data_TPI
# 
_chem_comp.id                                    TPI 
_chem_comp.name                                  "4-CARBAMOYL-4-{[6-(DIFLUORO-PHOSPHONO-METHYL)-NAPHTHALENE-2-CARBONYL]-AMINO}-BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H17 F2 N2 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-08-24 
_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                        430.297 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TPI 
_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        1BZC 
_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 
TPI P    P    P 0 1 N N N -20.528 58.443 12.069 -1.145 0.236  -5.750 P    TPI 1  
TPI O1   O1   O 0 1 N N N -20.441 56.979 11.460 -2.372 -0.123 -4.773 O1   TPI 2  
TPI O2   O2   O 0 1 N N N -21.334 59.323 11.198 -0.924 1.831  -5.770 O2   TPI 3  
TPI O3   O3   O 0 1 N N N -19.069 59.041 12.246 -1.448 -0.237 -7.119 O3   TPI 4  
TPI C1   C1   C 0 1 N N N -21.333 58.372 13.669 0.370  -0.578 -5.148 C1   TPI 5  
TPI F1   F1   F 0 1 N N N -21.442 59.627 14.164 1.455  -0.192 -5.942 F1   TPI 6  
TPI F2   F2   F 0 1 N N N -22.553 57.871 13.466 0.212  -1.967 -5.218 F2   TPI 7  
TPI C2   C2   C 0 1 Y N N -20.874 56.131 14.847 0.096  -0.917 -2.707 C2   TPI 8  
TPI C3   C3   C 0 1 Y N N -20.617 57.514 14.715 0.624  -0.173 -3.718 C3   TPI 9  
TPI C4   C4   C 0 1 Y N N -19.725 58.145 15.601 1.395  0.955  -3.452 C4   TPI 10 
TPI C5   C5   C 0 1 Y N N -19.100 57.425 16.618 1.643  1.348  -2.173 C5   TPI 11 
TPI C6   C6   C 0 1 Y N N -18.754 55.357 17.817 1.346  0.986  0.228  C6   TPI 12 
TPI C7   C7   C 0 1 Y N N -18.998 53.991 18.000 0.813  0.226  1.255  C7   TPI 13 
TPI C8   C8   C 0 1 Y N N -19.862 53.313 17.108 0.036  -0.911 0.974  C8   TPI 14 
TPI C9   C9   C 0 1 Y N N -20.489 54.016 16.050 -0.202 -1.291 -0.306 C9   TPI 15 
TPI C10  C10  C 0 1 Y N N -20.244 55.395 15.879 0.329  -0.544 -1.373 C10  TPI 16 
TPI C11  C11  C 0 1 Y N N -19.365 56.059 16.766 1.115  0.605  -1.102 C11  TPI 17 
TPI C12  C12  C 0 1 N N N -18.324 53.268 19.156 1.058  0.617  2.659  C12  TPI 18 
TPI O4   O4   O 0 1 N N N -17.608 53.925 19.900 1.729  1.600  2.908  O4   TPI 19 
TPI N1   N1   N 0 1 N N N -18.539 51.832 19.352 0.537  -0.115 3.664  N1   TPI 20 
TPI C13  C13  C 0 1 N N S -17.824 51.253 20.500 0.780  0.272  5.055  C13  TPI 21 
TPI C14  C14  C 0 1 N N N -16.323 51.418 20.518 2.034  -0.398 5.553  C14  TPI 22 
TPI N2   N2   N 0 1 N N N -15.724 52.071 21.663 2.399  -1.597 5.056  N2   TPI 23 
TPI O5   O5   O 0 1 N N N -15.621 50.987 19.617 2.715  0.140  6.399  O5   TPI 24 
TPI C15  C15  C 0 1 N N N -18.142 49.748 20.641 -0.406 -0.159 5.919  C15  TPI 25 
TPI C16  C16  C 0 1 N N N -19.628 49.505 20.944 -1.679 0.522  5.415  C16  TPI 26 
TPI C17  C17  C 0 1 N N N -19.866 48.031 21.082 -2.848 0.097  6.266  C17  TPI 27 
TPI O6   O6   O 0 1 N N N -21.139 47.677 21.233 -2.679 -0.672 7.182  O6   TPI 28 
TPI O7   O7   O 0 1 N N N -18.955 47.204 21.068 -4.076 0.573  6.006  O7   TPI 29 
TPI HO11 1HO1 H 0 0 N N N -19.922 56.413 12.020 -3.152 0.326  -5.127 HO11 TPI 30 
TPI HO21 1HO2 H 0 0 N N N -21.386 60.198 11.562 -0.731 2.098  -4.861 HO21 TPI 31 
TPI H21  1H2  H 0 1 N N N -21.563 55.628 14.147 -0.499 -1.790 -2.929 H21  TPI 32 
TPI H41  1H4  H 0 1 N N N -19.512 59.222 15.496 1.803  1.526  -4.273 H41  TPI 33 
TPI H51  1H5  H 0 1 N N N -18.399 57.933 17.301 2.243  2.225  -1.981 H51  TPI 34 
TPI H61  1H6  H 0 1 N N N -18.074 55.884 18.507 1.938  1.861  0.448  H61  TPI 35 
TPI H81  1H8  H 0 1 N N N -20.047 52.233 17.237 -0.374 -1.491 1.787  H81  TPI 36 
TPI H91  1H9  H 0 1 N N N -21.168 53.489 15.358 -0.800 -2.167 -0.507 H91  TPI 37 
TPI HN11 1HN1 H 0 0 N N N -19.138 51.279 18.738 0.002  -0.899 3.465  HN11 TPI 38 
TPI H131 1H13 H 0 0 N N N -18.207 51.851 21.359 0.899  1.354  5.116  H131 TPI 39 
TPI HN21 1HN2 H 0 0 N N N -16.310 52.431 22.415 3.206  -2.029 5.376  HN21 TPI 40 
TPI HN22 2HN2 H 0 0 N N N -14.710 52.182 21.675 1.852  -2.029 4.382  HN22 TPI 41 
TPI H151 1H15 H 0 0 N N N -17.812 49.177 19.741 -0.524 -1.240 5.859  H151 TPI 42 
TPI H152 2H15 H 0 0 N N N -17.487 49.264 21.403 -0.225 0.129  6.955  H152 TPI 43 
TPI H161 1H16 H 0 0 N N N -19.977 50.076 21.835 -1.560 1.604  5.475  H161 TPI 44 
TPI H162 2H16 H 0 0 N N N -20.297 49.973 20.185 -1.859 0.234  4.379  H162 TPI 45 
TPI HO71 1HO7 H 0 0 N N N -19.105 46.270 21.155 -4.825 0.300  6.552  HO71 TPI 46 
# 
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 
TPI P   O1   SING N N 1  
TPI P   O2   SING N N 2  
TPI P   O3   DOUB N N 3  
TPI P   C1   SING N N 4  
TPI O1  HO11 SING N N 5  
TPI O2  HO21 SING N N 6  
TPI C1  F1   SING N N 7  
TPI C1  F2   SING N N 8  
TPI C1  C3   SING N N 9  
TPI C2  C3   DOUB Y N 10 
TPI C2  C10  SING Y N 11 
TPI C2  H21  SING N N 12 
TPI C3  C4   SING Y N 13 
TPI C4  C5   DOUB Y N 14 
TPI C4  H41  SING N N 15 
TPI C5  C11  SING Y N 16 
TPI C5  H51  SING N N 17 
TPI C6  C7   DOUB Y N 18 
TPI C6  C11  SING Y N 19 
TPI C6  H61  SING N N 20 
TPI C7  C8   SING Y N 21 
TPI C7  C12  SING N N 22 
TPI C8  C9   DOUB Y N 23 
TPI C8  H81  SING N N 24 
TPI C9  C10  SING Y N 25 
TPI C9  H91  SING N N 26 
TPI C10 C11  DOUB Y N 27 
TPI C12 O4   DOUB N N 28 
TPI C12 N1   SING N N 29 
TPI N1  C13  SING N N 30 
TPI N1  HN11 SING N N 31 
TPI C13 C14  SING N N 32 
TPI C13 C15  SING N N 33 
TPI C13 H131 SING N N 34 
TPI C14 N2   SING N N 35 
TPI C14 O5   DOUB N N 36 
TPI N2  HN21 SING N N 37 
TPI N2  HN22 SING N N 38 
TPI C15 C16  SING N N 39 
TPI C15 H151 SING N N 40 
TPI C15 H152 SING N N 41 
TPI C16 C17  SING N N 42 
TPI C16 H161 SING N N 43 
TPI C16 H162 SING N N 44 
TPI C17 O6   DOUB N N 45 
TPI C17 O7   SING N N 46 
TPI O7  HO71 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 
TPI SMILES           ACDLabs              10.04 O=C(N)C(NC(=O)c1ccc2c(c1)ccc(c2)C(F)(F)P(=O)(O)O)CCC(=O)O                                                                                                                                              
TPI InChI            InChI                1.02b InChI=1/C17H17F2N2O7P/c18-17(19,29(26,27)28)12-4-3-9-7-11(2-1-10(9)8-12)16(25)21-13(15(20)24)5-6-14(22)23/h1-4,7-8,13H,5-6H2,(H2,20,24)(H,21,25)(H,22,23)(H2,26,27,28)/t13-/m0/s1/f/h21-22,26-27H,20H2 
TPI InChIKey         InChI                1.02b OWWCIKSGGKYNHT-JDUQIDKEDI                                                                                                                                                                              
TPI SMILES_CANONICAL CACTVS               3.341 NC(=O)[C@H](CCC(O)=O)NC(=O)c1ccc2cc(ccc2c1)C(F)(F)[P](O)(O)=O                                                                                                                                          
TPI SMILES           CACTVS               3.341 NC(=O)[CH](CCC(O)=O)NC(=O)c1ccc2cc(ccc2c1)C(F)(F)[P](O)(O)=O                                                                                                                                           
TPI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc(cc2)C(F)(F)P(=O)(O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N                                                                                                                                         
TPI SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc2c1cc(cc2)C(F)(F)P(=O)(O)O)C(=O)NC(CCC(=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 
TPI "SYSTEMATIC NAME" ACDLabs              10.04 N~2~-({6-[difluoro(phosphono)methyl]naphthalen-2-yl}carbonyl)-L-alpha-glutamine                     
TPI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S)-5-amino-4-[[6-(difluoro-phosphono-methyl)naphthalen-2-yl]carbonylamino]-5-oxo-pentanoic acid" 
# 
