10.923 -11.070 3.491  -2.780 -0.235 H23 4S2 52 
4S2 H2  H2  H 0 1 N N N 30.129 9.440  -7.391  0.625  -0.948 0.070  H2  4S2 53 
# 
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 
4S2 C28 C29 DOUB Y N 1  
4S2 C28 C27 SING Y N 2  
4S2 C29 C30 SING Y N 3  
4S2 C27 C24 DOUB Y N 4  
4S2 C30 C25 DOUB Y N 5  
4S2 C24 C25 SING Y N 6  
4S2 C24 S23 SING Y N 7  
4S2 C25 N26 SING Y N 8  
4S2 S23 C10 SING Y N 9  
4S2 N26 C10 DOUB Y N 10 
4S2 C10 C06 SING N N 11 
4S2 O09 C05 DOUB N N 12 
4S2 C06 C05 SING N N 13 
4S2 C06 C01 DOUB N N 14 
4S2 C05 N04 SING N N 15 
4S2 N07 C01 SING N N 16 
4S2 N07 C11 SING N N 17 
4S2 C01 N02 SING N N 18 
4S2 C15 C11 SING N N 19 
4S2 C15 C14 SING N N 20 
4S2 C11 C12 SING N N 21 
4S2 N04 C03 SING N N 22 
4S2 O19 C18 SING N N 23 
4S2 N02 C03 DOUB N N 24 
4S2 C14 C18 SING N N 25 
4S2 C14 C13 SING N N 26 
4S2 C03 N08 SING N N 27 
4S2 C12 C13 SING N N 28 
4S2 C12 O16 SING N N 29 
4S2 C13 O17 SING N N 30 
4S2 N08 C20 SING N N 31 
4S2 C20 C21 SING N N 32 
4S2 C20 C22 SING N N 33 
4S2 C21 C22 SING N N 34 
4S2 N04 H1  SING N N 35 
4S2 N08 H3  SING N N 36 
4S2 C11 H4  SING N N 37 
4S2 C12 H5  SING N N 38 
4S2 C13 H6  SING N N 39 
4S2 C14 H7  SING N N 40 
4S2 C15 H8  SING N N 41 
4S2 C15 H9  SING N N 42 
4S2 O16 H10 SING N N 43 
4S2 O17 H11 SING N N 44 
4S2 C18 H12 SING N N 45 
4S2 C18 H13 SING N N 46 
4S2 O19 H14 SING N N 47 
4S2 C20 H15 SING N N 48 
4S2 C21 H16 SING N N 49 
4S2 C21 H17 SING N N 50 
4S2 C22 H18 SING N N 51 
4S2 C22 H19 SING N N 52 
4S2 C27 H20 SING N N 53 
4S2 C28 H21 SING N N 54 
4S2 C29 H22 SING N N 55 
4S2 C30 H23 SING N N 56 
4S2 N07 H2  SING N N 57 
# 
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 
4S2 SMILES           ACDLabs              12.01 "C=2(N=C(NC1CC1)NC(C=2c3sc4c(n3)cccc4)=O)NC5C(C(O)C(CO)C5)O"                                                                                                                                     
4S2 InChI            InChI                1.03  "InChI=1S/C20H23N5O4S/c26-8-9-7-12(16(28)15(9)27)22-17-14(18(29)25-20(24-17)21-10-5-6-10)19-23-11-3-1-2-4-13(11)30-19/h1-4,9-10,12,15-16,26-28H,5-8H2,(H3,21,22,24,25,29)/t9-,12-,15-,16+/m1/s1" 
4S2 InChIKey         InChI                1.03  FXWUDZUPMZEZQL-NRXFTUCASA-N                                                                                                                                                                      
4S2 SMILES_CANONICAL CACTVS               3.385 "OC[C@H]1C[C@@H](NC2=C(C(=O)NC(=N2)NC3CC3)c4sc5ccccc5n4)[C@H](O)[C@@H]1O"                                                                                                                        
4S2 SMILES           CACTVS               3.385 "OC[CH]1C[CH](NC2=C(C(=O)NC(=N2)NC3CC3)c4sc5ccccc5n4)[CH](O)[CH]1O"                                                                                                                              
4S2 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)nc(s2)C3=C(N=C(NC3=O)NC4CC4)N[C@@H]5C[C@@H]([C@H]([C@H]5O)O)CO"                                                                                                                      
4S2 SMILES           "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)nc(s2)C3=C(N=C(NC3=O)NC4CC4)NC5CC(C(C5O)O)CO"                                                                                                                                        
# 
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 
4S2 "SYSTEMATIC NAME" ACDLabs              12.01 "5-(1,3-benzothiazol-2-yl)-2-(cyclopropylamino)-6-{[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]amino}pyrimidin-4(3H)-one"     
4S2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "5-(1,3-benzothiazol-2-yl)-2-(cyclopropylamino)-4-[[(1R,2S,3R,4R)-4-(hydroxymethyl)-2,3-bis(oxidanyl)cyclopentyl]amino]-1H-pyrimidin-6-one" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
4S2 "Create component" 2015-05-17 RCSB 
4S2 "Initial release"  2015-09-02 RCSB 
# 
