data_DFM
# 
_chem_comp.id                                    DFM 
_chem_comp.name                                  N-ACETYL-L-PHENYLALANYL-4-[DIFLUORO(PHOSPHONO)METHYL]-L-PHENYLALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H24 F2 N3 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "DIFLUOROMETHYLPHOSPHONIC ACID ANALOG" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-05-04 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        483.402 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DFM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye OEToolkits" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2CMC 
_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 
DFM C1   C1   C 0 1 N N N 26.072 31.429 19.610 -1.433 4.925  -3.910 C1   DFM 1  
DFM O6   O6   O 0 1 N N N 25.173 33.282 21.665 -2.762 5.332  -6.196 O6   DFM 2  
DFM O7   O7   O 0 1 N N N 24.567 30.581 21.940 -1.172 3.366  -6.060 O7   DFM 3  
DFM O9   O9   O 0 1 N N N 27.237 31.551 22.272 -3.450 3.245  -4.758 O9   DFM 4  
DFM C11  C11  C 0 1 Y N N 24.911 31.360 18.742 -0.754 4.080  -2.886 C11  DFM 5  
DFM C12  C12  C 0 1 Y N N 24.507 32.599 18.105 0.581  3.714  -3.057 C12  DFM 6  
DFM C13  C13  C 0 1 Y N N 23.302 32.562 17.274 1.216  2.923  -2.100 C13  DFM 7  
DFM C14  C14  C 0 1 Y N N 22.577 31.304 17.109 0.508  2.508  -0.983 C14  DFM 8  
DFM C15  C15  C 0 1 Y N N 22.981 30.039 17.723 -0.819 2.864  -0.799 C15  DFM 9  
DFM C16  C16  C 0 1 Y N N 24.192 30.093 18.556 -1.454 3.655  -1.757 C16  DFM 10 
DFM C21  C21  C 0 1 N N N 21.335 31.240 16.241 1.195  1.652  0.053  C21  DFM 11 
DFM C22  C22  C 0 1 N N S 21.580 31.681 14.784 1.057  0.152  -0.231 C22  DFM 12 
DFM C25  C25  C 0 1 N N N 22.622 30.788 14.105 2.114  -0.631 0.533  C25  DFM 13 
DFM O26  O26  O 0 1 N N N 23.762 31.188 13.878 1.966  -1.036 1.684  O26  DFM 14 
DFM N27  N27  N 0 1 N N N 22.270 29.540 13.789 3.241  -0.884 -0.221 N27  DFM 15 
DFM N45  N45  N 0 1 N N N 20.288 31.636 14.073 -0.231 -0.364 0.174  N45  DFM 16 
DFM C47  C47  C 0 1 N N N 20.054 32.519 13.111 -1.107 -0.996 -0.698 C47  DFM 17 
DFM C48  C48  C 0 1 N N S 18.767 32.392 12.335 -2.411 -1.387 -0.013 C48  DFM 18 
DFM O49  O49  O 0 1 N N N 20.852 33.412 12.877 -0.896 -1.187 -1.894 O49  DFM 19 
DFM N51  N51  N 0 1 N N N 18.121 33.708 12.323 -3.472 -1.183 -0.966 N51  DFM 20 
DFM C4   C4   C 0 1 N N N 19.041 31.987 10.887 -2.342 -2.839 0.475  C4   DFM 21 
DFM C5   C5   C 0 1 Y N N 19.814 30.696 10.765 -3.376 -3.151 1.529  C5   DFM 22 
DFM C30  C30  C 0 1 Y N N 19.190 29.441 11.170 -3.061 -2.964 2.866  C30  DFM 23 
DFM C31  C31  C 0 1 Y N N 19.962 28.201 11.110 -4.016 -3.252 3.840  C31  DFM 24 
DFM C6   C6   C 0 1 Y N N 21.342 28.297 10.636 -5.275 -3.723 3.465  C6   DFM 25 
DFM C33  C33  C 0 1 Y N N 21.973 29.552 10.221 -5.577 -3.906 2.116  C33  DFM 26 
DFM C34  C34  C 0 1 Y N N 21.190 30.791 10.278 -4.622 -3.618 1.142  C34  DFM 27 
DFM C67  C67  C 0 1 N N N 17.013 33.901 13.031 -4.115 0.030  -1.139 C67  DFM 28 
DFM O70  O70  O 0 1 N N N 16.397 32.936 13.517 -3.884 1.067  -0.528 O70  DFM 29 
DFM C71  C71  C 0 1 N N N 16.491 35.310 13.214 -5.182 0.013  -2.183 C71  DFM 30 
DFM F66  F66  F 0 1 N N N 27.084 32.428 19.132 -2.413 5.727  -3.418 F66  DFM 31 
DFM F67  F67  F 0 1 N N N 26.828 30.159 19.461 -0.604 5.726  -4.628 F67  DFM 32 
DFM P68  P68  P 0 1 N N N 25.744 31.724 21.398 -2.323 4.124  -5.215 P68  DFM 33 
DFM H12  H12  H 0 1 N N N 25.083 33.530 18.241 1.134  4.041  -3.934 H12  DFM 34 
DFM H16  H16  H 0 1 N N N 24.563 29.176 19.044 -2.494 3.935  -1.615 H16  DFM 35 
DFM H13  H13  H 0 1 N N N 22.944 33.478 16.775 2.256  2.642  -2.242 H13  DFM 36 
DFM H15  H15  H 0 1 N N N 22.414 29.105 17.571 -1.372 2.537  0.077  H15  DFM 37 
DFM H211 1H21 H 0 0 N N N 20.504 31.827 16.697 2.256  1.931  0.118  H211 DFM 38 
DFM H212 2H21 H 0 0 N N N 20.882 30.222 16.274 0.772  1.897  1.036  H212 DFM 39 
DFM H22  H22  H 0 1 N N N 21.953 32.732 14.785 1.159  -0.060 -1.302 H22  DFM 40 
DFM H45  H45  H 0 1 N N N 19.586 30.937 14.317 -0.508 -0.260 1.145  H45  DFM 41 
DFM H271 1H27 H 0 0 N N N 22.964 28.945 13.337 3.997  -1.418 0.194  H271 DFM 42 
DFM H272 2H27 H 0 0 N N N 21.324 29.208 13.977 3.340  -0.557 -1.177 H272 DFM 43 
DFM H48  H48  H 0 1 N N N 18.100 31.643 12.822 -2.601 -0.698 0.818  H48  DFM 44 
DFM H51  H51  H 0 1 N N N 18.519 34.470 11.775 -3.762 -1.971 -1.542 H51  DFM 45 
DFM H4C1 1H4C H 0 0 N N N 19.554 32.810 10.336 -1.339 -3.062 0.864  H4C1 DFM 46 
DFM H4C2 2H4C H 0 0 N N N 18.092 31.938 10.303 -2.486 -3.533 -0.364 H4C2 DFM 47 
DFM H30  H30  H 0 1 N N N 18.144 29.428 11.519 -2.083 -2.598 3.167  H30  DFM 48 
DFM H34  H34  H 0 1 N N N 21.622 31.757 9.966  -4.867 -3.763 0.093  H34  DFM 49 
DFM H31  H31  H 0 1 N N N 19.522 27.235 11.409 -3.781 -3.110 4.891  H31  DFM 50 
DFM H6   H6   H 0 1 N N N 21.941 27.372 10.588 -6.019 -3.947 4.224  H6   DFM 51 
DFM H33  H33  H 0 1 N N N 23.019 29.565 9.872  -6.557 -4.272 1.824  H33  DFM 52 
DFM H711 1H71 H 0 0 N N N 15.561 35.472 13.808 -6.170 0.285  -1.779 H711 DFM 53 
DFM H712 2H71 H 0 0 N N N 16.360 35.777 12.210 -4.989 0.735  -2.993 H712 DFM 54 
DFM H713 3H71 H 0 0 N N N 17.305 35.940 13.643 -5.332 -0.955 -2.688 H713 DFM 55 
DFM HO6  HO6  H 0 1 N N N 25.065 33.425 22.598 -3.310 5.128  -6.983 HO6  DFM 56 
DFM HO7  HO7  H 0 1 N N N 24.726 30.371 22.853 -1.433 2.807  -6.823 HO7  DFM 57 
# 
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 
DFM C1  C11  SING N N 1  
DFM C1  F66  SING N N 2  
DFM C1  F67  SING N N 3  
DFM C1  P68  SING N N 4  
DFM O6  P68  SING N N 5  
DFM O6  HO6  SING N N 6  
DFM O7  P68  SING N N 7  
DFM O7  HO7  SING N N 8  
DFM O9  P68  DOUB N N 9  
DFM C11 C12  SING Y N 10 
DFM C11 C16  DOUB Y N 11 
DFM C12 C13  DOUB Y N 12 
DFM C12 H12  SING N N 13 
DFM C13 C14  SING Y N 14 
DFM C13 H13  SING N N 15 
DFM C14 C15  DOUB Y N 16 
DFM C14 C21  SING N N 17 
DFM C15 C16  SING Y N 18 
DFM C15 H15  SING N N 19 
DFM C16 H16  SING N N 20 
DFM C21 C22  SING N N 21 
DFM C21 H211 SING N N 22 
DFM C21 H212 SING N N 23 
DFM C22 C25  SING N N 24 
DFM C22 N45  SING N N 25 
DFM C22 H22  SING N N 26 
DFM C25 O26  DOUB N N 27 
DFM C25 N27  SING N N 28 
DFM N27 H271 SING N N 29 
DFM N27 H272 SING N N 30 
DFM N45 C47  SING N N 31 
DFM N45 H45  SING N N 32 
DFM C47 C48  SING N N 33 
DFM C47 O49  DOUB N N 34 
DFM C48 N51  SING N N 35 
DFM C48 C4   SING N N 36 
DFM C48 H48  SING N N 37 
DFM N51 C67  SING N N 38 
DFM N51 H51  SING N N 39 
DFM C4  C5   SING N N 40 
DFM C4  H4C1 SING N N 41 
DFM C4  H4C2 SING N N 42 
DFM C5  C30  SING Y N 43 
DFM C5  C34  DOUB Y N 44 
DFM C30 C31  DOUB Y N 45 
DFM C30 H30  SING N N 46 
DFM C31 C6   SING Y N 47 
DFM C31 H31  SING N N 48 
DFM C6  C33  DOUB Y N 49 
DFM C6  H6   SING N N 50 
DFM C33 C34  SING Y N 51 
DFM C33 H33  SING N N 52 
DFM C34 H34  SING N N 53 
DFM C67 O70  DOUB N N 54 
DFM C67 C71  SING N N 55 
DFM C71 H711 SING N N 56 
DFM C71 H712 SING N N 57 
DFM C71 H713 SING N N 58 
# 
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 
DFM SMILES           ACDLabs              10.04 FC(F)(c1ccc(cc1)CC(C(=O)N)NC(=O)C(NC(=O)C)Cc2ccccc2)P(=O)(O)O 
DFM InChI            InChI                1.02b 
InChI=1/C21H24F2N3O6P/c1-13(27)25-18(12-14-5-3-2-4-6-14)20(29)26-17(19(24)28)11-15-7-9-16(10-8-15)21(22,23)33(30,31)32/h2-10,17-18H,11-12H2,1H3,(H2,24,28)(H,25,27)(H,26,29)(H2,30,31,32)/t17-,18-/m0/s1/f/h25-26,30-31H,24H2 
DFM InChIKey         InChI                1.02b KPMMESISHWWXNM-BEDRWNMRDT 
DFM SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc2ccc(cc2)C(F)(F)[P](O)(O)=O)C(N)=O 
DFM SMILES           CACTVS               3.341 CC(=O)N[CH](Cc1ccccc1)C(=O)N[CH](Cc2ccc(cc2)C(F)(F)[P](O)(O)=O)C(N)=O 
DFM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc2ccc(cc2)C(F)(F)P(=O)(O)O)C(=O)N 
DFM SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC(Cc1ccccc1)C(=O)NC(Cc2ccc(cc2)C(F)(F)P(=O)(O)O)C(=O)N 
# 
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 
DFM "SYSTEMATIC NAME" ACDLabs              10.04 N-acetyl-L-phenylalanyl-4-[difluoro(phosphono)methyl]-L-phenylalaninamide                                               
DFM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[4-[(2S)-2-[[(2S)-2-acetamido-3-phenyl-propanoyl]amino]-3-amino-3-oxo-propyl]phenyl]-difluoro-methyl]phosphonic acid" 
# 
