data_NAT
# 
_chem_comp.id                                    NAT 
_chem_comp.name                                  "ETHYL 4-(3-HYDROXYPHENYL)-6-METHYL-2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H16 N2 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         MONASTROL 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-07-21 
_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                        292.353 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     NAT 
_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        1Q0B 
_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 
NAT C1   C1   C 0 1 Y N N 18.944 14.071 112.221 -0.027 -1.936 -0.875 C1   NAT 1  
NAT C2   C2   C 0 1 Y N N 17.944 13.443 111.365 0.397  -1.135 0.170  C2   NAT 2  
NAT C3   C3   C 0 1 Y N N 16.900 12.619 111.914 1.707  -1.199 0.604  C3   NAT 3  
NAT C4   C4   C 0 1 Y N N 16.870 12.448 113.360 2.595  -2.075 -0.003 C4   NAT 4  
NAT C5   C5   C 0 1 Y N N 17.841 13.103 114.210 2.168  -2.877 -1.051 C5   NAT 5  
NAT C6   C6   C 0 1 Y N N 18.913 13.916 113.664 0.858  -2.806 -1.485 C6   NAT 6  
NAT C7   C7   C 0 1 N N R 18.023 13.606 109.893 -0.570 -0.188 0.833  C7   NAT 7  
NAT N8   N8   N 0 1 N N N 19.321 13.198 109.344 -1.867 -0.874 0.954  N8   NAT 8  
NAT C9   C9   C 0 1 N N N 20.214 14.045 108.786 -2.947 -0.312 0.377  C9   NAT 9  
NAT N10  N10  N 0 1 N N N 19.883 15.340 108.645 -2.875 0.845  -0.293 N10  NAT 10 
NAT C11  C11  C 0 1 N N N 18.539 15.829 108.947 -1.722 1.557  -0.455 C11  NAT 11 
NAT C12  C12  C 0 1 N N N 17.604 14.993 109.455 -0.555 1.120  0.067  C12  NAT 12 
NAT O13  O13  O 0 1 N N N 15.941 11.646 113.916 3.883  -2.143 0.425  O13  NAT 13 
NAT C14  C14  C 0 1 N N N 16.171 15.386 109.676 0.641  1.856  -0.100 C14  NAT 14 
NAT O15  O15  O 0 1 N N N 15.866 16.700 109.588 1.763  1.476  0.547  O15  NAT 15 
NAT C16  C16  C 0 1 N N N 14.532 17.333 109.727 2.786  2.403  0.179  C16  NAT 16 
NAT C17  C17  C 0 1 N N N 14.610 18.847 109.433 4.092  2.027  0.882  C17  NAT 17 
NAT C18  C18  C 0 1 N N N 18.356 17.298 108.628 -1.751 2.850  -1.228 C18  NAT 18 
NAT O19  O19  O 0 1 N N N 15.349 14.546 109.933 0.659  2.832  -0.827 O19  NAT 19 
NAT S20  S20  S 0 1 N N N 21.695 13.517 108.229 -4.460 -1.103 0.503  S20  NAT 20 
NAT H1   H1   H 0 1 N N N 19.726 14.665 111.771 -1.050 -1.881 -1.215 H1   NAT 21 
NAT H3   H3   H 0 1 N N N 16.167 12.145 111.278 2.037  -0.573 1.419  H3   NAT 22 
NAT H5   H5   H 0 1 N N N 17.766 12.984 115.281 2.858  -3.558 -1.527 H5   NAT 23 
NAT H6   H6   H 0 1 N N N 19.651 14.382 114.300 0.525  -3.430 -2.300 H6   NAT 24 
NAT H7   H7   H 0 1 N N N 17.291 12.909 109.459 -0.202 0.015  1.838  H7   NAT 25 
NAT HN8  HN8  H 0 1 N N N 19.561 12.228 109.386 -1.942 -1.713 1.435  HN8  NAT 26 
NAT HN10 HN10 H 0 0 N N N 20.575 15.987 108.325 -3.689 1.198  -0.686 HN10 NAT 27 
NAT HO13 HO13 H 0 0 N N N 16.308 10.779 114.047 4.384  -1.496 -0.090 HO13 NAT 28 
NAT H161 1H16 H 0 0 N N N 13.837 16.865 109.015 2.489  3.409  0.478  H161 NAT 29 
NAT H162 2H16 H 0 0 N N N 14.180 17.191 110.759 2.933  2.374  -0.900 H162 NAT 30 
NAT H171 1H17 H 0 0 N N N 13.593 19.260 109.363 3.945  2.057  1.962  H171 NAT 31 
NAT H172 2H17 H 0 0 N N N 15.155 19.350 110.245 4.389  1.022  0.583  H172 NAT 32 
NAT H173 3H17 H 0 0 N N N 15.137 19.009 108.481 4.872  2.735  0.602  H173 NAT 33 
NAT H181 1H18 H 0 0 N N N 17.283 17.526 108.551 -1.464 2.661  -2.262 H181 NAT 34 
NAT H182 2H18 H 0 0 N N N 18.803 17.905 109.429 -2.757 3.267  -1.200 H182 NAT 35 
NAT H183 3H18 H 0 0 N N N 18.850 17.530 107.673 -1.052 3.556  -0.780 H183 NAT 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 
NAT C1  C2   DOUB Y N 1  
NAT C1  C6   SING Y N 2  
NAT C1  H1   SING N N 3  
NAT C2  C3   SING Y N 4  
NAT C2  C7   SING N N 5  
NAT C3  C4   DOUB Y N 6  
NAT C3  H3   SING N N 7  
NAT C4  C5   SING Y N 8  
NAT C4  O13  SING N N 9  
NAT C5  C6   DOUB Y N 10 
NAT C5  H5   SING N N 11 
NAT C6  H6   SING N N 12 
NAT C7  N8   SING N N 13 
NAT C7  C12  SING N N 14 
NAT C7  H7   SING N N 15 
NAT N8  C9   SING N N 16 
NAT N8  HN8  SING N N 17 
NAT C9  N10  SING N N 18 
NAT C9  S20  DOUB N N 19 
NAT N10 C11  SING N N 20 
NAT N10 HN10 SING N N 21 
NAT C11 C12  DOUB N N 22 
NAT C11 C18  SING N N 23 
NAT C12 C14  SING N N 24 
NAT O13 HO13 SING N N 25 
NAT C14 O15  SING N N 26 
NAT C14 O19  DOUB N N 27 
NAT O15 C16  SING N N 28 
NAT C16 C17  SING N N 29 
NAT C16 H161 SING N N 30 
NAT C16 H162 SING N N 31 
NAT C17 H171 SING N N 32 
NAT C17 H172 SING N N 33 
NAT C17 H173 SING N N 34 
NAT C18 H181 SING N N 35 
NAT C18 H182 SING N N 36 
NAT C18 H183 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 
NAT SMILES           ACDLabs              10.04 S=C2NC(c1cc(O)ccc1)C(=C(N2)C)C(=O)OCC                                                                                                 
NAT InChI            InChI                1.02b InChI=1/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)/t12-/m0/s1/f/h15-16H 
NAT InChIKey         InChI                1.02b LOBCDGHHHHGHFA-VYSIWCKPDR                                                                                                             
NAT SMILES_CANONICAL CACTVS               3.341 CCOC(=O)C1=C(C)NC(=S)N[C@H]1c2cccc(O)c2                                                                                               
NAT SMILES           CACTVS               3.341 CCOC(=O)C1=C(C)NC(=S)N[CH]1c2cccc(O)c2                                                                                                
NAT SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCOC(=O)C1=C(NC(=S)N[C@H]1c2cccc(c2)O)C                                                                                               
NAT SMILES           "OpenEye OEToolkits" 1.5.0 CCOC(=O)C1=C(NC(=S)NC1c2cccc(c2)O)C                                                                                                   
# 
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 
NAT "SYSTEMATIC NAME" ACDLabs              10.04 "ethyl (4S)-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate"     
NAT "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "ethyl (4S)-4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate" 
# 
