data_S27
# 
_chem_comp.id                                    S27 
_chem_comp.name                                  N-[[2-METHYL-4-HYDROXYCARBAMOYL]BUT-4-YL-N]-BENZYL-P-[PHENYL]-P-[METHYL]PHOSPHINAMID 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H27 N2 O3 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        374.414 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     S27 
_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        1B3D 
_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 
S27 C1   C1   C 0 1 Y N N -21.978 30.314 1.813  1.228  -0.060 2.415  C1   S27 1  
S27 C2   C2   C 0 1 Y N N -22.120 29.262 2.814  1.031  0.376  3.712  C2   S27 2  
S27 C3   C3   C 0 1 Y N N -21.830 29.554 4.211  1.046  -0.529 4.756  C3   S27 3  
S27 C4   C4   C 0 1 Y N N -21.385 30.863 4.644  1.256  -1.871 4.504  C4   S27 4  
S27 C5   C5   C 0 1 Y N N -21.220 31.902 3.644  1.452  -2.309 3.207  C5   S27 5  
S27 C6   C6   C 0 1 Y N N -21.512 31.627 2.244  1.433  -1.404 2.163  C6   S27 6  
S27 P7   P7   P 0 1 N N R -22.644 30.141 0.094  1.209  1.127  1.045  P7   S27 7  
S27 O8   O8   O 0 1 N N N -22.288 31.309 -0.726 2.595  1.541  0.732  O8   S27 8  
S27 C9   C9   C 0 1 N N N -24.492 30.197 0.204  0.232  2.590  1.523  C9   S27 9  
S27 N10  N10  N 0 1 N N N -22.175 28.758 -0.800 0.518  0.409  -0.310 N10  S27 10 
S27 C11  C11  C 0 1 N N N -22.693 27.427 -0.362 0.824  1.280  -1.452 C11  S27 11 
S27 C12  C12  C 0 1 Y N N -23.807 26.867 -1.218 1.116  0.435  -2.665 C12  S27 12 
S27 C13  C13  C 0 1 Y N N -24.339 27.503 -2.403 0.120  0.188  -3.591 C13  S27 13 
S27 C14  C14  C 0 1 Y N N -25.445 26.897 -3.126 0.388  -0.587 -4.704 C14  S27 14 
S27 C15  C15  C 0 1 Y N N -26.011 25.646 -2.649 1.652  -1.115 -4.890 C15  S27 15 
S27 C16  C16  C 0 1 Y N N -25.477 25.001 -1.461 2.648  -0.866 -3.965 C16  S27 16 
S27 C17  C17  C 0 1 Y N N -24.369 25.612 -0.740 2.381  -0.087 -2.855 C17  S27 17 
S27 C18  C18  C 0 1 N N R -20.793 28.899 -1.338 -0.937 0.460  -0.119 C18  S27 18 
S27 C    C    C 0 1 N N N -19.696 29.018 -0.263 -1.618 -0.259 -1.254 C    S27 19 
S27 NA   NA   N 0 1 N N N -18.853 30.053 -0.334 -2.800 0.187  -1.723 NA   S27 20 
S27 OA   OA   O 0 1 N N N -17.571 29.819 0.235  -3.441 -0.489 -2.789 OA   S27 21 
S27 OB   OB   O 0 1 N N N -19.463 28.116 0.571  -1.103 -1.241 -1.746 OB   S27 22 
S27 C7   C7   C 0 1 N N N -20.511 27.698 -2.263 -1.302 -0.214 1.204  C7   S27 23 
S27 C8   C8   C 0 1 N N N -19.230 27.682 -3.103 -2.817 -0.159 1.404  C8   S27 24 
S27 C10  C10  C 0 1 N N N -19.196 28.914 -3.988 -3.197 -0.961 2.651  C10  S27 25 
S27 C23  C23  C 0 1 N N N -19.179 26.421 -3.954 -3.256 1.295  1.580  C23  S27 26 
S27 H2   H2   H 0 1 N N N -22.445 28.250 2.516  0.867  1.425  3.909  H2   S27 27 
S27 H3   H3   H 0 1 N N N -21.951 28.758 4.965  0.893  -0.187 5.770  H3   S27 28 
S27 H4   H4   H 0 1 N N N -21.177 31.063 5.708  1.268  -2.579 5.320  H4   S27 29 
S27 H5   H5   H 0 1 N N N -20.871 32.903 3.948  1.616  -3.358 3.010  H5   S27 30 
S27 H6   H6   H 0 1 N N N -21.377 32.427 1.496  1.586  -1.745 1.150  H6   S27 31 
S27 H91  1H9  H 0 1 N N N -24.893 30.092 -0.831 -0.788 2.285  1.753  H91  S27 32 
S27 H92  2H9  H 0 1 N N N -24.908 29.440 0.909  0.679  3.055  2.401  H92  S27 33 
S27 H93  3H9  H 0 1 N N N -24.868 31.107 0.726  0.220  3.304  0.699  H93  S27 34 
S27 H111 1H11 H 0 0 N N N -21.857 26.692 -0.287 -0.029 1.926  -1.656 H111 S27 35 
S27 H112 2H11 H 0 0 N N N -23.010 27.468 0.706  1.695  1.893  -1.218 H112 S27 36 
S27 H13  H13  H 0 1 N N N -23.900 28.451 -2.755 -0.867 0.600  -3.445 H13  S27 37 
S27 H14  H14  H 0 1 N N N -25.851 27.382 -4.029 -0.390 -0.781 -5.427 H14  S27 38 
S27 H15  H15  H 0 1 N N N -26.851 25.182 -3.192 1.861  -1.721 -5.759 H15  S27 39 
S27 H16  H16  H 0 1 N N N -25.911 24.050 -1.107 3.635  -1.279 -4.111 H16  S27 40 
S27 H17  H17  H 0 1 N N N -23.958 25.127 0.161  3.160  0.106  -2.131 H17  S27 41 
S27 H18  H18  H 0 1 N N N -20.753 29.864 -1.894 -1.265 1.499  -0.099 H18  S27 42 
S27 HNA  HNA  H 0 1 N N N -19.154 30.923 -0.772 -3.213 0.972  -1.329 HNA  S27 43 
S27 HOA  HOA  H 0 1 N N N -16.971 30.554 0.184  -4.263 -0.013 -2.969 HOA  S27 44 
S27 H71  1H7  H 0 1 N N N -20.551 26.763 -1.656 -0.808 0.305  2.025  H71  S27 45 
S27 H72  2H7  H 0 1 N N N -21.384 27.557 -2.941 -0.975 -1.254 1.184  H72  S27 46 
S27 H8   H8   H 0 1 N N N -18.342 27.688 -2.427 -3.315 -0.586 0.533  H8   S27 47 
S27 H101 1H10 H 0 0 N N N -18.263 28.902 -4.599 -4.264 -0.850 2.843  H101 S27 48 
S27 H102 2H10 H 0 0 N N N -20.112 29.008 -4.616 -2.963 -2.013 2.491  H102 S27 49 
S27 H103 3H10 H 0 0 N N N -19.306 29.857 -3.403 -2.633 -0.590 3.507  H103 S27 50 
S27 H231 1H23 H 0 0 N N N -18.246 26.409 -4.565 -2.691 1.749  2.394  H231 S27 51 
S27 H232 2H23 H 0 0 N N N -19.286 25.497 -3.338 -3.071 1.845  0.658  H232 S27 52 
S27 H233 3H23 H 0 0 N N N -20.092 26.304 -4.583 -4.320 1.328  1.815  H233 S27 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 
S27 C1  C2   DOUB Y N 1  
S27 C1  C6   SING Y N 2  
S27 C1  P7   SING N N 3  
S27 C2  C3   SING Y N 4  
S27 C2  H2   SING N N 5  
S27 C3  C4   DOUB Y N 6  
S27 C3  H3   SING N N 7  
S27 C4  C5   SING Y N 8  
S27 C4  H4   SING N N 9  
S27 C5  C6   DOUB Y N 10 
S27 C5  H5   SING N N 11 
S27 C6  H6   SING N N 12 
S27 P7  O8   DOUB N N 13 
S27 P7  C9   SING N N 14 
S27 P7  N10  SING N N 15 
S27 C9  H91  SING N N 16 
S27 C9  H92  SING N N 17 
S27 C9  H93  SING N N 18 
S27 N10 C11  SING N N 19 
S27 N10 C18  SING N N 20 
S27 C11 C12  SING N N 21 
S27 C11 H111 SING N N 22 
S27 C11 H112 SING N N 23 
S27 C12 C13  DOUB Y N 24 
S27 C12 C17  SING Y N 25 
S27 C13 C14  SING Y N 26 
S27 C13 H13  SING N N 27 
S27 C14 C15  DOUB Y N 28 
S27 C14 H14  SING N N 29 
S27 C15 C16  SING Y N 30 
S27 C15 H15  SING N N 31 
S27 C16 C17  DOUB Y N 32 
S27 C16 H16  SING N N 33 
S27 C17 H17  SING N N 34 
S27 C18 C    SING N N 35 
S27 C18 C7   SING N N 36 
S27 C18 H18  SING N N 37 
S27 C   NA   SING N N 38 
S27 C   OB   DOUB N N 39 
S27 NA  OA   SING N N 40 
S27 NA  HNA  SING N N 41 
S27 OA  HOA  SING N N 42 
S27 C7  C8   SING N N 43 
S27 C7  H71  SING N N 44 
S27 C7  H72  SING N N 45 
S27 C8  C10  SING N N 46 
S27 C8  C23  SING N N 47 
S27 C8  H8   SING N N 48 
S27 C10 H101 SING N N 49 
S27 C10 H102 SING N N 50 
S27 C10 H103 SING N N 51 
S27 C23 H231 SING N N 52 
S27 C23 H232 SING N N 53 
S27 C23 H233 SING N N 54 
# 
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 
S27 SMILES           ACDLabs              10.04 O=C(NO)C(N(P(=O)(c1ccccc1)C)Cc2ccccc2)CC(C)C                                                                                                                  
S27 InChI            InChI                1.02b InChI=1/C20H27N2O3P/c1-16(2)14-19(20(23)21-24)22(15-17-10-6-4-7-11-17)26(3,25)18-12-8-5-9-13-18/h4-13,16,19,24H,14-15H2,1-3H3,(H,21,23)/t19-,26-/m1/s1/f/h21H 
S27 InChIKey         InChI                1.02b KGUVBHLPMGERAT-DHPUCBKNDQ                                                                                                                                     
S27 SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@@H](N(Cc1ccccc1)[P@](C)(=O)c2ccccc2)C(=O)NO                                                                                                          
S27 SMILES           CACTVS               3.341 CC(C)C[CH](N(Cc1ccccc1)[P](C)(=O)c2ccccc2)C(=O)NO                                                                                                             
S27 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@H](C(=O)NO)[N@@](Cc1ccccc1)[P@@](=O)(C)c2ccccc2                                                                                                      
S27 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC(C(=O)NO)N(Cc1ccccc1)P(=O)(C)c2ccccc2                                                                                                                  
# 
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 
S27 "SYSTEMATIC NAME" ACDLabs              10.04 N~2~-benzyl-N-hydroxy-N~2~-[(R)-methyl(phenyl)phosphoryl]-D-leucinamide               
S27 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-N-hydroxy-4-methyl-2-[(methyl-phenyl-phosphoryl)-(phenylmethyl)amino]pentanamide 
# 
