data_MSD
# 
_chem_comp.id                                    MSD 
_chem_comp.name                                  1-[2-(3-ACETYL-2-HYDROXY-6-METHOXY-PHENYL)-CYCLOPROPYL]-3-(5-CYANO-PYRIDIN-2-YL)-THIOUREA 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H18 N4 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-05-22 
_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                        382.436 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MSD 
_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        1IKY 
_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 
MSD C2   C2   C 0 1 Y N N -6.745  144.932 173.087 0.372  0.388  -5.783 C2   MSD 1  
MSD C3   C3   C 0 1 Y N N -8.038  144.423 173.434 -0.681 -0.193 -5.076 C3   MSD 2  
MSD N4   N4   N 0 1 Y N N -8.691  143.587 172.534 -0.757 -0.068 -3.767 N4   MSD 3  
MSD C5   C5   C 0 1 Y N N -8.154  143.204 171.290 0.146  0.615  -3.080 C5   MSD 4  
MSD C6   C6   C 0 1 Y N N -6.863  143.682 170.902 1.224  1.221  -3.720 C6   MSD 5  
MSD C7   C7   C 0 1 Y N N -6.161  144.549 171.806 1.346  1.112  -5.079 C7   MSD 6  
MSD N8   N8   N 0 1 N N N -8.922  142.344 170.438 0.018  0.724  -1.700 N8   MSD 7  
MSD C9   C9   C 0 1 N N N -10.242 142.031 170.576 -0.932 0.021  -1.054 C9   MSD 8  
MSD S10  S10  S 0 1 N N N -10.804 141.236 169.725 -1.893 -1.106 -1.910 S10  MSD 9  
MSD N11  N11  N 0 1 N N N -10.912 142.595 171.640 -1.126 0.207  0.266  N11  MSD 10 
MSD C12  C12  C 0 1 N N R -12.298 142.322 171.873 -2.160 -0.556 0.969  C12  MSD 11 
MSD C13  C13  C 0 1 N N N -13.066 143.356 172.701 -2.969 0.173  2.044  C13  MSD 12 
MSD C14  C14  C 0 1 N N R -13.023 141.817 173.067 -1.925 -0.869 2.448  C14  MSD 13 
MSD C15  C15  C 0 1 Y N N -12.226 141.441 174.357 -0.647 -0.370 3.071  C15  MSD 14 
MSD C16  C16  C 0 1 Y N N -12.406 140.102 174.828 -0.692 0.415  4.213  C16  MSD 15 
MSD C18  C18  C 0 1 Y N N -11.719 139.655 176.028 0.484  0.880  4.794  C18  MSD 16 
MSD C19  C19  C 0 1 Y N N -10.862 140.531 176.757 1.694  0.572  4.244  C19  MSD 17 
MSD C20  C20  C 0 1 Y N N -10.643 141.886 176.321 1.759  -0.215 3.086  C20  MSD 18 
MSD C21  C21  C 0 1 Y N N -11.327 142.357 175.108 0.572  -0.686 2.497  C21  MSD 19 
MSD O22  O22  O 0 1 N N N -11.143 143.650 174.660 0.622  -1.449 1.378  O22  MSD 20 
MSD C23  C23  C 0 1 N N N -9.710  142.804 177.129 3.057  -0.547 2.493  C23  MSD 21 
MSD O24  O24  O 0 1 N N N -9.534  143.954 176.734 3.109  -1.229 1.492  O24  MSD 22 
MSD C25  C25  C 0 1 N N N -8.992  142.354 178.397 4.327  -0.041 3.128  C25  MSD 23 
MSD O41  O41  O 0 1 N N N -13.224 139.269 174.147 -1.889 0.727  4.771  O41  MSD 24 
MSD C42  C42  C 0 1 N N N -5.920  145.859 173.961 0.458  0.247  -7.205 C42  MSD 25 
MSD N43  N43  N 0 1 N N N -5.411  146.642 174.689 0.526  0.135  -8.334 N43  MSD 26 
MSD C44  C44  C 0 1 N N N -12.998 138.049 173.942 -1.612 1.530  5.920  C44  MSD 27 
MSD HC3  HC3  H 0 1 N N N -8.528  144.673 174.389 -1.437 -0.752 -5.606 HC3  MSD 28 
MSD HC6  HC6  H 0 1 N N N -6.421  143.390 169.934 1.957  1.772  -3.149 HC6  MSD 29 
MSD HC7  HC7  H 0 1 N N N -5.165  144.923 171.514 2.174  1.574  -5.598 HC7  MSD 30 
MSD HN8  HN8  H 0 1 N N N -8.421  141.456 170.404 0.614  1.305  -1.203 HN8  MSD 31 
MSD H11N NH11 H 0 0 N N N -10.382 143.213 172.254 -0.582 0.846  0.751  H11N MSD 32 
MSD H12C CH12 H 0 0 N N N -12.279 141.868 170.854 -2.679 -1.306 0.371  H12C MSD 33 
MSD H131 1H13 H 0 0 N N N -12.836 144.319 173.212 -4.020 -0.097 2.154  H131 MSD 34 
MSD H132 2H13 H 0 0 N N N -13.851 144.125 172.514 -2.732 1.220  2.229  H132 MSD 35 
MSD H14C CH14 H 0 0 N N N -13.763 140.999 173.226 -2.288 -1.826 2.823  H14C MSD 36 
MSD H18C CH18 H 0 0 N N N -11.851 138.623 176.395 0.439  1.488  5.686  H18C MSD 37 
MSD H19C CH19 H 0 0 N N N -10.363 140.156 177.667 2.603  0.937  4.700  H19C MSD 38 
MSD H22O OH22 H 0 0 N N N -10.568 144.235 175.139 0.742  -2.364 1.668  H22O MSD 39 
MSD H251 1H25 H 0 0 N N N -8.315  143.019 178.982 5.184  -0.387 2.551  H251 MSD 40 
MSD H252 2H25 H 0 0 N N N -9.767  141.966 179.098 4.315  1.048  3.144  H252 MSD 41 
MSD H253 3H25 H 0 0 N N N -8.416  141.433 178.144 4.399  -0.419 4.148  H253 MSD 42 
MSD H441 1H44 H 0 0 N N N -13.672 137.361 173.380 -2.549 1.807  6.404  H441 MSD 43 
MSD H442 2H44 H 0 0 N N N -11.996 137.984 173.456 -0.996 0.963  6.619  H442 MSD 44 
MSD H443 3H44 H 0 0 N N N -12.821 137.582 174.939 -1.080 2.431  5.615  H443 MSD 45 
# 
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 
MSD C2  C3   DOUB Y N 1  
MSD C2  C7   SING Y N 2  
MSD C2  C42  SING N N 3  
MSD C3  N4   SING Y N 4  
MSD C3  HC3  SING N N 5  
MSD N4  C5   DOUB Y N 6  
MSD C5  C6   SING Y N 7  
MSD C5  N8   SING N N 8  
MSD C6  C7   DOUB Y N 9  
MSD C6  HC6  SING N N 10 
MSD C7  HC7  SING N N 11 
MSD N8  C9   SING N N 12 
MSD N8  HN8  SING N N 13 
MSD C9  S10  DOUB N N 14 
MSD C9  N11  SING N N 15 
MSD N11 C12  SING N N 16 
MSD N11 H11N SING N N 17 
MSD C12 C13  SING N N 18 
MSD C12 C14  SING N N 19 
MSD C12 H12C SING N N 20 
MSD C13 C14  SING N N 21 
MSD C13 H131 SING N N 22 
MSD C13 H132 SING N N 23 
MSD C14 C15  SING N N 24 
MSD C14 H14C SING N N 25 
MSD C15 C16  DOUB Y N 26 
MSD C15 C21  SING Y N 27 
MSD C16 C18  SING Y N 28 
MSD C16 O41  SING N N 29 
MSD C18 C19  DOUB Y N 30 
MSD C18 H18C SING N N 31 
MSD C19 C20  SING Y N 32 
MSD C19 H19C SING N N 33 
MSD C20 C21  DOUB Y N 34 
MSD C20 C23  SING N N 35 
MSD C21 O22  SING N N 36 
MSD O22 H22O SING N N 37 
MSD C23 O24  DOUB N N 38 
MSD C23 C25  SING N N 39 
MSD C25 H251 SING N N 40 
MSD C25 H252 SING N N 41 
MSD C25 H253 SING N N 42 
MSD O41 C44  SING N N 43 
MSD C42 N43  TRIP N N 44 
MSD C44 H441 SING N N 45 
MSD C44 H442 SING N N 46 
MSD C44 H443 SING N N 47 
# 
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 
MSD SMILES           ACDLabs              10.04 S=C(Nc1ncc(C#N)cc1)NC3CC3c2c(OC)ccc(C(=O)C)c2O                                                                                                                             
MSD InChI            InChI                1.02b InChI=1/C19H18N4O3S/c1-10(24)12-4-5-15(26-2)17(18(12)25)13-7-14(13)22-19(27)23-16-6-3-11(8-20)9-21-16/h3-6,9,13-14,25H,7H2,1-2H3,(H2,21,22,23,27)/t13-,14+/m0/s1/f/h22-23H 
MSD InChIKey         InChI                1.02b FSRLCMRWYUJTNT-NJRZNQJTDN                                                                                                                                                  
MSD SMILES_CANONICAL CACTVS               3.341 COc1ccc(C(C)=O)c(O)c1[C@H]2C[C@H]2NC(=S)Nc3ccc(cn3)C#N                                                                                                                     
MSD SMILES           CACTVS               3.341 COc1ccc(C(C)=O)c(O)c1[CH]2C[CH]2NC(=S)Nc3ccc(cn3)C#N                                                                                                                       
MSD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)c1ccc(c(c1O)[C@H]2C[C@H]2NC(=S)Nc3ccc(cn3)C#N)OC                                                                                                                     
MSD SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)c1ccc(c(c1O)C2CC2NC(=S)Nc3ccc(cn3)C#N)OC                                                                                                                             
# 
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 
MSD "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R,2R)-2-(3-acetyl-2-hydroxy-6-methoxyphenyl)cyclopropyl]-3-(5-cyanopyridin-2-yl)thiourea    
MSD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-(5-cyanopyridin-2-yl)-3-[(1R,2R)-2-(3-ethanoyl-2-hydroxy-6-methoxy-phenyl)cyclopropyl]thiourea 
# 
