data_C4M
# 
_chem_comp.id                                    C4M 
_chem_comp.name                                  N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H28 N2 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "INHIBITOR OF THROMBIN" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-12-09 
_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                        392.512 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     C4M 
_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        2C93 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
C4M C1   C1   C 0 1 N N N -1.833 20.049 47.224 4.326  4.011  -0.745 C1   C4M 1  
C4M O2   O2   O 0 1 N N N -0.829 20.048 46.185 4.743  3.123  0.295  O2   C4M 2  
C4M C3   C3   C 0 1 Y N N 0.337  19.453 46.592 4.099  1.944  0.086  C3   C4M 3  
C4M C4   C4   C 0 1 Y N N 0.451  18.958 47.875 3.232  1.807  -0.989 C4   C4M 4  
C4M C5   C5   C 0 1 Y N N 1.607  18.338 48.318 2.579  0.608  -1.200 C5   C4M 5  
C4M C6   C6   C 0 1 N N N 1.588  17.843 49.751 1.638  0.458  -2.367 C6   C4M 6  
C4M C7   C7   C 0 1 Y N N 2.695  18.184 47.468 2.789  -0.455 -0.340 C7   C4M 7  
C4M C8   C8   C 0 1 Y N N 2.596  18.682 46.164 3.651  -0.320 0.732  C8   C4M 8  
C4M C9   C9   C 0 1 N N N 3.755  18.547 45.191 3.877  -1.480 1.667  C9   C4M 9  
C4M C10  C10  C 0 1 Y N N 1.422  19.306 45.726 4.312  0.875  0.943  C10  C4M 10 
C4M C11  C11  C 0 1 N N N 1.334  19.828 44.309 5.252  1.021  2.112  C11  C4M 11 
C4M S12  S12  S 0 1 N N N 4.177  17.378 48.028 1.955  -1.983 -0.611 S12  C4M 12 
C4M O13  O13  O 0 1 N N N 3.865  16.831 49.314 2.760  -2.977 0.007  O13  C4M 13 
C4M O14  O14  O 0 1 N N N 4.620  16.588 46.941 1.565  -1.973 -1.978 O14  C4M 14 
C4M N15  N15  N 0 1 N N N 5.331  18.501 48.352 0.546  -1.939 0.259  N15  C4M 15 
C4M C16  C16  C 0 1 N N N 5.146  19.470 49.437 -0.498 -0.971 -0.085 C16  C4M 16 
C4M C17  C17  C 0 1 N N R 6.532  20.000 49.843 -1.808 -1.371 0.595  C17  C4M 17 
C4M O18  O18  O 0 1 N N N 7.070  20.840 48.808 -1.658 -1.276 2.013  O18  C4M 18 
C4M C19  C19  C 0 1 N N S 6.426  20.773 51.153 -2.927 -0.433 0.137  C19  C4M 19 
C4M N20  N20  N 0 1 N N N 7.758  21.245 51.519 -3.082 -0.530 -1.320 N20  C4M 20 
C4M C21  C21  C 0 1 N N N 5.515  21.995 50.995 -4.238 -0.833 0.817  C21  C4M 21 
C4M C22  C22  C 0 1 Y N N 4.058  21.678 51.278 -5.312 0.164  0.463  C22  C4M 22 
C4M C23  C23  C 0 1 Y N N 3.077  22.077 50.366 -5.513 1.275  1.260  C23  C4M 23 
C4M C24  C24  C 0 1 Y N N 1.738  21.816 50.595 -6.495 2.192  0.933  C24  C4M 24 
C4M C25  C25  C 0 1 Y N N 1.363  21.155 51.752 -7.282 1.991  -0.186 C25  C4M 25 
C4M C26  C26  C 0 1 Y N N 2.329  20.750 52.661 -7.085 0.877  -0.979 C26  C4M 26 
C4M C27  C27  C 0 1 Y N N 3.678  21.013 52.434 -6.100 -0.037 -0.655 C27  C4M 27 
C4M H1C1 1H1C H 0 0 N N N -2.461 19.151 47.128 4.596  3.589  -1.713 H1C1 C4M 28 
C4M H1C2 2H1C H 0 0 N N N -2.460 20.947 47.127 3.246  4.146  -0.696 H1C2 C4M 29 
C4M H1C3 3H1C H 0 0 N N N -1.343 20.049 48.209 4.819  4.975  -0.618 H1C3 C4M 30 
C4M H4   H4   H 0 1 N N N -0.384 19.057 48.552 3.069  2.637  -1.661 H4   C4M 31 
C4M H6C1 1H6C H 0 0 N N N 0.685  18.217 50.256 2.162  -0.014 -3.198 H6C1 C4M 32 
C4M H6C2 2H6C H 0 0 N N N 2.482  18.210 50.277 0.791  -0.161 -2.073 H6C2 C4M 33 
C4M H6C3 3H6C H 0 0 N N N 1.583  16.743 49.759 1.281  1.441  -2.674 H6C3 C4M 34 
C4M H9C1 1H9C H 0 0 N N N 4.307  17.620 45.405 4.635  -2.142 1.248  H9C1 C4M 35 
C4M H9C2 2H9C H 0 0 N N N 4.429  19.409 45.302 4.215  -1.107 2.634  H9C2 C4M 36 
C4M H9C3 3H9C H 0 0 N N N 3.368  18.514 44.162 2.945  -2.030 1.795  H9C3 C4M 37 
C4M H111 1H11 H 0 0 N N N 0.416  19.450 43.836 6.257  0.730  1.808  H111 C4M 38 
C4M H112 2H11 H 0 0 N N N 2.209  19.486 43.737 5.259  2.059  2.445  H112 C4M 39 
C4M H113 3H11 H 0 0 N N N 1.313  20.928 44.323 4.919  0.380  2.928  H113 C4M 40 
C4M H15  H15  H 0 1 N N N 6.157  17.987 48.582 0.413  -2.555 0.996  H15  C4M 41 
C4M H161 1H16 H 0 0 N N N 4.654  18.991 50.296 -0.200 0.021  0.255  H161 C4M 42 
C4M H162 2H16 H 0 0 N N N 4.512  20.301 49.094 -0.638 -0.957 -1.166 H162 C4M 43 
C4M H17  H17  H 0 1 N N N 7.212  19.148 49.985 -2.060 -2.396 0.324  H17  C4M 44 
C4M H18  H18  H 0 1 N N N 7.189  21.721 49.144 -1.436 -0.356 2.209  H18  C4M 45 
C4M H19  H19  H 0 1 N N N 6.007  20.109 51.923 -2.675 0.593  0.408  H19  C4M 46 
C4M H201 1H20 H 0 0 N N N 7.683  22.125 51.987 -3.314 -1.491 -1.524 H201 C4M 47 
C4M H202 2H20 H 0 0 N N N 8.312  21.353 50.694 -3.892 0.021  -1.563 H202 C4M 48 
C4M H211 1H21 H 0 0 N N N 5.587  22.333 49.951 -4.536 -1.824 0.477  H211 C4M 49 
C4M H212 2H21 H 0 0 N N N 5.846  22.769 51.703 -4.097 -0.846 1.898  H212 C4M 50 
C4M H23  H23  H 0 1 N N N 3.370  22.598 49.467 -4.898 1.432  2.134  H23  C4M 51 
C4M H24  H24  H 0 1 N N N 0.992  22.125 49.878 -6.649 3.063  1.552  H24  C4M 52 
C4M H25  H25  H 0 1 N N N 0.320  20.955 51.947 -8.052 2.705  -0.440 H25  C4M 53 
C4M H26  H26  H 0 1 N N N 2.032  20.224 53.556 -7.700 0.720  -1.853 H26  C4M 54 
C4M H27  H27  H 0 1 N N N 4.422  20.702 53.152 -5.945 -0.908 -1.275 H27  C4M 55 
# 
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 
C4M C1  O2   SING N N 1  
C4M C1  H1C1 SING N N 2  
C4M C1  H1C2 SING N N 3  
C4M C1  H1C3 SING N N 4  
C4M O2  C3   SING N N 5  
C4M C3  C4   DOUB Y N 6  
C4M C3  C10  SING Y N 7  
C4M C4  C5   SING Y N 8  
C4M C4  H4   SING N N 9  
C4M C5  C6   SING N N 10 
C4M C5  C7   DOUB Y N 11 
C4M C6  H6C1 SING N N 12 
C4M C6  H6C2 SING N N 13 
C4M C6  H6C3 SING N N 14 
C4M C7  C8   SING Y N 15 
C4M C7  S12  SING N N 16 
C4M C8  C9   SING N N 17 
C4M C8  C10  DOUB Y N 18 
C4M C9  H9C1 SING N N 19 
C4M C9  H9C2 SING N N 20 
C4M C9  H9C3 SING N N 21 
C4M C10 C11  SING N N 22 
C4M C11 H111 SING N N 23 
C4M C11 H112 SING N N 24 
C4M C11 H113 SING N N 25 
C4M S12 O13  DOUB N N 26 
C4M S12 O14  DOUB N N 27 
C4M S12 N15  SING N N 28 
C4M N15 C16  SING N N 29 
C4M N15 H15  SING N N 30 
C4M C16 C17  SING N N 31 
C4M C16 H161 SING N N 32 
C4M C16 H162 SING N N 33 
C4M C17 O18  SING N N 34 
C4M C17 C19  SING N N 35 
C4M C17 H17  SING N N 36 
C4M O18 H18  SING N N 37 
C4M C19 N20  SING N N 38 
C4M C19 C21  SING N N 39 
C4M C19 H19  SING N N 40 
C4M N20 H201 SING N N 41 
C4M N20 H202 SING N N 42 
C4M C21 C22  SING N N 43 
C4M C21 H211 SING N N 44 
C4M C21 H212 SING N N 45 
C4M C22 C23  SING Y N 46 
C4M C22 C27  DOUB Y N 47 
C4M C23 C24  DOUB Y N 48 
C4M C23 H23  SING N N 49 
C4M C24 C25  SING Y N 50 
C4M C24 H24  SING N N 51 
C4M C25 C26  DOUB Y N 52 
C4M C25 H25  SING N N 53 
C4M C26 C27  SING Y N 54 
C4M C26 H26  SING N N 55 
C4M C27 H27  SING N N 56 
# 
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 
C4M SMILES           ACDLabs              10.04 O=S(=O)(c1c(cc(OC)c(c1C)C)C)NCC(O)C(N)Cc2ccccc2                                                                                                       
C4M InChI            InChI                1.02b InChI=1/C20H28N2O4S/c1-13-10-19(26-4)14(2)15(3)20(13)27(24,25)22-12-18(23)17(21)11-16-8-6-5-7-9-16/h5-10,17-18,22-23H,11-12,21H2,1-4H3/t17-,18+/m0/s1 
C4M InChIKey         InChI                1.02b HORGTFOBJRCVMO-ZWKOTPCHBY                                                                                                                             
C4M SMILES_CANONICAL CACTVS               3.341 COc1cc(C)c(c(C)c1C)[S](=O)(=O)NC[C@@H](O)[C@@H](N)Cc2ccccc2                                                                                           
C4M SMILES           CACTVS               3.341 COc1cc(C)c(c(C)c1C)[S](=O)(=O)NC[CH](O)[CH](N)Cc2ccccc2                                                                                               
C4M SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc(c(c(c1S(=O)(=O)NC[C@H]([C@H](Cc2ccccc2)N)O)C)C)OC                                                                                               
C4M SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc(c(c(c1S(=O)(=O)NCC(C(Cc2ccccc2)N)O)C)C)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 
C4M "SYSTEMATIC NAME" ACDLabs              10.04 N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-4-methoxy-2,3,6-trimethylbenzenesulfonamide   
C4M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 
# 
